Giant Robots Smashing Into Other Giant Robots

Today's conversation revolves around the importance and challenges of goal setting within organizations. It highlights how identifying and articulating real problems can be transformative, turning abstract desires for growth into concrete plans for improvement. Host Victoria Guido and special guest Evan Hammer discuss the nuances of leadership and organizational self-awareness, emphasizing the need for honesty and a growth mindset when addressing weaknesses. They touch on Evan's role as an OKR Coach in fostering alignment, focus, and excitement around goals, particularly in small to mid-sized companies. Evan shares his enthusiasm for goal setting and believes his passion can inspire others. He points out the positive outcomes when employees engage with goals that address problems they care about. Victoria and Evan agree that success is not solely measured by hitting OKRs but also by engagement and alignment within the team. They discuss the ideal organizations for Evan's work, which include small to medium-sized companies seeking to improve focus and alignment, as well as start-up teams needing more straightforward goal statements and go-to-market strategies. Evan also recounts his experience as a Techstars mentor, noting that a common issue across companies is the lack of clear goals, and he emphasizes the power of focus as a lever for growth. Follow Evan Hammer on LinkedIn or X. Visit his website at evanhammer.com. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Evan Hammer, OKR and personal goals coach. Evan, thank you for joining us. EVAN: Thank you for having me. I'm excited to be here. VICTORIA: Wonderful. Me too. And I wanted to ask you first, before we dive into business, tell me a personal goal that you've achieved recently that you're most proud of. EVAN: I guess a couple of months ago, I did a 100-mile loop of Mount Rainier. So, it was a 10-day backpacking trip. My younger brother, I went with him, and it's the kind of thing he does more regularly. Yeah, it was something I was kind of excited to do but really unsure of, and worked super hard between the gear and the training and just, like, the mindset. But it was also just awesome being out in the woods for ten days. VICTORIA: I also love being out in the woods for long periods of time. I guess, like, how long did your brother plan this trip for? And how long were you involved before you decided to go? EVAN: You know, it was something he was planning to do since the spring. He won a lottery to be able to do it. And I was going back and forth for a few months. And I think it was just maybe in the end of June where I was like, okay, I'm doing this. I need to put together a gear list, figure out a training plan. I live in Fort Greene in Brooklyn. And it was a lot of, like, waking up early and going up and down the steps in Fort Greene Park, which is, like, you know, 6, 10 flights of steps, something like that outdoors -- VICTORIA: [laughs] EVAN: With a heavy backpack on for two to three hours, like on weekends. VICTORIA: Oooh. Wow. EVAN: Yeah, it was one of those things I was like, you know, you don't know when you do something like this how it's going to go until you're there doing it or how your body is going to respond. So, it was a little bit of, like, trying to train as much as possible but also being aware that I just have to deal with whatever will happen on the trip. VICTORIA: I love that, at first, it sounds sort of, like, fun. Like, "Oh, do you want to go on this trip with me?" And you're like, "Yeah, okay." And then you look at the training plan, and it's like, "We'll wake up at 6:00 a.m. every day and walk up and down ten flights of stairs [laughs] with a heavy backpack on," you know, like, "Oh okay, [laughs] a lot of prep work to have this trip." [laughs] EVAN: It's fun in that you're doing something amazing, and it's beautiful. And it was just one of the more beautiful places I've ever been. It was really interesting and meaningful to me to kind of be detached from everything that I normally do and just focus on being in the woods and hiking these mountains. But yeah, you don't know how it's going to go. So, it's like you're putting yourself in an extreme physical situation. I think that's anxiety-inducing, and it feels good and is healthy and protective to train for it. VICTORIA: I agree. Yeah, I mean, I totally relate to that. I'm a rock climber and hiker myself. And sometimes I spend all this time, you know, on gym memberships, climbing in the gym, running up and down hills. And then, I get all the way out to rock, and I'm about to start my climb, and I'm like, why am I doing this? [laughs] This is a lot of work to get to this point. But then it is all fun, and it's super worth it. And I always feel restored whenever I come back from being a long time in nature. It's really great. I think maybe to get towards, like, a metrics conversation that we talk about a lot in climbing is the type of fun something is. So, there's three types of fun levels. Have you heard this framework before, Evan? EVAN: I have not. VICTORIA: Okay, so there's three levels of fun. Level one fun is, like, you're having fun while you're doing it. We're, like, laughing and enjoying recording a podcast together. Like, oh my God, it's so much fun, super easy, not stressful. Maybe it was a little stressful for you, I don't know. [chuckles] It's a little stressful for me. Level two fun is it's a little difficult while you're doing it, but you're still looking back on it and having fun, but you're never really in any kind of intense danger, right? Like, you're going on a backpacking trip. It's relatively within your health expectations, and the trail is walkable. You're not, like, going to fumble and fall down a cliff. It's level-two fun. So, you're mostly enjoying it. Like, it's kind of difficult, and there's some effort involved, but it's still fun. Level three fun is when it's very dangerous, and you're really scared the whole time [laughs], and, like, you maybe, like, could have died. But looking back on it, it's fun. So, how would you rate your Mount Rainier trip? EVAN: It's funny because we actually...we didn't come up with the levels, but we spoke about how when you're hiking, often, in your head, you're just trying to figure out how much longer you have to hike as if the whole point was not to be hiking. And then you finish hiking for the day, and you're like, "Oh, that was so great. I'm so looking forward to waking up tomorrow and hiking some more." VICTORIA: Yeah [chuckles], exactly. EVAN: That fits the level two fun pretty explicitly. VICTORIA: That's great. Yeah, it's a very, you know, I've found it to be pretty useful. And, you know, as I get older, I tend to try to avoid level three fun more often [laughs]. Like, I don't really need to be frightened [laughs]. I have enough stress in my life. I don't need to also endanger myself too aggressively. But, you know, everyone has their own risk level as well, right? Like, someone else might think the type of climbing and hiking that I'm doing is level three fun, but, for me, it's more...and, like, there's other things like skateboarding and riding a bike where, for me, is level three. I'm scared and [laughs] -- EVAN: Right. And I think you also frame level three as, like, sort of physical safety. But, you know, people have different risk tolerances and classifications across the board. So, like, for me, I try to stay away from things that I would consider physically dangerous. But I'm very comfortable, like, taking financial or social risk, where I know other people have an inverted kind of spectrum where, like, social risk is, like [laughs], you know, is a terror to them when physical risk doesn't seem that scary to them, you know, so... VICTORIA: That's so interesting. And especially for me, I do a lot of networking. And I'm, of course, been really active in San Diego Startup Week this week. We're recording this in October. So, for some people, going to an event where there's going to be hundreds of people, you maybe have met some of them before, but you really don't have a buddy that you are coming to this event with. You're on your own. You're going to have to walk up to people, start conversations, figure out who is who, and, like, find your people. That's terrifying for a lot of people. And they're like, "Absolutely not." [laughs] EVAN: Well, it's interesting how, like, level one and level three can be inverted. I went to a conference last fall by myself, and I actually had some voice issues. So, I couldn't talk for a little bit before this, so it was like...or even that well, during, you know, it was kind of an environment that I think a lot of people might be feeling like, oh, that's level three social experience. And I just remember how much fun I had there. Like, for me, it was totally a level one thing. But, you know, there's definitely moments on this hike where I was like, oh, this is level three. This feels physically scary, even though most of the time it wasn't. VICTORIA: Yeah, no, I think it's helpful. So, maybe that helps us segue a little bit into telling me more about what you do and how you came to do what you do. What's your background? EVAN: What do I do? I'll give you, like, a list of the things that I do. I will say I help people focus and maybe communicate better. You know, the list is, like, I am an OKR coach, right? That's objectives and key results, coaching business leaders on how to set goals and get everybody aligned towards the same goals. I do personal goals coaching, and that's, like, helping individual people set goals that are meaningful to them and live more intentionally. I'm a Techstars mentor, where I mentor companies. And I also do, like, a fractional head of product role. And it's a little all over the place. I mean, it's something that, obviously, a lot of that is, like, business coaching but really focused around focus and how you can use goal setting to accelerate growth for a business or an organization or for yourself personally. VICTORIA: How did it get started? What led you to be the coach that you are today? EVAN: Yeah, you know, I get asked this question. And I feel like there's a story about how I kind of tested goal setting. I was a founder. I went to Techstars in, like, 2013. And I was running the company. So, I had to, like, mess around with goal setting and then ended up being at Codecademy and Vimeo. They were doing OKRs. And there were certain things I liked and certain things I didn't. And there was, like, this progression. But I think the truth is that I just really like systems and organizing things, and I think I've always been like that. And OKRs are a way of taking something that's really messy, which is, like, a group of people running together in some direction and saying, "Oh, well, what if we come up with, like, some agreed plan here, and some rules, and some guidance? And we can split this out between what, like, the company and the organization is doing versus what individual people are doing or what the department's doing." I think I just find that process comforting. It's just, like, gleeful for me to be working with people on how they're going to focus and organize themselves, and then also how they're going to communicate that focus to each other, which I think is, like, a key part of people staying on the same page. VICTORIA: I love that. And I really want to dig into some examples of OKRs and maybe even get some free OKR coaching for myself on this episode. But, you know, but with your background, I wanted to start with looking at the founder experience versus being someone in a larger organization. How do you bring in that context of where you are in your journey into how you think about setting goals for an individual? EVAN: I think it's a hard question for me because my viewpoint on how goal setting and strategy and achievement in organizations has changed over this whole time, right? So, I was a founder, then at these larger organizations. I think I've tried to synthesize some, like, through line rather than difference between them. So, let me start there. I think when you look at a founder, or a founding team, or a larger organization, the key thing to figure out is where you're going and coming up with really clear goals. And then, depending on the size of the organization, there's different tactics you can use, right? So, if you're a founder, it might be just sitting down with your co-founders once a week, having a clear Northstar metric, and having a clear goal, and then everybody's running, and that works. Zoom to a 100-person company, which is, like, I probably focus on, like, 20 to 100-person companies. And now you have a lot of confusion between departments because you have people who are working on very different parts of the business. So, I think OKRs, at that point, are really great because it is this, like...and we will talk more about OKRs. But it's this cascading goal-setting technique where you have company goals that everybody understands and agrees to, and then each department is carving out how they're going to support that, which is, like, less necessary for a small company. But I still think the key thing is to know what you want, what your biggest problem is in getting there, and what your approach is going to be in overcoming that problem, which is, you know, is, like, I guess, strategy 101. VICTORIA: I like that. And it's funny; it makes me think of a tarot card layout. That's a situation I'll come and approach. Anyways, I wanted to get, like, down to the basics. I think we said OKRs earlier, but what is an OKR, if you can define that? EVAN: Yeah, so objectives and key results. An objective is any goal you have, so that can be launch a feature, revamp your sales process, or achieve some sort of milestone or some capability, right? So, often, that's, like, build a new department, or come up not just with a specific feature but a new offering, like launch a whole product line. Anything that's important to you can be a goal. It should be clear and inspiring. And that's the objective piece. Key results answer the question: how will you know if you're successful in reaching that goal? That might be if you're building a new department, a certain number of hires. If you're launching a feature or want to have a new offering, that might be some KPI for the product team, like, you know, onboarding rates or retention rates. VICTORIA: Yeah, and let's maybe even go into a real example: myself, I'm a managing director here at thoughtbot. People who aren't familiar with thoughtbot...I'm sure everyone listening has [laughs] familiarity with what we do as a product and business consultancy. And our team at Mission Control, the goal was to innovate on our approach to how we were deploying and managing software. So, over 20 years, the trends and modernization of infrastructure was something we wanted to be a part of, and we wanted to enable and accelerate not just our own development teams but our clients' teams in deploying software securely and efficiently and meeting everything that we need to do. Like, it's an incredibly complex environment. And there's lots of choices to make. So, that's, like, the big vision of what we're trying to do at thoughtbot. It's a new service. It's touching not only our internal processes but also, like, the growth of our business overall. So, what I've done as a managing director I talk with my team. I work with the CTO of thoughtbot, Joe Ferris. He's my acting director [chuckles] on identifying what is our overall approach? What's our strategy? So, one of the things we do at thoughtbot, one of our strategies, is to put content out there. So, we want to build stuff that works for us, and we want to share and talk about it. And we believe that by putting good stuff out there, good stuff will come back to us [laughs]. So, really just increasing the amount of blog posts, increasing the amount of open-source contributions and [inaudible 13:03] people we talk to and hear about what their problems are. We think that that will be an indicator for us of whether or not we're being successful in growing this business. So, that's just, like, one small strategy, but I've got five other ones if you want to talk about them. EVAN: Yeah, I mean, you highlighted a large goal that you have, and then some of the, like, sub-objectives in reaching that goal. And you could imagine key results being metrics along number of blog posts, audience size, number of readers, engagement. I mean, all those have different values, depending on what your goals are. VICTORIA: Exactly right. Like, there's the overall leading indicators we have of, like, whether or not we're successful as a business [laughs], which is, like, revenue, and, like, margins of profit, which really aren't going to change. And as a company, we don't change our policies or things that often to where those costs are ultimately going to change. It's all about, like, are we bringing in new business? Are we retaining the clients we have? And are we able to sustain, you know, work that centers around this problem area? So, that kind of, like, makes our goal tracking, like, the numbers month to month somewhat easy. Although those individual strategies and how they all line up to meet, that is something I think I'm curious to hear about how you facilitate those discussions with teams. How would you, like, begin an engagement with a team where you have a company like thoughtbot [laughs]? How are you going to coach us to get better at our goals? EVAN: Well, one thing I do is I pull apart KPIs, Key Performance Indicators, from OKRs, which you actually implied. KPIs are metrics you use to judge the health of your business, when OKRs are the goals that are going to transform your business. They fit well together. But, you know, for a founding team, they're still trying to figure out, well, how do we actually measure if this is going well? What does that mean? And I have a whole technique for that. But for a larger company, something like thoughtbot, you probably have pretty clear KPIs for the business and for each department. And you can look each month to make sure that those are in a healthy band or each week. And then, when you go to set goals, one of the things you can say is, "Hey, what's not working well? Why are the KPIs not where they should be?" And there's other ways of coming up with good goals, but I do think that's one of the starting points for goal setting. Another one, and I'm curious if you all have this here, is, like, a sense of what's holding back your growth. So, if you have a clear goal of growing your business year over year; usually, people in different departments have a sense of what challenges they're facing in executing towards those growth goals. And, fundamentally, there's usually some sort of competitive or market conditions or customer conditions that are concerning to you as a business in terms of where you're currently at. So, do you all have that type of, I guess, angle on thoughtbot's growth at all? VICTORIA: You know, for me, it's my first year as managing director. And experiencing how thoughtbot does planning, I appreciated our approach this year was to ask each managing director more like a retro style, like, "What should we do more of? What do we like doing? What didn't really work, and what should we do less of? And what other things do we want to start doing?" So, it's kind of similar to start, stop, continue but, you know, just really reflecting on, like, what's working? What should we do more of? What doesn't work, and we should just stop [laughs], or change, or figure out how to improve? And then, what should we start doing? And what kind of new behaviors do we need to practice and learn to build a better system? Which I think when you talk about what's holding people back, I think it's difficult to understand in a complex organization of 100 people how all these departments work together and how they contribute and support teams. So, I'm curious, from your experience, and you like to come in and organize and get focused, so if you have that level of complexity in an organization, how do you start to get people organized and understanding how they all work together and what's working and what's not? EVAN: Yeah, that's a good question. I might punt that to the second half of my answer here and answer an earlier question [inaudible 17:08] how we get started. Because I think that actually comes up as, like, the second piece. I think the first piece is, like, when I start with an organization, I usually sit down with the CEO. Maybe there's a founding team. Maybe it's a leadership team. And I try to understand their vision for where the company's going and, one, how clear and actionable it is. So, does it feel like, oh, I get exactly how they're going from point A to point B to point C, or is it a little bit murkier? And trying to nail that down. And sometimes I do, like, a strategy workshop around that. But the next piece is understanding if they have a clear plan for the next quarter, next year. When I come into companies, I'm doing OKRs quarterly. So, even if they don't have a clear strategy, we still need to set goals for the next quarter. I then have them just kind of draft goals with not that much guidance here. I might do some sort of training so everybody, like, understands what OKRs are. And then, you know, I do...and this is a common thing, I think, like, my background is in product, is trying to understand the root cause of things. So, usually, there's some goal that I can ask. And, usually, there's a goal that's, like, something that seems very strategic, like a new offering, or changing how the business is organized, or it's very growth revenue-oriented. Those are, like, the two types of goals that people usually come up with. So, there's a lot of just, like, asking why this is valuable, and kind of going up the ladder, down the ladder asking why it's valuable, and understanding what their root motivation is for doing this. And then going the other direction and saying, "Oh, if we did this, then what would happen?" And trying to just understand how they're thinking of this goal and how it fits in a longer chain of events. And, usually, through that process, we shift the focus point. So, it's rare that somebody comes up with, like, exactly the right goal. I think when they start understanding what would the effect be of that goal, sometimes one of those things is the actual goal. Or if there's a root cause, it doesn't always mean that we go to the root cause, right? If somebody wants to, like, fix their onboarding, and that's really, like, their whole focus point, you know, when you say, "Why?" and they talk about helping a certain customer get more focused. And then you may say, "Well, why?" And they say, "Oh, well, you know, we have this revenue model that involves helping them, and we make money." And "Why?" "So we can grow our business at a certain clip." And that's the arc that we build. That doesn't mean we go to, oh, well, you're trying to make more money faster. That might not be really what the focus should be for the quarter. So, we have to always start just trying to, like, dial in with what the right angle is. That's both...I think you want to choose the thing that's the most fundamental to the business that still feels attainable and focusable, if that's a word, in the short term, right? That's like, oh, this is a good target for a quarter or a year, if you're doing it on an annual basis. So, that's, like, how I usually get started with folks, which, you know, depending on how much thought there is around strategy, like, it goes in different ways. Sometimes, the company has a very, like, clear strategy, and then everything I said works pretty smoothly. And you get to a goal very quickly that you kind of orient the company around. If the strategy is either not explicit or maybe the CEO has a different vision for it than, you know, CTO or the head of sales, then there's more negotiating between folks and getting on the same page. And I think that's a whole, like, can of worms that we can dive into, but that's, like, a different type of exploration. VICTORIA: Yes, I love all that. I have so many follow-up things I want to ask. Just to play it back a little bit, too, I really resonated with some of what you're saying around it's kind of better to draft it; just write it. Like, the act of planning is more valuable than the plan itself. Like, get as close as you can as fast as you can [laughs]. That makes sense. Like, something that feels, like, good enough and, like, kind of go with it and, like, see how it goes. You know, like, I think that's a mindset that can be difficult to implement in an organization, especially if there's been, like, past trauma with, like, not meeting your goals. And how does that flow down to the organization? EVAN: That's a hard thing. VICTORIA: And it makes me think of, like, what you started with, like, talking about getting to the root of what's happening. Like, what are the motivations of individual people? Like, what's happened in the past? Like, trying to take an approach that's...I prefer blame-aware to blameless. You can't get away from the tendency to blame people. So, you just have to accept that that happens and kind of move on and, like, quickly go past it [laughs] and just, like, really get to, like, what are the facts? What does the data say about this organization? So, anyways, I think that that was where I went to. I think -- EVAN: One thing I did...I started with a new company; I guess, two or three quarters ago around the OKR coaching. And, you know, I think there was this expectation. We've been doing OKRs. There's issues we need you to come in and solve and fix everything. And the tone I tried to set was, hey, I'm not here to set great goals for you. You're going to set the best goals you can. And I'm here to help support that process and teach you a lot about goal setting. And we're going to do this every quarter. And after two or three quarters, things are going to start becoming a lot easier. People are going to communicate better. Everybody's going to be on the same page. And it's going to feel like, oh, we're getting really good at goal setting. And then, like, I try to set that tone when I start working with the CEO of, like, the point here is to make your whole leadership team good at goal setting so that you have this skill as an organization, rather than set just the right goals with the right language in the right way right now, right? We want to timebox everything. So, we're moving forward using this tool to make progress throughout the quarter, and then each quarter, revisiting it and getting better. MID-ROLL AD: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at tbot.io/entrepreneurs. VICTORIA: And I'm curious if there's anything else when you're evaluating whether or not someone might be a good fit for the work that you want to do with them. Are there, like, some red flag, green flag energy that you check for with executives when you're deciding whether or not to work with them? EVAN: Yeah, there are two flags that come up; one is, are they clear with what they're saying? I think a lot of leaders want to sound good. So, that doesn't mean that they need to be clear right off the bat. But in a conversation where someone says, "This is our vision," and you say, "Hey, I don't understand X, Y, and Z," or "This part didn't make sense to me. Can we dive into it?" And yeah, if someone through a conversation can be really clear about what's important to the company and where they're going, I think that's, like, key. Because if someone's talking around issues all the time and when you kind of bring up things they don't really address it, it's very hard to make any progress. It's like, you know, the lack of specificity ends up being a defense towards maybe dealing with some of the difficult conversations. But, like, at the end of the day, like, one of the major things that happens with goal setting that makes it, I think, feel exciting to people when it does—it always feels exciting to me [laughs]—when it feels exciting to other people is that they say, for the first time, "Oh, this is actually the thing holding us back. This is the problem. Yeah, we want to grow our business." But when you say, "Well, what are all the things you do to grow your business?" All of a sudden, you start talking through things, and someone says, "Hey, this is the real problem. This is why we're struggling to grow our business." And, you know, that transforms the conversation. People who are avoiding being specific, that can be really hard. That's one thing. And the other thing is around responding to feedback. And, you know, you can just...and this is a common interview question, right? You can ask somebody, "What do you think the weaknesses of your organization are?" And if somebody doesn't know, but they're, like, open to it, that's, I think, totally fine. But if it seems like they're constantly kind of, like, filibustering the answer there, it's like, hey, the main thing you're bringing me on to do is to make sure that you communicate the weaknesses of your organization to everybody else because that's what goals are about. They're about overcoming the weaknesses of your organization. So, those are two areas. And they also speak to, like, I think, rapport with the people that I'll be working with. VICTORIA: I agree. And I like that, you know, you're asking really for people, are you going to be honest about what's happening in your organization? Are you honest with yourself about where you're not doing well? And I think I also pay attention to the language people use to describe those problems. And are they really speaking with a growth mindset or a fixed mindset? Because that's a really hard thing to change [laughs]. Naturally, I think people who are good leaders and run successful companies have a growth mindset. So, I think that's usually there. But that would be some yellow-flag stuff for me. EVAN: You know, when people are looking to hire an OKR coach, they usually already are looking for improvement. And it's not like they're hiring a product manager, right? You have to be saying to yourself, hey, I believe that if we did better around goals, our company would grow better. We'd have better focus. We'd have better alignment. Like, there's already a belief that people have that is usually pretty self-aware of the limits of both the people there and the organization where it's at today, and they're looking for help. So, I think I come across what you brought up more in individual people on a leadership team that, like, feel more coachable or less coachable depending on how interested they are around expanding how they think about things and growing. And, you know, obviously, [inaudible 27:01] lots of opinions that are wrong, and I love the disagreement that comes up there. But you want to, you know, you want to be speaking to people that are generally open to learning through a conversational process. VICTORIA: Right. Yeah, I think it's like a confirming thing. Like, if they're reaching out to a goals coach, they probably do have a growth mindset. And if the top leadership does, then that means that there's an opportunity for other people to come along as well. So, I like opening it up that way and getting people to get specific about their goals as well. I think that's a real challenge. Like, it's either too vague or too specific, not inspiring enough. Some people still bring up SMART goals with me. I like to prefer HARD goals, but you probably need those. And I'm curious if you're familiar with those acronyms. I can spell them out. And I'm sure you've heard of both of these [laughs]. A lot of people are familiar with the SMART goals and the specific, measurable, actionable. I forget what the Rs and Ts are. But then HARD goals are heartfelt and more around, like, the big vision. And it's something that you want to get people excited about, which is something that you said earlier. Like, how do you get people excited? And some people would think of a corporate goal-setting event as a level three fun [laughter]. So, how do you make it more like a two or a one? EVAN: I don't know, a lot of what I hope I offer to folks...and I've gotten good feedback here is that I enjoy goal setting a lot. So, talking through all these problems, talking through challenges, doing workshops, having these conversations. Like, whenever I'm doing that, it's my favorite thing to be doing. So, I think, hopefully, some of my joy just rubs off on the people around me. Because I do think talking to somebody who's excited about what you're talking about is helpful. The other thing is, usually, at a decently small company, under 100 people, I'm working with the CEO and the leadership team; you know, people are there because they care about the company. They care about the mission of the company. They care about the people in the company, and they care about the growth of the company. So, I get why goal setting has, I think, can have a bad rap. But if you're fundamentally solving problems that people care about, there should be some, like, glee that comes in when people say, like, "Oh, yeah, I thought this was going to be about, like, how do we grow more? And that felt very generic to me." And it turns out when we actually think about how we grow more, and we talk through what's holding back our growth and what we can do to overcome that, and we have the top few ideas that we've all come up with, usually, those feel really relieving to people. And there's a company I'm working with now that I think is struggling to shift their target market a bit because...and there's awareness that the target market needs to shift, but there isn't so much knowledge around the new target market. There's a lot more knowledge around the old target market. And so, we're doing a bunch of research and talking to folks. And I know once we're able to say, "For this target market, we need to do X," there is going to be, like, a huge amount of excitement and relief at the organization because people will feel like, oh, we've crossed that bridge, that bridge that we were kind of in the middle of crossing and didn't really know where the other side was. We now can see that other side, and we're going there. So yeah, I think there can be a lot of excitement around this stuff when it's real, and it's important work that you're doing. VICTORIA: Right. Like, maybe there's a good factor of, like, how do you measure if what you've done with a company is successful? Is there a glee scale that you [laughs] use to evaluate? EVAN: You know, for me, it's still probably more subjective than I want it to be. You know, I'd love it to be like, what percentage of people's OKRs did I [laughs] hit each quarter? And when I work with them, it gets better. But I think that's, like, a pretty short-sighted view in terms of my role. So, you know, I'm looking for people who were maybe disengaged to be more engaged, people who didn't see the value of OKRs to see and be able to articulate how their daily work is different because of the OKRs we set. Yeah, and obviously, there's excitement when we're solving real problems. And we're changing the problems each quarter, and people are seeing growth increase. You know, like, all that stuff, I guess there's, like, a tangible excitement with. But I hope folks can, like, just connect the dots between the work, which can be tedious work around goal setting and negotiating with people. And often, it pulls you out of other day-to-day work that you're doing, especially for a small company, with the excitement towards the end of the quarter of reaching these goals and moving on to the next challenge. VICTORIA: I think that's great. I think that was a perfect answer. It's kind of not always easy to know what [laughs]...like, sometimes there's a sense of it, like, you have a feeling, and sometimes you can get data to back that up. And other times, you know you're doing the right thing by the people's faces around you at the end of the workshop [laughs]. So, I think that's great. And so, maybe my final question would be is, like, what would be the ideal organization that you would want to work with? Like, who's your ideal customer right now? EVAN: Yeah, I guess I have two ideal customers based on these, like, two things that I'm doing. In terms of the OKR coaching, I usually look for CEO or founding team of a company that's now, like, 20-plus people who's saying, "Oh, we have these departments," or "We have this leadership team. And we need to really get all on the same page at the beginning of the quarter because then everybody's going to consistently be talking to each other but has other people that they need to organize." That's definitely for the OKR coaching where, like, 20 to 30 people is where that starts. That probably goes up to 100 in terms of where I focus. For the other work I do as a Techstars mentor and the coaching I do through that, that's really for founding teams. And that's more focused on how do you take your vision and make that a clear goal statement, which is around, like, behavior change, usually, in a certain population you're targeting? How do you turn that into a go-to-market plan? How do you turn that into a product roadmap? So, for that, that's just much smaller teams. I actually think that work often needs to be done at larger organizations, too. That's, like, a common thing that comes up. And that can bleed into strategy at large organizations. But yeah, I know that's probably a pretty broad bucket, but groups of people that believe that focus is a key lever towards faster growth. VICTORIA: Thank you for that. And I guess I said that was my final question, but I'll add two more questions. Can you share an anecdote from being a mentor at Techstars that you think will be interesting for our audience? EVAN: I think I was struck the first time I did the mentoring. They do, like, a Mentor Madness. So, it's like, you know, six companies in a row, and every company they all have different challenges. But a lot of them, it's, like, helping them articulate what they're doing a little bit more clearly. And often, there's a question around sales and growth and maybe fundraising. So, there's just, like, a focus in that direction. And I found that every company, even though they had kind of different questions, I was giving the same answer to, which was, I don't think your goal is clear to you or to me. And so, there's this framework that I would use with each company that there was, like, this aha moment. And I picked this up from a person named Matt Wallaert. It was a book, "Start at the End." It's called a behavioral statement. And it's when population wants to motivation, and they have limitations, they do behavior as measured by data. And the kind of conceptual version is, oh, you're trying to get some group of people to change their behavior. And that's only going to happen if you can tap into a motivation that happens to them as frequently as the behavior you want to change. So, it's like a formalization of that. And each group, I'd like bring up the statement; we work on filling it quickly. And there was just, like, a clarity that would develop around what they were doing and how to orient themselves both on the growth and marketing side and on the product development side. I guess it just struck me how much that little framing was transformative to [laughs] accelerating both focus and alignment but, more importantly, like, getting somewhere that they wanted to get to. VICTORIA: It sounds almost like building a mental model of what you're trying to do [laughs], right? Like, it was a mental model that you referenced in your mind that helps you make decisions every single day. So, I really appreciate that. And we are about out of time. So, let me ask you, is there anything else that you would like to promote today? EVAN: Sure. Looking for a couple more OKR coaching clients for the new year, and just happy to chat with anybody who has questions around OKRs or goal setting for their organization. I also do personal goals coaching, which is a little different from the OKR coaching that I help individual people with their goals. But it's also similar. It's a lot of like...it's a lot more, like, reflection, and getting to know oneself, and coming up with goals that are really meaningful. And then the other half of, like, I think you alluded to this earlier around systems. Like, how do you take a goal that's important to you and actually act every day in ways that move you towards that goal? So yeah, interested in talking to people about both of those. I do some workshops as well, so people can reach out to me at evan@evanhammer.com. I can also put anybody on my mailing list. I do some workshops around both those things. VICTORIA: Wonderful. Thank you so much, Evan, for joining us today. You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guest: Evan Hammer.Sponsored By:thoughtbot: Are you an entrepreneur or start-up founder looking to gain confidence in the way forward for your idea? At thoughtbot, we know you’re tight on time and investment, which is why we’ve created targeted 1-hour remote workshops to help you develop a concrete plan for your product’s next steps. Over four interactive sessions, we work with you on research, product design sprint, critical path, and presentation prep so that you and your team are better equipped with the skills and knowledge for success. Find out how we can help you move the needle at: tbot.io/entrepreneursSupport Giant Robots Smashing Into Other Giant Robots

If you missed the first episode with thoughtbot Incubator Program partcipant and founder Josh Herzig-Marks of Knect, you can go here first to catch up. A key focus of Josh's second episode is the importance of user research and customer discovery. Josh stresses that talking to users is crucial, as it grounds the development process in reality. thoughtbot's Director of Product Strategy, Jordyn Bonds, adds that direct engagement with users builds empathy and understanding within the team, making it more effective. They also discuss the challenges of identifying a product's target audience and the importance of iterative customer feedback. Josh and Jordyn highlight the need for founders to be resilient and open to feedback, even when it's negative. Transcript: JOSH: We're live. DAWN: Welcome. Thanks, everyone, for joining. I'm Dawn. I am going to be emceeing today, facilitating, really just asking questions and letting these great people talk. Filling in for Lindsey, who is usually here. Thanks for being here. We're excited to talk to everyone and hear your comments and questions. You might be familiar with thoughtbot. We're a product design and development consultancy. And we like to help people make products or make products better. We are currently in our third incubator session. And today, we're talking to one of two founding teams. And in case you aren't familiar with the incubator, it's an eight-week program that we run with founders. We pair founders up with a product quad from thoughtbot. And we undergo market research, customer discovery, basically market and product validation exercises to help us hone in on a solution, a potential solution for the problem that we're trying to solve, and build a product plan with the founder, basically set them off on a path for success, hopefully, and next steps. Do you want to kick us off, Jordyn? JORDYN: Yes. DAWN: Tell the people about yourself. JORDYN: I'm Jordyn. I'm the Director of Product Strategy on Dawn's team. Dawn is my boss. And I sort of run the incubator. I have also founded two startups and been the first head of product at two others, so four early-stage startups. JOSH: I'm Josh. I am the founder part of this who is working with the thoughtbot incubator. I founded a startup. I wasn't very good at it. I was very lucky at it. I was head of product at a whole series of other startups. And I enjoy that a lot. A few folks have asked me why I wanted to join the thoughtbot incubator if I've done this before. I'm, like, moderately techie for a non-technical person. And I coach other founders in doing the sorts of things that Jordyn and her team are coaching me on. So, I'm doing this thing for a few reasons. One is being a founder is really, really lonely. But the other one is that there's just a huge value in bringing together the diverse set of perspectives. And we're doing that with a company that's really good at getting complicated things out the door, having them be successful through a focus on who the end user is. It kind of felt like a no-brainer because I felt like—and we talked about this last week—I had the Josh problem that I wanted there to be a solution to. And trying to figure out, is there a larger opportunity that this represents? DAWN: Thanks. Well, you cued us up well for the topic, at least that we're going to start with today, which is user research or customer discovery. I think it probably goes by several names. That's another interesting topic we [laughs] could get into. But what is this user research that you're doing? Why is it important? What's it doing for this team at this stage? JOSH: One of the founders I work with asked me a couple of months ago, "Just remind me again, what are the things I have to do to build a product?" And I'm like, "It's actually really easy," right? My, like, standing on one foot advice is talk to users, mostly customers. Bring your engineers along when you can. And if you do those things, mostly everything will work out. But I think it's actually, like, there's some subtlety in all of those things, right? It's not that talking to users or customers is going to solve all of your problems. It's just that you're not going to make any progress in the absence of doing that, right? Because then you're just talking to yourself. And I don't know about everybody else here in this group or who might be listening, but it's really easy to get yourself all spun up inside of your head if you're only talking to yourself. Users are the ones who ground you, right? And ultimately, users are the ones who could turn to customers. So, why customers, right? As the people you really want to be talking to. Now, we don't have any customers yet, so we can't do that. But you know something about customers more than anybody else, and that's they're willing to pay for the thing, for the problem you're trying to solve. They could be paying in money. They could be paying in time. They could be paying in reputation. Oftentimes, they'll be paying in all three of those things or two out of three of those things. But they have an expressed willingness to pay. And that's really the magic of, like, having a product and having those conversations. Now, why do you bring along your engineers? It's because the most effective tech companies...and I think thoughtbot is maybe unusual in design-build firms in really internalizing this, but the most successful tech companies are the ones where the entire organization is aligned around understanding who is our market? Who is our customer? What is their problem, and what does it take to solve that problem for them? And too often, all that stuff is, like, stuck inside of the founder's head, or the sales team's head, or the marketing team's head, or the product manager's head, or little bits of stories are stuck other places. But when we're all listening to the same conversations, that's when it's most effective to build alignment around who's the customer? What are their needs? What would they pay for? JORDYN: I agree. And I would add some detail there that why does it work like that? How does having everyone at the organization talk to users and customers build that alignment? And it's one of those things that's kind of, like, it has to be seen to be believed in a certain way. But, like, you can break it down. You know, we can all sit in a room and argue about what reality looks like out there. But it's a lot more efficient if we're all living in that reality together. There's a lot less bringing everyone along. If you've got skeptics on your team, and I hope that you do because they're very useful people, they want to hear it from the source. So, great, go have them hear it from the source. And there's nothing that's more motivating as an engineer, having been an engineer, than seeing someone live fail to achieve their goal in the piece of software you're working on. You will turn around and go fix that bug right then. A bug that has maybe been sitting at the top of the backlog for, like, six weeks or six months, when you see someone struggling with it [laughs] in action, you'll be like, oh, I see. Okay, this is actually causing a lot of angst out there, and I... So, anyway, building that empathy, it's always easiest to build it directly. And it's harder if I am here and if I'm having to triangulate empathy through someone else. Like, if only one person on your team is talking to users and listening to users, and then they come back to the team, and they're like, "Here's what I'm hearing," maybe the team believes you. Maybe they hear the same things out of your mouth that they would have heard directly out of the user, but probably not [laughs]. So, it sounds less efficient. People resist it because it feels intuitively, I think, to a lot of people like a waste of time to have engineers doing user interviews or having anyone else. There's a lot of pushback at organizations for doing this for different reasons. If you're doing, like, an enterprise SaaS thing, sales might really not want anyone else talking to customers because they worry it's going to erode that relationship that they feel like they have. Nothing could be further from the truth in my experience. Customers feel valued. The more people on your team they talk to, the more they are listened to, the more they are taken seriously, and, like, have people engaging with them, that only bolsters your relationship with them, not the opposite. But either way, it's just much more efficient when everyone is hearing the thing from the people it's impacting directly. I get that that does not intuitively feel true, but I assure you that it is true. DAWN: So, -- JOSH: And even more so at this stage where our experience as designers or engineers is much less important than our experience as team members who are trying to find who is that initial audience going to be who is so motivated they will let us build a product for them? DAWN: That's exactly what my follow-up question was related to, which is there's this sort of perception that you sort of stay in your lane, right? With the different roles that you occupy [laughs] in an organization, whether it's early stage or later stage. And even for people who are participating in that customer discovery, you kind of want to, like, ask questions that are most relevant to your role. So, how do you, like, prepare teams or, you know, offer guidance to teams to help them sort of get into the right mindset going into those conversations, not so that they execute it perfectly because they have to have some UX design background, but so that you can learn the important things? JOSH: I think it is totally natural for someone to feel unprepared coming into these, but that's okay, right? Their job is to develop this as a skill, and the only way they're going to do that is by actually doing it. I am certain there were people on the thoughtbot team who felt uncomfortable doing this for the first time, talking to somebody who wasn't even a user, a rando who Josh found on the internet who was willing to chat and go talk to them. And I know they got better at it because I get to watch everybody's interview recordings, and I get to watch the notes they're taking. And I get to watch my own. And we have, like, a team of five of us who, like, are all getting better at this, and that's good. These things are skills, and you got to practice them, which, putting on my friends of thoughtbot hat, is, I think, one of the reasons why thoughtbot likes to do these things because it's a chance to develop these skills in a really intense way, which we may not otherwise get to. And it's a thing that, you know, as a founder, I want everybody on my team to be getting good at as quickly as possible. So, sure, prep work. You read a book. It's like baking a cake, right? You know, you can read cookbooks. You can walk up and down the aisle at the supermarket, right? You can go to the bakery and try other people's cakes, but until your arms are deep in flour, butter, and sugar, like, you've no idea what you're really talking about. And I just want to get people making a mess in the kitchen as fast as possible. Nothing bad happens if you have a bad interview. Lots of bad things happen if you never interview. That's my very strong opinion. JORDYN: I share the opinion and its intensity. That is exactly how I would have answered. JOSH: [laughs] JORDYN: There's no substitute for doing the thing. And you can spend your whole life feeling like you're not ready to do the thing. You're not going to learn and get better at it until you just start doing it. It's like...and, Josh, you are right. That is partly what this incubator is for, both internally and externally. One of the main differentiators of what we're doing here with this incubator from other incubator programs out there is we get into the kitchen with you and get our arms and elbow deep in flour with you so that we can help founders, not necessarily Josh who has brought some skills into this with him, but, like, so that you know what it feels like to do the thing. There's a lot of content out there about how to start a company, how to do customer discovery, all this stuff, and you can read all of that stuff. You can also listen to people talk about it all the livelong day. There are tons of people out there who do this all the time. They are on podcasts. They are here on this live stream. That's cool [laughs]. Like, listen to them. But really, there's no substitute for you getting out there and talking to people. And this, I just cannot stress this, like, so many people...given my role here and what I do, people often bring their startup ideas to me. People at thoughtbot, people outside of thoughtbot they say, "I have this idea." I ask, "Who is it for?" They tell me. I say, "Have you talked to those people?" and they say, "I'm not ready to start talking to people yet." And I'm like, "That is incorrect. You're talking to me. The only way you're going to get to a thing is if you start talking to people, like, yesterday." And they resist. "Well, I still need to figure out." And I'm like, "No, you don't need [laughs] to figure anything out." If you're going to build something for someone, go engage with them, learn what their life is like, what their work is like today. Hello, people listening to this, do this today. JOSH: Jordyn talks a lot about the emotional labor of being a founder, and I think it's really important. Like, hey, founders out there who hear this and they feel a bit overwhelmed, that's okay, right? The thing which you're going to learn how to do as a founder is talk to people about the thing you're trying to do and have people give you feedback you don't like, and it's not fun. You know, I work with a lot of very technical founders, and it's amazing the things people will do to avoid that. They will take their savings, their retirement money out of the bank and plow it into design-build firms. They will quit their jobs to build this thing themselves just to avoid having that potentially unpleasant conversation. So, potential founders, if you want to prepare yourself for being a successful founder or even a mediocre founder, the thing which you need to do is [laughs] improve your frustration tolerance. Get really good at people telling you your idea is bad, or your process is bad, or something else is bad. And maybe they're right, and maybe they're wrong, and it doesn't matter. But you got to be able to tolerate that. JORDYN: Yes, you have to be able to tolerate that. And you have to be able to actually, like, listen for the relevant feedback that's buried in there. So, the founder Josh just described was me, P.S. JOSH: [laughs] JORDYN: The first time. JOSH: Not just you. JORDYN: And not just me, not merely me, but it was me. You know, technical background definitely plowed my meager savings—because I'd already been working in startups, which does not pay well, newsflash [laughs]. I don't know if any of you know this; they don't pay well—into a product that I hadn't really spoken to very many people about. But I knew that I needed to start talking about it with people, but I didn't know how to do that well. That's okay. So, I started talking to people about it after the fact. I should have done this sooner. That's cool. My first company was this product called TallyLab. Like, you can think of it like a data diary app. Basically, it's a place you can go and collect small data to kind of figure out, like, if you think you have a food allergy. Think of it like a food allergy notebook but a digital app for it. I think that when the moon is full, and I eat over a pint of strawberries, I get a stomach ache, whatever it is. So, you need to track the cycles of the moon and how much strawberries you ate and when, and then you can do this analysis. Anyway, if you're thinking to yourself, that doesn't sound like a business, you are correct. Anyway [laughs], I was describing this to my friend's dad. My friend had just had her first kid. I was over meeting this baby. Her dad was there. And he was just like, "What do you do?" And I was like, "Oh, I have a startup." He's like, "What's your startup do?" And I told him. And he was like, "Sounds like you're just feeding people's OCD to me." Like, I felt physical pain at that reaction to this. Like, he was like not only...his tone was so derisive [laughs]. But, like, there was information for me in that. First of all, I needed to think about who is this guy. Where is he coming from? Does this have anything to do with his life at all? Should I even listen to this? In fact, maybe he's, like, my anti-ideal customer. And this feedback is great for me because it means my ideal customer is a good fit, whatever. There's information in there, right? But this was some of the first feedback I was getting on this from someone in the wild [laughs]. So, I had to dig that dagger right out of my heart. So, it's going to happen. It's going to happen, but you got to, like, steel yourself for it, like Josh says. And you also find a way to respond to it with curiosity. So, if I could go back in time to that conversation...I just changed the subject immediately, I think, at the time. I was like, "Cool. Let's talk about something else [laughs]." What I should have done is been like, "Tell me more. Why does it strike you like that? Tell me more about this problem in your life," right? That was an opportunity for me to have a customer interview, and I just totally whiffed it [laughs]. DAWN: Hopefully, it didn't harm your relationship with your friend [laughs]. JORDYN: Not at all. Not at all. I think she felt somewhat aghast. She was like, "Dad, lay off." [laughs] JOSH: Which is actually the other lesson to take from this, which is these things all feel really important and personal and, like, present to you as the founder. Nobody else gives a shit. JORDYN: No. And this was a lesson for me. I at least didn't have that problem because I had been in a series of touring rock bands, and I had learned over and over again how little anything I was doing mattered to anyone. Like, you know, you get to the point where, like, you walk offstage, and you're like, "That was the worst set we ever played." No one knows that. No one cares. They were, like, talking to their girlfriend at the bar the whole time, like, whatever, man [laughs]. Like, whatever is going on with you, you as a human are maybe this big in their purview. What you're doing professionally is even smaller. So, like, don't sweat it. They're not going to be thinking about it again, ever [laughs]. DAWN: That's the thing. Maybe your startup idea doesn't matter, but you matter. Everyone here matters. Okay? JORDYN: Yes. DAWN: So, I want to go back to the users or the particular customers in this case. Have there been any surprises? Have there been any daggers out there or any delights? What have you been learning? JOSH: Last time we were speaking, we were basically talking to a convenient sample of people who, let's be honest, look a lot like Jordyn and myself, right? They are people in mostly U.S. tech companies, mostly early-stage ones, not necessarily programmers, but maybe they found the company. Maybe they work in product management, or they have other kinds of executive roles. Maybe they change their job every couple of years because that's what people in tech companies do. Maybe they like, you know, they carry around a smartphone. They live out of their smartphone. They care about building a network. They attend in-person things when they can. They're in a bunch of, like, networking Slacks, and WhatsApp groups, and things like that. And they all kind of look the same. And I think the last time we spoke two weeks ago, we were noticing that this thing we were trying to work on was a problem for all of them but not necessarily a problem that they were, on average, investing a whole lot of time and energy into. We recognized this as a group largely because everybody was participating in the conversations and getting better and better at it and getting better and better at kind of, like, pulling out the insights. So, we experimented with a couple of other audiences. And the reminder here is the idea isn't to build a product for one of these audiences; the idea is to build the first version of the product for one of these audiences who feels the need so intensely they're actually going to use the damn thing and give you some feedback. So, the audience has to have a real pain–a willingness to do some work. And we have to be able to find them, so some attribute that allows us to identify where they are. They all hang out at the playground after recess is, like, a good attribute, or they all search for the same kinds of things using the same language or a comparable language on Google, or they all follow the same people on TikTok. They are all examples of audiences that we could somehow identify and address. People who, you know, deep down, are worried that their second-grade teacher didn't like them enough, right? Probably not an addressable audience, even though you can imagine, you know, all sorts of potential problems and potential solutions you can build for those folks. So, we got to find that. So, we've experimented with a few other groups. One is we identified early on in kind of our broader conversations that journalists might have a need for this, journalists or folks that have a broad network, and they check in with those people frequently. And the other one was people who do Biz Dev, or partnerships work at tech companies as well. And we reached out to a bunch of people. And we discovered that both those groups are probably also a little bit too big for us to be focused on. It's not that nobody in those groups had a burning need for the thing that we're trying to do; it's that people in those groups overall didn't. And now we got to go figure out, like, okay, is there, like, a subgroup inside of there that we can identify? Just sports journalists, just investigative journalists, just journalists who don't have a salary who work freelance, just radio journalists, you know, just journalists who went to specific schools. Hard to know what that's going to be, and that's the work that we're doing, like, literally right now. JORDYN: We actually published our methodology for doing this recently. People should go to thoughtbot.com and look at our Playbook, our Customer Discovery Playbook, if you want to know how to do this. It is not black magic or something. Basically, you just think about the dynamics that matter that create a need for the thing that you're contemplating building, and then you just generate giant lists of the people who might need that thing. And guess what? It's going to be totally wrong and weird, and a bunch of different shaped groups of people. It is going to be like people who hang out at the playground and also dog walkers, and just, like, some weird random assortment of personas, individuals, groups of people, but that's where you start. And then you start learning. You take what you know about those people today, and you find the best place to start. And then you start talking to them, and then you learn why they are or are not a good fit, and you keep going through the list. So, it's not mysterious, but it is work. It is hard work. Synthesizing on a team what you're hearing is part of that hard work, but it's really invaluable because everybody, like Josh mentioned earlier, brings something different to the conversation, thinks about it from a different vantage, brings different life experiences. And that is just invaluable to unlocking insights, perspectives, directions to pursue. It really is very much a...I don't know what we would call it. It's like a real...it's the hard work. You go talk to a bunch of people. You get together as a group, and you talk to each other about what you're hearing from all the other people [laughs]. You go back and talk to more people or the same people if you realized you weren't asking them the things that you needed to be asking them. You come back together. And out of that process, the patterns emerge. DAWN: This is also kind of meta, the fact that y'all are doing so much customer discovery with potential customers who their entire work lives [laughs] are managing conversations, both the frequency and timing of that, but also, like, what they're learning from those conversations. So, that's super interesting. It sounds like, obviously, there are still many conversations to be had. But what else is next? I know we're about halfway through the program. So, what are y'all looking into for the next week or two? JOSH: I mean, we don't yet have that audience, which is, I think, a really important part of this and something which I think about all the time as the founder. What does this mean that it's hard to find the audience? Like, what does that tell about the idea, about the opportunity? But I think we've had enough conversations with enough people who have enough similarities in the problems we're trying to solve that I think we're getting good insights into if we knew who would really want this thing; we have some good ideas about how we might be able to help them out. So, we're starting to actually go through the process of, you know, the really early sketches, the wireframes. And what might a solution look like? Which I think is doing two things, right? One, it helps us to sharpen our thinking a fair amount, right? There's, like, a thing which we can react to as a group, which is not as amorphous as an interview. Like, a sharp, pointy thing we can react to. The second is we're going to start showing this to people. And not everybody we talk to is going to be, like, our final audience we're building for. That's okay. They can still, like, give us thoughts and give us feedback. And it'll probably change the tenor of the conversations we're having with them. And that's also okay, too, right? We're going to learn different kinds of things than we would in the absence of this. JORDYN: Yeah. And that is super exciting. And then the other side of that coin becomes feasibility questions. So, this thing that we're imagining, how would we build it? Can we build it? What do we need in order to build it? And so, those conversations are really starting to fire up as we start to imagine a solution. DAWN: I know there's a really awesome blog post to come from Jordyn that I reviewed [inaudible 22:27] JORDYN: Wow. Public nudging. DAWN: [laughs] JORDYN: I'm late with this blog post, and I'm being publicly nudged. This is so intense; you're right. DAWN: [laughs] But it's so relevant to exactly what y'all have been talking about. JORDYN: I know. I know. [laughs] DAWN: So, [crosstalk 22:40] retroactively point everyone to it. It's really good stuff. JORDYN: How would you state the problem, Josh, if anyone out there has the problem? JOSH: The problem we're looking at is people who have a hard time managing their social network in general but their professional social network in particular. You know, that might be, you know there's people you wish you were keeping in touch with, but you just forget to keep in touch with them. Or, you know, you tell somebody to do something in some thread, or some channel, on some social network, or some direct message, and you just kind of forget about that because you don't go back to it. Or maybe, you know, you're making friends on Discord. You're making friends on Slack. You're making friends out in the real world, but you don't actually, like, add them into your LinkedIn, something like that. Somebody who's having problems like that that's actually done something about it. Did you go and build yourself, like, a spreadsheet? A baby CRM in Notion, or in Coda, or in Airtable? Do you search out a purpose-built tool? You know, if you think you've ever tried, whether you've been successful or not, to actually solve this problem for yourself, I'd love to talk to you, or Jordyn would love to talk to you. Dawn would probably love to talk to you also. But reach out to any of us any way you can. I got a super Googleable SEO-compatible name, as does Jordyn. So, like, reach out to one of us, and we'd love to chat. DAWN: Awesome. Well, thanks, y'all. This has been wonderful, as always. And if anybody has questions for the team, feel free to comment on the post afterwards. And we'll see y'all next time. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at: tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Support Giant Robots Smashing Into Other Giant Robots

Host Victoria Guido and special guest Regina Nkenchor discuss the evolution and impact of Regina's work with the GNOME Project and OpenKids Africa. Regina explains how the GNOME Project is advancing its Global Inclusive Initiative, aiming to amplify diverse voices within the community and contribute to GNOME's development. She expresses enthusiasm for OpenKids Africa's efforts to incorporate technology education in rural communities, primarily through engaging early childhood teachers in understanding and teaching tech like virtual reality and robotics. Victoria probes into strategies for sparking children's interest in technology, with Regina advocating for a co-creative, experience-based approach that includes real-life applications and interactive participation. They also touch on the challenges of balancing professional and personal commitments. Regina shares her ongoing journey to find balance by prioritizing and delegating while still maintaining her nonprofit work and her role at the GNOME Project. They also talk about personal growth and community engagement. Regina advises newcomers to leverage open-source tools and be open to change while encouraging fair treatment within the open-source community. Victoria reflects on her experiences with Women Who Code, highlighting the importance of community involvement and networking for career advancement. Both emphasize the significance of creating safe, welcoming spaces in tech communities to foster inclusion and support, especially for women in tech. GNOME Follow GNOME on X, Facebook, LinkedIn, YouTube, or Mastodon. OpenKids Africa Follow OpenKids Africa on LinkedIn, X, YouTube, Facebook, or Instagram. Follow Regina Nkenchor on LinkedIn. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Regina, Board Vice President of the GNOME Foundation and Founder at OpenKids Africa. Regina, thank you for joining me. REGINA: Thank you so much for having me. It's such a great opportunity to be here today. VICTORIA: That's wonderful. So, what's going on in your world, anything fun or exciting happening? REGINA: You know, I actually work in Sweden. And this period is actually one of the...let me say the peak period, beginning of a new year, beginning of a new year for my job. So, there's so much around projects, projects, projects. So, I wouldn't say this is more like a fun period because, after the summer, it's a different time here when you're working in Europe. VICTORIA: Yes, working in Sweden must be so interesting. I'm wondering if you found any cultural differences that were really surprising about working there. REGINA: Oh yes. I think there are so many cultural differences, one of it is...I come from Nigeria, and we have more, like, a particular way...we don't have a schedule for having breakfast. So, we can have breakfast anytime we want to, and we don't feel any problem by it. So, I could decide to have my breakfast by 12:00 or by 1:00 and have my lunch by 4:00 p.m., you know, it just depends. But here, it's more like you have to have your breakfast early. And by 11:00, 12:00, 1:00, you should be having your lunch. I'm still trying to get used to that one anyway. And also, another cultural difference that I've seen here that is very, very obvious to me compared to where I'm coming from, and I think this is basically the work culture around here, so they have, like, a work culture of taking certain timeouts for vacations, which is not the same thing for me when I was working back in Nigeria. I mean, you could just pick your vacations anytime you want to have them. But here, it's more like you have to have them around the summer somehow so that you could basically have much fun and get the time required. So, I think these basic two things are things I've had to adjust to working here now for over two years, so yeah. VICTORIA: So, more rigid timeframes for lunch, and breakfast, and vacation [laughs]. REGINA: Yes, yes. And, you know, it's quite funny because even when my colleagues are like, "Let's go and have lunch," and I'm not ready. And they feel like, "Are you okay? Like, you should be having lunch." [laughs] So, it's really rigid timeframe here, I would say that. VICTORIA: I like that. You know, working in a remote world, it's so easy to just work through lunch or skip breakfast and just go straight to your computer and work. So, I kind of like it. They're looking out for you and making sure that you're taking your breaks. REGINA: Yes. Yes. And it's actually also making me self-conscious. Because, you know, working daytime as a software engineer, you don't know when to eat. You don't know when to take a break. So, that realization, I'm beginning to more, like, take it more in and adapt to the culture here. Now, I'm always looking out for myself. And when I wake up in the morning, I remember that I need to, you know, grab something, no matter how small. And then, when it's around lunchtime, I'm also preparing to have something as well. So, I think it's really good. And it also keeps me more healthy, I would say [laughs], compared to me just eating anytime I want to eat. So, I think it's a very good culture. VICTORIA: That's wonderful. And I really want to hear more about your journey and your career. I first heard about you and invited you to the podcast when you were a speaker for Open Source Festival in Nigeria earlier this year. So, I'm curious how you went from being in Nigeria and how did you get into software engineering and get to where you are today with the GNOME Project and everything else. REGINA: Well, thank you so much for that. I actually started my technology career path...that's about...I would say around about 10-11 years ago. So, I graduated with a public administration bachelor's, so a bachelor's in public administration. I really did not think that I would be doing what I'm doing today. But so, when I graduated years ago, that was 2010, I needed more opportunity. And at the time, in Nigeria, technology was not something that was very available to everyone. What I mean is technology was mostly found around those that are privileged, those with more advantage, and all of that. And I wasn't around the set of people that had...those privileged to have computers in their homes or to have parents that has the money to buy these kinds of resources. But I had always known as a child that I was very good with my hands. And I could remember when I was quite younger, I was the one that my dad would go to to repair his phone when it's not working well. So, I had this thing with my hands that I couldn't really explain that I like to repair things. And so, when I graduated from the university, I got an opportunity to attend more like a program, a computer program, where they would teach stuff around IT for beginners and all of that. So, I enrolled, and when I enrolled for that particular program, I can remember they would show us more like a slideshow of different programs that you would like to learn, and then give you more like, insight into job opportunities available for those programs. So, when I sat in that class as a beginner, and I was watching the slideshows, one of the courses that caught my interest was Linux administration and database administration, so I opted in for that particular course. And that was basically how my journey began. When I began to learn about Linux, I began to use it to basically manage databases; then, I was managing databases in Oracle. And I found that one of the things that I needed to learn was basically knowing how to administer the Linux OS. From there, I began my first job. I worked as a faculty, more like a lecturer teaching Linux administration. So, this time, I had learned, and now I have to help other students learn as well. So, because of this, I began to use more of open-source tools. Now, just to do a little bit of realization check here, at the time when I was basically lecturing years back as a Linux administrator, I did not know that the concept open source existed. I knew that I was using Linux, but I did not really understand the concept of what open source is. So, going forward now, as I began to use these tools and began to teach students how to administer databases and use more of Linux operating system tools, I somehow, a particular year, stumbled on the GNOME Project. Because GNOME is more like a feature of the Linux OS—it's a desktop application—I was already familiar with it. I just decided to make my contributions there anyway since I had been using the GNOME Project over the years with the Linux operating system. So, I was basically fascinated to see that everything I had done as a user in my career was basically using open source to basically teach Linux and to teach my students. So, that's, in some way, how I got into technology, how I got into open source, and all of that. So, going into how I found myself [laughs] in the Open Source Festival and how I found myself in GNOME Project, I chose to contribute to the GNOME Project, one, because GNOME is one of the basic...I'll say a very good feature of the Linux OS. It's a desktop application––allows usability in a way that Linux seems like a Windows operating system. And so, I decided to go into GNOME just to learn more about community, how the community looks like and also contribute my quota to outreach and engagement. So, what it means is that there are different areas you can contribute to in the GNOME project, one of it is community and engagements, which means you basically help to do outreach, marketing, and events. So, I wanted to basically bring the GNOME project down to my location, and that's Africa, Nigeria. I wanted people to basically see the benefits of what the GNOME Project is to the Linux ecosystem and how they can also contribute to it. So, because of this, I created a chapter of GNOME in Africa. Right now, we have a community of GNOME Africa. And basically, that is how I started. So, this particular Open Source Festival that just completed for 2023 was not my first, although I was a keynote for this particular one. I had attended Open Source Festival in 2020, where I shared as a workshop speaker, and I shared more about improving Linux experience for African users. And one of the demos I did was basically showcasing the GNOME Project to the users. VICTORIA: I love that. And maybe you can say more about what the GNOME Project is and the kind of impact it can have on communities like the one that you're from. REGINA: One of the things with GNOME Project, in some way, it's a desktop application, a desktop application that features in the Linux operating system. So, like you know, we have the Windows operating system, and then we have user-friendly desktop that allows us to be able to basically use Windows without going through command lines all the time. GNOME is like that desktop application to Linux operating system. So, it's a feature of distros of Linux that decides to basically use it. So, what does it do to a community like mine? I think it is very clear, usability, and allows people as well to be able to contribute to the GNOME shell. Like any other open-source projects, one of the things is that you don't just become a user. But also, you can contribute to the innovation of that particular project, so not just having to be consumers of products but also become creators of those products by contributing to what the community is doing. So, I think what it has done to a community like mine is basically given people the opportunity and the free will to become creators for something that is quite unique to the Linux operating system and allowing them to also become part of a community, bringing diversity to the global community globally. VICTORIA: So, how does GNOME benefit as a project from having these additional communities in areas where they may not have had before? REGINA: I think the key thing here is diverse voices. The key thing here is bringing in people to create more diverse GNOME Projects. And it's not a buzzword. I think creating better technologies is allowing for diverse users' views to be heard. So, before I came into the GNOME project, they had presence around Europe and the U.S. but not so much around Asia and Africa. What this means is that the design, the usability, the culture around the community is not going to be that that is very friendly towards these communities that they are not part of, these communities that doesn't really know what is happening in the GNOME Project. So, having to bring in diversity, bringing in somebody like myself, community like myself, into the GNOME Project, what this means is that there will be more opportunities for GNOME to evolve around what they have in the previous years into something that is more global, something that is more inclusive, you know, a project that allows people to become contributors and designers of the GNOME shell. So, I would say this: when I got into the board...this is my second time in the board. We've had several discussions around how to bring in diversity into the GNOME Project and also allow users, newcomers to feel welcomed in the GNOME Project. And that is a discussion and an action that is basically progressive here. We are having these conversations because I have now come into the project. There is now space for the GNOME Project to see that we need to be more inclusive. We need to be more diverse in our approach, in our design, in the basically way we listen to users right now. So, this was not the case before I came in. So, it's basically just allowing more diversity into the GNOME Project. VICTORIA: I love that. And I think there's been a lot of studies and evidence that have shown that projects and companies with more inclusive and more diverse voices perform better business-wise afterwards. So, it's not only, like, a moral imperative but just smart business decisions. REGINA: Yes, yes, yes, yes. Yes. VICTORIA: And I'm curious, as a community organizer myself [chuckles], what surprised you about the early stages of starting up this community in Africa, or maybe even joining the board of this community now that you've become there? Anything that surprised you in the process there? REGINA: I think one of the first things that surprised me is that it was more like I was the only one that knows that GNOME exists [laughs]. So, it's me having to first always explain, giving onboarding sections to newcomers to basically explain to them what the GNOME Project is, and doing multiple demos to show how the GNOME desktop works within Linux. And I thought that people would just know these things and people would just understand how the Linux project works. So, that basically surprised me because I had to always have to...even up until now, I always have to more, like, introduce, guide, and explain what GNOME is and help users to basically or newcomers basically decide if it is something that they will want to contribute to, right? So, that's one thing that surprised me. And I think the second thing that surprised me was mainly about when I came into the GNOME Project; for a project that global, I thought that there would be some certain level of diversity around the projects. And I thought that I would see more of people like myself or more of people from maybe, you know, Asia or something like that. But I realized that that wasn't the case. Instead, I remember when I was being introduced to the project, I was introduced to other two Africans, and that made us three. And it was shocking for me that there was less presence for Africans within the GNOME Project. And I think that's one of the basic motivation for me to build a community in Africa and to see that they know that a project like GNOME exists. VICTORIA: I love that, and it reminds me of when I was running DevOps groups with Women Who Code and DevOps DC, how frequently you have to do just a 101, like, a 101, like, here's the basics. Here's the introduction. And getting really good at that and just knowing you're going to have to keep doing that and to bring in new people. Yeah, that's interesting; that was the point for you. Mid-Roll Ad: When starting a new project, we understand that you want to make the right choices in technology, features, and investment but that you don’t have all year to do extended research. In just a few weeks, thoughtbot’s Discovery Sprints deliver a user-centered product journey, a clickable prototype or Proof of Concept, and key market insights from focused user research. We’ll help you to identify the primary user flow, decide which framework should be used to bring it to life, and set a firm estimate on future development efforts. Maximize impact and minimize risk with a validated roadmap for your new product. Get started at: tbot.io/sprint VICTORIA: I'm curious; maybe we can dive more into open source in general and how it can be more inclusive and more diverse. Because I think what I see with open source is, you know, often, it's people doing maintenance on their own free time. They're not getting paid for it. And, of course, there's all the existing access and issues with enabling women to be more into technology careers. So, I'm curious if you have anything else that you think we should talk about with open source and how to make it more inclusive and have more voices at the table. REGINA: One of the things here is...and I feel like discussion there is a progressive discussion as open-source communities begin to grow, open-source ecosystem continues to grow. So, one of the things here is, basically, having programs that is geared towards under-representation people within the open-source ecosystem. And this program, I feel like, should be a program that encourages some certain level of incentives, you know, stipends for people that are going to be contributing. Because, like I said, in the past, open source has thrived more within Europe and the U.S. area. But in these areas, there are certain levels of opportunities that is presented. It's either the maintainer has good jobs, or they have projects that pays them on the side. So, they could easily give their free time to open-source contribution. But looking at the economy side of things and problems we have within areas like Africa and Asia, if you see people contributing or you want people to contribute to open source, there must be some other level of motivations that would get them to basically contribute to your project. So, there are programs like Outreachy. Outreachy is basically a program that helps women to contribute to open source, and they are paid a certain level of stipends at the end of three months, at the end of their contribution. We need to have more of such programs to encourage inclusive contribution into open source-projects. Because this way, we get more people that would not necessarily have an opportunity to become open-source contributors to come in to contribute. And also, [inaudible 18:29] more diverse voices in the open-source ecosystem. Another thing here is also that we need to also talk about one of the problems within open source at the moment, which is that we have less women representation, and I'm very glad you're very deep within community and Women Who Code as well. So, you will basically relate with this one. So, there are less women within the open-source ecosystem. And even the women that are contributing––they have challenges within the ways they are treated amongst maintenance. They have challenges even with how to prioritize what they are doing and to be able to also give their time to open source. So, these all challenges we need to begin to, you know, address them by giving voices to women within open source and helping them to solve some of these problems that they have within, you know, the communities that they are serving in. Another thing is to have representation in leadership, and I really cannot stress this enough. When I mean representation, it's having more women leaders because this is where the gap is here at the moment. I think the Linux Foundation had a particular research; I'm not very sure about the year. But it shows that we have about 93% of men in the open-source ecosystem, and that tells you what is left of women, you know, the percentage of women that we have within the open-source ecosystem. So, there's a whole lot of work we need to do to bring in more inclusiveness, to bring in more women into the open-source ecosystem. I'm not particularly sure about the exact statistics for that research, but I know it's around that range. Another thing is that we should encourage communities, open-source communities, to have separate channels where diverse voices can basically have their views about their community, so whether it is having to have a pool of questions geared towards, how do you think we are diverse? How diverse are we in this community? What can we do better? You know, taking metrics of your community is one way we can also bring in inclusivity into the open-source ecosystem. One of the last thing here that I would mention is events also––open-source events, has to also be conscious around people that are attending their events, around the different races, the different genders. This matrix needs to be taken to basically help to solve and bring more inclusivity into open-source community and open-source events. VICTORIA: You raised a lot of really great points there. And I won't even try to recap them all because I think I'll miss them [laughs]. But I think you're spot on with everything. It resonates with me, especially, like, working through Women Who Code; what you'll see is there's lots of people interested in joining. There's a drop-off rate around the mid-level of your career because of some of the things that you mentioned, the way that they're treated in the environments and in the communities, and not seeing a path forward to leadership. So, I think you're spot on with everything that you said there. And I'm curious; I want to make sure we make time to also talk about OpenKids Africa and your founding of that. And what was the goal or the idea behind it? REGINA: The idea behind it was basically my journey into tech. If you recall, I said I started my journey into tech after my bachelor's degree in public administration. And I felt like I could have done more with technology if I was aware about technology a bit more earlier in life. So, I wanted to create something and to build something that would give children an opportunity to have better career choices and possibly become technologists, or software engineer, or robotics engineer, or developers in future. But giving them the opportunity to know that this set of careers exist and they could actually make their choices from it. So, I grew up in Nigeria, like I said. And at the time I grew up, the trending careers were doctors, engineers, lawyers. And my parents actually wanted me to be a lawyer because, at the time, they believed that I was very good at arguments [chuckles]. I could argue a lot. And that basically quickly transcends to I can be a better lawyer. And also because lawyers, in those times, lawyers were very respected in the society. Now, don't get me wrong, lawyers are still respected. But at that time, it felt as though being a lawyer or being a doctor is the only way you're ever going to have a career in Nigeria. Having to feel like I disappointed my parents because I couldn't get into law...I had a diploma. I did a diploma in law program, but I did not get into my degree. So, I had to do something close, which was the public administration I took. Having to go through those whole process in my career and then finish my bachelor's and realizing that I was a bit better in a technology career, I felt like it was a bit late for me and that I would have taken a better chance at my career choices if I had known about technologies earlier. So, this is the motivation of creating OpenKids Africa is basically giving children an opportunity to know what they can do with technology, to know how technology cuts across different careers, and to make them realize that technology is no longer an option in your career choices; it's something that needs to be part of your career journey, whether they want to become doctors, whether they want to become technologists in future. Whatever they want to become, they need to have this basic foundation to thrive. So, that's basically what brought about OpenKids Africa. And my target is basically children in rural communities. And so, we are teaching children in rural communities several skills: how to code, how to understand basically foundational courses within technology. Recently, we went to different schools and giving them an experience of how virtual reality looks like. And it was really fun for these children because, like I said, they are in rural communities. They don't even have these opportunities in the first place, and except it is provided to them here. So, that's basically what we're doing. We're giving children in rural community an opportunity to experience technology and to make better career choices in the future. VICTORIA: I love that. And so, you found that the kids are really excited about learning about computers. Do you feel that the parents agree that technology is a good path for them to follow and study? REGINA: Well, I think that that's another part of OpenKids Africa. So, when I started OpenKids Africa, I wanted to explore the rural community and understand, basically, what are the unique cases that we have here? So that's part of those...I was exploring, basically. We found that some of the children would tell us that, "I like this, but my mom or my parent would not allow me to do this. They will not allow me to know how to use computers or to become maybe a technologist in future because my mom or my dad thinks I should be a doctor," and all of that. So, we had to remodel our strategy in a way that we now go to parents' associations in schools in rural communities. And we talk to them about technology, benefits of technology, and how they can encourage their children to learn technology, and also the future career choices for their children. And when we do this, when we speak to parents, we see the excitement of "Oh, so, my child can actually become this with this technology thing." And we also give them safety measures because, of course, there's so many things on the internet here. And there's safety tips for parents to know about, even if they want to allow their children to basically use computers and all of that, child control and all of those things. So, by talking to parents, we've realized that we have to have a two-model approach in OpenKids Africa, where we don't just teach the children and encourage the teachers to learn more about technology, but we also have to talk to the parents to allow their children to basically explore technology careers in the future, and also, showing them the opportunities that it will pose to them. So yeah, to be honest, this is one of the surprising things that I found, and it has continued to surprise me as a founder of OpenKids. VICTORIA: Well, that's, I think, a very common thing for founders is that you think you have one set of users, but there's actually another one [laughs] where it impacts you. REGINA: Exactly. Exactly [laughs]. VICTORIA: That's wonderful. Are you excited about on the horizon with either the GNOME Project or OpenKids Africa? REGINA: I will start with the GNOME Project. Right now, we are looking towards things like the Global Inclusive Initiative. And it's basically an initiative that we are looking to put together all the communities we have globally, giving more voices to diverse users to be able to contribute into GNOME. That is something on the pipeline that we're looking to plan. And I'm also excited for OpenKids Africa. So, right now, we are exploring how to get teachers in rural communities involved with what we're doing and basically train them separately as well to know the benefit of technology to children. So, the target teachers here are teachers that basically...early child education teachers and helping them to understand how to teach technology to children, and how to inspire children to appreciate technology innovation we have around the world, innovations like virtual reality, you know, robotics, and all of that. So, I'm really excited about that one because I feel like if you can tell the teachers how these things are and the benefits, and then they can better pass the message across to the children, making our work more easier when we have workshops and demos to do in schools, yeah. VICTORIA: And I've actually gotten this question quite a few times from people, which is, how do you get kids interested in learning [laughs] technology and learning how to code? REGINA: I think it's basically having a practice that is more child-friendly, co-creative. So, co-creation is basically, you are not the only one doing it. You're involving the children in it as well, and you give them the real-life experiences. So, for instance, when we went to talk about virtual reality to children, and we showed them what virtual reality does in the presentation, we engage with the kids. We make them give us their own ideas. We even go as far as allowing them to draw what they see and give us what they think about it. But we don't stop there. We get virtual sets and show them exactly...give them a real-life experience of what virtual reality is. So, children are very, very creative, and they also have a very fast mind to pick pictures. But not only that, they can also store experiences very, very fast. So, we utilize every area that makes children excited in our workshops. After we are done, we do practices, and we give them gifts as well for engaging in those practices. So yeah, we just co-creation [laughs]. VICTORIA: Wow. And you're doing so much because you have a full-time job. You're on the board for GNOME Project, and you have your non-profit, OpenKids Africa. So, how do you find a right balance in your life of work, and extra stuff, and your regular life [laughs]? REGINA: Honestly, I would say that the word balance I wouldn't use balance for me at the moment because I feel like I've not basically found the balance I'm looking for, but I've been able to prioritize. So, what that means is that I've been able to know what is important part-time and know when to take certain engagements. So, my full-time job is more, like, a priority right now because, of course, we need a job to be able to sustain our lives. So, I take that as my priority. And I have different schedule of days for other things like the GNOME community and working with my team in OpenKids Africa. So, I would say I'm quite lucky to have a very good team. And also, being part of GNOME board, the commitments are not as demanding as you would expect, you know, maybe a regular board. There are fixed schedules on things, and they have flexible time for contribution as well. I'm also part of the GNOME Africa community. And I recently just on-boarded a community manager because I realized that I need more, like, to take a step back so that I don't get burned out and all of that. So, I think it's basically prioritizing for me at the moment to gain the balance that I'm looking for. So, I think if I have a conversation with you maybe months after now, I would be able to know what balance feels like. So, I'm really experimenting with prioritizing at the moment. VICTORIA: We'll have to check back in in a few months and see how things are going. But I think that's a very honest answer, and I appreciate that. And I think that probably relates to how a lot of people feel, honestly, even having less on their plate that it's hard to find that balance. So, I appreciate you sharing that. And I wonder, too, if you had any advice for yourself. If you could go back in time, either when you were first starting on your journey or when you were first starting on either of these projects, what advice would you give yourself? REGINA: I think one of the things...I will talk about first starting on my technology career. I didn't have the opportunities that many young people had at the time because I didn't come from a background where my parents had the finances to basically give me the opportunity to learn technology the way I wanted to. But, I was able to make do with the resources I had at the time to learn and to basically grow. So, an advice I will give to my younger self and to anybody that wants to come into technology that do not have the resources, I would say leverage open-source tools as much as you can because now I realize that that's basically what helped me. And also, allow yourself to grow; it will always get better. Advice I would give to somebody coming into an open-source project like me at the GNOME Project. I think that one of the things that...understand why you're contributing to that project, and always seek to be treated fairly, always seek to be treated nicely. And also treat other people nicely and fairly as well. I think if we have these both balance, we'll have a better, healthy community within open source. And don't be scared to share your view. Don't be scared to basically be yourself wherever you are found in the community that you're representing. And if I would like to add: OpenKids Africa, for me, if anyone would be...it's, I would say, it's still young because we are going, I think, about our third year now. So, I will say it's still young. But what I would say to any founder that wants to basically found a non-profit or do something in the society, I think, is just to get your motivation, understand why you're doing them, and be open-minded to what you'll learn along the way. That's it. VICTORIA: I think that's great. Yeah, I love that. And I like that you mentioned that there are open-source tools out there. I'm trying to use those more, and I think I always try to iterate that for people, too, is, like, there's free training. There's free resources. There's free tools. And there are lots of people who want to see you succeed, no matter your background, or where you're from, or what you look like. So, I think that that's a really powerful message. So, I appreciate that. And do you have anything else that you would like to promote? REGINA: I think before that, I would like to learn more about the Women Who Code. As a community builder, what basically surprised you the most? VICTORIA: Yeah. So, what I loved about Women Who Code is that it was really aimed at helping women get started in careers in technology and maintaining careers in technology. So, I think what was interesting for me...I think I started doing it back in 2017 or 2018, and I just loved it. I loved going to a tech meetup with a room where it's all women [laughs]. Because, normally, and I'm sure you've had this experience, you go to a tech meetup, and you're maybe one of two, at the best, of women in the group. I just really enjoyed that. And I've been really surprised and happy to see how the women, including myself, who started running the meetups, and doing trainings, and helping other women learn how to code have really advanced in their career and become directors, or engineering managers, or really senior contributors in different companies. So, I think that that was a really interesting and surprising thing for people is, like, well, if you want to grow in your career, it helps to be active in your community and to be someone that people know and to have those connections. And I think it still surprises me to this day how my network that I got from investing in all of those meetups and all that time is still paying off [laughs]. Like, I could still, like, reach back into my network and find someone who is an expert on a particular subject or works at a company that I want to talk to or something like that. So, I think that that's been a really wonderful aspect of it. REGINA: Wow, that's quite interesting. And I really think, also I agree with you. One of the beautiful things around communities and meetups is basically networks, the people that you get to meet, the people that you get to know along the way. VICTORIA: Absolutely. Yeah, and those are the people that you want to keep working with. So, it helps you find jobs. It helps you find people to hire if you're hiring. It's worth it. Like [laughs], it can feel like, ugh, am I really going to go to this meetup [laughter], like, after work, after a long day? And, you know, maybe the topic is even something I'm not interested in. But it does pay off if you keep showing up and continue to invest in it. Yeah, I think that's smart. And make people feel safe, too. I think that was a big part of it is, you know, going to a meetup and meeting someone maybe like me who's nice and friendly and wants to hear your voice. I think that has a big impact for people, especially if they're, you know, the only woman at their company. And now they have a whole set of friends [laughs]. That's, yeah, how powerful that can be for people. REGINA: Exactly. Exactly. And you just said one of the most important things, and that's basically making people feel safe, making them welcomed as well. Interesting. Thank you for sharing that one because I was quite curious, and I wanted to really learn more. VICTORIA: Yeah, I'm very lucky. And we actually had the CEO and founder of Women Who Code on our podcast lately. So, you're in good company [laughs]. REGINA: Nice. VICTORIA: Yeah, it's wonderful. Do you have any other questions for me? REGINA: My last question, and I'm going to be asking again that I will be inviting you on my podcast as well [inaudible 37:32] [laughs] VICTORIA: Yes. Of course, yes. Absolutely. Send me the details. I'd be happy to join. All right. Well, thank you so much again for joining us. I really appreciate your time. And for our listeners, you can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thank you for listening. See you next time. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guest: Regina Nkenchor.Sponsored By:thoughtbot: When starting a new project, we understand that you want to make the right choices in technology, features, and investment, but that you don’t have all year to do extended research. In just a few weeks, thoughtbot’s Discovery Sprints deliver a user-centered product journey, a clickable prototype or Proof of Concept, and key market insights from focused user research. We’ll help you to identify the primary user flow, decide which framework should be used to bring it to life, and set a firm estimate on future development efforts. Maximize impact and minimize risk with a validated roadmap for your new product. Get started at: tbot.io/sprintSupport Giant Robots Smashing Into Other Giant Robots

We released episode one of this podcast on June 11, 2012. Now, more than a decade later, we're celebrating the 500th episode of our show. In honor of this milestone, Victoria, Will, and Chad caught up with each of the past hosts of the show: Ben Orenstein, Chris Toomey, and Lindsey Christensen. We chatted about what they’re up to now, what they liked and learned from hosting the show, their time at thoughtbot, and more! Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. WILL: And I'm your other host, Will Larry. CHAD: And I'm your other host, Chad Pytel. We released episode one of this podcast on June 11, 2012. Now more than a decade later, were celebrating this: the 500th episode of our show. In honor of this milestone, Victoria, Will, and I caught up with each of the past hosts of the show: Ben Orenstein, Chris Toomey, and Lindsey Christensen. We chatted about what they’re up to now, what they liked and learned from hosting the show and their time at thoughtbot, and more. First up: Ben Orenstein. Ben was the very first host of the show back in 2012 when he was a developer at thoughtbot. He is now the co-founder and Head of Product at Tuple, a remote pair programming tool for designers and developers. Ben, it's great to talk to you again. It's been a while since you and I talked. How have you been? BEN: I've been decent, yeah. It's fun to be back to my roots a little bit. I told some folks that I work with that I was coming back to the pod for the 500th Episode, and they were stoked. So, it's kind of a treat to get to be on these airwaves again. CHAD: What have you been up to since you left this show and thoughtbot? BEN: Well, I started a company. So, I was at thoughtbot for a while; I think it was seven years. And I eventually sort of struck out to start my own thing–had a false start or two here and there. And then, I ended up starting a company called Tuple, and we still exist today, fortunately. Tuple is a tool for doing remote pair programming. We started off on macOS and then wrote a Linux client. And we're launching a Windows client now. But it's sort of, like, screen sharing with remote control for developers who are actually writing code and want to have great, low latency remote control and who care about screen share quality and that sort of thing. I started that about five years ago with two co-founders. Today, we are a team of 11, I think it is. And it's been going well. Our timing was really great, it turned out. We launched a little bit before COVID. So, remote work turned into a lot more of a thing, and we were already in the market. So, that helped us a ton. It was quite a wild ride there for a bit. But things have calmed down a little lately, but it's still fun. I'm, like, really enjoying being a co-founder of a software company. It was what I've always sort of wanted to do. And it turns out it actually is pretty fun and pretty great. Although there are, of course, the ups and downs of business ownership. It is never quite as calm or relaxing as being an employee somewhere else. CHAD: You started Tuple instigated by...full disclosure: thoughtbot's an early customer of Tuple. We're still a customer. We use it a lot. BEN: Woo-hoo. I appreciate that. Thank you. CHAD: If I remember right, you started and were sort of instigated to create Tuple because there was a prior product that then Slack bought, and then it started to degrade. And now, it no longer exists in the same way that it did before. BEN: Yeah. So, there was this tool called Screenhero, which I actually started using -- CHAD: [inaudible 02:14] BEN: Yeah, first at thoughtbot. Some other thoughtboter introduced me to it, and we would use it for pair programming. And I was like, oh, this is nice. And then yeah, Slack kind of acqui-hired it and more or less ended up shutting the product down. And so, there was this gap in the market. And I would ask my friends, I would ask thoughtboters and other developers, like, "What are you using now that Screenhero is gone?" And no one had a good answer. And so, after a while of this thing sort of staring me in the face, I was like, we have to try to solve this need. There's clearly a hole in the market. Yeah, so we were heavily inspired by them in the early days. Hopefully, we've charted our own path now. But they were definitely...the initial seed was, you know, let's do Screenhero but try to not get bought early or something. CHAD: [laughs] How did you or did you feel like you captured a lot of the Screenhero customers and reached them in those early days? BEN: I think so. The pitch for it was sort of shockingly easy because Screenhero had kind of blazed this trail. Like, I would often just be like, "Oh, we're making a thing. Do you remember Screenhero?" And they'd go, "Oh yeah, I loved Screenhero". I'd be like, "Yeah, we're going to try to do that." And they'd be like, "Nice. Sign me up." So, it for sure helped a ton. I have no idea what percentage of customers we converted. And they were a pretty large success, so probably a small fraction, but it definitely, like, made the initial days much easier. CHAD: Yeah. And then, like you said, COVID happened. BEN: COVID happened, yeah. I think we had been around for about a year when COVID hit. So, we were getting our feet underneath us. And we were already, like, the company was already growing at a pretty good rate, and we were feeling pretty good about it. I don't think we had quite hit ramen profitable, but we were probably pretty close or, like, flirting with it. Yeah, the business, like, I don't know, tripled or quadrupled in a matter of months. We had a few big customers that, like, just told everyone to start using Tuple. So, we had, like, thousands and thousands of new users kind of immediately. So, it was a crazy time. Everything melted, of course. We hadn't quite engineered for that much scale. We had a really rough day or so as we scrambled, but fortunately, we got things under control. And then had this, like, very nice tailwind. Because we started the company assuming that remote work would grow. We assumed that there would be more remote developers every year. And, you know, it's probably maybe 5% of dev jobs are remote or maybe even less, but we expect to see this number creeping up. We don't think that trend will reverse. And so, COVID just, like, it just yanked it, you know, a decade in the future. CHAD: You haven't tripled or quadrupled your team size, have you? BEN: No. Well, I mean, I guess, I mean, we started as 3, and now we're 11, so kind of. CHAD: [laughs] Yeah, that's true. BEN: Expenses have not grown as fast as revenue, fortunately. CHAD: That's good. That's basically what I was asking [laughs]. BEN: Yeah, yeah. We're still a pretty small team, actually. We have only, like, four or five full-time engineers on the team at the moment, which is kind of wild because we are now, you know, we have three platforms to support: Linux, Windows, and Mac. It's a pretty complicated app doing, like, real-time streaming of audio, webcams, desktops, caring about OS-level intricacies. So, I think we will be hiring more people soon, although we haven't said that for a long time. We sort of have always had a bit of a hire-slow mentality to try to get the right team members and, like, feel a real pain before we hire someone into it. But we have been getting a bit more aggressive with hiring lately. VICTORIA: Well, I really appreciate Tuple. I installed it when I first started working here at thoughtbot. And we have random pairings with everyone across the company. So, I'll randomly get to meet someone halfway across the world who's working on similar projects. And I think they really enjoy that I have a tool they like working to share what they're working on. So, I want to thank you for that. And I'm curious about when you really started to scale during COVID, what were some of the technology architecture trade-offs you came across, and where did you land with it? BEN: Well, we got fairly...I don't know if it was lucky, but we...for a long time, for years, even through COVID, maybe the first four years of the company, all Tuple calls were purely peer-to-peer. And there was no server that we owned intermediating things. This was, like, kind of one of the keys of, like, not having expenses. The scale of revenue was we could have lots more calls happen. And it wouldn't cost us bandwidth or server capacity. To this day, still, for any calls with three or fewer participants, they're purely peer-to-peer. And this is nice for latency purposes because it just...we can find the most direct path to the internet between two people. It's also nice from our cost perspective because we don't need to pay to send that data. And that was hugely useful as call volume went up immensely. Didn't have to worry too much about server load and didn't have to worry too much about bandwidth costs. CHAD: Today, is there a central service that makes the initial connection for people? BEN: Yes, yeah, yeah. So, there is a signaling server. So, when you launch the app, you sign in, and you see, like, oh, which of my co-workers are online? So, there is actually a Rails app that handles that, actually, increasingly less the Rails app. We have now...I think it's a Go service that actually manages all those. I'm further and further from the code every year. Some of the technical questions might be a little bit beyond me, or I might have slightly out-of-date info. But back to the architecture question for a second, we did a pretty big refactor when we decided to go from just being a Mac client to supporting other platforms, where we split out a cross-platform real-time communication engine written in C++ so that we could use that for all of the heavy lifting, all the managing of the connections, and the tricky bandwidth estimation, and all this stuff, and use that across different platforms. And so, today, you have the cross-platform engine, and then on top of that is a, like, a less specific layer for each of the operating systems that we support. CHAD: So, you mentioned you're less and less in the code these days. So, what do you spend your time doing then? BEN: It's a mix of things. These days, it's basically mostly -- CHAD: Just cocktails on the beach, right? BEN: Cocktails, yes [laughs], cocktails on the beach, appearing on podcasts trying to sound important and impressive, yeah. Mostly product work. So, right before this, I just got off a call with some folks from The Browser Company. They are some of our first alpha users for our new Windows clients. So, I hopped on the call with them and, like, watched three of them install the product and inevitably run into some bugs. And, you know, chatted through those with the engineer that was working on it, prioritized some stuff, made some decisions about what's coming up next, and what we're going to ignore. So, mostly product work these days. For the first five years of the company, I was CEO, so I was doing kind of everything: marketing, and also hiring, and also product. About two months ago, I stepped down as CEO, and one of my other co-founders, Spencer, stepped up. And so, now my focus has narrowed to be mostly just product stuff and much less on the marketing or hiring side. VICTORIA: Yeah, you mentioned that it was a little more comfortable to be an employee than to be a founder. I don't know if you could say more about that because, certainly, a lot of engineers are smart enough and capable enough to run their own company. But what really informed your choice there, and do you regret it? [laughs] BEN: I definitely don't regret it. thoughtbot was a close second in terms of wonderful professional experiences. But running my own thing has been the most interesting professional thing I've done by a big margin. It has also been more stressful. And, Chad, I don't know if you remember, I think, like, maybe eight years ago, you tweeted something like, if you want to sleep well at night, and, like, value that, like, peace of mind, like, don't start a company or something. I have experienced that. CHAD: [laughs] BEN: A lot more, yeah, like waking up in the middle of the night worrying about things. It feels a little bit like the highs are higher; the lows are lower. Being an employee somewhere, it's like, if this company fails, I know I can go get another job, right? Like, you're a developer. You're extremely employable. But as the owner of the company, if the company fails, like, a huge chunk of your net worth is gone. Like, this thing you poured your life into is gone. It's way more stressful and traumatic to have that happen, or have that threatened to be happening, or just imagine that happening. So, overall, I have found the trade-off to be totally worth it. It's awesome to make your own decisions and chart your own path. And when it works, it can work in a way that being a salaried employee can't. So, I'm happy with those trade-offs. But I think that is a good question for people to ask themselves as they consider doing something like this is, like: is that the kind of trade-off that you want to make? Because it has significant downsides for sure. WILL: I am a big fan of Tuple also. I love it. It [inaudible 10:08] easy, especially with remote work. You hit the jackpot with COVID and remote work, so kudos for that [laughs]. Was there anything...because I know from our previous companies, about over...hopefully a lot more of the good stuff than the bad stuff. But was there anything that you learned? Because you were at thoughtbot for seven years. Was there anything that you're like, oh my gosh, I learned that, and it's helped me till this day while I'm running my company? BEN: Yeah, quite a bit, actually. I think it'd be hard to tease apart exactly which lessons, but I do...so I ran Upcase for thoughtbot and also FormKeep. So, I got a chance to kind of run a small division of the company, while still being a normal employee and, like, having not much of that risk. And I think that was a really wonderful opportunity for me to, like, practice the skills that I was interested in. Just, like, how do you market a thing? How do you design a product and have it be good? How do you prioritize user feedback? There were a ton of lessons from those days that I feel like made me better at running our company when we actually took a shot at it. So, there were, like, the specific things that I learned by the work I was doing there. But then just, like, I mean, I think I am the programmer I am today because of, like, the weekly dev discussions that happened. Like, spending so much time with Joe Ferris and, like, trying to copy as much of his brain as possible, like, really, like, imprinted on me as, like, a programmer. And also, just, like, a lot of the sort of cultural things from my time at thoughtbot of, like, you should be sharing the things you're learning. Like, writing blog posts is a great use of time. Like, doing open-source work is a great use of time. And maybe you can't directly trace how doing, like, working in public or sharing information benefits the company. It's hard to, like, attribute it from a marketing sense. But if you sort of have faith that in the large, it's going to work out, it probably will. That feels like a thoughtbot lesson to me, and I think it has served us really well; where I recorded a weekly podcast for a long time called The Art of Product. I'm recording a new podcast called Hackers Incorporated with Adam Wathan of Tailwind fame. And I don't ever think, like, hmm, how many new leads do we think we get per episode, and how many hours has that taken? What's the ROI? I just have this sort of reflex that I developed from thoughtbot time of, like, you should be putting stuff out there, or you should be giving back. You should help other people. And that will probably help your business and make it work in the long term. CHAD: That's a good lesson [laughs]. One of the other things, you know, while you were a host of Giant Robots, you were the first host. I remember, you know, encouraging you to be the first host, and I think we talked about that in one of the episodes along the way. But we also transitioned the format a little bit, especially as you started to work on products here; you know, it was more about the building of those products and following along with those. And one of the things that sort of half-jokingly defined, I think, your impact on a lot of products was pricing, experimenting with pricing, learning about pricing, increasing prices more than people were maybe comfortable doing so. How has that worked out with Tuple, pricing in particular? BEN: It's really hard to say. It's hard to know what, like, the other path would have been through the world-. We sort of decided from, like, the early days that we wanted to have, like, a fairly premium price. Like, we wanted to be the product that was really good and was, like, a little bit annoyingly expensive, but you still paid for it because it felt worth it. And I think people could debate in both directions whether we nailed that or not. We have had a price increase that we ended up rolling back. We went, like, a little too far one time and said, "You know what? I think we're a little bit over," and we reverted that. But I would say even today, we are still a fairly pricey product. I mean, I'm pretty happy with how the company has done. I can't prove to you that, like, if the price were half what it is, we would have, you know, better success or not. CHAD: I think it'd be very hard to make the argument that if it was half that, you would have double the number of customers. BEN: Yeah, that's probably not true. CHAD: Not with the customers that you have, who are companies that will pay for products that they use as much as Tuple. BEN: Yeah, I'm happy serving the kind of companies, and they end up being mostly tech companies that really value developer happiness. When their developers come to them and they say, "We don't want to pair over Zoom. We like this thing. It's better. It feels nicer to use," they say, "Okay," and they buy the tool for them. There are places where that's not the case. And they say, "We already have a thing that does screen sharing. You're not allowed to buy this." We don't invest a lot of time trying to sell to those people or convince them that they're wrong. And I'm pretty happy serving sort of the first group. CHAD: So, you've mentioned that you've still been podcasting. To be honest, I didn't realize you were starting something new. Is it live now? BEN: It is live now, yeah. CHAD: Awesome. Where can people find that? BEN: hackersincorporated.com. It's about the transition from developer to founder, which is kind of what we've been touching on here. Yeah, hopefully, the audience is developers who want to start something or have started something who are maybe a little bit further behind progression-wise. And it's kind of, like, I have some lessons, and Adam has some lessons, and, you know, we don't think that we're experts. But sometimes it's useful to just hear, like, two people's story and sort of see, like, what seemingly has worked for them. So, we've been trying to share things there. And I think people will find it useful. VICTORIA: I was going to ask you for a lesson, maybe give us a little sample about how would you advise someone who's built a product and wants to market it, and it's targeted towards developers since you mentioned that previously as well. BEN: Yeah, in a way, the question already contains a problem. It's like, oh, I built the product; now how do I market it? It's a little bit indicative of a very common failure mode for developers, which is that. They sort of assume, okay, after you make the product, you then figure out how you're going to market it. And marketing is sort of a thing you layer on later on when you realize that just, like, throwing it on Twitter or Product Hunt didn't really work. When we started building Tuple, I was out there marketing it already. So, I had two co-founders, so this is a luxury I had. My two co-founders were writing code, and I was out doing stuff. I was recording podcasts. I was tweeting about things. I was making videos. I was giving conference talks. And I was getting people to hear about our product well before it was done. In fact, I was even selling it. I was taking pre-orders for annual subscriptions to the app while it was still vaporware. So, I would say, like, you basically can't start marketing too early. If you start marketing early and no one really cares, well, then you don't really have to build it probably. I would actually even go a little further and say, like, I started marketing Tuple before we had a product available. But in reality, I started marketing Tuple seven or so years before that when I started publishing things through thoughtbot. It's like when I was traveling around giving talks about Ruby, and when I was making screencasts about Vim, and when I was running Upcase, I was, over time, building an audience. And that audience was useful for thoughtbot, and it also was useful for me so that when I left, I had something like 10,000 Twitter followers or something, a few thousand people on our mailing list. But there were a lot of developers that already sort of knew me and trusted me to make fairly good things. And so, when I said, "Hey, I've made a new thing, and it's for you," I really benefited from those years of making useful content and trying to be useful on the internet. And in the early days, we had people sign up, and they would say, "I don't even really think I'm going to use this. But I've learned so much from you over the years that I want to support you, so I'm going to pay for a subscription." VICTORIA: I like your answer because I think the same thing when people ask me, like, because I am an organizer for Women Who Code, and I know all these great people from showing up for years in person months over months. And so, then people will ask, "Oh, how do I recruit more women in my company?" I'm like, "Well, you got to start showing up [laughs] now and do that for a couple of years, and then maybe people will trust you," right? So, I really like that answer. WILL: How has your relationship with Chad continued to grow since you left? Because seven years at the company is a lot. And it seems like you're still on really, really good terms, and you're still friends. And I know that doesn't happen at every company. BEN: I mean, it was tough deciding to leave. I think, like, both of us felt pretty sad about it. That was the longest I'd ever worked anywhere, and I really enjoyed the experience. So, I think it was tough on both sides, honestly. But we haven't kept in that much touch since then. I think we've emailed a handful of times here and there. We're both sociable people, and we sort of get each other. And there's a long history there. So, I think it's just easy for us to kind of drop back into a friendly vibe is sort of how I feel about it. CHAD: Yeah. And the way I explain it to people, you know, when you're leading a company, which Ben and I both are, you put a lot of energy into that and to the people who are on that team. If you're doing things right, there's not really hard feelings when someone leaves. But you need to put in a lot of effort to keep in touch with people outside of the company and a lot of energy. And, to be honest, I don't necessarily do as good a job with that as I would like because it's a little bit higher priority to maintain relationships with them, the people who are still at thoughtbot and who are joining. BEN: What you're saying is I'm dead to you [laughter]. That's CEO, for you're dead to me. CHAD: No. It's just...no hard feelings. BEN: Totally. CHAD: I think one of the things that has been great about the show over the years is that we haven't been afraid to change the format, which I think has been important to keeping it going. So, there is sort of; in fact, the website now is organized into seasons. And I went back and re-categorized all the episodes into seasons. And when the seasons were made up of, like, sort of the format of the show or particular hosts...when we started, it was just an interview show, and it was largely technical topics. And then we started The Bike Shed, and the technical topics sort of moved over there. But it also went with your interests more under the product and business side. Then you started working on products at thoughtbot, so it started to go even more in that. And I think Chris joined you on the show, and that was sort of all about those topics. BEN: Yeah, that makes sense. I think if you don't let the hosts kind of follow their interests, they're going to probably burn out on the thing. It's not fun to force yourself, I think, to record a podcast. CHAD: Yeah. And then when you left, you know, I took over hosting and hosted by myself for a while, went back to the interview format, but then was joined by Lindsey for a little while. We experimented with a few different things: one, interviews, but then we did a whole, just under a year, where we followed along with three companies. And each month, we would have an interview episode where we talked to them, all three companies, about the same topic. And then, we also did an episode with just Lindsey and I talking about that topic and about what we learned from the startup companies that we were following along with for the year. And now we're back to interview freeform, different guests, different topics. It seems like we're going to stick with that for a little while. But, obviously, as Will and Victoria have said, like, we'll probably change it again in some way, you know, a year, two years, three years from now. VICTORIA: Yeah, and I'm definitely bringing my interest around DevOps and platform engineering, so you'll see more guests who have that focus in their background. And with that, sometimes my interview style is more; how do I ask a question that I can't read from your developer docs and that I might not understand the answer to? [laughs] That's kind of where I like to go with it. So yeah, I'm really excited about...it's probably one of my favorite parts of my job here at thoughtbot because I get to meet so many interesting people. And, hopefully, that's interesting to everyone else [laughs] and our guests, yeah. BEN: Totally. Well, I dramatically underestimated how awesome it would be to meet all kinds of cool people in the industry when I started the podcast. I didn't truly connect in my head, like, wait a second, if I have a 45-minute conversation with, like, a lot of prominent, awesome people in our field, that's going to be really interesting and useful for me. So, I think, yeah, it's nice to be in the hosting seat. VICTORIA: And it's so surprising how I'll meet someone at a conference, and I'll invite them onto the podcast. And the way it winds up is that whatever we're talking about on the show is directly relevant to what I'm working on or a problem that I have. It's been incredible. And I really appreciate you for coming back for our 500th Episode here. CHAD: Ben, thanks very much again for joining us, and congratulations on all the success with Tuple. And I wish you the best. BEN: Thank you so much. Thanks for being a continuing customer. I really appreciate it. CHAD: Next, we caught up with Chris Toomey, who had a run as co-host of the show with Ben throughout 2016. CHRIS: Hi there. Thanks for having me. So, we're talking with all of the past hosts. I know you joined the show, and you were on it with Ben. And then you moved over to The Bike Shed, right? CHRIS: Yeah. So, I had co-hosted with Ben for about six months. And then I think I was transitioning off of Upcase, and so that ended sort of the Giant Robots “let's talk about business” podcast tour for me. And then, I went back to consulting for a while. And, at some point, after Derek Prior had left, I took over as the host of The Bike Shed. So, I think there was probably, like, a year and a half, two-year gap in between the various hostings. CHAD: Are you doing any podcasting now? CHRIS: I'm not, and I miss it. It was a lot of fun. It was, I think, an ideal medium for me. I'm not as good at writing. I tend to over-edit and overthink. But when you get me on a podcast, I just start to say what's in my head, and I tend to not hate it after the fact. So [chuckles], that combination I found to be somewhat perfect for me. But yeah, lacking that in my current day-to-day. CHAD: Well, what's been taking up your time since you left? CHRIS: I had decided it was time to sort of go exploring, try and maybe join a startup, that sort of thing. I was sort of called in that direction. So, just after I left thoughtbot, I did a little bit of freelancing, but that was mostly to sort of keep the lights on and start to connect with folks and see if there might be an opportunity out there. I was able to connect with a former thoughtbot client, Sam Zimmerman, who was looking to start something as well. And so, we put our act together and formed a company called Sagewell, which was trying to build a digital financial platform for seniors, which is a whole bunch of different complicated things to try and string together. So, that was a wonderful experience. I was CTO of that organization. And I think that ran for about two and a half years. Unfortunately, Sagewell couldn't quite find the right sort of sticking point and, unfortunately, shut down a little bit earlier in this year. But that was, I would say, the lion's share of what I have done since leaving thoughtbot, really wonderful experience, got to learn a ton about all of the different aspects of building a startup. And I think somewhat pointedly learned that, like, it's messy, but I think I do like this startup world. So, since leaving Sagewell, I've now joined a company called August Health, which has a couple of ex-thoughtboters there as well. And August is post their Series A. They're a little bit further along in their journey. So, it was sort of a nice continuation of the startup experience, getting to see a company a little bit further on but still with lots of the good type of problems, lots of code to write, lots of product to build. So, excited to be joining them. And yeah, that's mostly what's taking up my time these days. CHAD: So, I know at Sagewell, you made a lot of technical architecture, team decisions. It was Rails in the backend, Svelte in the frontend, if I'm not mistaken. CHRIS: Yep, that's correct. CHAD: You know, hindsight is always 2020. Is there anything you learned along the way, or given how things ended up, that you would do differently? CHRIS: Sure. I was really happy with the tech stack that we were able to put together. Svelte was probably the most out there of the choices, I would say, but even that, it was sort of relegated to the frontend. And so, it was a little bit novel for folks coming into the codebase. Most folks had worked in React before but didn't know Svelte. They were able to pick it up pretty quickly. But Inertia.js was actually the core sort of architecture of the app, sort of connected the frontend and the backend, and really allowed us to move incredibly quickly. And I was very, very happy with that decision. We even ended up building our mobile applications, both for iOS and Android. So, we had native apps in both of the stores, but the apps were basically wrappers around the Rails application with a technology similar to Turbolinks native–if folks are familiar with that so, sort of a WebView layer but with some native interactions where you want. And so, like, we introduced a native login screen on both platforms so that we could do biometric login and that sort of thing. But at the end of the day, most of the screens in the app didn't need to be differentiated between a truly native mobile app and what like, mobile WebView would look like. So, we leaned into that. And it was incredible just how much we were able to do with that stack and how quickly we were able to move, and also how confidently we were able to move, which was really a nice thing. Having the deep integration between the backend and the frontend really allowed a very small team to get a lot done in a short time. CHAD: Does that code live on in any capacity? CHRIS: No. CHAD: Oh. How does that make you feel? [chuckles] CHRIS: It makes me feel very sad, I will say. That said, I mean, at the end of the day, code is in service of a business. And so, like, the code...there are, I think, probably a couple of things that we might be able to extract and share. There were some interesting...we did some weird stuff with the serializers and some, like, TypeScript type generation on the frontend that was somewhat novel. But at the end of the day, you know, code is in service of a business, and, unfortunately, the business is not continuing on. So, the code in the abstract is...it's more, you know, the journey that we had along the way and the friends we made and whatnot. But I think, for me, sort of the learnings of I really appreciate this architecture and will absolutely bring it to any new projects that I'm building from, you know, greenfield moving forward. VICTORIA: I'm curious what it was like to go from being a consultant to being a big player in a startup and being responsible for the business and the technology. How did that feel for you? CHRIS: I would say somewhat natural. I think the consulting experience really lent well to trying to think about not just the technical ramifications but, you know, what's the business impact? How do we structure a backlog and communicate about what features we want to build in what order? How do we, you know, scope a minimal MVP? All those sorts of things were, I think, really useful in allowing me to sort of help shape the direction of the company and be as productive of an engineering team as we could be. CHAD: A lot of the projects you worked on at thoughtbot were if not for startups, helping to launch new products. And then, a lot of the work you did at thoughtbot, too, was on Upcase, which was very much building a business. CHRIS: Yes. I definitely find myself drawn in that direction, and part of like, as I mentioned, I seem to be inclined towards this startup world. And I think it's that, like, the intersection between tech and business is sort of my sweet spot. I work with a lot of developers who are really interested in getting sort of deeper into the technical layers, or Docker and Kubernetes and orchestration. And I always find myself a little bit resistant to those. I'm like, I mean, whatever. Let's just...let's get something out there so that we can get users on it. And I am so drawn to that side, you know, you need both types of developers critically. I definitely find myself drawn to that business side a little bit more than many of the folks that I work with, and helping to bridge that gap and communicate about requirements and all those sort of things. So, definitely, the experience as a consultant really informed that and helped me have sort of a vocabulary and a comfort in those sort of conversations. WILL: How did Upcase come about? Because I know I've talked to numerous people who have gone through Upcase. I actually went through it, and I learned a ton. So, how did that come about? CHRIS: I think that was a dream in Ben Orenstein's eye. It started as thoughtbot Learn many, many years ago. There was a handful of workshops that had been recorded. And so, there were the video recordings of those workshops that thoughtbot used to provide in person. Ben collected those together and made them sort of an offering on the internet. I think Chad, you, and I were on some podcast episode where you sort of talked about the pricing models over time and how that went from, like, a high dollar one-time download to, like, $99 a month to $29 a month, and now Upcase is free. And so, it sort of went on this long journey. But it was an interesting exploration of building a content business of sort of really leaning into the thoughtbot ideal of sharing as much information as possible, and took a couple of different shapes over time. There was the weekly iterations of the video series that would come out each week, as well as the, like, longer format trails, and eventually some exercises and whatnot, but very much an organic sort of evolving thing that started as just a handful of videos and then became much more of a complete platform. I think I hit the high points there. But, Chad, does that all sound accurate to you? CHAD: Yeah, I led the transition from our workshops to Learn, which brought everything together. And then, I stepped away as product manager, and Ben took it the next step to Upcase and really productized it into a SaaS sort of monthly recurring billing model and took it over from there. But it still exists, and a lot of the stuff there is still really good [laughs]. CHRIS: Yeah, I remain deeply proud of lots of the videos on that platform. And I'm very glad that they are still out there, and I can point folks at them. VICTORIA: I love that idea that you said about trying to get as much content out there as possible or, like, really overcommunicate. I'm curious if that's also stayed with you as you've moved on to startups, about just trying to get that influence over, like, what you're doing and how you're promoting your work continues. CHRIS: I will say one of the experiences that really sticks with me is I had followed thoughtbot for a while before I actually joined. So, I was reading the blog, and I was listening to the podcasts and was really informing a lot of how I thought about building software. And I was so excited when I joined thoughtbot to, like, finally see behind the curtain and see, like, okay, so, what are the insider secrets? And I was equal parts let down...actually, not equal parts. I was a little bit let down but then also sort of invigorated to see, like, no, no, it's all out there. It's like, the blog and the open-source repos and those sort of...that really is the documentation of how thoughtbot thinks about and builds software. So, that was really foundational for me. But at the same time, I also saw sort of the complexity of it and how much effort goes into it, you know, investment time Fridays, and those sort of things. Like, a thoughtbot blog post is not a trivial thing to put up into the world. So many different people were collaborating and working on it. And so, I've simultaneously loved the sharing, and where sharing makes sense, I've tried to do that. But I also recognize the deep cost. And I think for thoughtbot, it's always made sense because it's been such a great mechanism for getting the thoughtbot name out there and for getting clients and for hiring developers. At startups, it becomes a really interesting trade-off of, should we be allocating time to building up sort of a brand in the name and getting ourselves, you know, getting information out there? Versus, should we be just focusing on the work at hand? And most organizations that I've worked with have bias towards certainly less sharing than thoughtbot, but just not much at all. Often, I'll see folks like, "Hey, maybe we should start a blog." And I'm like, "Okay, let's just talk about how much effort that [laughs] actually looks like." And I wonder if I'm actually overcorrected on that, having seen, you know, the high bar that thoughtbot set. CHAD: I think it's a struggle. This is one of my [laughs] hot topics or spiels that I can go on. You know, in most other companies, that kind of thing only helps...it only helps in hiring or the people being fulfilled in the work. But at most companies, your product is not about that; that's not what your business is. So, having a more fulfilled engineering team who is easier to hire—don't get me wrong, there are advantages to that—but it doesn't also help with your sales. CHRIS: Yes. CHAD: And at thoughtbot, our business is totally aligned with the people and what we do as designers and developers. And so, when we improve one, we improve the other, and that's why we can make it work. That is marketing for the product that we actually sell, and that's not the case at a SaaS software company. CHRIS: Yes, yeah, definitely. That resonates strongly. I will say, though, on the hiring side, hiring at thoughtbot was always...there was...I won't say a cheat code, but just if someone were to come into the hiring process and they're like, "Oh yeah, I've read the blog. I listen to the podcast," this and that, immediately, you were able to skip so much further into the conversation and be like, "Okay, what do you agree with? What do you disagree with? Like, let's talk." But there's so much. Because thoughtbot put so much out there, it was easy to say, like, "Hey, this is who we are. Do you like that? Is that your vibe?" Whereas most engineering organizations don't have that. And so, you have to try and, like, build that in the context of, you know, a couple of hour conversations in an interview, and it's just so much harder to do. So, again, I've leaned in the direction of not going anywhere near thoughtbot's level of sharing. But the downside when you are hiring, you're like, oh, this is going to be trickier. CHAD: Yeah. One of the moments that stands out in my mind, and maybe I've told this story before on the podcast, but I'll tell it again. When we opened the New York studio, it was really fast growing and was doing a lot of hiring. And one of the people who had just joined the company a couple of weeks before was doing an interview and rejected the person was able to write an articulate reason why. But it all boiled down to this person is, you know, not a fit for thoughtbot. Based on what they were able to describe, I felt very confident with the ability or with the fact that they were able to make that call, even though they had been here only a couple of weeks, because they joined knowing who we were, and what we stand for, and what our culture and our values are, and the way that we do things, and all that kind of thing. And so, yeah, that's definitely a huge benefit to us. VICTORIA: I've certainly enjoyed that as well, as someone who hires developers here and also in meeting new companies and organizations when they already know thoughtbot. That's really nice to have that reputation there, coming from my background—some really more scrappier startup kind of consulting agencies. But, you know, I wanted to talk a little bit more about your podcasting experience while you're here. So, I know you were on both The Bike Shed and Giant Robots. Which is the better podcast? [laughter] So, what's your...do you have, like, a favorite episode or favorite moment, or maybe, like, a little anecdote you can share from hosting? CHRIS: Well, I guess there's, like, three different eras for me in the podcasting. So, there's Giant Robots with Ben talking more about business stuff, and I think that was really useful. I think it was more of a forcing function on me because I sort of...Both Ben and I were coming on; we were giving honest, transparent summaries of our, like, MRR and stats and how things were growing, and acted as sort of an accountability backstop, which was super useful but also just kind of nerve-wracking. Then, when I joined the Bike Shed, the interviewing sequence that I did each week was just a new person that I was chatting with. And I sort of had to ramp them up on, hey, here's a quick summary on how to think about podcasting. Don't worry, it'll be great. Everybody have fun. But I was finding each of the guests. I was sort of finding a topic to talk about with them. So, that ended up being a lot more work. And then, the last three years chatting with Steph that was by far my favorite. There was just such a natural back-and-forth. It really was just capturing the conversations of two developers at thoughtbot and the questions we would ask each other as we hit something complicated in a piece of code or, "Oh, I saw this, you know, article about a new open-source repository. What do you think about that?" It was so much easier, so much more natural, and, frankly, a lot of fun to do that. And, two, I actually do have an answer to the favorite podcast episode, which is the first episode that Steph was ever on. It was before she actually joined as a co-host. But it was called “What I Believe About Software.” And it was just this really great, deep conversation about how we think about software. And a lot of it is very much, like, thoughtbot ideals, I would say. But yeah, Steph came in and just brought the heat in that first episode, and I remember just how enjoyable that experience was. And I was like, all right, let's see if I can get her to hang out a little bit more, and, thankfully, she was happy to join. WILL: What was your favorite position, I guess you can call it? Because you say you like the mixture of business and, you know, development. So, you've been in leadership as development director, CTO. You've been a web developer. You've been over content, like, with Upcase. What was your favorite position [inaudible 16:43] you were doing, and why was it your favorite? CHRIS: The development director role feels like sort of a cheating answer, but I think that would be my answer because it contained a handful of things within it. Like, as development director, I was still working on client projects three days a week. And then, one day a week was sort of allocated to the manager-type tasks, or having one-on-ones with my team sort of helping to think about strategy and whatnot. And then, ideally, still getting some amount of investment time, although the relative amounts of those always flexed a little bit. Because that one sort of encompassed different facets, I think that's going to be my answer. And I think, like, some of what drew me to consulting in the first place and kept me in that line of work for seven years was the variety, you know, different clients, as well as, even within thoughtbot, different modes of working in podcasts or video. Or there was a bootcamp that I taught, a session of Metis, which that was a whole other experience. And so, getting that variety was really interesting. And I think as sort of a tricky answer to your question, the development director role as a singular thing contained a multitude, and so I think that was the one that would stand out to me. It's also the most, you know, the one that I ended on, so [laughs] it might just be recency bias, but yeah. VICTORIA: Oh, I love that. Is there anything else that you would like to promote on the podcast today? CHRIS: No, although as you ask the question, I feel like I should, I don't know, make some things to promote, get back into some, I don't know, content generation or something like that. But for now, no. I'm, you know, diving into the startup life, and it's a wonderful and engrossing way to do work, but it does definitely take up a lot of my headspace. So, it's an interesting trade-off. But right now, I don't know; if folks are online and they want to say hi, most of my contact information is readily available. So, I would love to say hi to folks, anyone that listened in the past or, you know, has any thoughts in the now. Would love to connect with folks. But otherwise, yeah, thank you so much for having me on. CHAD: In 2017, I took over from Ben as solo host of the show but was joined by Lindsey Christainson as cohost in 2019. After some time away from thoughtbot, Lindsey is back with us and we sat down to catch up with her. VICTORIA: Why don't you tell me about your current role with thoughtbot? LINDSEY: I am currently supporting marketing and business development at thoughtbot, as well as working as a marketing consultant for thoughtbot clients. VICTORIA: Great. And I understand that you had worked with thoughtbot many years ago, and that's when you also came on as a co-host of Giant Robots. Is that right? LINDSEY: Yeah, a couple of years ago. I left thoughtbot in spring of 2021. And I forget how long my stint was as a co-host of Giant Robots, but over a year, maybe a year and a half, two years? CHAD: Yeah, I think that's right. I think you started in 2019. LINDSEY: Yeah. Yeah, that sounds right. And Chad and I were co-hosts, I think, similar to the setup today in which sometimes we hosted together, and sometimes we were conducting interviews separately. CHAD: And then we sort of introduced a second season, where we followed along with a batch of companies over the course of the entire season. And that was fun, and we learned a lot. And it was nice to have consistent guests. LINDSEY: Yeah, that was a lot of fun. I really liked that format. I don't know; they almost were, like, more than guests at that point. They were just like other co-hosts [laughs] that we could rely on week in, week out to check in with them as they're working on early-stage companies. So, every time we checked in with them, they usually had some new, exciting developments. WILL: I really like that idea. How did y'all come up with that? CHAD: I'm not sure. I think a few years before I had taken over hosting of the show, and I forget...my memory maybe is that I went to Lindsey and said, "You know, let's do something different." But I'm not sure. Does that match your memory, Lindsey? LINDSEY: Yeah, I think there were two main drivers; one was I think you were feeling like you were having similar conversations in the interviews every time. Like, you couldn't get to a certain depth because every time you were interviewing someone, you were doing, like, the, "Well, tell me your founding story." And, you know, how did you raise funding? It kind of got a little bit repetitive. And then, on the side, the few we had done together, I think we both really enjoyed. So, we were thinking, like, what's the format in which the two of us could co-host together more regularly? Because I'm a pleasure to talk to [laughter]. I think you were like, I need to talk to Lindsey more. [inaudible 3:13] VICTORIA: What is your hosting style? How would you describe your approach to hosting a podcast? LINDSEY: I mean, obviously, it's a podcast about products and business. I think as a marketer, I am, you know, drawn a lot to the marketing side, so tending to ask questions around go-to-market audience, users. That's always just, like, a particular interest of mine. But then also, like, the feelings. I love asking about the feelings of things, you know, how did it feel when you started? How did it feel when you made this tough decision? So, that's another thing I think I noticed in my interviews is asking about some of the emotions behind business decisions. VICTORIA: And I like hearing about how people felt at the time and then how they felt afterwards [laughs]. And, like, how people around them supported each other and that type of thing. That's really fun. I'm curious, too, from your marketing background and having to do with podcasts like; some founders, I think, get the advice to just start a podcast to start building a community. But I'm curious on your thoughts about, like, how does podcasting really play into, like, business and marketing development for products? LINDSEY: Oh yeah. It's become definitely, like, a standard channel in B2B these days. I feel like that it's pretty typical for a company to have a podcast as one way that they engage their audience and their users. In marketing, you're really vying for people's attention, and people's attention span is getting shorter and shorter. So, like, if you have an ad or a blog, you're getting, like, seconds, maybe minutes of someone's attention. And whereas something like a podcast offers a unique channel to have someone's undivided attention for, you know, 30 minutes, an hour, and if you're lucky, you know, checking back in week over week. So, it became a really popular method. That said, I think you're probably also seeing the market get saturated [laughs] with podcasts now, so some diminishing returns. And, you know, as always, kind of looking for, you know, what's the next way? What's the next thing that people are interested in in ways to capture their attention? CHAD: What is the next thing? LINDSEY: I don't know, back to micro-content? TikTok videos -- CHAD: Yeah, I was going to say TikTok, yeah. LINDSEY: Yeah, you know, 10-30 seconds, what can you communicate? VICTORIA: I see people live streaming on Twitch a lot for coding and developer products. LINDSEY: Yeah, I think we've seen some of that, too. We've been experimenting more at thoughtbot with live streaming as well. It's another interesting mechanism. But yeah, I don't know, it's interesting. It's another form of, like, community and how people engage with their communities. So, it's always evolving. It's always evolving, and sometimes it's not. Sometimes, people just do want to get in a room together, too, which is always interesting. WILL: What has been, in your experience, the good the bad? Like, how do you feel about the way that it has shifted? Because I think you started in, like, 2000, like, kind of earlier 2000, 2005, something around there. And it was totally different than now like you're saying. Because I feel like, you know, Channel 5 30-second ad, you know, with some of the marketing depending on what you're doing, to now to where you're, like, you're paying influencers to advertise your product, or you're doing an ad. Or it's more social media-driven and tech-driven. What has been your opinion and feelings on the way that it has grown and evolved? LINDSEY: Marketing, in general, yeah, I graduated college in 2005 and started my marketing career. And yeah, you could, like, actually get people to click on banner ads back then, which was pretty [inaudible 07:14] [laughs]. WILL: I forgot about banner ads [laughs]. LINDSEY: I don't know, yeah. I don't know. In order for myself to not just get too frustrated, I think I've got to, like, view it as a game kind of. What new things are we going to try? You know, what do we see work? But it can really depend. And I've always been in B2B side of things. And consumer, I'm sure, has its own kind of evolution around how people engage and how they consume content and byproducts. But in B2B, you know, it can really depend on industry too. You know, I'm working with a client right now in the senior living space, and they're really big in in-person conferences. So, that's how people consume, get a lot of their information and, make connections, and learn about new products. So, it's been interesting to work in an industry that what might be considered, like, a little bit more old-school channels are still effective. And then just thinking about how you weave in the new channels with the existing ones without ignoring them. They might get information in conferences, but they're still a modern human who will then, you know, search online to learn more, for example. VICTORIA: It reminds me of a phrase I like to say, which is that, like, technology never dies; you just have more of it. There's just more different options and more different ways to do things. And some people are always, you know, sometimes you have to be flexible and do everything. CHAD: So, tell us more about what you did in between...after you left thoughtbot, what did you do? LINDSEY: I was heading up B2B marketing for a company called Flywire, which is headquartered in Boston but is a global company now. And they were just kind of starting their B2B business unit, which, as I mentioned, B2B is my personal specialty. I had been connected to their CMO through the Boston startup community. And yeah, I was helping them kind of launch their go-to-market for B2B. The industries they were in before...they got their start in higher education and then expanded in healthcare and found a niche in luxury travel, and then we were figuring out the B2B piece. But yeah, I was there for about a year and a half. They actually went public the second week I was there, which was an interesting [laughs] experience. I knew they were, like, on that journey, but it was kind of funny to be there the second week, and people were, like, "Congrats." And I was like, "Well, I definitely didn't have anything to do with it because I just finished my onboarding, but thank you," [laughs]. CHAD: One of the things that really impressed me when you joined thoughtbot was the way in which you learned about who we were and really internalized that in a way where you were then able to pretty meaningfully understand our market, our positioning in the market, and come up with new strategies for us. I assume that's something you're good at in general [laughs]. How do you approach it? How did you approach it when you joined Flywire, for example? And how was it the same or different than how you approached thoughtbot? LINDSEY: Ooh, yeah, that's a good question. And I appreciate that comment because it's difficult. But I think, yeah, with any new organization that I'm joining, you know, I think starting out with your kind of mini-listening tour of your key stakeholders across, you know, the different departmental focuses to get a sense of, what are the challenges? What are the opportunities? It's actually like, you know, it's the SWOT analysis, kind of trying to fill in your own mind map of a SWOT analysis of where the company is. What are the major hurdles you're facing? Where are people trying to go? What have they tried that's worked? What have they tried that's failed? But then, like, I think for the culture component, I think a part of that maybe is, like, feel, and maybe something that I do have a knack for. Again, maybe this is, like, you know, emotional intelligence quotient, where it's like, you know, but it's the company, you know, who is this company? What is important to them? How do they work and go about things? I know thoughtbot is certainly very unique, I think, in that arena in terms of being, like, a really value-driven company, and one where especially, like, marketing and business work is, like, distributed across teams in a really interesting way. You know, I'm sure the fact that it fascinated me and was something I could get passionate and get behind was something that also helped me understand it quickly. CHAD: I was excited that...or it was sort of a coincidence because I had reached out to you and without realizing that you had left Flywire. And Kelly, who had been doing a combined sales and marketing role, was going on parental leave. And so, it was fortuitous [laughs] that you were able to come back and help us and provide coverage, like, Kelly was out. LINDSEY: Yeah, it definitely felt like stars aligned moment, which, you know, I'm pretty woo-woo, so I believe in [laughter]...I believe in that kind of thing. You know, yeah, it was wild. It really did feel like your email came out of nowhere. And, you know, I mentioned it, obviously, to my partner and my friends. And they were like, "Oh, he definitely knows, like, that you left your last company." And I'm like, "I actually don't think he does [laughter]. I actually don't think he does." Yeah, and then we started chatting about me coming back to help. And it was great. thoughtbot makes it hard to work anywhere else [laughs]. So, I was happy to come back. I missed the team. CHAD: And one of the exciting things, and you've mentioned it, is you're not just doing marketing for thoughtbot now. We have started to offer your services to our clients. LINDSEY: Yeah, I'm super excited about this. And it's something I'd started thinking about. I had decided to take some time off between Flywire and my next thing and had started thinking about doing marketing, consulting. And as I'm doing that, I'm thinking a lot about how thoughtbot does consulting and, you know, wanting to emulate something like that. So, I started back up at thoughtbot. That wasn't part of the plan. I was just going to, you know, fill in for Kelly and help with marketing things. But then, you know, a good opportunity arose to work on a client, and I was really excited. When, you know, Chad, you and I chatted through it, we came to the conclusion that this was something worth exploring under the, you know, thoughtbot umbrella. And it's been a really great experience so far. And we now have brought on another client now. And if you're listening and need early-stage B2B marketing support, reach out to lindsey@thoughtbot.com. CHAD: Definitely. And Lindsey is pretty good, so you're going to like it [laughs]. LINDSEY: Yeah, you're going to like the way you look. WILL: Yeah, definitely. Because I can even feel your presence here, you know, coming back. Because even like, you know, the market where it's at now and some of the suggestions that, you know, you've been helping us. For example, like, I do a lot of React Native, and you're like, "Hey, you know, blog posts have done a lot of traction, you know, let's get some more blog posts out in the market to help with the traffic and everything." So, the question I have with that is, like, thank you for even suggesting that because it's, like, those little things that you don't even think about. It's like, oh yeah, blog posts, that's an easy transition to help the market, clients, things like that. But with the market the way it is, what has been your experience working during this time with the market? I don't know if you want to call it struggling, but whatever you want to call it that, it's doing [laughs]. LINDSEY: Yeah, I mean, the economy is difficult now. We also went through a really tough spot when I was here last time. During COVID, you know, we faced a major company challenge. And, I mean, I'll let Chad speak to it, but I would imagine it's probably one of the bigger, like, economic inflection points that you faced. Would you say that? CHAD: Yeah, definitely. The thing about it that made it worse was how quickly it happened. You know, it was something that you didn't see coming, and then, you know, about 40% of our business went away in a single month. That's the kind of thing that was a real shock to the system. I think the thing that made it difficult, too, was then the aspects of COVID, where we were no longer able to go into our studios. We were all working remotely. We were isolated from each other. And so, that made executing on what needed to be done in order to make the company survive additionally challenging. LINDSEY: Yeah, so I think, like, going through that experience, also, and seeing how the team and the leadership team rallied together to get through it. And then, you know, ultimately, I think 2021 and 2022 have, like, really good years. That was a really positive experience. And something I'll definitely take with me for a while is just, like, keeping a cool head and just knowing you have, like, really smart, talented folks with you working on it and that you can get through it. And just, like, doing some, I mean, we relied on what we did best, which was, like, design thinking, using design exercise to think about, like, how we might re-organize the company, or what other services we might try launching, or how might we re-package, you know, larger services into smaller more palatable services when people have, like, kind of tighter purse strings. So, that was, like, a great educational experience, and I think something we just continue to do now: be open to change, be open to changing how we package services, what clients we go after, and coming at it with, like, an agile, experimental mindset and try to find out what works. VICTORIA: I really appreciate that. And it aligns now with the new service we've developed around you and the marketing that you provide. And I'm curious because I've had founders come up to me who say they need help with marketing or they need to, like, figure out their marketing plans. So, say you've met a founder who has this question, like, what questions do you ask them to kind of narrow down what it is they really need and really want to get out of a marketing plan? LINDSEY: I've been thinking about this a lot recently. And, like, obviously, I see other marketing leaders in the market. Marketers like to talk about what they do on LinkedIn [laughs], so I get to...I read a lot about different people's approaches to this. And some people kind of go in and are like, okay, this is what you need. This is how we're going to do it, and they start executing on it. And I really do take a very collaborative approach with founders. I think they're, especially in early stage, they're your most important asset in a way, and a lot of their intuition around the market and the business, you know, it's gotten them to where they're at. And so, I think starting from the point of, like, taking what they view as priorities or challenges, and then helping them better explore them or understand them with my own marketing experience and expertise, to narrow in on work that's going to be valuable for them, is kind of my starting point with early-stage companies. Again, a little bit of that, like, listening tour kind of attitude of, like, what do you think is important? And there's probably data points behind that. And then helping you as a company frame that into, you know, what's going to be the most valuable? Like, is it an awareness campaign, or a lead-generating campaign, or a content strategy? Do we actually need to take a look at the data you have and spend a little bit of effort cleaning that up so that we understand what we're working with better? Is it sales enablement? You know, do you have existing salespeople, but maybe they're struggling or don't have unified tools and messaging that they're using? That's how I kind of first approach it with the founder, very much kind of in lockstep. VICTORIA: I appreciate that little preview of what your services would be like. And I always really appreciate when you help me with my marketing plans around our Mission Control team and platform engineering and how to really refine our message and make sure it reaches the right people. LINDSEY: Yeah, I think another thing I used at thoughtbot in the previous time that I've taken with me to Flywire and now with clients is, like, the idea of, like, mini-briefs and working on them with the key stakeholder, whether that's you the head of, you know, a business unit or a founder, which is, like, let's just take the, however long, 30 minutes to talk about, who's the audience? What's our goal? You know, what are the elements that might help us achieve that goal? What are some of the metrics that we might use to measure whether or not we were successful in reaching that goal? And it sounds really basic, but a lot of people can skip it. And I think then there's confusion around who you are targeting, or people have different ideas in mind of, like, what you are actually trying to achieve. VICTORIA: I like that. And to pivot a little bit, I wonder if you have any thoughts on our podcast here at Giant Robots. What do you think the benefit of it is to thoughtbot, actually? LINDSEY: I think it's been a brand builder and a way to, again, like, another channel to engage with our audience. It's been so long-standing now, you know. I talked about how most companies have a podcast now. But this is what? The 500th Episode, right? Over years and years, which is really impressive that it's been going that long. So, it's a way to bring the brand to life. I think one of my first insights coming into the thoughtbot team is, you know, as a consulting organization, when I interviewed clients about what they loved about thoughtbot, I thought they were going to say that they ended up with amazing products. And they did. They did say that. They said they ended up with amazing products. But I said, "You know, what was the biggest benefit, or what stood out to you the most?" And they all said it was the people, you know, they loved the people. They loved learning from thoughtboters. They were, like, you know, teachers and mentors, and so smart, but also, like, very kind and helpful. So, when you think about it like that, podcasts or videos and ways you're able to, like, better see and hear and feel the person on the other side is a really great way of, you know, continuing to make that connection with folks. VICTORIA: I love that answer. I wish we had little heart emojis we could share, like in Google Meets with Zencastr. So, what do you think...Maybe this is a question for everyone on here, too, that we're asking is, like, where do you think we should go with the podcast? What should we change? What should we think about for future episodes? LINDSEY: I think you should ask the listeners if possible. We tried, in the past, surveying. And it's hard because you don't have, like, necessarily an email list of listeners. But there does tend to be some overlap of, like, our newsletter subscribers with podcast listeners. So yeah, I'd go straight to the audience and just learn more about...ask them what they care about and what they want to learn. Because at the end of the day, it's really for them, providing value for them and something they want to come back to listen to week after week. CHAD: Oh, when we've done the surveys in the past, we've had very few people [laughs] respond. So, you can always email us at hosts@giantrobots.fm if you have feedback on the show, questions for people, questions for the hosts, or opinions on, you know, who would make a great guest or a direction we should take the show. All that is super valuable. And we definitely would take it to heart. VICTORIA: Yes, please send me your feedback. I will read your emails and incorporate it into the show. So, it'd be great. I wonder, Lindsey, do you have any questions for us? LINDSEY: How do y'all like hosting the podcast? [laughs] How's it going? WILL: I feel like I'm starting to find my style and the way that it works best for me, so that's exciting. I do want to engage more with the listener. So, that's one thing that I'm trying to brainstorm on what's the best way to do that. Also, you know, inviting just different types of guests, trying to think through what's some different type, a different angle that we can invite for the podcast? But as far as how do I like doing the podcast, I really enjoy it. It's pushed me out of my comfort zone. But it was a good thing for me. So, I'm really enjoying it. LINDSEY: How long have you been doing it, Will? WILL: A little over a year. So, I think I started after I went on parental leave with my youngest child. And then when I came back, I took a couple of weeks, and then I started. So yeah, about a year, a little over a year. LINDSEY: That's fun. What's your favorite part about doing it? WILL: I love talking to the guests. And I love learning, like, people's stories. And so, that has been the most exciting thing for me, like, because especially with the founders, like, it's not easy to be a founder. But people they go all out, and they make a difference. And even through the heartache, and the pain, and just all different levels, but they're willing to endure it because they believe in their product. They believe it's going to make a difference. So, I think the stories, the stories, and the people, meeting new people, and hearing their stories is what I love. VICTORIA: And I'm the same as Will. I've been on the show for about a year now. And the first episode I recorded with Chad, I think afterwards, he said, "Oh, you didn't ask any questions [laughs]. Like, you were too quiet." But then I think I got a hang of it. And now I really like making people feel comfortable and opening up about their story and hearing, yeah, like the emotions and what it really felt like to go through that. Because, you know, if it's interesting for me to hear that, then I think that our audience will also appreciate it and to feel like you're not alone, right? To build that community and hear those same stories and people going through similar things. Yeah, some of the guests that we've had on have just been really incredible. And they are people who I admire in the industry, and to have them on the show and to be a part of it has been really special. LINDSEY: Yeah, that's cool. That reminds me another kind of underlying thing I love about the podcast and the interviewing. It's also low-key, like, market research [laughs], which is interesting, like, better understanding the types of people we provide services to and their kind of drivers and challenges. There's, like, an interesting element there. And yeah, at the end of the day, you get really interested and into it, and you're just, like, having a conversation with them, probably makes for the best kind of episode. VICTORIA: Right. And then afterwards, you have to, like, pace around the room to, like, decompress [laughs] because you're operating at, like, such a level, at least, that happens to me; I don't know about anybody else. LINDSEY: No, totally. I would also...if we had, like, an episode scheduled and then it got, like, rescheduled at the last second, I would find I had all this, like, pent-up energy that my body was, like, preparing me to, like, go into the interview. VICTORIA: Yeah, sometimes I have to get hyped. Like, you got to do some movement right before because you got to get into the zone. But I'm curious, Chad, this is, you know, you've been a host for a number of years now, too. Like, how do you feel about the podcast? Do you still like hosting it? CHAD: No [laughs]. I'm kidding. I have taken a little bit of a break recently from the ongoing continuous hosting because I was really busy. And it was hard to create the time and dedicate the time to it. But I really like hosting the show. I love talking to different people and learning about their stories. I also really like the episodes where it's able to be more of a conversation with people, and I get a lot of enjoyment out of that. LINDSEY: We've seen, also, some trends in, like, the episodes where Chad will talk about, like, the business of thoughtbot perform well, too. Because I know there's, like, a lot of folks, who listen who also own agencies or consultancies and always appreciate Chad's transparency around how we run thoughtbot. VICTORIA: That's interesting. And yeah, I think one of the ways that we've been experimenting with getting the episodes to be more conversational is to have more than one host in the episode. So, Chad or Lindsey, if you're ever wanting to rejoin an episode or invite a founder on and be one of the co-hosts, you're always welcome. LINDSEY: I'm always down. I love talking. That actually...that does remind me we were thinking...we've been doing live streams that cover thoughtbot's new startup incubator. So, we have the second session currently in progress. But repurposing some of those live streams into, like, mini–Giant Robots episodes. So, that may happen soon. We may do a little bit of that and then give some insight into what it's like week in, week out for founders going through the startup incubator. It's super, super interesting if you're a startup nerd like me. VICTORIA: That would be great, yeah. We did an episode with Agnes for the first incubator round, and I think that was really interesting. And something we've been experimenting with a little bit is having that diverse group of founders. So, there's founders from companies who the company has managed to survive and excel, and they've been around for ten years or so. Then there's other people who are just starting out. And, like, hearing those stories, too, and, like, the things they're thinking about and what challenges they're facing has been super interesting. Anything else you'd like to promote Lindsey? LINDSEY: Hire me for all your marketing consulting needs. CHAD: It was great to catch up with everyone in celebration of our 500th episode. Thank you to Ben, Chris, and Lindsey. But most of all, that you to you. We make the show, but you make the show possible. You can subscribe to the show and find notes, along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. This podcast is brought to you by thoughtbot, and produced and edited by Mandy Moore. Thanks for listening, and here’s to the next 500 episodes! AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us.More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Support Giant Robots Smashing Into Other Giant Robots

This episode introduces the second participants of the season's thoughtbot's Incubator Program, Mike Rosenthal and Chris Cerrito. Mike has a background in music industry marketing, and Chris is a maker and tinkerer with experience in exhibit development. They're developing a product combining physical objects with digital content, starting with music. Their concept involves creating physical items like wooden mixtapes with NFC chips linking to digital playlists. This blend of physical and digital aims to revive the tangible aspects of fan engagement in a digital era. Their project, named Goodz, is the first pure consumer product in the Incubator program, adding complexities like supply chain and manufacturing considerations. The team is conducting user interviews to validate market interest and refine their messaging. They aim to have a functioning physical product and a supporting digital backend by the end of the program. Challenges include defining the target market and understanding how to attract customers to a new product type. The thoughtbot team is excited about the project due to its fun nature and technical aspects, offering a fresh perspective compared to problem-focused startups. The conversation also explores the broader implications of bridging the digital and physical worlds in fan engagement, with the potential to collect valuable data for artists and create lasting, meaningful connections for fans. Follow Josh Herzig-Marx on LinkedIn or X. Visit his website at joshua.herzig-marx.com. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: LINDSEY: All right. I'm going to kick us off here. Thanks, everyone, for tuning in. We're doing our first update with two founders that are now going through the Startup incubator at thoughtbot. thoughtbot, if you're not familiar, product design and development consultancy. We'll help you on your product and make your team a success. One of the very fun ways we do that is through the startup thoughtbot incubator, which is an eight-week program. So, with us today, I myself am Lindsey Christensen, marketing for thoughtbot. We also have Jordyn Bonds, who is our Director of Product Strategy and runs the thoughtbot incubator. And then, as I mentioned, we've got two new founders who are going to tell us a little bit about themselves and what they're working on. Mike Rosenthal, let's kick off with you. Can you tell us a little bit about maybe your background and what brings you to present day? MIKE: Sure. First of, thanks for having us. It's been a lot of fun doing this over the last [inaudible 01:03]; it's only two weeks, two and a half weeks, something like that. It feels like a lot more. I come from a music industry background, so worked in sort of marketing and strategy for artists for a long time; worked with a band called OK Go back, sort of starting in 2009 or so. I did a lot of early kind of viral music video stuff. And we were sort of early to the idea of sort of leveraging fan engagement and revenue, honestly, kind of beyond sort of just selling their music and touring, so sort of exploring other ways that artists can make money and connect with their fans and was with those guys for five years. And then, I went on and worked at an artist management company in Brooklyn called Mick Management and ran the marketing department there, so doing similar type of work but for a roster of 2025 major label bands. And so, really got to see fan engagement on all different levels, from really large bands down to baby bands who were just getting started. And then, yeah, started my first startup in 2018, so doing sort of fan engagement work, and NFTs, and blockchain-type stuff working with bands, but then also sports and entertainment properties. Yeah, that kind of brings me here. So, always been sort of on the music side of things, which ties into a lot of what Chris and I are working on now, but more generally, sort of fan engagement and how to, you know, drive revenue and engagement for artists and deliver value for fans. LINDSEY: Very interesting. All right, Chris, going to head over to you. Chris Cerrito, can you tell us a bit about your background? And it sounds like yours and Mike's paths; this isn't the first time you've crossed. CHRIS: No. Mike and I have been working together since 2007, I believe. Yeah, that's a great place to start. I've always been kind of a maker and a tinkerer, always been interested in art materials, how things are put together. And that kind of culminated at grad school, where Mike and I met at NYU, where we both studied physical computing and human-computer interaction, making weird things that kind of changed the way that people interact and play with technology in their day-to-day lives. I think the first project he and I worked on together was a solar robotic band that we played with light in front of a bunch of people. It was very wonderful and confusing at the same time. After grad school, I was lucky enough to become a resident artist and then an exhibit developer at a museum in San Francisco called the Exploratorium, which is a museum of science, art, and human perception. I spent ten years there working on exhibits, teaching people things ranging from, let's see; I built a dueling water fountain to teach visitors and users about the prisoner's dilemma. I built a photo booth that used computer vision to teach people about the microbiome that lives on their face, like, just all kinds of weird things like that that fuse the digital and the physical worlds. I loved my time there. And then kind of COVID hit, and I realized that everything I had been working on for ten years was locked up in a museum that I no longer had access to. And it really gave me a desire to kind of bring my ideas into the physical world. I wanted to make things that people interact with and use in their lives on a day-to-day basis. And I would say that's really what brought me here to this point. LINDSEY: Very cool. Very interesting backgrounds, in my opinion. What is the new idea? What is the thing that you're bringing into the incubator? Mike, I'll start with you. Tell us a bit about what you're working on. MIKE: Chris and I are working on physical objects that connect to digital content is sort of the broadest way that I could describe it. I think, you know, as Chris kind of mentioned, you know, we've both been working on sort of physical things that have interactivity for a lot of our careers. I think we both come from an era of a lot more physical objects in your life, whether that's, you know, VHS cassettes at your parent's house growing up, or records and tape cassettes, and just sort of physical things that remind you of the things that you love. And I think that, you know, cell phones are great, and the sort of the smartphone era is amazing and having, you know, every single song, and movie, and television show and podcasts, et cetera, in a black box in my pocket is great. But I think we've sort of gotten to a point where it's more of an organizational problem now than anything else. And we sort of forget the actual things that we love in this world. And so, we're working on basically making physical objects to tie to digital content, and we're starting with music. And that's what we've been working on at thoughtbot is sort of how we can create physical things that basically you can tap, and that will take you to streaming content. One of the first things we're working on literally looks like sort of a little mixtape on a piece of wood, and you can just load that up with any sort of playlist that you might have on Spotify, or Apple Music, or YouTube, or whatever, and tap it, and it will take you there. And so, it's just sort of that idea of like, oh, we used to be able to sort of flip through a friend's music collection and judge them ruthlessly, or become even better friends with them based on kind of what you saw there. And we think that the time is ripe for, I don't know, a blend of that nostalgia with actual sort of, like, real-world utility that people could be into this right now. Chris, what am I missing there? CHRIS: I'd say just to expand on that a little bit, it's, you know, we spend so much time in the digital world, but we still exist in the physical. And a lot of the things, like, you might spend a really long time editing a photo for your parents or making a playlist for a friend, and there's, like, a value there that might not translate because it's digital. It's ephemeral. And I think tying these digital assets to a physical thing makes them special. It gives them, like, a permanent place in your life, something to respect, to hold on to, and maybe even pass down at some point. LINDSEY: Yeah, and I think before we logged on, we actually had Jordyn and Mike grabbing cassette tapes from the room there and to show us -- MIKE: [inaudible 06:49] LINDSEY: What [laughs] was some of their collection and to prove some of the power of these physical –- MIKE: Nothing, like, just old mixtapes. LINDSEY: Mementos. MIKE: Yeah. We were just talking about this on our sync with the thoughtbot crew. They're, like, there's sort of two levels of nostalgia. There's nostalgia for people like us who, yeah, [crosstalk 07:09] mixtapes, right? For people who actually grew up with this stuff and still have it lying around or don't but, like, look at something like that that gives you, like, instant flashbacks, right? You're like, oh my God, I remember scrolling on that little j-card or, like, getting a mixtape for my first, you know, boyfriend or girlfriend, and having it just mean everything. So, there's people for whom that was a thing. And there's, you know, generations of people for whom that is, like, their only connection to that is, you know, Stranger Things or, like, you know, the mixtape exists in pop culture as a reference. So, there's still, like, a very strong attachment there, but it's not a personal one, right? It's a cultural one. But I think everybody has that connection. So, that's kind of why we're starting with the mixtape, just because I think everyone can kind of relate to that in some way. LINDSEY: Yeah, no, yeah. When I hear mixtape, it goes immediately to crushes. You make a mixtape for your crush. CHRIS: Exactly. LINDSEY: It's a huge, powerful market, powerful. MIKE: Oh my God, so powerful. I mean, yeah, I don't know anybody -- LINDSEY: What's more motivating? MIKE: [laughs] Yeah, exactly. CHRIS: Or even just I have a really good friend who I don't get to see as often as I'd like. And he and I are constantly sending each other, you know, Spotify links and text messages. And it's great. I love that interaction. But at the same time, you know, I might forget to add that to a playlist, and then it's kind of lost. If I had taken the time to make something and send it to him physically or vice versa, it just becomes so much more special and so much more real. MIKE: Yeah. I mean, honestly, I first made these...I mean, we can go to this origin if we want. But, like, I literally just went on moo.com, right? The business card company. And they let you upload, you know, 50 different images, and they'll send you all of those as business cards. And so, I literally went on and just made business cards of all the album covers of, like, albums that I loved growing up, right? And their cheapest is this little piece of cardboard. But I had 50 of these, and I'd put them all out on my coffee table, just as something I wanted to have around. And people kept coming, you know, friends would come over, and you would just have these conversations that I haven't had in 10 or 15 years, right? Because no one's going to come to my house and pick up my phone and look at my Spotify collection. But if these things are all just sitting out, they're like, "Oh shit, you're into that? Like, I haven't thought about that album in 15 years." Or like, "Oh, I didn't know you were into that. I'm, like, a crazy super fan of that artist as well." And all of a sudden, we're having these conversations that we just weren't having. Yeah, there's something there where it's all been nostalgia coupled with the kind of prompting of conversation and connection that we've kind of lost, I think. CHRIS: And I think just to clarify a little bit on what Mike's saying, is, you know, this mixtape will be our first product launch, and then we're hoping to move into collectibles for artists and labels. So, shortly after we launch this tape, we're hoping to launch some kind of pilot with a label where you will be able to buy a version of this for your favorite music artist at a merch table in a concert, possibly online. Our dream is to have these sitting there on the table with T-shirts, and records, and other things that artists sell so you can express for the artists that you love. This is a way of expressing your fandom. LINDSEY: Jordyn, heading over to you, this feels like maybe the first consumer product that has gone through the incubator, would you say? Or how do you think about it? JORDYN: Yeah, if you're a consumer -- LINDSEY: Or is it different than other types of products? JORDYN: Yeah, the first incubator project we did with Senga was, I think, what you would call prosumer. So, it was sort of a consumer thing but directed at folks who had kind of freelancing in sort of a business context. It's got a lot of dynamics of the consumer. But this one, for sure, is the first pure consumer play. Though now that I'm thinking about it, you know, AvidFirst had some consumer elements to it, but it was, you know, it was, like, more complex tech [laughs] [inaudible 10:46] totally different thing -- LINDSEY: But definitely the first of the physical, physical [inaudible 10:52] JORDYN: Oh, sure, the first of the physical thing. Right. Absolutely. LINDSEY: Does that change any of, like, the approach of the programming, or it's kind of -- JORDYN: I mean, no, not fundamentally, though it does add this layer of operations that you don't have with a pure software play. So, we have to be, there is a thing that needs to get shipped to people in the world, and that takes timelines, and it takes -- LINDSEY: Supply chain. JORDYN: Yeah, exactly. And Chris is doing most of that stuff. I don't want to, you know, this is not, like, the main focus of our team necessarily, but it intersects, right? So, this isn't the first one of these types of products I've worked on personally in my career. But there's something, like, really, for me, very fulfilling about, like, there's software. There's a big component of software. There's also this physical object that needs to exist in the world. And partly, what's so compelling about Goodz is that it gives you the promise of a physical, like, the sort of good aspects of a physical product, a thing you can hold in your hand and look at and really connect with in that physical way. But it has this dynamic digital, like, essential quality as well. So, it's very compelling as a product because it sort of marries the things that we like about both the physical world and the digital world, which is partly why the team was really excited about working on it [laughs]. LINDSEY: Well, that was going to be my next question is, you know, what stood out to you about the Goodz application for the incubator and the interview process that made you and the team feel like this was going to be a great project to work on? JORDYN: Yeah. So, I think just the team really resonated with the sort of idea in general, and it seemed fun. There was, like, it's a very positive thing, right? It isn't so much about solving problems and pain points. And, sometimes the, you know, when you're very focused on solving problems, it can feel a little doomy because you actually have to, like, immerse yourself in the problems of the people that you're making software for. And sometimes, you start to feel like the world is just full of problems. What Goodz is doing is sort of it is solving a problem in a sense, but not in that kind of way. It's really, like, a fun upside kind of thing, which I think a lot of the folks on the team were very excited about. But, like, the software component, actually, is very interesting to us from a technological standpoint as well. There's a lot of opportunity here to do interesting things on the backend with an object that's essentially functioning as a bookmark out in the world. What all can you do with that? There's something super compelling and technically interesting about it. And I think, also, the team was just sort of excited by Chris and Mike, you know, the energy and the kind of background they were bringing to the table was also super interesting. And then, above all else, what I say every time you ask me this question, which is stage fit, y'all, good stage fit. They're right at the beginning. They haven't built the product yet [laughs]. Gotta say it. It's a good stage fit. They know who they're building for broadly but not super specifically. Got a good vision but, like, haven't made that first step with the software. Perfect stage fit for us [laughs]. LINDSEY: Great. So, Chris, we were talking a bit before about how you two have been collaborators in the past, worked on business ideas before. Why bring this idea into the thoughtbot incubator? What are you hoping to, you know, achieve? CHRIS: One of the main reasons why we wanted to bring this into the incubator was just for support, momentum, and then, also, I would say, validation for our idea. I mean, we came to the incubator with a very, yeah, I would say it was a fairly developed idea that needed to be proved, and we, quite frankly, needed help with that. You know, Mike and I have our own expertises, but we don't know how to do everything. We're more than willing to jump in where we need to go. But having people with expertise to work with has proven to be incredibly helpful, and just having kind of fresh faces to bat ideas around with after he and I have been staring at each other for months now on Zoom calls and meetings. And just, you know, being able to talk about these ideas with fresh faces and new people and get new perspectives has been so very, very helpful. I think something that's also great from the momentum standpoint is that because there's a time limit to this experience, we've got the time that we have with you guys, and we've been able to set goals that I think are very achievable for things we want to occur in the next couple of months, and it feels like we're going to get there. And I think by the end of this, I mean, our hope, and I think we're on track, is to have a functioning physical product that we're going to offer to consumers with a digital backend to support it, which is, in my mind, amazing. That'll totally validate this idea and prove if we have something or not. LINDSEY: I was going to ask if you're open to sharing what those goals specifically are. Is that it? Is it that by the end, you have -- MIKE: Is that it? Lindsey, that's a lot. [laughter] CHRIS: It's a lot. I mean, yeah. I mean, we're going to have a physical object in the world that you can buy via an e-commerce site -- JORDYN: Sounds like we need Lindsey on the team if Lindsey feels like this is so achievable. [laughter] CHRIS: Yeah, yeah. Lindsey...yeah. We're in the beginning [crosstalk 15:47] LINDSEY: I meant, is that the goal? CHRIS: That is the goal. LINDSEY: Is that all? CHRIS: I was going to –- LINDSEY: Is that all you got? CHRIS: Mike, do you agree? MIKE: Yeah. Is that the goal? Yes, that is the goal. I mean, you know, when we sat down with the thoughtbot team kind of week one, you know, they're sort of like, "All right, let's define kind of the experiment." So, we refer to them as experiments, which I think is helpful because, like, what are the experiments that we want to be doing during our time here? And, you know, we talked about it a lot. And yeah, I think it's, you know, having a physical product out in the world, having a website in which to sell it. But also, it's really like Chris was saying, it's like, it's market validation, and just making sure we actually have something that people want. It's like, you know, running a startup takes so long and, like [laughs], you know, you'll do it for so many years. It's like bands when people say, like, "Oh, that's an overnight sensation." It's like, you know, that band has been slogging it out in tiny, little venues for four years before you ever heard of them. It's like, that's what so much of the startup world feels like to me, too. It's like, "Oh, you're just getting started as a startup?" It's like, "Well, we've been working on this forever." And I know how long this can take. And so, I think we want to learn as early as possible, like, is this something people actually want? Because if they don't, like, we'll just go do something else. I don't want to spend years making something that people don't want. So, I think the biggest goal, for me, is just validation, and then that is sort of how we get there is like, okay, how do we validate this? Cool. Let's identify some, you know, assumptions of personas that we think are people who do actually want this and then try to go sell it to them. And all the implications from that are, okay, well, you need a website where somebody can buy it. You need a physical product that somebody can actually buy. So, all those things sort of come out of that, but, for me, it's like, proving that assumption, is this thing real? Do people actually want this? And everything else is like, okay, how do we prove that? LINDSEY: Jordyn, what does that look like in these first few weeks here? User interviews, I assume, how are the user interviews going? JORDYN: Always. Always. So, you know, we kick it off by just, like, doing the exercise where we list everybody who might want this. And the team, you know, it's a fun product. Everybody brought their own assumptions and ideas to the table on that. You know, we had a lot of different scenarios we were imagining. It's super fun getting that stuff out of people's heads, just, like, what are we all thinking? And then, you know, we get to negotiate, like, okay...I always encourage everyone to think, like, if everyone else on the team was on the moon, you had to make a decision about a market segment to pick; which one would you pick? And then we kind of argue about it in a productive way. It really helps us get at, like, what are the dynamics that we think matter upfront? And then we pick one, or, in this case, we have a few. We have a handful. And we're running interview projects where we just recruit people to talk about people that meet this persona, talk about a specific problem. We're in the middle of that right now. And it's fun, fantastic. These conversations are super interesting. We're validating a lot of the things that Mike and Chris, you know, walked into this with, but we're learning a bunch of new things as well. And, like, really, part of the aim there is to validate that there's a hole in the market that we might fill but also to hear the language people are using to describe this stuff. So, when people talk about buying music, merch, you know, making playlists, et cetera, like, what language do they use to talk about that? So that we make sure we're speaking the language that our customer uses to describe this stuff. And we're, you know, we're right in the pocket of doing that, learning stuff all the time. And it helps us kind of hone the messaging. It helps us know where to go talk to people about it, how to talk about it, but it's, you know, it all kind of fits together. And it's just this, really...the early stages. It's just a bunch of us in a room, a virtual room, in this case, sort of, like, tossing ideas around. But out of it crystallizes this sense of alignment about who this is for, how to talk to them about it, and with a goal. And, you know, Mike and Chris walked in with the exact right mindset about this, which is, yes, it's experiments. We need to validate it. Let's make sure there's a there-there. If there's a there-there, let's figure out where it is [laughs], like, all those things. And we're running these experiments, and it was really [inaudible 19:36]. We got down to business quite quickly here. It was really great. LINDSEY: Like you said, it's not necessarily a problem or, you know, the typical framing of a problem. How do you start those user interview questions around this? Do you feel a gap between the physical and the digital sound? [laughter] JORDYN: No, no. LINDSEY: It's maybe not it [laughs]. JORDYN: Yeah, no. Well, I can tell you what our startup questions are. One of them is, tell me about the last time you bought music merch. Go for it, Lindsey. Tell us. LINDSEY: The last time I bought music merch, I went to a Tegan and Sara concert a few weeks ago, and I bought a T-shirt. JORDYN: Tell me about buying that T-shirt. Why'd you buy it? LINDSEY: Because I wanted to remember the show and my time with my friends, and I wanted to support the artists. I know that buying merch is the best way to support your favorite touring artists. JORDYN: So, it's just, you know, we could spend the rest of this time talking [laughter] [crosstalk 20:34], and it would be awesome. So, it's really a lot of things like that. LINDSEY: Gotcha. JORDYN: You don't ask, "What problem are you trying to solve by buying this t-shirt?" Right? Like, that's not, you know, but we ask you to tell us a bunch of stories about when you did this recently. You know, and if you make playlists for friends, you know, that's a different persona. But we would have asked, you know, like, "Tell me about the last playlist you made. You know, who did you share it with? You know, what happened after that? What happened after that? What happened after that?" It's a lot of questions like that. And there's just nothing better. People love to tell you what's going on with them. And it's great [laughs]. LINDSEY: Yeah. As you all have been doing these interviews, Mike and Chris, have you been surprised by anything? Any interesting insights that you're seeing already? CHRIS: I mean, I haven't done really much in the way of user interviews in the past. This is a really new experience for me. And then we're, obviously, not on the calls because that would be weird and probably intimidating for people. But we're getting lots of highlights from folks who are doing them, you know, in our daily sync. And I'm surprised at how many, like, really intense, like, playlist nerds we have found even just in, like, the few people we've talked to, like, in the best possible way. Like, people who are like, "I make playlists all the time." Like, you're talking about, like, a vinyl fan or, like, a...Jordyn, what's the story? It's, like, the guy who there was so much out-of-print vinyl that he started a vinyl label just to get the albums in vinyl. [crosstalk 21:56] JORDYN: Yeah. There were a bunch of releases that he feels really passionately about that were never released on vinyl that he knew would never be released on vinyl. And so, he started a vinyl record label. And we just found this guy [laughter]. CHRIS: Is that indicative that that's, like, an entire persona we're going to, like, target? Absolutely not. But it's just, like, it's amazing that even just in the few user interviews we've done, that we've found so many very passionate people. And it's sent me down, like, a TikTok rabbit hole of, like, TikTok, like, music nerd influencer-type folks who are posting playlists. And they, like, hundreds of thousands of likes on these videos that are literally just, like, screen with text on it that you're supposed to, like, pause the video [laughs] and, like, look at, like, the songs that they're recommending. And it's like, who does that? And it was like, these people do that. And it's like, so there are...it's been very encouraging to me, actually. I was worried that we were going to find not as much passion as we had suspected, and I think the opposite has proven to be true. So, it's exciting. CHRIS: Yeah, I completely agree with Mike. It's been so encouraging. I think, for me, what we're doing is an idea that I'm very excited about and have been very excited about for a long time. But hearing the responses that we're getting makes me confident in the idea, too. That's great. I mean, I think that is everything that a founder needs, you know, is excitement and confidence. MIKE: Well, and just the whole user interview experience has, like, made a lot of my other conversations sort of I've tried to frame parts of them as user interviews because I'm talking to a lot of, like, label folks now, and artists, merch people. And, you know, I ended up just sort of, like, asking them, I mean, yes, trying to explain the product and work on kind of partnership stuff, but a lot of it is really just geeking out with them. And just, like, hearing their thoughts about, like, what they love about merch because these are people that clearly think about this stuff all the time. So, it's definitely kind of, like, tuned my other conversations into trying to get unbiased feedback. LINDSEY: Yeah. Everything is a little user interview now. MIKE: Yeah, exactly. LINDSEY: Get that angle in there. All right, so some early validation and excitement. That's really cool to hear. Any challenges or, you know, other kinds of learnings early on? Anything that's been invalidated? MIKE: I don't know that we're there yet. [inaudible 24:02] Chris, I don't know. I'm happy to find that some things are invalidated, but I don't really feel...you know, some of the personas that we decided or maybe just one of the personas we decided to pursue, I think we're having a hard time having those user interviews kind of really bear fruit, but that's helpful, too, actually. I mean, it's like, okay, well, maybe that's not a group that we target. JORDYN: Yeah. It's about, like, [inaudible 24:24]. I encourage folks not to think about this like a 'no, not that,' and instead think of it as like a 'not yet.' And that's, I think, the dynamic here with a couple of the personas we were interested in. It's just been turned into kind of, like, a not yet for reasons that we very quickly figured out, but we'll get there. It's just a matter of figuring out we had some other personas take precedence because they're more sort of red, hot in a way, right? It's just easier to get in contact with these people, or it's, like, clear what they're going for or what they need from the market. So, you know, we have this whole list, and it was not clear at first who was going to kind of stand out. But we've kind of found some focus there, which means, invariably, that there's things that are falling out of the frame for now, and you're kind of de-prioritizing them. But it really is, like, a we'll get to that [laughs]. We'll eventually get to that. LINDSEY: Yeah. And part of the process, who's going to rise to the top right now? JORDYN: Yeah, exactly. LINDSEY: Do you have anything you can show and tell with us today or not yet? MIKE: So, Chris has been hard at work on all the physical side of this stuff and going back and forth with our manufacturing partner and all that good stuff. But we have a final version of the mixtape product. LINDSEY: For when this gets pulled into the podcast, Mike's showing us a physical card. CHRIS: It's a small card, and we call them Goodz. And it's printed on three-millimeter plywood using a UV printing process, super durable. And this is something you can put in your pocket. You're not going to wreck it. I think you could actually (Don't quote me on this.), but I think you can even, like, put it through a washing machine, and it would be fine. Embedded in this card is a chip that can be read by your phone, and that's pretty much what we're working with. MIKE: Yeah, so the idea is you just sort of tap this, and it'll take you to a streaming version of a playlist. And then Chris has also been making these adorable crates. And [crosstalk 26:10] LINDSEY: The little crates I love. MIKE: And we actually have some wooden ones, too, in the testing that's [crosstalk 26:15] LINDSEY: And then the mixtapes get stored in the little crates [crosstalk 26:19] MIKE: Yeah. So, you could have -- LINDSEY: Throw it on your desk. CHRIS: Each crate can hold about, I think, 15 of these things. What's really cool about this product on the physical side is we are using a tried-and-true technology, which is NFC chips. These are things that make Apple Pay work, make Google Pay work. They are in your E-ZPass when you drive through a toll booth. This is stuff that's been around for years. So, we're just kind of leveraging this technology that's been around for so long in a new way. MIKE: Yeah, I think it's similar to kind of the evolution of QR codes, right? It's like they were sort of around forever, and then it was, like, COVID and restaurant menus kind of kicked those into mainstream. Like, NFC has been around for a long time. It's very tried and true. It's affordable. But I want to say Apple only turned it on by default, like, the NFC reader in the iPhone in the last, like, 18 to 24 months, right? Like, it started...like, it's been around for a while, but they're sort of slowly kind of...and now you just sort of see it everywhere. People are using it on the subways in New York to scan for tickets or for accessing stuff. I was also just showing Chris has been prototyping with the ability to sort of keep these on a key ring. So, we have, like, a little chain hole on them. It is [inaudible 27:22] to sort of have this on your backpack or, you know, on a key ring, or something like that. And friends could kind of, like, come up to you and just, like, scan one that looks interesting. CHRIS: And yeah, something that's awesome about this is you don't need an app. You don't need to download anything. As long as your NFC reader is on when you scan this, it will bring you to the music that it's linked to, which I think is awesome. So, I mean, my dream is to have these, like, hanging off of people's backpacks so I can, like, scan them in the subway or, you know, it's such, like, an easy thing to do. And it requires so little technical time on the user's end to be able to do it. LINDSEY: Oh, we got a question here. "So, Moo used to offer NFC cards. What made you decide to do the thicker plywood model?" CHRIS: Durability is really what it comes down to. We wanted something that felt like an object that you can have and treasure. Like, these have weight, you know, these feel like something, not just a piece of paper. This is something that you can have and [inaudible 28:22] your desk, and it's not going to fade in the sunlight. It's not going to disintegrate over time. This is something that's going to last. MIKE: Yeah, the cards would definitely, like, as I would sort of carry them around and show them to people and stuff, the cards would start, you know, breaking. It's like having a business card in your pocket, right? Eventually, it's going to kind of wear out. And plus, we had, like, the stickers were visible on the back of them. And we were, like, having the sticker just completely disappear inside the wood; it just feels a little bit more like magic. LINDSEY: Well, thanks for demoing there. I put you on the spot a little bit. But they are...I had seen them in the Slack, and they're very cool [laughs]. So, I had to ask if we could show them off a bit. MIKE: Of course. CHRIS: I think another thing to think about, too, is we've been talking a lot about the user experience. But if and when we get to the point of making these for artists, artists will be able to collect so much data off of the way that people buy and collect and use these things over time, which is something that we're really, really excited about. And also, you know, we're working on a way to make the link in the object updatable over time. So, artists will be able to change what a card points do to inform their users about the latest and greatest thing. LINDSEY: Very cool. Jordyn, what's next on the programming agenda for Chris and Mike? JORDYN: It's really sort of we're in this, like, iterative cycle. So, we're talking to folks. We're working on the website. The conversations we're having with people are informing how we're framing this first experiment with the mixtape, how we're marketing it, who we're marketing it to. I think next up is probably a Google Ad experiment to really see if we can piggyback on some stuff or at least figure out a new consumer product. It's so tough, right? It's also not a thing people are searching for. So, we have to come up with some experiments for how we get people to that website [laughs]. So, you know, Google Ads funnels is just something you kind of have to do because it's very interesting to figure out what people are responding to, what people are searching for. But we're going to have a bunch of other experiments as well and non-experiments. Outbound experiments: can we go to people? Can we get listed in a gift-buying guide for the holidays? Or, like, we don't know. There's a bunch of experiments we need to do around that, which is really just this iteration. We won't stop talking to users, but, you know, everything we're hearing from them will inform where we go and how we talk to the folks in those places where we end up. And really, it's just about starting...once this is up and, you know, there's, like, an orderable thing, there's, like, a whole data cycle where we start to learn from the stuff we're testing; we actually have some real data for it, and we can start to tweak, iterate and change our strategy. But the bigger thing, also, is this bigger platform. So, the next thing really, the big next thing, is to sort of start to scope and create an architecture idea. What's it going to take to build the actual backend thing? And it's the thing that thoughtbot really [laughs] excels at, which is software. So, you know, that's the big next kind of project. Once the mixtape experiment is sort of out and in flight and we're getting data, we really need to turn our attention to the technical backend. LINDSEY: Exciting. Another comment/question from Jeff, who maybe needs a user interview. "Love the crate more than the actual albums. Maybe offer collections of artists." MIKE: Yeah, that's the plan. CHRIS: Yeah, definitely. It's a good idea. Yeah, it's, I mean, and labels get to, especially, like, small indie labels get really excited about doing, like, crates worth of collections of different artists or, like, you know, digging through their back catalog, their subscription services. There's a lot of different angles for sure about that idea. LINDSEY: [inaudible 31:55] Chris and Mike, going into this next section of the programming, for anyone watching right now, or watching the recording, or listening to the recording, any action items from them? You know, are you looking for any user interviews or have any survey or any destinations you'd like to send people yet? CHRIS: Not quite yet, but soon, I would say. Well -- MIKE: I mean, [inaudible 32:19] plug the website, I mean, you know, I think we've got, like, an email to sign up from there, right? The URL is getthegoodz.com and I [crosstalk 32:27] LINDSEY: Goodz with a Z. MIKE: Goodz with a Z. CHRIS: With Z. MIKE: So yeah, if you want to go there, you can sign up. I think there's an email signup on there to learn more. LINDSEY: Perfect. All right. getthegoodz.com email sign up. To stay up to date on Goodz and the incubator, you can follow along on the thoughtbot blog. You know, as always, send us any questions you might have, and we're happy to get to those. But otherwise, thanks for listening. And thank you all — Jordyn, Chris, and Mike. Thanks so much for joining today and sharing and being open about your stories so far. MIKE: Thank you. CHRIS: Yeah, thank you, Lindsey. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guests: Chris Cerrito and Mike Rosenthal.Support Giant Robots Smashing Into Other Giant Robots

Jamon Holmgren is the founder of Infinite Red, a consultancy specializing in React Native. He discusses his journey and insights into technology and leadership and highlights how Infinite Red stands as a testament that businesses can be run ethically while still achieving success. The conversation shifts to leadership styles and the principle of "one-minute praise" from the book "One Minute Manager." Both Jamon and Will agree that acknowledging others' efforts openly can make a significant difference, enhancing leadership skills and building stronger relationships. Will points out how this simple principle has been a game-changer for him in various aspects of life, including his personal relationships. Towards the end, the focus turns to motivation and long-term strategy. Jamon is driven by his enthusiasm for learning and the thrill of tackling diverse challenges in his consultancy work. He also shares his philosophy of keeping the company "10 degrees above the horizon," emphasizing steady, sustainable growth rather than erratic leaps and bounds. Infinite Red Follow Infinite Red on LinkedIn, X, YouTube, GitHub, Facebook, or Instagram. Follow Jamon Holmgren on LinkedIn or X. Visit his website at jamon.dev. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: WILL: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Will Larry. And with me today is Jamon Holmgren, Co-Founder and CTO of Infinite Red, a software consulting agency that specializes in React Native. Jamon, thank you for joining me. JAMON: Yeah. Thanks for having me. I really appreciate it. WILL: So, Jamon, what's going on in your life? How's everything going? JAMON: You know, things have been obviously very busy, like, I guess, pretty much everybody. You know, school has started. I have four kids, so that keeps me quite busy, going to various school events, going to volleyball, you know, bringing kids here and there, running the company. I have some side projects I'm doing. I am playing hockey. So, it just seems like every waking hour is filled with something. [laughter] WILL: I totally understand that. I have three kids of my own. So, they're a little bit younger than yours, so mine is 4, 3, and, like, 17 months, so... JAMON: Okay. Yeah, so you're just getting started. And you're doing all of the, like, physical labor associated with being a parent. WILL: Yes, yes, yes. So, I want to start there. Tell me a little bit about your kids. I know their ages are 10 to 18. JAMON: Yeah, so I have a boy, Cedric. He's actually a programmer as well. He's just starting his career. He is the oldest, and then we have three girls. We have a 15-year-old who's a sophomore in high school. And then we have a 12-year-old who's in middle school and a 10-year-old who is in fifth grade in elementary school. And it's a lot. My wife and I both came from very large families, so we're kind of used to it. And it's a lot of fun. A lot of challenges at this age, I mean, teenagers especially, you know, as they kind of all come into that same era, you know, it's more of a challenge. I guess the thing that I think about it is a lot of the skills that I learned as a young kid parent don't really translate super well to being a teenager parent. And I'm having to learn a lot of new skills. And I actually talked to a guy the other day. His kids are, I think, 32 and 28, or something like that. And he said, "Yeah, the learning never stops." [laughs] WILL: So, I'm going to ask you for the secret sauce because I'm still in the temper tantrums and those type of emotions and stuff. So, how is it different in the teenage years from the temper tantrums? JAMON: Well, I think that they can act like adults in a lot of cases, and you start thinking of them as adults, and you start developing a relationship there. But their brains are also not fully developed. And so, they will also do things that are very inexplicable, like, you'll just be like, why? Why would this be a thing? Like, I don't get it. Like, you act like an adult for half the time, and then the other half, you act like a kid. Navigating that, and the fact that they change all the time, and all the other challenges. And they're all different. Like, if we had only had one kid, you know, my boy was pretty easy. He was pretty straightforward. It would have been like, well, shoot, being a parent is pretty easy. Like, I don't know what everybody else is complaining about. Like, he never did tantrums. He was just a really quiet, you know, like, well-behaved kid and kind of went through life like that. But then, obviously, developing a relationship with him is more of the challenge because he's quieter, where with my girls, it's easier to develop the relationship, but then you [laughs] deal with a lot more volatility as well. So, they're all different. Every kid's different. It's hard to really apply that directly. I would say that the thing that I've learned the most in the last few years is just kind of continuing to be, like, even through some of the tougher times, continuing to be there, continuing to develop that relationship. A lot of times, it feels like you're not getting anywhere, but you are. It is actually happening. You just don't see it until later. WILL: I'm writing that down. That's great advice [laughter]. You mentioned hockey. Tell me about it. I've never played hockey. I grew up in the South, so we didn't have that. So, tell me about it. And you're a goalie also, correct? JAMON: Yeah, I play goalie. I didn't discover hockey...I played basketball in high school. I played four years of high school basketball. I even played a little bit at college. And I didn't really discover hockey until I moved to Southwest Washington, about an hour away from where I grew up in the coast of Oregon. When I got there, a lot of my friends that I made were playing hockey. And one friend, in particular, he was a goalie, and he had grown up in Upper Michigan. So, you know, like, he grew up playing hockey. He was a very good skater and things like that. But there was one weekend I was coming to watch him play just rec hockey. And he's like, "You know what? I can't make it. Would you want to jump in and, like, be my sub?" And it was just a pick-up game. So, it wasn't like there was anything on the line. And I was like, "All right, I'll give it a try." You know, put on the gear. He showed me what to do to put on the gear. He kind of gave me some tips. Like, in the living room where we were, he was, like, showing me how to play. We were, like, I would say, 19, I think. Nineteen years old, something like that. Anyway, I show up, and I put on the gear, and I go out there. And I actually had a decent game, considering I barely knew how to skate and barely knew how to do anything. But I'm kind of big; I'm six foot four, almost six foot five. And having all that gear and everything, I filled up a lot of the net. And it wasn't a very high-level game, so I did pretty well. And after that, the team was like, "Well, we'd love to have you back." And then my friend really was not interested in continuing, so he was like, "You can have it, like, just roll with it." I kept playing for about three years, and then, I don't know, I took over a decade off. The team dissolved. It wasn't even a league team. It was just, you know, pick-up hockey. And then a friend called me and was like, "Hey, I'm starting up a game. It's going to be Finnish Americans," because I'm half-Finnish myself. "So, it's going to be all Finnish Americans. We're going to call it the [Foreign language]," which is the Finnish boys in sort of Finnish. It's not exactly supposed to be like that in Finnish. Anybody listening who's Finnish is going to be like, "Yeah, that's bad Finnish." But it kind of means Finnish boys or Finland boys. And we put together the team, and I've been playing for the last three-plus years. It's been kind of, like, a rec league team. We've won the championship four times, which was really fun. This year, I'm actually playing in two leagues. I'm playing in rec league, and I'm also playing the next league up, so a little bit faster, better skaters, better shooters, things like that. And I just love it. It's so much fun. WILL: Wow, that's amazing that you started later and that you're still playing it. Because when I look at hockey, I'm like, that's really hard. I don't know if I could do that. I can skate. I can't stop. JAMON: [laughs] WILL: Like, I can get a lot of speed [laughs]. But it's just something about turning sideways and thinking I'm going to fly over the skates. JAMON: [laughs] WILL: And yeah, it's a whole thing [laughs]. Is goalie harder than playing any of the other positions? JAMON: I would say it's different. Like, I don't have to be as good of a skater, you know, things like hockey stops are still not supernatural for me. I don't skate backwards super-fast. You know, I'm not a fast skater in general. But the difference is, of course, you have to be reading the flow of the game. You have to know the body language of the players that are coming at you. You have to kind of see what's happening. At the end of the day, lots of things can happen, so you try to put yourself in the best position. It's a lot of, like, positional, like, where are you in the net? What does your position look like? And then, once they shoot, how do you react? Are you dropping down, or are you staying up? Are you using your glove? Are you using your blocker? Are you just trying to block with your body using your stick? Then, once the puck hits you, then what do you do? How do you control the rebound? Are you trying to cover it up and ice the puck so they do a face-off? Are you trying to kick it out to one of your skaters? And then, once that happens, you have a little bit of a rest, hopefully, while they're down on the other side. But you're continually alert and watching to see what's going to develop because it could be a breakaway. And then it's just you and the skater and trying to anticipate what they're doing and try to make it so that they have to make a play. Like, just be big, be in position. Don't get out of position. Don't make a mistake. And I've had really great games where I've, you know, had 45 shots on me, and I've only let one in or something like that. And I've had some bad games too. I know there's one game in a championship where they only had six shots on me. But we ended up losing because I let in two, so that was not a fun game. I only had six opportunities, and I failed on two of them. But that happens, and so you just have to be mentally tough. WILL: Wow, that's amazing. The limited knowledge of hockey...I'm going to assume here, so I hope it's right. With you being 6'4, 6'5, I'm guessing that the five-hole, if I'm correct, was probably your toughest position to defend. JAMON: You know, you would think so. And just for the audience, the five-hole is, like, between your legs, you know, the puck going between your legs underneath. But I play a style...a little bit older style of goalie because that's what I watched. You know, in, like, the early 2000s, I watched Patrick Roy of the Colorado Avalanche, one of the greatest goalies of all time, and he played what's called a butterfly style. So, as the play develops, you're standing, but then you go down fairly early, and you're protecting the bottom. You have your stick in front of you protecting the five-hole, and you have your legs, you know, spread out. So, I used my height really more for blocking as I'm down rather than standing because when I'm standing, I'm above the net. It's better for me to get down. And I think that that's worked out pretty well. You know, Patrick Roy was a pretty big goalie as well. Most modern goalies play a more hybrid style. But, you know, we could get into all that. I'm a big kind of hockey nerd in this way. But that's what I do. I play butterfly, so most of the time, people don't beat me five-hole; when they do, it's usually they're picking a corner. WILL: Wow. Now that you've painted the picture, I can see how that's smart because you do have the goal, I mean, the gloves plus the stick and then your height. Yeah, I can see how...that's smart. That's very smart [laughs]. JAMON: Yeah, that's right. Yeah, that's kind of the goal. And also, because I wasn't a great skater, it sort of played into it as well, playing down on the ice where I was just more comfortable that way. It's worked out. I've had a pretty decent record over my career here [laughs]. WILL: That's awesome. Well, let's transition a little bit into consultant agencies. You've been doing it for 18 years. Tell me about that. How did you get started? JAMON: Well, when I started, I was working in construction. I was working for a home builder. And, you know, everybody I knew pretty much worked in construction, including my dad, who owned a business. And I went on my own. I had always dreamed of owning my own business, but I didn't start really thinking about websites. I was coding. I loved coding, and I was coding since I was 12. So, when I got to 23 years old, I thought, I'll start a business, and I'll do home design because that's what I was doing for the builder was, I was drawing homes. I was designing homes and remodels and things like that. And so, I started it doing that. But I also needed a little bit extra work. I didn't have enough work. Like, I had people, you know, sending me work, you know, home design and whatnot, but I didn't have quite enough. So, I would also build websites on the side, PHP and HTML, MySQL, and JavaScript. And I just sort of continued to do that. But in 2008, there was the housing crisis, and all of the design work for homes just dried up. There wasn't much there. In fact, it actually really dried up in 2007 because things kind of started a little early for designers. And so, I was like; I got to do something to stay busy. I've got a wife. I've got a young kid (Actually, at that point, I had two kids.), and I need to make sure that I'm staying busy. And so, I really ramped up trying to find work, you know, as a programmer, as a web developer. And there were plenty of companies at that time that were really trying to drum up business. So, they were putting money into their websites trying to get new projects, and they were all construction companies. And so, that's how I started. And I started doing more things like internal web apps for managing orders and managing sales leads, and that sort of thing. And that led me into web apps and eventually to Ruby on Rails, which became sort of my bread and butter for a while. As I was doing Ruby on Rails, you know, obviously, the iPhone was out, but the iPad came out. And I was more of an Android guy at that point. But I bought an iPad because it looked really cool, and my dad had one. When I started playing around with it, I'm like, I need to build apps for this. This is super cool. So, I took some Stanford courses online, which you could do back in those days, iTunes U, and learned how to use Objective-C. This was previous to Automatic Reference Counting and stuff. So, you had to manage your own memory, and this was a lot of manual work; very different environment than JavaScript, and PHP, and Ruby. But I actually enjoyed it quite a bit and then eventually transitioned into React Native later. But really, getting over to mobile and that sort of thing was...once I found mobile, I really didn't want to do web anymore. Mobile is what I really enjoy doing. WILL: Wow, I love that. If I'm following you correctly, you said in 2007, that's kind of when everything dried up. So, you were almost forced to find something different, correct? JAMON: Yeah, that's right. I mean, I kind of sat around feeling sorry for myself for a while. And then I was like, well, it's my business. I got to figure out what to do. It's not anybody else's fault. Like, you know, it doesn't matter that this is forces out of my control. I do have control. I have the ability to go in there and figure out, okay, what do I do next? Well, I know how to program, and it seems like people want me to program. So, let's lean into that. WILL: Wow. I love that. Because it's funny, that's how I got started in programming. I lost my job. And I was working at Buckle, the clothing store. If you know me, that is not me at all, like, at all [laughter]. I love gym shorts and athletic clothes. Like, fashion is not my thing. It's just not. So [laughs], I got into programming because I was just struggling. And it was a very pivotal moment in my life. And I'm thankful that I lost my job. Losing your job is just hard, and I think it makes you rethink things. JAMON: Yeah, absolutely. It was a growth moment for me as well, one of many. But that was definitely a point that I look back on and say, I mean because I can actually point at almost the day when it all dried up. It was, like, April 2007. And my uncle had been sending me a lot of work, you know, he had extra work. He didn't have barely enough for himself anymore at that point. And I finished up my last project, and he's like, "I don't have anything else." And I had some other clients as well and called them up, and they were like, "No, we don't have anything. Like, nobody is buying right now." And it just kept going like that. And it was weird because 2005, 2006, most of 2007, it felt like things were really rolling, but it just dried up all at once. And so, I was really lucky that I did end up getting a bunch of web work to do in 2008. I was still doing home design till probably late 2008, 2009. But then I eventually just hung that up and was like, okay, this is over. I'm definitely focusing on programming. WILL: Wow, how was the initial traction when you moved into ramping up the web development? JAMON: It was really good because it didn't take much to keep me busy. And I ended up getting some big contracts from, like, a cabinet manufacturer was a big one. I did some other things as well. And I ended up hiring my first employees in 2009. So, really, less than two years later, I was starting to hire employees. And I just hired, like, junior developers who had barely learned to code and taught them to code. So, I hired probably, over the years, next few years, like, ten programmers, many of whom are actually still with me today, and I taught them to code back in the day. And as time went on, they became senior and really high-level programmers who are now leading projects for big companies that you've heard of. But they started with me building, you know, PHP and MySQL and whatnot for small, like, regional construction companies. And we learned together. So, it was definitely a progression you can go look back and see. WILL: Yeah, I saw a tweet that you tweeted, and I loved it because I totally understand. JAMON: [laughs] WILL: And so, I'm glad you mentioned the junior devs and stuff. The tweet that I'm talking about was, "I got into this industry to code; ended up becoming a founder because I was the only person who would hire me." JAMON: [laughs] WILL: I want to ask you about that. [laughter] JAMON: Yeah, it's really that I grew up in a small logging town, like, very tiny logging town in Northwest Oregon. I didn't know...I knew one programmer, and the guy was, like, an incredible genius. And I just thought that that was the only way that you could professionally be a programmer was to be an incredible genius. I was coding, but I was, like, coding games, you know, in QBasic. And so, for me, every time I looked around, it was just, like, construction, or logging or, you know, blue collar, like, working at a mill. Like, these were the things that I saw around me. And so, that was the path I went. And I didn't really think of using this passion that I had for coding to turn it into, like, actual money. And when I did start thinking about it, I was like, I don't know anybody who does software. Like, even when I moved to Southwest Washington, I was closer to Portland. But I thought you had to have a CS degree, and I didn't have a CS degree. So, I was like, okay, well, I'll start my own business then, and that will be the thing that kind of leads me into tech. And that's what ended up happening. And it's kind of funny because I did go to, you know, one semester of community college for basketball and for...until I got cut. And then I studied some things there. But I never finished for the community college. What's kind of cool, though, is today, I'm actually on their, like, tech advisory committee. Like, they actually have me advising their professors on the current state of tech, which is kind of cool. WILL: Wow, that is really cool. It is interesting because I remember when I first started out and that feeling of probably over 300 applications just trying to get a job. And it was just hard. And my first job, to be honest, I think it was because of networking is why I got the job. If I didn't know the person that introduced me to the company, I probably wouldn't have gotten the job, if I'm being honest. But I am very sympathetic for junior devs anytime. If a junior dev asks me a question, I will take time, help them out. Because I remember...it's very hard as a junior dev trying to get that first job. So, when you said that, I was like, yeah, I can see your heart towards junior devs. JAMON: Absolutely. That's where I started. You know, the first developers that I hired were all juniors. We don't hire juniors anymore because of the style of business that we are. But I miss that. I miss that to some degree. We really can't. And we've looked at it from just about every angle. But I did my time [laughs]. I spent a lot of hours teaching junior developers when I could have done it quicker myself. WILL: Definitely. Like, you end up losing some money when you do a junior dev and you're hiring for the future. So, like, in a consultant agency, I totally understand that, yeah. JAMON: Yeah, absolutely. MID-ROLL AD: Now that you have funding, it's time to design, build, and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Liftoff brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we'll help launch your new product and guide you into a future-forward business that takes advantage of today's new technologies and agile best practices. Make the right decisions for tomorrow today. Get in touch at thoughtbot.com/liftoff. WILL: So, I want to ask you about the transition from ClearSight Studio to Infinite Red. How did that happen? JAMON: ClearSight was my first company. And it sort of evolved from being a, you know, a home design/website company to just a website and web app company, and then mobile apps. And, at a certain time, we had, I think, around 12 employees, something like that. I had a design department. We were building websites and whatnot. And I was really interested in iOS development. That was really my passion. And so I actually ended up working on some open source with iOS developers across the globe and then got invited to a conference down in San Francisco in 2014. And I went and gave a talk there. It was my first tech conference that I'd ever been to, much less given a talk, and I was the first talk [laughs]. So, that was kind of an interesting little anecdote there. And as I did it, I got to know some other developers. I had one in particular, Todd Werth, who I really hit it off with, and we ended up chatting a lot after the conference. And it felt like he and I had a very similar outlook. And he had an iOS agency. That's all they did. Well, 2015 rolls around, and I had had some rough times toward the end of 2014 in terms of the business, and I was kind of complaining to Todd. He had had some issues as well, and we started commiserating. And he's like, you know, he just started joking. I still have this conversation in Slack way back if I go look. And he's like, "Well, maybe we should just merge our businesses together," because it felt like we had maybe complementary skills. And we had a similar outlook on what we wanted from our businesses. And so, we ended up eventually solidifying that. I flew down there, talked to him and his business partner, Ken, at the time. We ended up making that happen later that year. So, just a few days ago, October 1st was our eighth anniversary running the companies, running the new company, the merged company, which is Infinite Red. So, that was kind of how that all came together. Eventually, Ken left, and we had a new business partner who was our top employee buy-in; that's Gant Laborde. And so, there are still three owners. We have three directors and then the rest of the team. We're about 30 people altogether, and we focus entirely on React Native. WILL: Wow, congratulations on eight years. That's a lot. That's amazing. JAMON: Yeah, thank you. I was just thinking the other day that I ran ClearSight for ten years. Infinite Red is getting close to how long I ran my first business. And, like, my youngest is, like I said, 10. So she was only two years old when I merged the company. She does not remember my old company, which is weird to me. [laughter] WILL: Wow. So, can you walk me through your decision to go here with React Native and specialize in that? Because it sounds like right around the time when React Native was created, and people started using it in production. JAMON: That's right. The iOS technology that we had sort of bonded over at that conference was called RubyMotion. But in 2015, the founder ended up going to work for Microsoft for a while and then went back to Apple. He had been from Apple before. So, it was sort of going down. And we were looking for a different technology, both of our companies were, and then, of course, the merged company. React Native looked interesting, but it didn't have an Android version yet. But then, in September of 2015, Android came out, so it was iOS and Android. So, we were able to take a look at that one month before we ended up solidifying the actual merger. So, basically, day one, October 1st, 2015, we were, like, we are now doing React Native for mobile, but we kept doing web. We kept doing Ruby on Rails. We did some Elixir. We did some Elm. We did some...I think we had some old Ember stuff going on. We had all kinds of things going on. But over time, we got more and more traction with React Native because that's really where our interest was. And so, we ended up saying, okay, well, this is where we really want to be. It took us a few years. It took us probably five years, six years, something like that, to really develop the confidence to say, "Hey, this is all we want to do," because it's a risk. Like, you put yourself on one technology. We had that before with the other technology that went down. But we had the confidence that we knew we could step off of a sinking ship onto another one if we needed to. So, we said, "You know what? Let's do this." And I got to give my co-founder, Todd, a lot of credit because he was the first one to say, "Let's go all React Native. Anywhere that React Native is, React Native is on a lot of different platforms. You can do tvOS. You can do Mac. You can do Windows. You can do web with React Native web, all kinds of things. So, let's just focus on React Native. Our team will just focus on that. We will only hire React Native developers. All of our marketing is going to be around React Native. Let's just focus on that." And it ended up being a great call. We did that. We made that happen. And for probably the last, I would say, three, four years, something like that, that's all we've been doing. WILL: So, what's your opinion on, I guess, the argument that's being held right now with native iOS and Android, even the Flutter, and I think Ionic is the other one that I've heard of, versus React Native? What's your pitch on React Native over those? JAMON: There's definitely reasons to use any of those. But I wrote this article a while back. It was specifically about Flutter, but I think it applies to a lot of the other competitors as well. The title of the article was provocatively titled, "Flutter Is Better Than React Native in All the Ways That Don't Matter." And the idea behind this is that, yes, Flutter gets a lot of things very right. A lot of their developer experience is actually better than React Native; some is worse, but, you know, some is better. But really, when it comes down to it, the things that matter are more business level. React Native is good enough. It's like native views. So, you have the native performance. With Hermes, you have really good performance in JavaScript. So, you know that you can get really high-level JavaScript performance. You can ship JavaScript, which really helps because then you can bring in JavaScript developers, and specifically React developers. So, a lot of companies already use React. It's a no-brainer to then use React Native if you're already using React Web. It doesn't really make sense to go to Flutter. It makes maybe some sense to write it in native, but then you have to write it twice. And you have three teams. You have a web team. You have an iOS team, and you have an Android team. And you also have three codebases, and one's always lagging behind. That's always what's happening. Marketing is like, "Okay, when can we announce this?" "Well, iOS isn't done," or "Android is not done," or "Web is not done." Where if you can combine all of those things and combine just the culture of your team, then it becomes more tight-knit because everybody's working on all aspects at one time. You can take a feature, and you can build it in web, and you can build it in iOS, and you can build it Android with all the same skills. Now, there are some deeper parts of React Native. It goes really deep. But in terms of just being productive out of the gate, a React developer can be productive in week one, and that's, I think, a huge deal. So, it really comes down to is the performance and developer experience good enough? And the answer is absolutely yes. And then, secondly, like, what's the business case for React Native? Well, you can have the same developers doing iOS, Android, and web, and even if you don't, you can share techniques. You can be like, "Hey, here's this cool JavaScript thing," and the Kotlin developers aren't just like, "Ugh, you know, JavaScript." Or you can be like, "Hey, here's our TypeScript configuration across the whole codebase." You can even have a monorepo with everything in it. It just makes a lot of sense that way. And especially now with Expo, it makes it even more that way because Expo removes a lot of the barriers for web developers that they would have coming into native. So, with that in mind, I still see React Native dominating the apps that are at the top of the App Store. One of the Expo developers, Evan Bacon, has put out a bunch of tweets about, you know, like, 24 out of the top 100 food and drink apps are written in React Native, as opposed to 8 in all the other options combined other than native, you know. So, it gives a good sense that React Native is still growing and continuing to. It has a lot of steam behind it. WILL: Yeah, I totally agree with you. I'm a big React Native fan, and I do a lot of React Native work here. So, yes, totally agree with you. And one of the most frustrating things that I've come across is, I'm a big researcher, and so I'll research things, and I'm like, oh, there's an app for this. And I'm a big Android fan, so when I go to them, it's like, oh yes, I can use this app. And then it's like, no, I can't. It's only for iOS. Okay, like, you lost me as a customer. JAMON: [laughs] WILL: I was willing to pay whatever on this because I've been looking for it. So yeah, I like how you said that. JAMON: Yeah. It treats all of the platforms as first-class citizens. WILL: Yes. Yes, yes, yes. Totally agree. How does your company handle the backend? Do y'all do any of the backend, or how is that handled at Infinite Red? JAMON: We used to do that, like I mentioned. But a few years ago...we had a very, very small back-end team by then. Most of the time, and now pretty much 100% of the time, when someone comes to us, they already have a back-end team, so we work directly with them. A lot of our developers were back-end developers, and so they understand the backend really well, but they're obviously React Native specialists now. So, you know, I came from that. I did PHP. I did Ruby, Ruby on Rails, Elixir, Node, all kinds of back-end technology. So, I understand it really well as well. But yeah, we lean on our clients for that. We might partner with an agency like you folks over there at thoughtbot and have them do the backend, or just have the client, you know, come up with their own solution. WILL: Yeah, I love that, yeah. And we've done that with numerous agencies, so yeah, that's awesome. What does success look like for Infinite Red now versus, you know, six months or five years from now? Do y'all have any goals in mind that you're trying to hit? JAMON: In the Infinite Red leadership, we are currently reading John Maxwell's 21 indisputable Laws of Leadership, which is a good book. And we had this really great conversation at our first book club meeting in leadership, which John Maxwell defines success in a very different way than we do. You know, he measured it as, like, McDonald's, or Starbucks, or something like that, like, giant, becoming huge, becoming big, making tons of money. And it was sort of just implicit in the book that that was the case. We had this great talk internally. Why didn't this resonate with us? And that's because we don't really measure success that way. So, I love that question, Will, because measuring success is you really have to start there. Like, you have to start there and say, "What do we want from this?" So, ultimately, we want to build cool things with our friends. I'm a coding nerd. I want to code. I want to be in the code. That's why we're an agency. Like, if we were a product company, if we were building, I don't know, podcasting software or something, we'd have to become experts in podcasting rather than experts in React Native, or experts in TypeScript, or whatever we want to do. So, we really love code. We want to build that. We want to have an amazing family-first environment. We want to treat everybody super well. We want to have really low turnover, which we've been able to achieve. Hardly anybody leaves Infinite Red. Maybe every other year, we might lose one person. And even with those people, they tend to come back [laughs], which is a great sign. They go out and find out that, yeah, actually, Infinite Red is pretty awesome, and they come back. So, we really look for that. We really focus on that. We want that to happen. And it's really less about making the most money we can. Obviously, everybody wants to be well paid. And so, we're going to try to make sure we have a successful business in that way and that we want to be around for a long time. But, really, measuring success is less about business success and it's more about life success. It's really more about family success, being with my four kids, being there for them when they need me to be. That's why we're remote, you know, as another example. So, everything really hinges off of that. It's around happiness. It's around fulfillment. It's not around financial success. WILL: I'm a huge John Maxwell fan, by the way. JAMON: [laughs] There you go. WILL: So, yes, I love it. And I love how you explained, you know, because one of my questions I was going to ask you is about the core values, but I'm going to switch it up a little bit. So, I'm just going to say, in my opinion, I feel like there's almost leadership talk void at times, especially in the tech space. Like, we don't talk about leadership a lot. But it plays a huge part in what we do day to day. Like, you named a couple of core values and principles that you're following because of the leadership. So, for you, why is the leadership so important and I guess you can say have a seat at the table at Infinite Red? JAMON: I'm a strong believer, and I've become more of a strong believer over time, that it all starts at the top. If you don't have buy-in from your top leadership, it does not really matter what happens otherwise because they will continually undermine, and they have the power to continually undermine that. So, these core values have to apply to the top leaders. They have to be held accountable to that. And these leaders also need to be developed. So, we have three owners. We have three directors. And the three directors who are underneath us were not directors when we hired them; you know, they started out as developers. They started out as designers. They started out as project managers. But they became Director of Operations, Director of Engineering, Director of Communications. And we developed them. We poured a lot of time into them, and we continue to do that. In fact, even reading this book with them and going through that exercise is continuing to invest in them. Not that we as owners don't have growth to do; we also do. And so, we learn from them, and we learn from our team. So, you have to start there. And on that same vein, we do have some core values. We call them our foundation and our pillars. We have three foundational things, and we have four pillars. So, the three foundations are: one, we control our own destiny. We are not going to be beholden to some other company. We're not going to ride someone else's coattails. We're not going to be in a situation where someone else can kill us. And it can be easily done that way where we're in a position where, you know, we're too reliant on one whale client or something like that. We just won't do it. The second foundational thing is that we have...it's a word bonitas, which means kindness, friendliness, benevolence, blamelessness. And it's basically just being a good person to everybody and doing the right thing. And the third one is having a significant positive impact. That's why we do so much media. That's why we try to have an impact outside. And we're only 30 people, but people think we're way bigger because of how we kind of present ourselves in the world. And then our pillars all support those things, so high personal support. We support each other. We have high expectations, but we also support each other not just at work but also as a whole person. Long-term viewpoint, we think way beyond this year. We think about what is Infinite Red going to be when I retire? You know, I'm 41; that's a ways out, hopefully. But what's that going to look like? The next one is collaborative creativity. Creativity by yourself is just a solo thing. We're a team, so it has to be collaborative. We have to do it together. All our creative work, whether it's our conference, Chain React, or our work, it's all collaborative, and we love being creative. And the last thing is being pioneers, pioneering spirit. We like to be pioneers in technology. We put out a lot of open source. And we try to bring that pioneering spirit everywhere we go. And then, there's a lot of different things that kind of come out of that. For example, we have this internal saying, which is, "Don't do hard things alone." So, you have a hard thing coming up? And it could be hard in various ways. It could be a technically challenging thing. It could just be hard because of the mood you're in that day. But don't do it alone. Ask someone to help you, you know, jump in with you, pair with you. Do it together. And we love that. That's part of the high personal support and the bonitas. So, all these things come out of the foundation and pillars that we have. WILL: Wow, I love all those. I want to pick one of them out and ask you a question around it. So, you're talking about having an impact. I'm loving this conversation just talking to you. It's just been amazing. So, for you, what do you want the impact on the world to be from your perspective? JAMON: That's a hard question to answer, and it tends to be something that I think about a lot. I'm more of an opportunistic person. I react more than I plan ahead, that sort of thing. But with that said, I think that we have had significant positive impact through a lot of different ways. So, on Twitter, for example, I try to present a...and this is authentically who I am. But I try to present a positive force out there, someone who's excited and enthusiastic about the technology, who supports other people, even who you might consider competitors, for example. I just retweeted recently a Callstack thing. I mean, you might consider them a competitor. They're another React Native agency. But I love Callstack. They're great people. And I retweeted one of their really amazing resources, which is the ultimate guide to React Native performance, which, by the way, is really good. And if you do React Native, you should check it out. So, I think what goes around comes around, and I really want to have that positive impact out there. I want to give talks that inspire people. You know, I'm a nerd, and I'm going to nerd out about stuff. And I feel like that has an impact all of its own. So, that's kind of my personal side of it. And then Infinite Red is a showcase that you can run a company the right way. You can treat people the right way. And the company can be successful along our own metrics of success. WILL: So, one of my biggest principles that I've learned in life that's changed my leadership 100,000% is from this book called One Minute Manager. And I think it's called one-minute praise. And, essentially, the background behind it is, if you think something, just tell the person because so many times...and I get in my head, and I think amazing things about people, but I never say it. JAMON: [laughs] WILL: So, I want to just tell you, like, you said, the impact that you're making. You are doing that. Like, one of the reasons why I invited you on the show was because of your impact that I see that you're having on Twitter and LinkedIn and just everything that you're doing at Infinite Red. So, keep going. I want you to know that you are making a difference. I see you, and it's making a big difference in my life. JAMON: I love that, and it makes me feel great. And I appreciate you sharing that one-minute praise there. It is something that sometimes you put it out there, and you don't really know what the impact is, you know, it's sort of hidden in maybe the likes, or the replies, or whatever. As an example, I just reached out to my friend Aaron Francis last night, and I told him, "Hey, I love your videos." I don't even do the tech that he does. But I watch his videos on YouTube because I just love the vibe that he has. And I told him that. I was like, "You're doing a great job. You're being a very good advocate for your company." And I agree with you; I think that just taking the moment to reach out and say, "Hey, I think you're doing good work," it encourages people to do more of it. So, I appreciate it a lot, Will. That's really nice of you to say. WILL: Yeah, definitely. If you can go back, what is some advice that you would give yourself? We could do both at the beginning when you did ClearSight and whenever you merged and did Infinite Red. Was there any advice that you're like, wow, I learned these lessons, and they were game changers for me? JAMON: [laughs] Boy, this could be a whole nother podcast, to be honest. There are so many different things that I've kind of learned over the years. I feel like, you know, there's value in, you know, there was actually...I forget exactly where I heard this, but it was about Cloudflare, the company. And a long time ago, as they were sort of launching, one of the people that worked on the...I think it was their founder, actually. One of their investors told him, "Hey, running a company is sort of like flying an airplane. You want to make sure that it's well-maintained at all times. And then, when you're flying, you keep the wheel steady and the nose 10 degrees above the horizon so you continue to rise. And you don't need to shoot for the moon. We're not a rocket here. Just continue to execute well, make sure that it's well maintained, make sure that you're continually rising." And Cloudflare is a good example of this, and I think that Infinite Red is as well. Every year, we try to do something where we're continuing to keep that nose 10% above the horizon. That doesn't always mean growing. Like, we don't hire all that often. We don't grow in terms of headcount, but we grow in other ways. And you can see that looking back over the years. Every year, there was something that we continued to, you know, improve, keeping that nose 10 degrees above the horizon. And so, that's a big one. And you can just go do all the little things really well and continue to think long term and where are you headed. And if you do the right things long enough, good things happen. WILL: I love that because, especially when I'm working out, I try to shoot for the moon. JAMON: [laughs] WILL: I go all out. So, that was some amazing advice. I don't even remember who told me, but when I first started programming, I tried to shoot for the moon. And, oh, I crashed and burned so many times [laughs] because it's just something you can't just master it, and just like, I got it, da da da. And I love that advice. That's amazing advice. So, that's perfect. JAMON: Yeah, it really stuck with me, and I have so many more lessons. I have actually kept a notebook of profound things that I've heard over the years, and I actually really enjoy that minute praising you said. And I'm going to look up the quote after this, and I'm going to put it in my notebook. [laughter] WILL: Yeah, yeah. It's been a game-changer because I'm a very straightforward person. And so, a lot of times, like, I don't mind addressing an issue just head-on. But what I found is I'm just always doing that. And I never had equity in the bank at times. This is when I was a very young leader. I didn't have equity. And so, it was just hard to tell people, "Hey, can we tweak this? Can we do that?" And then I had to sit back and say, okay, what can I change to be a better leader? And it's like, I can connect better. And I see so many things. Like, I'm very observant, I think. To be honest, it's helped me in every area, even with my spouse, with my kids, with friends. It's just saying, "Hey, I see what you did. I see that you made breakfast." Or "My kids, I see that you made this beautiful mud pie for me. And it's amazing. So, thank you. Thank you." And so, yeah, it's been a game changer for me. JAMON: Yeah, one of my friends, his goal was...and he's a leader. And he said that his goal with everyone on one was to give them one thing to change and highlight one thing they did well like you said, equity in the bank. He was talking about when he was a leader of, like, a call bank. And he said, "No matter how bad the call was, I wouldn't give them more than two things to improve because there was no way that they could take ten critiques and improve. They would just be defeated." And then, he would review and see if they could improve one more thing, avoided negative language, things like that. So, that's a really interesting concept. WILL: Yeah, definitely, definitely. So, I have one other question for you. What motivates you? What's your wind in your sails? What keeps you going? Because I know running a consultant agency is not easy. What keeps you going? JAMON: For me, motivation tends to be enthusiasm for learning, really more than anything, like going into something new and, like, exploring. I see it more as exploring even than learning. With a consultancy, there's always so many different...it's never the same, you know, there's always some other challenge. And that's one of the reasons I've loved being, you know, a consultancy owner for so many years. You're never dealing with just the same stuff over and over. So, I would say it's really about the exploration that happens, and just loving code, and talking shop, and being around great people. To me, that continues to motivate me. WILL: I love that. Do you have anything that you would like to promote — personally, Infinite Red, anything? JAMON: Well, Infinite Red, of course. If you're looking for React Native, we are all senior-level React Native developers. We've been working together for a long time. So, big companies, the biggest ones you can think of, many of them have hired us to, you know, be the experts with their team. We usually put 2 or 3 people on a project, and then the client will come in with 2 to 10 people or whatever they have on their side. And we work with them side by side, teaching them as well as delivering code. So, that's really our bread and butter. We also put on the biggest and, I think, only U.S.-based React Native conference, and it's called Chain React. It's in Portland. Next year, it's going to be in July. So, go check it out: chainreactconf.com. We'd love to see you all there. I'd love to see you there, Will. And network with all these different React Native developers. There's people from Meta, and Microsoft, Amazon, all over the world, really. And they're some of the best React Native programmers you're going to ever meet, and some great talks, and great food, and a great city. WILL: Yeah, I would love to be there. Let me ask you this: how is Portland in July? JAMON: Portland is amazing in July. Sometimes, it can get hot, but for the most part, it's just beautiful. It'll be like 85 degrees, not really any humidity, nice, little breeze. It's just a beautiful weather pattern around Julyish. That's why we chose that time of year. So, definitely, if you're going to be coming to Oregon, Portland, you know, West Coast, July is a great time to come. It's not going to be super, super hot, usually. Sometimes, I mean, we get over 100 sometimes, but no worries, you know, there's AC as well. But for the most part, it's beautiful. WILL: You sold me already. JAMON: [laughs] WILL: So, I live in South Florida, so...[laughs] JAMON: Yeah, it's going to be different in South Florida in July. [laughter] WILL: Awesome. Well, this has been an amazing chat, and just great getting to know you and learning more about Infinite Red. Thank you for being a part of the podcast. JAMON: Yeah. Thanks for inviting me, Will. It was a lot of fun, and you're a great host. I appreciate it. WILL: I appreciate it. JAMON: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantrobots.fm. You can find me on Twitter @will23larry. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guest: Jamon Holmgren.Sponsored By:thoughtbot: Now that you have funding, it’s time to design, build and ship the most impactful MVP that wows customers now and can scale in the future. thoughtbot Lift Off brings you the most reliable cross-functional team of product experts to mitigate risk and set you up for long-term success. As your trusted, experienced technical partner, we’ll help launch your new product and guide you into a future-forward business that takes advantage of today’s new technologies and agile best practices. Make the right decisions for tomorrow, today. Get in touch at: thoughtbot.com/liftoffSupport Giant Robots Smashing Into Other Giant Robots

thoughtbot's Incubator Program is back for a third round! This episode introduces founder Josh Herzig-Marks of Knect, and he will be sharing his journey from freelance work to joining the program and what happens throughout! So far, he appreciates the deliberate communication practices required for practical remote work, despite remote work already being second nature to him, and he understands the importance of proactive and transparent communication in a team setting. One critical insight for Josh so far was the misconception surrounding the term "CRM" in personal relationship management. His moment involved mislabeling a survey, which led to confusion about the project's intent. As the Incubator Program progresses and continues to scale, Jordyn expresses excitement about involving more teams with different geographic focuses. The goal is to foster a collaborative environment within the thoughtbot Incubator Slack channel, encouraging past and present participants to share experiences and advice. We invite listeners who resonate with any of the challenges heard or have potential solutions to reach out! Our next Incubator episode will introduce our other Session 3 participants, Mike and Chris, founders of Goodz. Follow Josh Herzig-Marx on LinkedIn or X. Visit his website at joshua.herzig-marx.com. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: LINDSEY: My name is Lindsey Christensen, and I head up marketing for thoughtbot. For anyone listening or joining who isn't familiar with thoughtbot, we're a product design and development consultancy that helps you make great products and help make your team a success. One of the very cool ways we do that is with the thoughtbot Startup Incubator, which is a program that we launched this year and that Jordyn, who's with us today, has been heading up. What's up, Jordyn? And today, what we're going to be doing is catching up with one of the latest founders who's participating in the incubator and seeing what he's been up to since the kickoff over these last two weeks. JOSH: It's been two weeks. It's been two really fast weeks. LINDSEY: [laughs] Josh, could you give us a little introduction to yourself? JOSH: Sure. I'm Josh. Hi. I've been in tech product management for, like, 20-ish years, 15 or so of those were in head-of-product roles. And a bunch of those early on were my own startup, where I discovered I was a pretty mediocre founder but really liked this product leadership thing. I had a very lucky exit, which I leveraged into a series of first product manager, first head of product, first product leader roles at a series of early-stage companies across a ton of domains: B2B, B2C, FinTech, mobile, Revtech. And then, a little over a year ago, my partner and I got to do this thing we've been talking about for a while, which was we swapped who the primary parent was. We have two kids, two teens, 13 and 15, right now, so that's eighth grade and ninth grade. I wanted to take over primary parenting so that they could focus as much or as little on their career as they wanted to in the same way they had allowed me to do for the first 15-ish years of our kids being kids. And if I were a better person, I would have found some kind of job that allowed for work-life balance, but I'm not. I have a whopping case of ADD, which we'll probably come back to later on in this conversation. And the way that I knew I'd be able to actually fulfill my responsibility as a primary parent was by retiring from salaried work. So, I did that a little over a year ago, last summer. And kind of keep me busy and occupied in between 8:30 in the morning, you know, school drop off and 3:00 o'clock in the afternoon school pickup. And when I'm not doing shopping, and cooking, and lunches, and doctor's appointments, and dentist appointments, and orthodontist appointments, and play dates, and soccer practices, and basketball practices, and soccer games, and basketball games, and Bar and Bat Mitzvahs, and all the other things that we do, I built a very small niche coaching mentorship and advisory practice around founders, solo product managers, and first-time heads of product. And that's pretty much up until about two weeks ago what I had been doing with myself. LINDSEY: That's a great update. I especially liked all the practices that you have to go to. [crosstalk 02:54] JOSH: I do like practices. We went to a co-ed soccer game for my middle school kid. And it was the first time that the boys' team and the girls' team ever played together, and they got totally clobbered by this other team. And what I loved about it at the end was the kids weren't bummed. They were like, "That was really fun." And, you know, for a lot of these kids, they've been friends since kindergarten. So, this is, like, nine years of being friends and playing recess soccer together. And they're not very good at soccer, but they just really love all playing together so much. And they just bring so much sportspersonship to the field. It was really a pleasure. LINDSEY: Okay. So, you're doing all this fun primary parenting and going to all the fun practices. You've got a coaching business that you're working on as well. But there was this idea, this idea that's needling. What brings you to us? JOSH: I think before it was an idea, it was a problem. And I knew this was a Josh problem. And the Josh problem was that I have a really big network, you know, built over the past, you know, more than 20 years of professional life. And, you know, one of the joke lines I have is that the solution to almost any business problem is found in talking to more people. I really value being able to, you know, call people up, message them, text them, email them, get together with them, ask them lots of questions, listen hard. And I try really hard to reciprocate, doing the same thing. I don't know what your professional network looks like, Lindsey or Jordyn, over the past, I don't know, couple years, decade, however long it's been, you know. But what used to be email and LinkedIn, maybe, and maybe getting together in some local meetups, has really spiraled what, to me, feels, again, whopping case of ADD, completely out of control, right? I have my LinkedIn network, which has not gone away, right? And now I'm a member of, I don't know, Jordyn, we share these a lot, a dozen different professional networking Slacks. Those are the ones that Jordyn and I share, probably far, far more than that, right? Product management ones, entrepreneurship ones, product marketing ones, engineering ones, tech company ones, ones geographically based for the Boston area, ones that are focused on things like climate change and climate tech. So, a ridiculous number of these. And as somebody with some experience and the privilege to have some free time, it feels kind of like, I don't know, an obligation sounds too grandiose, but it feels like a nice way that I can give back is by participating and trying to be helpful inside of these. So, that's happened. And Discord became a thing, you know, certainly, it had been a thing for gamers since before that. But since the beginning of the pandemic, Discord became a thing. I'm in, like, I don't know, a dozen different similar Discord groups. And I'm in WhatsApp communities, and I'm in Telegram communities. And in-person meetups have started to happen again. And I found myself kind of losing control. I was telling people, whether, you know, over the phone, or in Zoom calls, or direct messages, that I'd make connections to them, make intros, and it was getting increasingly hard to do that. I was forgetting about people, you know, like, it's hard to remember to stay in touch with all of your colleagues when you move on from past roles. And, you know, I would try to make connections to people to be like, okay, Lindsey, you know, you wanted to meet somebody else in marketing in the Boston area. And I remember that, like, six years ago, they worked at Rocket, and now they've moved on to something else. I can't remember what it's called. And, like, how do you, like, you know, page through your email and your Slack connections and your LinkedIn to find that person? And that was really hard, too. So, I have ADD. My family would say that I'm, like, moderately functional. So, how do I achieve that? By creating systems for myself. And I did all the things which other people have tried to do. I built myself, like spreadsheets and Notion databases. I have an awful lot of, like, Notion databases now powered by forms. I'm like, just put your information in, and it'll appear magically into my database where I try to, you know, push the work onto other people. And none of it was really working for me. And that was kind of the genesis of the idea and then trying to figure out, is this a Josh problem, or is this a broader problem? That's kind of how I got started. LINDSEY: Lots of people, lots of channels, not a lot of tracking or confusing tracking. And we chatted briefly before, you know, you were starting the program. And this really resonated for me. And I also ended up doing a user interview [chuckles] with the team about it. JOSH: Yeah [laughs]. LINDSEY: Because yeah, in my role, and moving from different companies or doing mentoring on the side, and being in investor communities and marketing communities, it gets overwhelming for sure. And I feel the pain. And I've had the embarrassing moments of not remembering how I know someone or a conversation we had, or someone I really respect asking me for an intro, and I'm like, I don't remember anything about how I know that person. JOSH: I mean, that was both gratifying and disappointing. Gratifying, like, oh, it's not just a Josh problem; we all struggle with this, and disappointing, right? And as I've had more of these conversations, just to realize, like, I know almost nobody who doesn't struggle with this. There's a few. There's a few outliers, a few weirdos, a few superheroes who are able to do this really well and who feel in control. And, like, literally, as they describe it, it sounds like...Jordyn, you're nodding, right? It sounds like a superpower as they're describing how they do this, how they kind of manage it. JORDYN: [laughs] JOSH: But for the most part, thank goodness it's not a Josh problem. The bummer is, nobody has, like, you know, the magic incantation, right? The spell or the secret or, like, the one weird trick, or the tool or, like, could I just give you money and solve this thing? And none of this really exists today. And that was kind of a bummer. I was hoping for, you know, better news that this was a solved problem. LINDSEY: [laughs] Yeah. Jordyn, heading over to you for a minute, Josh applied for the incubator with this problem that he was working on. We had a lot of great applications, I think, for this session. What made you think or you and the team land on Josh as one of our session three founders that would be a great fit for the programming? JORDYN: I'd say it was probably two factors; one is the stage. What's really tough was figuring out who's a good stage fit for us. So, like, what that means is you've identified a specific enough problem. You're not just, like, I want to solve world hunger or something, like, super broad. There's enough of a specific pain point or a problem that you're trying to solve that there's, like, we might conceivably make progress on it in eight weeks. But you're not so far along that you are basically like, "Hey, I've got the specs for an MVP. Can you just build it?" Which is, like, too late for us. And part of that is a discovery mindset of, "Hey, I've identified this pain point. I think other people have it. But I am very open to how we solve the problem or learning new things about it, learning that it is a bigger need in a market I've never thought about," like being open to the things we might learn together. So those things: stage fit, mindset fit. But, also, like, it is a problem that is addressable with software, right? thoughtbot's focus is software. Like, yes, we have worked on products that are not software products, but, like, our bread and butter is software. And my personal bread and butter professionally is software. So, is the problem on the table something that, you know, software is a big component in meeting the need? So, it's, you know, it's stage. So, I guess it's three things: stage, founder mindset, which is this combination of having conviction but being open-minded, a very weird [laughs] thing to find in a person. And then, you know, can we conceive of a way to address this with software without jumping to a solutionizing? That's sort of what we're looking for, and Josh checked all of those boxes. And I think, also, just had a problem that people really resonated [laughs] with, which is clear from [laughs] what Lindsey was saying and for me personally as well, I think I should [laughter] say. This is a problem I have. So, when Josh and I first talked about it, I was just like, yes, I would love to solve this problem. I also wish there was some spell, or incantation, or weird trick, or existing products, et cetera. JOSH: We might have spent an hour nerding out over all of the things that we've tried, yeah. JORDYN: The things that we've tried, emphasis on the nerding. JOSH: On the nerding part, yeah. JORDYN: Any of you listening [crosstalk 10:45] JOSH: Or what if we get sneakier connect Google Sheets to this, like, really weird web query and [laughs] -- JORDYN: [laughs] Exactly. And then giving up because it's totally unmaintainable or, like, [laughter] impossible, yeah. So... JOSH: Right. Oh, and it's all crap, too [laughs]. JORDYN: Right, right. So, if anyone out there listening is like, "Oh yeah, that's me," first of all, you're not alone. Second of all, please reach out to us. We would like to interview you [crosstalk 11:09] JOSH: Or, if anyone out there is like, "Oh, I have this thing solved," right? If you got the solution, please reach out to us. JORDYN: [laughs] Yes, also, please. JOSH: You can save us six more weeks of work [laughs]. JORDYN: If you know the solution, definitely tell us. Anyway, so to your question, though, Lindsey, that's how this [inaudible 11:23], and it just seemed like a great fit along those lines. LINDSEY: Yeah. So but, Josh, you mentioned...well, I think you kind of downplayed your founder history a little bit. But you've been a founder who had success, certainly a product team leader who has been very successful in the early-stage teams. What were you looking for from thoughtbot? Like, what attracted you to working with the thoughtbot team on your problem when you have all this kind of past experience already? JOSH: I think there's probably three parts to it; one is I know a bunch of people in the thoughtbot team pretty well. In past roles, I have actually hired thoughtbot; I think it was twice. And I've referred a bunch of your current and past clients as well. Like, I'm just generally a big thoughtbot fan. I think I've even used thoughtbot products long before I even knew, like, Chad or Jordyn, some of your old products from, like, you know, the early 2000s. So, we're going really OG here. So, I knew thoughtbot really well and think really highly of everybody who I've interacted with there. Number two is, I know, you say incubator, but, for me, the word that's really been resonating has been accelerator. It can be really slow the early, I don't know, weeks, months, years to go from an idea to, hey, this is really an opportunity. And I didn't want to spend weeks or years at this. I have a full-time job. It's, you know, taking care of the family. Like, that's what I wanted to be focused on. And if this was really an opportunity, I wanted to figure this out relatively quickly. And I love the fact that thoughtbot has this eight-week accelerating program. And the third one is I had this...and, you know, not every assumption I came in with was one that I'm going to leave the program with. But I came in with the assumption that a lot of the risk was technology risk. I had a rough idea. I was quickly discovering this wasn't just a Josh problem; this was a broader problem, right? There's plenty of challenges beyond that, but it's good to discover that your problem is broad. But is it something which can actually get built and built relatively straightforward? Jordyn here [inaudible 13:27] this all the time. You know, I don't like science project problems, right? And thoughtbot is really, really good at building software and partnering with somebody who could help to remove that kind of risk as a non-technical founder, as somebody with literally zero technical skills, I find that very, I don't know, comforting, exciting. LINDSEY: Okay, writes down in marketing notebook: "Accelerator resonating more than incubator." [laughs] JOSH: I wanted to get to the decision...incubator is a better word for it. But I personally wanted to get to that is this a good opportunity or a bad opportunity decision faster. LINDSEY: To quickly validate invalidate. JOSH: Right. I wanted this, like, I wanted to timebox this thing, and eight weeks is a nice chunk of time. LINDSEY: Love that, yeah. JORDYN: I want to just, like, flag here that, like, all of these words are very frustrating [laughter]. And we had a really hard time picking one. LINDSEY: I know [laughs]. JORDYN: And we really actually, like, in literal terms, I think that program is way more, like, founder bootcamp than anything, but thoughtbot can't run a bootcamp without people thinking it's a Rails bootcamp, right? JOSH: Yeah. LINDSEY: [laughs] JORDYN: Like, if we just said, "thoughtbot bootcamp," people would be like, oh, as a developer, I should go to this bootcamp, and thoughtbot will teach me how to be a better engineer, which would be totally reasonable from a brand standpoint, right? So, we were like, all right, not bootcamp. And then accelerator typically comes with investment dollars, in my experience as a founder, and we don't invest cash in the companies that we work with yet. So, that was off the list. And that just left incubator, which, eh, like, I don't disagree that it's not the best word, but, whatever, we lack a good one. JOSH: I'll tell you one thing. So, I'm involved with other things in this space. I'm based in Boston but for Raleigh's brand-new Founder Institute chapter, which I think is a great program. And I'm really proud of the, you know, first cohort of founders that are going to the program down there. And I love them. And I love their energy, and enthusiasm, and focus and that we at Founder Institute are providing them with value. I think we really are, or I wouldn't be participating. But I wanted people to work alongside me. And I think that's actually one of the things which is really unique about thoughtbot's program. This isn't, like, you know, a bunch of other founders with varying amounts of experience working alongside you. This is, like, actual people who do things: designers and software engineers, developers who are working alongside you and learning alongside you. But it makes it, I would say, less of a lonely process. This is one of the things I remember. When I founded a company, the one time I did this prior, I did it with my best friend, which is about as unlonely as you can possibly get. And it still is really, really lonely. Having this like, you know, team backing you up and a company backing up that team and organization is nice. LINDSEY: Thanks for sharing that about the loneliness factor. That kind of reminds me, Jordyn; I know in the last session, you were trying out the idea of, like, this founder emotion tracker. Has that made its way to session 3? JORDYN: Not really, mostly because both of the teams we're working with, two teams, by the way, not just Josh, have been founders before. And so, the emotional rollercoaster of, like, literally every day, you know, Monday, you feel like a million bucks because you have a really great idea, and you're really excited about it. And then, Tuesday, you talk to a bunch of people who add some complexity to the assumptions that you had [laughs] made on Monday. And then you start to feel like maybe this isn't a thing, oh no. And then, Wednesday, you learn about some, like, technical thing that you didn't realize was a stumbling block. And so, by the end of Wednesday, you're like, everything is doomed. I shouldn't even be doing this. I've just wasted everyone's time. But then the team wakes up on Thursday and is like, "Actually, there's an easy solution to this. And we've found a new group of people to talk to who have this problem in a really clear way." And then you feel like a million bucks again. And then you just cycle through it. Like, that cycle is something that Josh and our other founding team have actually felt before. And so, we haven't really been, like, leaning on the emotional roller coaster timeline as much just because it hasn't been as relevant. And that's kind of what's tough about the program we're running, which is that everybody comes to it with different assets in hand. I always think of that scene in The Princess Bride when they're outside the castle, and Westley is like, "What do we have? What are our assets?" It's like you arrive to this with different assets in hand. You might have already talked to 50 people, but you have no technical background. So, you don't know what on earth to do about the information that you've learned. Or, you know, maybe you do have a technical background. And so, you've done a bunch of solutionizing, but you haven't talked to a single person about [laughs] whether they have the problem you're trying to solve. Anyway, it really runs the gamut. And so, the programming is designed to help teams find focus and find market message fit. But what people roll up with is very different. In this case, we have a cohort, so to speak, that has some prior startup experience, especially as founders. And so, they know a little bit more about how every day is going to emotionally feel different. And that emotional rollercoaster workstream is on the roadmap. But we don't spend as much time with it as we did with Ashley and with Agnes before in the first two sessions because they were first-time founders and really didn't know how they should be feeling. And that, to me, is one of the many value adds, including what Josh mentioned, like just having a team diligently focused on your problem space full-time is a huge boost of momentum and confidence. Just, like, people thinking about the same thing you're thinking about with you and bringing their earnest efforts to solving the problem has been one of the main things people have found valuable about it, in addition to the acknowledgement that, like, you're going to have a lot of different emotions. And it doesn't mean anything necessarily. Like, your day-to-day emotion does not mean that you are a failure or that this is a bad idea or that you're a success, and this is a good idea [laughs]. Like, neither of those things is necessarily true. LINDSEY: So, let's chat a little bit about what has actually been happening since kickoff. So, two weeks ago, started. Jordyn, maybe I'll start with you. What has the first two weeks of programming looked like? JORDYN: We have been really heads down on interviewing. Josh rolled up having done a survey, which yielded a bunch of conversations already, conversations [inaudible 19:34]. So, we iterated on the scripts. You know, part of the efforts of the first couple of weeks are really geared toward having our team understand the things that Josh understands already. We need to kind of get on the same page. And so, we try to talk to as many people as we can because there's nothing...One of our theses here, beliefs, I don't know what the right word is, is that there's really nothing that drives momentum quite like team alignment, and there's nothing quite like talking to customers and hearing for yourself what their pain points are. That drives alignment. So, it's like, everyone's talking to people. I'm sure people out there have been on teams where it's like one person talks to customers, and they're translating to everybody else. "Here's what I'm hearing. So, this is what we need to build." And it's like if everybody has first-hand experience with the conversations, alignment and conviction sort of grows organically out of it. It's a lot less work to align if everybody's talking to people. So, it's always, like, the first order of business is, how do we talk to people so that we know the things you know to the level that you know them? So, we've been doing a ton of interviewing. And then, that's about driving alignment and understanding, but it's also ultimately about trying to drive focus. So, as we are talking to people and listening to them, we're really trying to listen for patterns and to map those to the market segments these people inhabit. So, like, every one of us has our own network that we're bringing to this effort, and so we start there. And we start where you are with what you have, right? I think that's, like, a Teddy Roosevelt quote: start where you are with what you have. Somebody said that. Anyway, so we all do that. But really, ultimately, we want to...building software is all about a repeatable problem that you can address with a one-size-fits-all [laughs] more or less product. What we're trying to find is, like, we're trying to listen for patterns and listen for pain points that are addressable and really focus in on a narrow niche or a situation context that we can address in some repeatable way. And I would say, at this moment, we've done a bunch of that interviewing. And we're now like, okay, we're feeling the need to focus, but we have not quite started that dive. I don't know, Josh, maybe you feel the same or different. JOSH: No, I think that's right on. I mean, you know, the first thing we all had to do was develop our own [inaudible 21:45] understanding of the problem and the potential user, right? It wasn't going to happen from me talking to people. It was going to happen from us talking to people. And then, the next step is to start to align that empathic understanding, which sounds like a thing that gets finished, but really, it's only a thing that gets started and never really ends. And then, you know, we got to be willing to make some bets, right? We got to figure out, you know, what is our hypothesis? You know, what do we think are the risky bits? And what are the things that differentiate this from being a problem? Where I think we have broad agreement across the entire team. And, literally, everybody we spoke to, the only people who don't think this is a problem are the ones who have some complicated, ridiculous system they built themselves, which they will acknowledge is not going to apply to anybody else. So, the problem is broad, right? But where exactly is the opportunity? Because at the end of the day, we're looking to build a business. LINDSEY: Josh, I saw your head nodding during the alignment discussion. How has it been aligning with the team around the problem you've been thinking so much about? JOSH: I don't know, Jordyn, how you feel about it. I've found it really fun. And it's been fun for a couple of reasons. I think the number one reason that I really like it is this is a really diverse team, right? So, Jordyn and I are in Boston and have; I would say, fairly similar tech company entrepreneurish sort of, you know, hand-wavy, miscellaneous tech people, startup folks background. We have somebody in Denmark, but she's Spanish. We have someone in maybe London right now, but he's Nigerian. And we have a member of our team in Saudi Arabia. That's a lot broader perspective. And I think that comes to play in, like, at least three different ways. They come with their own perspectives, and their own world experiences, and lived experiences, and values, and ways they talk about those things, right? Number one. They come with their own networks of people to talk to you for whom it's easy to reach. So, it's not just all hand-wavy, tech startupy folks like I'd be talking to. And, like, literally, my entire list is, like, oh, they're all people like me. Like it was really easy to get 60 people to want to talk to me because they're all people I've been talking to for a while, which is awesome and maybe a little bit uninteresting. But more than that, they all bring different language. Like, we've been struggling. Like, this is what we did. We spent what? Two hours of our hour and a half meeting this morning struggling with, like, are we having a difference, like, meaning or a difference of words? And it's not an efficient way to use your time, but it really is an effective way to use your time. Because, like, that struggle of trying to communicate what we're hearing and try to communicate what we're thinking and what we're feeling, I think, has led to a much better understanding of the problem and maybe even the opportunity than we would have had otherwise. I'm a big fan of struggle. JORDYN: Definitely. And I do feel like there's an element of this where you can never understand your customers' problems in too much detail. It's like every pass we do at this, we kind of have a deeper, more granular, nuanced sense of the problems. And just in that conversation this morning, we, like, took a problem that we had understood one way and, like, were able to break it down, like, okay, what are the actual pieces of this? Oh, there's, like, many pieces of it, right? Like you said, Josh, it feels inefficient, or sometimes it just feels like you walk out of a call and you're like, what was that about? And then only later do you find, you know, maybe when we are ideating, like, ways we might solve a problem, that conversation we had that felt really murky and, like, are we just arguing about semantics here? Are we arguing [laughs]...I don't know, like, however, you might frame that, like, actually becomes really important where you're like, oh, well, I'm very glad we took the time to break this problem down because now that we're trying to develop a solution, it becomes clear that there are many, little things we're trying to solve. And we can't solve them all at once. And so, it's great that we all have a fluent understanding of the details of that because it makes those conversations much faster so [inaudible 25:30]. JOSH: Can I say a nice thing about thoughtbot? I know this isn't, like, the, you know, [crosstalk 25:34] LINDSEY: Please. Please do. Welcome, Josh. Yeah, the floor is yours. JOSH: Let me say a nice thing about thoughtbot. The last time I did this, I did this with my best friend, Ben, a person I had literally known since I was six years old, maybe five, I don't know, since first grade. And we were entering a new space. This was, like, grocery marketing. And we talked to a crap ton of people, a lot of them doing things like going to grocery store headquarters and just talking to people and meeting people who are, like, manufacturers of a grocery product and going to trade shows with 60,000 grocers all in one giant room. Remember those days pre-COVID? We would, like, you know, take the samples with your left hand and shake with your right hand, and don't get those two things mixed up because there's a lot of people in the room with you. And we talked to easily 1,000 people, and we knew how to establish that, like, shared empathic understanding of the market and the problem really well because we were side by side. We were really well-practiced at having those conversations. And, you know, after the day of, you know, shaking hands, and meeting people, and introducing ourselves was done, we'd go back to the hotel room, shared, of course, because we were young entrepreneurs who couldn't afford to get nice hotel rooms. And we'd spend the next couple of hours, like, talking about it. We, like, talked to each other all the time. One nice thing about thoughtbot is you're really good at working remotely and working asynchronously. And if, you know, it had been up to me by myself to be like, okay, you know, Josh, you have this, like, remote team in different time zones with, you know, non-overlapping hours. How are you going to, like, work together to establish this common understanding, this common semantic model, this common syntax for talking about the problem, and the users, and the needs, and the opportunity? I'd be like, I don't know, right? And this is somebody who's, like, worked remotely for the past, I don't know, 5,6, 7 years, I mean, most of his job. But, like, still, that early bit is a thing, which, you know, I've seen a lot of thoughtbot practice and skill around. And it's not an easy skill to master. And it's one that you practiced organizationally. And that's really valuable. And I don't think I fully appreciated that until we got started. LINDSEY: Oh, thanks. Jordyn, any thoughts on that? Were you thinking about remote setup of the program, or at this point, it's just everything is remote? JORDYN: Working remotely can really deepen, in good ways, one's communication practices because it forces you to be intentional about communicating in a way that when you are co-located with people, you kind of don't have to because there's people in front of you when you talk to them. So, I agree, Josh, that thoughtbot does a good job of making that work, the work to communicate and stay on the same page, like, tangible, visible, whatever it is. That's also just something I've given a ton of thought to because I've been working remotely, like, as a primary orientation since 2010. And so, this is just, like, how I work. And it's very; I don't know, organic to my mind now that it's basically, like, if I'm doing something and I don't tell someone about it, it's like a tree falls in the forest, you know, if there's no one around to hear it. If I'm working on something and I don't tell anyone about it, it's like I didn't do anything. Communication is, like, 60% of the job. And the setpoint is, oh, I did something. Oh, I emailed someone. Maybe I should tell the team about this [laughs]. Just literally because you're not in a situation where I'm going to overhear a phone call that Josh is having because he's at the desk next to mine, or I'm going to, like, ambiently be aware that, like, Carol and Toby went into a conference room to talk about something. Like, while I maybe didn't consciously think about that, it's sort of in my periphery. Like, none of that is happening because we're not in the office together, right? We don't get to do the thing that you did with Ben, where we just talk about stuff because we're near each other. So, you really have to get into this practice of externalizing very proactively the things going on in your own mind with the team. And it's a challenge. It's work. It doesn't just happen effortlessly, right? But yeah, to say it's critical or to say it's a critical piece of how we approach the work is an understatement. I don't know, it's like, it is the work [laughs]. The making of the software, whatever, that's easy [laughs]. Communicating about making software that's hard [laughs]. So, I don't know, it's very heartening -- LINDSEY: Yeah, that makes sense. JORDYN: To hear, Josh, that you think that we do a good job of that. I think we're constantly trying to do a better job of it, frankly. I don't know if you can do [crosstalk 29:28] JOSH: That's probably why you do a good job. LINDSEY: So, I know a lot of the early weeks, days has been around alignment and doing a lot of these user interviews. Have there been any moments yet, Josh, any new, like, light bulbs for you or insights, or are we not quite there yet; it's more kind of setting the scene? JOSH: I'll share one really embarrassing one. LINDSEY: Oooh. JOSH: Which keeps on coming back to bite me. When I sent out the survey and, of course, I [inaudible 29:57] for everybody listening, basically, surveys are useless, except they're really nice lead generation tools for people who are willing to talk to you. But when we sent out the survey, at the top, it says something like, "Personal CRM survey." And I'm pretty sure that when I set up the calendar invite system, which is, by the way, for folks listening out there, like, you want to get your, like, operational side of this thing done before you start sending emails out because you're going to quickly, like, lose the ability to keep track of stuff. I think the meeting of it also, I said something like personal CRM survey. And it was, I don't know, sometime in the middle of the first week, maybe later on, when, like, I think we all realized on the team that, like, CRM is the wrong framing for this thing, right? Nobody likes CRMS [laughs]. CRMs are transactional. They're tools to sell something to somebody. You know, they are tools for, like, auditing your behavior if you're a salesperson to make sure you're doing what you're supposed to be doing. They're, like, on a cadence. Like, CRMs are tools for a world, which is not what most people aspire for their personal relationships to be. And I don't think we've quite settled on what this thing actually is. And maybe there isn't a thing yet, right? Maybe that's part of the challenge that we're having, like, this thing doesn't exist, but it's not a CRM. And three-quarters of the way through the interviews is when I asked people like, "So, what question should I have asked you?" They all said, "Well, you didn't ask me about personal CRMs at all." I'm like, "Okay, that's a good point [laughs]." So, there have been plenty of pivots inside of my head around this and the way that I think about this problem, and some of these things are still embarrassing and still kind of coming back to haunt me and maybe haunt the rest of the team as well. I don't know, Jordyn, what [crosstalk 31:27] LINDSEY: Honestly, I was hoping for something way more embarrassing, but [laughs] -- JOSH: Way more embarrassing. JORDYN: If that's your embarrassing...[laughs] LINDSEY: Yeah, you're doing great. You're doing great. JORDYN: You're doing great. JOSH: Okay, the number of video calls where I'm not wearing pants. [laughter] LINDSEY: Okay, onto the next question, Jordyn –- JOSH: Embarrassing or awkward, I don't know, yeah. [laughter] LINDSEY: Jordyn, you mentioned that Josh is not the only participant in this [crosstalk 31:52] JORDYN: Great question. LINDSEY: Tell me about, why not just Josh? What's going on? What are the developments there? JORDYN: Yeah, this is really exciting. So, we wanted to scale this program from the moment that we ran single companies [inaudible 32:08] to start because we wanted to learn as much as we could in a kind of intense, focused way from developing a process and seeing what's valuable about it. So, this was always kind of on our minds to do. And the way it worked out was just that there were two teams at thoughtbot ready and willing to serve. And we had, you know, anytime we [inaudible 32:28] the application window, we always kind of have a list of folks that we're excited about. We can't take all of them. But in this case, we had the two teams. And it also kind of fell in this nice way where we've got this team with a center of gravity, you know, GMT center of gravity, essentially. And then we have another team, which has more of a, like, U.S. center of gravity. And so, the timing kind of worked out. And yeah, I don't know, it wasn't anything more complex than that. It's just we'd always been on the lookout for how we could scale this effort––bring it to more folks. And this was the first opportunity where it appeared like it would work out. I mean, TBD if it's working out [laughs]. We can decide at the end [laughs]. But it's very exciting. It's fun. And we're really looking for ways to help these teams collaborate, you know, we'll see how. Everybody's in a Slack channel together inside of thoughtbot's Slack called thoughbot incubator. And our past participants are in there as well. And we're really trying to create an atmosphere where people can help each other, share tips, talk about what they're working on. There is actually some intersection between what Josh is working on and what the other team is working on, I think, just because, Josh, what you're working on applies [laughs] to a lot of people. I think it applies to these people, too. Anyway, that's [crosstalk 33:42] LINDSEY: It's fun to see the incubator Slack start to build out and folks talking to each other, and more thoughtboters are trickling in there. Because, Josh, you mentioned you've been a client before and a thoughtbot fan in the past. And now you can officially live in thoughtbot Slack, too, and hang out with us 24/7. JOSH: Still just a guest. LINDSEY: [laughs] JOSH: Only got my two channels. Can't DM you unless you're in one of those two channels. LINDSEY: One [crosstalk 34:11] JOSH: But yes, it is very exciting. This is better than snacks at your downtown Boston office. LINDSEY: Yeah, that's great. JOSH: I think I even added an emoji to Slack. I was pretty happy with that. LINDSEY: Oh, nice. We've got a good custom emoji library. JOSH: I mean, that's what we have for company culture, right? Is company emojis. LINDSEY: To kind of finish this out here, Josh or Jordyn, do you have any calls to action for our viewers or listeners, maybe interviews or survey participants or anything else? JORDYN: Well, certainly, if the pain point we described resonates for you [laughs], reach out. We would love to interview you. Or, like Josh said, if you actually have solved this problem [laughs] -- LINDSEY: Oh yeah, that was a good one. JORDYN: Please reach out [laughs]. That would be amazing. JOSH: But I actually meant that. So, like, hey, if you out there are a software developer, an entrepreneur, own a company that you think has really solved this, I would love to learn from that if you want to talk to us. If you are a person who struggles with this and feels like you've tried really hard to solve this, I'd love to hear from you as well. You know, did you search for a tool? Did you ask your friends? Did you try to build something yourself? Do you still use that thing you built yourself? Did you try one of those CRMs? [crosstalk 35:26] Did you try a personal CRM tool out there, right? Clay, Dex, Monica, folk, if those names resonate with you, like, I want to hear, right? I want to hear about people who feel like they're doing this thing really well or people who don't feel like they're doing as well as they should but who feel like they've put, like, real effort into it. LINDSEY: Great. Well, we're going to be catching up with Josh here every other week. JOSH: Great. LINDSEY: We'll have some updates on the thoughtbot blog. And in our alternating week, we're going to be catching up with the other founders going through the incubator. So, next week, we're going to chat with Mike and Chris. And y'all will get to meet them and hear a little bit about their journey and what's led them to validating their idea in the thoughtbot incubator as well. JOSH: And strong rec people to tune in for that one. They are extremely photogenic and very funny, and they talk slower than me, too, so a greater chance for people to understand what they're saying. So, all in all, definitely tune in for that. LINDSEY: That's a great promo. If you want to stay up to date with the incubator or are thinking about applying for the next session, I think will be in the new year, you can go to thoughtbot.com/incubator. And you can also sign up for email updates. And we can make sure to send you recordings of these interviews as well as the blog updates and then keep you up to date about when applications open and end. Jordyn and Josh, thank you so much for joining today and sharing what's been going on in the early days. It's really exciting to follow along. All right, have a great day. Thanks, everyone, for watching. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guests: Jordyn Bonds and Josh Herzig-Marx .Support Giant Robots Smashing Into Other Giant Robots

In this episode, the focus is on RubyConf, the upcoming conference dedicated to the Ruby programming language. They start by talking about the origin and evolution of RubyConf, highlighting its growth in attendance and its impact on the Ruby community. Chelsea details how the conference has adapted to the digital format due to the COVID-19 pandemic but points out the value of in-person connections. They are looking forward to the Community Day event, which will feature various activities to encourage community interaction and an acknowledgment of scholarships that would help more people attend. The event will offer various programming options, workshops, and talks to cater to newcomers and seasoned professionals. There will also be some level of hands-on learning through hacking activities. The conference aims to be inclusive, offering opportunities for mentorship and growth, regardless of one's career stage. Towards the end, the discussion shifts to Ruby Central, the organizing body behind RubyConf and RailsConf. Chelsea and Allison describe multiple avenues for community engagement, ranging from board membership to open-source contributions. They also encourage donations and corporate sponsorships. Don't miss your chance to register for RubyConf and engage with the fantastic Ruby community! RubyConf Follow RubyConf on LinkedIn, X, YouTube, or Mastodon. Learn Academy Follow Learn Academy on Facebook, X, LinkedIn, or Instagram. Follow Chelsea Kaufman on LinkedIn or X. Follow Allison McMillan on LinkedIn or X. Visit her website at daydreamsinruby.com. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Allison McMillan and Chelsea Kaufman, Board Directors, and RubyConf '23 Co-chairs. Thank you for joining me. ALLISON: Hi, thanks for having us. CHELSEA: Thanks for having us. VICTORIA: Yes, I'm glad that you were able to make time to come on the show today. I understand, Allison, that you've been having very full weeks with family over the last month. Do you want to tell us a little bit more about that? ALLISON: Yeah, it's...we have just ended what I call the gauntlet of Jewish holidays. But, basically, there are four Jewish holidays starting with Rosh Hashanah, which many folks know that's the Jewish New Year. But what a lot of folks don't know is that there are actually four holidays that are all in a row, each about a week apart. And you do different celebratory things for each of them. And so, it's been really amazing and fun, and lots of, like, sharing our home with others and meals and seeing lots of people. But it is also exhausting. And they basically all fell on weekends this year, which was nice from sort of a scheduling perspective but was exhausting in the fact that I basically have not had a weekend in over a month. So, it was wonderful and tiring. And I am, I guess, both happy and sad that they're over now. VICTORIA: Yeah, that does sound like a lot of quality family time, which has its pros and cons [laughs], right? So, after going through that, do you feel more rested? Or what do you feel like you need to do in order to recuperate and return to your normal energy levels after having every weekend full after that? ALLISON: Oh, that's a great question. I've been looking at my calendar to be like, I should take a day off. I should take a break. I'm working for myself and [inaudible 02:02] entrepreneur consultant. So, I do have the flexibility to do so, but it is hard to look at my calendar and be like, yes, I will take this day off because I deserve it. But, ideally, I would take a day or multiple days off. VICTORIA: Yes. And some of us are lucky enough to have a reason to travel for work purposes and to sneak in a little vacation and be productive [laughs] in our companies. So, I'm curious, Chelsea, if you can tell me a little bit about the option for people to come to San Diego in November and take a restful vacation by the beach and learn a little bit more about Ruby. CHELSEA: Yeah, so RubyConf will be in San Diego this year. As a native San-dieagan, I am a bit biased, but November is a beautiful time to be in San Diego. And we're going to be at the Town and Country, which feels a little bit like we're going to be in a, like, Palm Springs resort. They just went through a major renovation. And there's these really awesome, like, lounge areas with fire pits and just places for people to gather, which really kind of aligns itself with some of the stuff that we're planning because we're really trying to focus in on just connecting Rubyists together. So, to me, it feels like the perfect place because I think San Diego is, one, we're a little bit more low key, a little chill. And it's a great place to just gather and connect and share with people that have, you know, similar interests. VICTORIA: Yes, I live in San Diego now, but I was from Washington, D.C., And I would come and visit my family in San Diego once a year. And they would always go on about how great it is and how beautiful, and everyone is so happy and chill. And I was like, sure, whatever. And then we [chuckles] had the opportunity to move here, and now I'm one of those people who says that [laughs]. Like, it's great, especially in November. Everywhere else is getting a little cold and fall. And San Diego has a little bit of fall, but it's still 75 degrees out. I forget what that is in Celsius. But yes, I'm also super excited. CHELSEA: We have, like, fake fall activities that you can go do. Like, Allison, when you're talking about doing all the family activities and things like that, you know, this is when we start thinking about, oh, we need to go to, like, the pumpkin patch and apple picking and do all these things, but it's not cold or, like, fall weather at all. So, you want to get all, like, bundled up in your cute fall clothes or, like, put my kids and bundle them up in cute things. But then they're, like, sweating and trying to do [laughs] all these funny activities. But I think that there's so many beautiful things to do here that we, like, try and do these, like, fall activities. But then we just end up at the beach and play in the sand [laughs]. VICTORIA: Yeah, I will go out in, like, shorts and a T-shirt because it's that kind of weather. And my neighbors will be wearing full puffy jackets and [laughs], like, long pants and a hat. And they're like, "You're not from around here, are you?" [laughs]. It's like, you guys are silly. But it's fun. Yeah, there's seasons, I think, you know, in November...I made a list of suggested activities for my team members since thoughtbot is sponsoring RubyConf this year. And we're going to have a couple of speakers at the event. And we'll have other thoughtboters available at our booth for people to come up and chat with us. So, I'm really thrilled to be hosting everyone. And I made a list of, like, activities, and most of them were about where to see cool animals [laughs]. I was like, of course, there's the zoo, which is the obvious one, but then there's baby leopard sharks, and there's a season for them. I think they will still be around in November; I'm curious if you know, Chelsea, actually. And then there's, like, the safari parks, and whale watching, and the sea lions at La Jolla and, like, just a bunch of cool animals to see that I think it makes San Diego really special. CHELSEA: I agree. The zoo, the safari park are great places to just hang out and see some really cool exhibits. Balboa Park, the museums there are amazing. Liberty Station is one of my favorite places to go; that it's an old historic naval training center that's been converted into an arts and culture area. So, they have, like, little shops. They have...there's museums. There's brew pubs. There's coffee shops. And then there's beautiful, like, grassy areas, and right by the water, it's one of my favorite places to just go and hang out. ALLISON: This is great. I've done zero research on San Diego so far. So, just, like, I'm writing notes of what things to do and see while I'm there. CHELSEA: Yeah, I know the San Diego Ruby group is trying to put together some, like, local events and things that people can gather and do together. I know that there was a talk about doing a taco crawl. I think if I say that on the podcast, it might actually push them to do it because there are some amazing tacos in San Diego to be had. VICTORIA: Yes, I love that taco crawl. I'll reach out to them because I'll help put something like that together. I'm writing a blog post right now about all of these things and about all the other kind of events that are coming up in San Diego this fall. Great location, great time of year to be here. Tell me a little bit more about RubyConf specifically. And what are you all trying to do different this year than in past events? ALLISON: There are a bunch of things that we're doing differently. Our goal this year with this RubyConf is really to sort of focus on more ways to bring the community together. I think in the last little bit so much excitement around Ruby and Ruby Central and just sort of the community in general. It's a hard time in tech. I think people need to be sort of choosier about sort of what they attend and why they're attending something. And so, we really wanted to help folks connect with each other, help folks get to know other people, help folks sort of reconnect to ways that they love Ruby and the Ruby community and being a Ruby programmer. So, one of the things that we're doing differently is we have a three-day conference. And the way that that sort of broken down is the first day is a Community Day. And the first day is comprised of the workshops, as well as sort of this Hack Day, where people can bring their own projects. We're going to have people there that folks can hack with, sort of open-source projects that folks can work on, all sorts of different stuff. So that people can really sort of get to know one another, work with one another, work with people that they might, you know, admire or have followed in the community for a while, and have that sort of really special experience that doesn't feel as conference-y, right? It feels a little bit more sort of organic in terms of the way that the day will flow and, the options that people have, and sort of what that day looks like. And then following that, we have two days of sort of RubConf with talks and speakers, et cetera. And I'll let Chelsea add anything to Community Day and then also jump into some of the sort of new and different things we're doing at RubyConf. CHELSEA: I agree with Allison in that we've really wanted to focus in on the connection side of things. But I think coming out of the last few years, out of even the last year that's been tough in the industry, just finding ways for people to connect, support, lift up each other, I think that that was something we really wanted to do. And we didn't want it to just be about going and seeing speakers. We wanted to find more ways for people to learn from each other, to connect. And so we added in quite a few of these community connection points. So, on that first day, there's a lot of community aspects to it. We have a lot of learning happening with our workshops and also working on projects, hacking together, showing off what you're working on, connecting with people in the community. It's going to be really focused in on everyone's own skills and talents and coming together and supporting each other in where we're at in our careers, in our learning. And then, the next couple of days will look a little bit familiar in the way that it is structured with some new aspects kind of woven in. We'll have our Community Room, where we're bringing different community groups together so that people can learn more about what is going on in the community, how they can support, how they can connect. And in addition to seeing and learning about some of the new things happening in the Ruby community, we'll also have our Career Pathways room again, which will be a place for people to support their own careers. And that room was really set up so that it wasn't just about early career, but also about folks in their mid and senior careers, and finding the advice, finding the resources, finding the mentorship that they might need in whatever stage of their career that they're at, and figuring out how we can together as a community grow as a whole. VICTORIA: I really appreciate the focus on community. And, for me, as managing director at thoughtbot, in deciding to invest in which conferences we want to attend and sponsor, we find more value in groups that are trying to bring people together around a common passion and purpose versus a particular product. But I'd like to hear from each of you if you can tell me, what does the community mean to you? And I'm looking for, like, a personal story on how you've benefited or how you've engaged with the Ruby community in the past. And what makes you motivated as CEOs and founders of your own companies [laughs] to spend all this time organizing a conference? ALLISON: Many, many, many years ago, I did a Rails Girls workshop. It was actually my first introduction into the tech community, into programming in general. And, for me, really, I did Rails Girls. I did not actually expect to like programming. But I was sort of launching a startup, and I wanted to learn more about tech and blah, blah, blah. And at the end of the day, I was, like, so energized and so excited about what I had built and what I had done. The Ruby community in D.C., who I always think is just a group of really special individuals, was so supportive, was so wonderful, was so, like, "Here's where we co-work on Wednesdays. Come to this coffee shop. Here's how you can keep learning," just was so encouraging. You know, I went to the local Ruby meetup sort of really not knowing anything. And they were excited about, you know, newbies being there and asking questions and, you know, really sort of getting to know folks who are just starting out in their programming journey. And really, through that, I mean, I went to my first RubyConf as a scholar. Was strongly encouraged to do a lightning talk, did a lightning talk. That's how I, you know, sort of ended up having a whole bunch of informational interviews and having conversations with folks. And really, that's how I got my first real job in tech. And so, you know, I want people that are coming into the industry now to have that same support, to have those same opportunities, to have that same encouragement. And, for me, sort of planning RubyConf, planning these conferences, being a part of Ruby Central is really me giving back to the community that has gotten me to where I am today, right? And it's amazing, also, to just...I'm still in touch with the people that were at my table, sort of guiding and mentoring at that first Rails Girls session or the people who I met at the first-ever Ruby meetup that I went to. I still talk to them. I'm still in touch with them. We still get together. I still ask them for, you know, advice and guidance sometimes. And sometimes, they ask me, at this point, for advice and guidance, which is fun. But yeah, it just means so much to me that I have really been able to get to where I'm at because of the support and encouragement of the community. CHELSEA: I have a similar story. I guess over, gosh, over a decade ago, I also went to my first RailsBridge and got introduced to the community there at RailsBridge. And, you know, at the time, I wasn't in tech. I was in the theater. I come from the performing arts. I had spent a very long time executive leadership in the theater. And I got introduced to this community that was so warm and welcoming to people wanting to learn and grow. And I was so interested in how communities are built and how people connect together that I started getting more and more involved in the Ruby community here in San Diego. And just like Allison was saying about the welcoming and warmth that she felt from the D.C. community, I felt the same way here in San Diego. Before that, you know, I had spent so many years being the only woman in a room. I had been in an industry that made me feel like my voice was not always heard. And when I walked into this room, I felt like I mattered. I felt like people wanted to hear what I had to say. And they wanted to learn from my experiences. And in 2014, San Diego hosted RubyConf here. And at that point, my business partner and I launched our business, LEARN Academy, and it's still running strong today. But it was about creating that on-ramp for people and a launchpad into this industry where they could make a difference and they could have their voice heard. And they could be a part of a conversation, even if they hadn't been a part of that community for many, many years, that their background mattered, that their growth mattered. And helping people find their voice at a table is something that is so important to me that I love being able to bring that into the planning of this conference, into a lot of the work that I've done with Ruby Central, with LEARN academy. And really just helping people understand that just because you don't have the traditional background, maybe you didn't start programming at the age of two, you can have a different background and a different path and still provide so much value. And I think that that is the thing that I wanted to continue to be a part of and to make sure was a part of the conversation, that we need so many different types of people at the table. And I want to make sure that our community is responsive to that, that it's inclusive to that, that it's equitable as best we can, and just allows people to share their own experiences. And so, you know, I feel like, for me, we're, you know, almost at our 10-year mark at LEARN academy and that we were launching the company at RubyConf in 2014. To have it here again this year is so special to me. I remember being at the conference many years ago; you know, we spend a lot of time helping companies figure out how to work with early-career developers and to create those pipelines for them so that there's career growth for them. And, you know, I remember sitting around the table and just saying, "Hey, who wants an internship? Who wants to, you know, help these early-career developers?" And everyone raised their hand, and we found some of our very first partners at that conference. And it's always been such a warm and welcoming community that has allowed me to feel like I have a voice and then allows me to help other people find theirs. VICTORIA: Wow, thank you both for sharing that. I totally relate to that feeling of a welcoming community and just getting the sense that, like, wow, everyone who does Ruby is really nice [laughs]. And I think that you know, for me, same as Allison, starting in D.C., there were quite a few people who were involved in Women Who Code who were running Ruby meetups. And that's where I met Valerie Woolard, who I think is also coming to San Diego for RubyConf. I'm excited to see her again. And it's interesting for me coming from that perspective and hearing that from both of you because I've also heard a viewpoint on Ruby community as being highly opinionated and causing certain amounts of consternation. So, I'm curious if you have any comments on that. If not, otherwise, I'm grateful that there are people working to bring that better community in the community that I'm more familiar with more to the forefront and making it more inclusive and open for everyone. So, to, like, bring the question all the way back, it's like [chuckles], do you have any comments on, like, if there's a tendency for Rubyists to be really highly opinionated? Or what else can we do to make it more open and inclusive for people to join the community? CHELSEA: I mean, I think that people are going to be opinionated about something that they care a lot about. And I think that the thing that I've noticed in the Ruby community is people love this language. They love programming in this language, and I think that there's something very powerful about that. And it does, you know, lend itself to people [laughs] having very strong opinions about what they think needs to be out there. And, to me, it's not a matter of, like, whether we have strong opinions or not. It has more to do with whether we're listening or not. But I think it's really important for those of us who are leading to be the listeners, and that we should be there to make sure that there is space for people to be heard, whether their opinion is loud or not. And I think that there are people that are going to be louder than others; that is going to be true no matter where we go. But I think that as long as there is intention around making sure that we are listening to even the quietest voices and that we are creating space for the quietest voices, that's where we're going to find more collaboration. But if we're only going out there and saying, "This is the way it needs to be," and we're not willing to listen to anything else, then I think that growth will stop happening because we need to listen to everyone. We need to be able to create some kind of place for people to come together and share ideas; you know, you don't get the perspectives of all these amazing people in the industry. So, that's why I feel like, you know, I've been on the board at Ruby Central for about a year now, and the biggest thing that I feel like I can contribute is to simply listen. If I can help in any way of filtering ideas or creating connections with people because I've been putting my ear to the ground and saying, "Okay, these people are talking about this, and we're expanding here." And we just want to make sure that we're doing the best we can at being open to all different kinds of ideas and not closing anyone off. Maybe your opinion is really strong. It doesn't mean that we should shut you down. It just means that we need to make sure that there's space for other people, too. And I think that that's the part that, you know, as someone who has always been a bit of an introvert, a bit of a wallflower, I understand how hard it is to get my voice out there. And so, I often fight for the quiet people. I think in every language and any space where it's a craft, it's something that we're creating, people get really passionate about it. And that's going to happen. And I think there's something powerful in that because there's going to be change that happens from that. But if we're not doing our part in the listening and making sure that there isn't just one voice, that there's a collective voice, that's the part that I felt so powerful when I joined the community so many years ago was that, even though I had, you know, months of experience, my questions mattered. And as long as we hold on to that, the community will continue to grow. But those of us at Ruby Central and some of the other organizations, if we're creating space to allow people to question, allow people to speak their opinions and listen, then I think that the industry, the community will just continue to thrive because of that. But we have to be open, and we have to be compassionate when we're doing our listening. ALLISON: Yeah, I agree with all of that. And I would just add in safe places, in a way that we're creating sort of safe structures and safe places for folks to communicate. MID-ROLL AD: Are your engineers spending too much time on DevOps and maintenance issues when you need them on new features? We know maintaining your own servers can be costly and that it’s easy for spending creep to sneak in when your team isn’t looking. By delegating server management, maintenance, and security to thoughtbot and our network of service partners, you can get 24x7 support from our team of experts, all for less than the cost of one in-house engineer. Save time and money with our DevOps and Maintenance service. Find out more at: tbot.io/devops. VICTORIA: What, if you could tell me, what does Ruby really have going for it? Like what makes Ruby a good choice for tech founders or for new companies would make someone decide they want to build with Ruby? ALLISON: First, it's a little bit about just sort of the ease of the language to jump into and to understand, right? There's a lot that you can get done very quickly with Ruby and Rails. And in addition to sort of individuals being able to work in it, there's a whole community of resources, and support, and podcasts, and tutorials, and all sorts of stuff. I know that as an engineering leader at any company, when engineers are coming to me with, like, the desire to use a new language or try something new, part of what I look at is, if I'm going to hire, like, what would hiring look like? What does it look like for engineers to have to ramp up in this area? How long does that take? What resources are available? What sort of community am I pulling from and looking at? And that's both community in terms of sort of technical experience, expertise, years, et cetera, but also non-technical skills, right? What does the community look like in terms of some of those ideals around communication, collaboration, just sort of general pieces like that? And so, I think that, given sort of the strength of open source, strength of community, community contributions, ways to contribute, etcetera, I think that's one of the reasons that it still makes Ruby a really strong choice for folks to build in and to work with. VICTORIA: What type of people, what personas do you think will be the most interested in attending RubyConf? Is it all just going to be, like, senior or super Ruby developers, or what? CHELSEA: Oh, I don't think so. I mean, this RubyConf, in particular, is great for anyone on a learning journey. We've worked really hard to make sure there's a good breadth of programming for different folks in different stages of their careers. I think that, you know, those of you that are maybe earlier on there, this is a great opportunity to meet people who are maybe even a step or two ahead of you. I think that the best mentorship that you can find is someone who is only maybe a year ahead of you because they're going to recognize where you're at and help you along the way. And I think that there's a lot of opportunities here for that. I think that with our Community Day, the hacking that's going to be involved, like, maybe, as a new developer, you wouldn't be able to come in and, like, get your hands really dirty. But you'll get to sit next to somebody who has been through all the different stages and get to watch, and explore, and learn. I think that making those connections could be really great for anyone's career. I think that our mid-level developers, folks that are our management, there's great resources for them to connect with other developers in similar stages. There's great workshops. Because of our focus on the community, I think that it's going to be a place where you can really connect with other Rubyists. And so, if you are at a stage in your career that you want to figure out what that next spring is, where that next ladder step is, this is a good place to see all the different options because you're going to be surrounded by people in all different stages of their careers. And what we've, I think, said now quite a few times is so many people there are just so excited to help people continue that growth. And so, I think that no matter what stage you're in, you're going to find people there that are excited to help you along the way. That being said, I think for our more senior, more advanced, our executive leadership, this is going to be a great place to, one, meet some really great talent, and, two, I think, learn from other folks in the industry of, like, where people are at, what we're struggling with, and how we're changing and doing things differently. So, I really do think there's going to be a little bit of everything for people. And what I love about that is really that it gets to the core and heart of the Ruby community because we're so excited about new folks coming in that that growth continues, that you have folks like Allison who started out as a scholar and want to give back. And then because we have folks at all those different stages, you can find people that are, you know, maybe a step or two ahead of you that are going to be able to help bring you up to that next level. So, I think it's an exciting opportunity for people to really meet new people, learn some new things, maybe find a little bit of encouragement, empowerment on where you're going to go next on your career. VICTORIA: Yeah, absolutely. And it reminds me of an article I read while I was at RailsConf earlier this year about why we do conferences and what's the whole point. And, you know, for me, all of those things are true, like, all those values. As an executive, I'm going to meet a lot of great talent. I'm going to connect with other companies. I'm just going to get to show up and say hi to people and ask them questions in a way that's very informal. And that's so valuable to have that. I think where I was going to go next with this was with Ruby Central, which I believe organizes both RailsConf and RubyConf. (And you can correct me if I'm wrong on that.) I'm curious if there are anything else you want to talk about with, like how the community can engage in support and how other companies could get involved with the community and show their support. CHELSEA: I think that there's quite a few different ways for folks to get involved. We are currently recruiting board members. We just finished a round just now. But I know that in our planning, that we're likely going to bring on at least one, maybe two more, in the next six months. So, I definitely...for folks in the community that want to get involved, that is a really great place to really get involved with Ruby Central. We also have a really strong open-source community. And we're working, oh gosh, with quite a few different companies now that are really helping to support our open-source efforts. And those are also good ways to get involved. You know, we do plan both RailsConf and RubyConf. RailsConf will be in the spring again. And, you know, it takes a village to put on a conference like this and that, you know, we also look for programming committee members to help us shape the program of the conferences. So, if you are interested in any of that, that's also another great way to get involved in the community. We have an amazing programming committee that's helped us with RubyConf. And I'm excited to see what we do next with RailsConf. And I think that you know if you're one that's going to the conference and are saying, "Man, I wish that they would do this," or "I wish I could see that," come and talk to us because that's the best way for us to learn, that we want to hear all of those pieces. But don't be surprised if we then send you an email and say, "Hey, you want to be on our programming committee with us?" ALLISON: I'll add that we also, through our website, we take donations. So, if you want to help monetarily, there's the option to do that on the website. And if you're a company, I mean, we're always looking for conference sponsorships. But if your company also is interested in getting involved in sort of more of a corporate sense of sponsoring or supporting Ruby Central, we are always open to those conversations. You can send an email to contact@rubycentral.org. VICTORIA: That's great. I have a fun question about the conference because I'm leading the event with thoughtbot since I live here. And I'm thinking about some fun swag to give away. Rank your preferences on what kind of swag you'd like to see at the thoughtbot sponsor booth: a thoughtbot-branded surfboard or, a boogie board, a bucket hat, or a pickleball paddle. Any of those interesting for you? ALLISON: Wait, when you say surfboard, like, how am I going to get a surfboard back to D.C.? [laughter] VICTORIA: Okay. I think it's, like, kind of funny because if you win it, it's like, well, what do you do? [laughter] You got to shake it back. That sounds like maybe a boogie board. CHELSEA: Yeah, I'm down for a boogie board. VICTORIA: Thank you so [laughs] much for entertaining me on that one. Is there anything else that you would like to promote today? ALLISON: We would love to see everybody at RubyConf. You can register. Check out the program speakers, et cetera, at rubyconf.org. You can learn more about Ruby Central at rubycentral.org. Those are, I think, the two things that we'd love to make sure everybody knows about. CHELSEA: And if you're here in San Diego, come say hello. VICTORIA: Yes, I have met up with a few random people from the internet [laughs] who have said like, "I'm in San Diego. Who should I say hi [inaudible 34:02]?" I was like, "Me, me, me," [laughter]. So, yes, I'm very happy to meet up for drinks. Chelsea, you and I will have to get together sometime soon before the conference. And I'm super excited for RubyConf. And thank you both so much for being here today. ALLISON: Thanks for having us. CHELSEA: Thank you. VICTORIA: You can subscribe to the show and find notes along with a complete transcript for this episode at giantrobots.fm. If you have questions or comments, email us at hosts@giantsrobots.fm. And you can find me on Twitter @victori_ousg. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. See you next time. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guests: Allison McMillan and Chelsea Kaufman.Sponsored By:thoughtbot: Are your engineers spending too much time on DevOps and maintenance issues when you need them on new features? We know maintaining your own servers can be costly and that it’s easy for spending creep to sneak in when your team isn’t looking. By delegating server management, maintenance, and security to thoughtbot and our network of service partners, you can get 24x7 support from our team of experts, all for less than the cost of one in-house engineer. Save time and money with our DevOps and Maintenance service. Find out more at: tbot.io/devopsSupport Giant Robots Smashing Into Other Giant Robots

Dawn Delatte, Vendela Colavecchio, and Jordyn Bonds interview Ashley Sheble, the Founder of AvidFirst, about her experiences and progress in thoughtbot's Incubator Program, which aims to help founders like Ashley turn an idea into a viable product. The discussion covers various aspects of the program, including the evolution of the product idea, insights gained from industry conferences, the importance of listening to customers, and the ongoing development of the go-to-market strategy. Everyone emphasizes the value of the Incubator Program in helping founders connect with their market and refine their strategy. Just catching up? Listen to Part I, Part 2, and Part 3 of the Mini Incubator Series! Follow Ashley Sheble on LinkedIn. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: DAWN: Hello, everyone. So, since we have a bigger crew here today, slightly bigger crew, we should just jump right in, right? If you're not familiar with thoughtbot, we're a design and development consultancy who create and build products from the very earliest stages. We are currently in our second incubator session. This is actually our final week. We're wrapping up this week our second program with Ashley at AvidFirst. And I'll let everybody go around and say hi and give a little intro. Today, we're going to be chatting about how the program has been going, any new recent activity, and things that we've learned and done, and, you know, what's going to happen here after the session ends. I'm Dawn. I am a Managing Director here at thoughtbot. And I will shoot it over to you, Ashley. ASHLEY: Thanks, Dawn. And my name is Ashley Sheble. I'm the CEO and Founder of AvidFirst. AvidFirst is really focused on helping people save and spend for college in a modern way. We're simplifying the process, modernizing the experience, and really, with the end goal of helping families avoid student debt. So, I've been working with the thoughtbot team for the past eight weeks, really refining our strategy, and we'll talk about this here in a minute. But pivoting a little bit on the strategy just based on what we learn from the market from talking to users, from talking to experts, from talking to people with just insight around what's needed in the space. And so I'm excited to share more about the past eight weeks. DAWN: Awesome. Thank you. Jordyn, do you want to hop in? JORDYN: Sure. I'm Jordyn Bonds. And I'm the Director of Product Strategy on the Ignite team. And I am a two-time former co-founder of tech startups, so whence I come to this work. Vendela, I'll let you go. VENDELA: I'm Vendela Colavecchio. I'm the Design Director on our team here running the incubators at thoughtbot. And yeah, should I talk about my role on the incubator [chuckles] more? I guess the incubator is sort of funny because, you know, as a designer, typically, my tasks fall under more of a traditional design category. But I think with the incubator, we're, like, all hands on deck, just trying to get lots of things done and help out in any way that we can. So, definitely some design things, but also just a bunch of participating in discussions and getting all sorts of tasks done. DAWN: I'm sure we'll dive more into that. As usual, though, we're going to let Ashley kick us off, kick our discussion off with a little bit of an update on what's been going on in these past two weeks since we last chatted and, you know, where we are now. ASHLEY: Yeah. So, the past couple of weeks have been pretty exciting. I went to an industry conference. It was a 529 and ABLE conference. So, 529s are tax-advantaged savings accounts specific for education expenses. ABLE accounts are tax-advantaged savings accounts, specifically for people who have a disability. And so, spent a week learning from experts in both spaces, hearing from all the different stakeholders, so state agencies, program distributors, you name it, every sort of stakeholder in the whole industry was there. And it was amazing to just be able to go in and learn and meet people and hear their perspectives around what's going well, what's not going well. It could not have been more well timed because I think had the conference been earlier, I might not have been ready to ask the right questions from the different stakeholders. And had the conference been later, well, we couldn't have used any of that insight and learning to continue working on refining or pivoting the project. So, it was a great experience. People were so collaborative, so helpful. I think it's interesting that my perspective going in was, oh, people aren't going to want to talk to me. They're not going to want to share their insight. But it was quite the opposite. People were really happy to talk about what they thought could be improved or what they thought seemed to be going well. But it's only from one perspective. So, if you start asking questions around what you've learned from other people's perspectives, you kind of see this, like, aha moment. Like, oh, I hadn't thought about that before. Maybe that's something to consider. So, it was an amazing experience. So, as a result of that particular event last week, have really been synthesizing what we learned, filling in any gaps. And then just using that to think about a different strategy based on kind of the signals in the room, what people were really excited about, and what people really thought needed some work versus what we went into the conference thinking was the right answer, if that makes sense. DAWN: That's so exciting. Can you tell us more about this pivot? You mentioned a pivot. ASHLEY: Yeah. And I wouldn't call it maybe a full pivot. I would say it's more an expansion on the work we've already done, which is good. So, we're not just throwing away all the work we've done for the past seven weeks and saying, "Forget it." There are a lot of parallels in the 529 space and the ABLE space. A lot of the stakeholders are the same, and it's just a different target market with a little bit different need set. And so, really trying to understand what the differences are, and what the similarities are, and how we can replicate the work that we've already done for one space in the other space, and then build upon that a lot more rapidly than it took us to build the initial work for the 529. So, there's definitely some advantages that the two industries are really intertwined. But at the same time, there are some differences that we need to be keenly aware of and making sure that we're solving a problem meaningfully. DAWN: Jordyn and Vendela, how has this, not pivot, but new expansion or new strategy, how has this affected your work? VENDELA: What I'm thinking about on sort of a meta-level is how it's exciting to see that this new angle doesn't really change how we would approach the problem in terms of just running the incubator. So, it's almost, not in a discouraging way, but it's almost just like starting back from week one and kind of going through, what do we know? What do we need to find out? What kind of questions do we need to ask stakeholders, et cetera? And just seeing how having done that already together it makes it pretty clear what the path forward would be in terms of the process. In terms of information, who knows what we'll find out? But I think that's been exciting. The pivot doesn't feel so scary as it might sound [laughs]. JORDYN: Yeah, I would just build on that to say that it's giving us this really awesome opportunity to immediately run the same process that we just ran but, like, to see how much we've learned from doing it the first time. It's like you're starting over, but you're starting over from a better place, right? With more skills, way more understanding of sort of what's important and what's not important. And, you know, once you've run the process at least once, no part of it feels daunting, right? It just feels like work you know how to do, so it's like, okay, this is a really interesting additional sort of adjacent opportunity. We need to very quickly itemize all the things we don't know about it, and then figure out how to learn about it. Is it research? Is it interviewing? Is it testing? But none of those things feels unknown, right? It just feels like you get to do it faster and better. This is, like, a thing, you kind of can't convince someone without them having done it. And a lot of folks come to us, come to thoughtbot with a product idea. And we tell them like, "Okay, let's get in there and validate and invalidate things." And they're, like, "Invalidate? [vocalization] I don't want to invalidate my awesome, precious product idea [laughs]." And what we know that they don't know is that there are pieces that we're going to validate and pieces we're going to invalidate, but always you uncover new opportunities in that process. And you're just better and better at ascertaining what's promising about those things. So, it's only upside, but it feels like we're asking them to let go of something or to lose something, right? There's a feeling of like, it's like a scary...it's a feeling of like, I've built something, a tiny thing of value here, and you're asking me to risk that. And that couldn't be further from the truth. But it's, like, a really hard thing to convince someone until you've done it once. So, it's very fun, anyway, that we're getting to do this within one incubator cycle. Usually, it's, you know, it doesn't happen that quickly. ASHLEY: I like how you qualified that as fun. I will say...and Vendela and I were talking yesterday, and we were going through the sprints around, not starting over but beginning at the beginning with this new angle. And I was having the emotional rollercoaster of, like, what are we doing? Oh my gosh. And then, oh my gosh, this is so exciting. And then, oh my gosh, what are we doing? I feel very equipped now, having gone through this process once, to have the tools, the skills, the mindset to know, okay, it's part of the process. Here's what's going to happen. Here's what we'll probably learn. And just have a very structured way of approaching a new idea or a new angle, versus feeling like just thrown into the deep end and trying to figure out how to swim or which way is up. So, that's been pretty encouraging and eye-opening, too, that I developed all these skills that I didn't realize I had developed till we started redoing this, which is exciting. DAWN: I love that. It's kind of a testament to how valuable time spent is and how important it is to become really, like, more efficient with this process and the value of sort of rapidly being able to validate or invalidate different assumptions. I imagine that this might be a little bit different than what you expected. As Jordyn was saying, [laughs] most founders don't, you know, expect to have to loosen the grip on specific ideas. So, now that you're at week eight, how has this experience been overall for you? ASHLEY: It's been incredible. First of all, just the talented team that has been working on this project with me, I cannot say enough good, nice, positive things about that. I've heard horror stories about people working with teams that there's just a lot of dissension. There's lack of trust, all those things. And we had none of that, which is incredible. So, I feel very fortunate to have been with the team that I was with. I will also say that everybody had different strengths. And so, we're looking at an opportunity or a problem from a different lens in four ways, which is amazing because then you can cover so much more ground so much more quickly. I will also say, too, just the process: the thoughtbot program has for the eight-week structure is so intentional because sometimes I would think, well, wouldn't it make sense to do this thing before this thing? But just trusted the process, and the process was right. So, I would just say anybody that's thinking about going through the incubator or goes through the incubator next, just trust the process because you guys have a portfolio of success. You know what you're doing. I'm a testament to just really endorse the fact that each step is necessary in getting to the next step in a successful way. So, you're not taking two steps forward, one step back. You're constantly making forward progress. DAWN: That's awesome. What about you, Vendela, and Jordyn, how has this program and this session been this time around? VENDELA: I can talk about my experience as the first time going through the incubator, and then maybe, Jordyn, you have some insight on comparing the two or how you think it went in general. But I think one thing that has been really fun to do and participate in, and to Ashley's point about kind of having this environment of trust and just counting on each other that we're all distilling the information that we're hearing, I guess, accurately or in a way that aligns with how the rest of the team would perceive these things, is that we've had these really cool moments of not feeling like we 100% with complete certainty know exactly how something looks, but being creative about how we might get closer to that point. So, hearing a few tidbits here and there, thinking of ways that we're reading between the lines and interpreting that, and thinking about how we can narrow who we're talking to or approach the conversation slightly differently, so adjusting our script, or running some kind of other experiment, or structure things differently. And then, we might find that that angle wasn't exactly right, but by pursuing that angle, we learned something new that actually did get us closer in some way. And I think a lot of that was subtle throughout the process. But now, just thinking about this new kind of topic or pivot, whatever you want to call it [laughs], that we're pursuing, I think that lesson is going to be really valuable for Ashley moving forward, too, and just thinking, okay, I feel like what we're trying now isn't getting any closer. What have I heard that I could just grab, like, a small piece of string and pull on it, and see where that goes, and unravel something, and hopefully learn something new? So that there's just consistent kind of learning and not feeling like you're just totally blocked at any point. JORDYN: Yeah, to build on that a little bit, there's a real quality with this early work of just starting with what you have, where you are. And, you know, you don't have everything you need, like, you just don't, not in life and certainly not in [laughs] startup land. But the question is, like, figuring out what you need and figuring out how to get that from where you are. And that might be validation of a hypothesis you have, or it might be resources that you need that you don't have yet. And so, a lot of the work that we did together is to identify those things and to figure out ways to get them. And it's a real creative process because every problem is different. It's why it's really hard to talk about the programming in a specific way. It's like, you know, broadly, we're driving at the same outcomes every time. But every problem space, every industry requires a kind of different set of approaches, and, to me, that's really fun. It's like, okay, imagine as a metaphor, you know, that you are dropped from a helicopter into a jungle in Central America versus into Mongolia. Like, what you're going to need to survive in those two [laughs] environments is probably going to be pretty different, right? But that doesn't mean that your strategy for figuring those things out is going, like, the tactics you employ will be different. Yeah, I'm glad to hear, Vendela; that was a fun aspect of this. And sort of jumping off from that point, what was different this time? It's always different running this program. And every time, there's something new and different. But this was the first time we've run it with a FinTech product, and just learning about that ecosystem, the players, and the complex landscape of incentives and motivations, et cetera, was just, like, there was a steep learning curve for us at the beginning. And it was just super interesting and helpful to sift through that. It was like being, you know, dropped from a helicopter into a new sort of ecosystem. And we were like, all right, like, which berries are poisonous here? I don't know. But I also know that I need to eat something to survive [laughs]. So, it's like those kinds of questions, which is just super interesting. And then, what it always causes me to do is look at my own network anew. So, often, we find ourselves talking about, like, this question of starting with where you are with what you have. That includes with the network you have and the people you know. And it really depends on the problem you're solving, who you tap for what questions, right? And, suddenly, like, every one of these that we run, I get to turn to my own network. And I find new reasons to talk to different people about different things in my own network, which is really fun. It's like it allows me to get to know people in my own life in a new way. Like, every time this happens like, one of the first things we do is we turn to our own networks. Like, who do we know that has this problem or works in this industry, whatever? But having never worked on a FinTech product before, I didn't really need to do that with this lens. And it's like a whole new set of people lit up for me, and I got to have really interesting conversations with them. So, that was one thing that was different and really kind of fun. ASHLEY: It's funny to hear your take on the FinTech complexity because I feel like every time Vendela, or Jordyn, or Dave, who's not here, would ask me a question, it was, well, here's the answer, but if this, then that, or if this other thing, then that. It was never just a straightforward answer. And I was like, oh my gosh, they're just going to throw their hands up in the air at some point, but never did. They were just like, cool, that's fine. We'll figure out these different pathways, and if this, then we'll do that, and if this other thing, then we'll do this other thing. And I was just blown away by how nimble the team was and willing to just embrace the complexity. So, that, for me, was a huge positive. I don't know if you'll ever want to work in a FinTech product again; maybe yes, maybe no. DAWN: I would argue that we're more prepared now. You know, we've done a lot of FinTech work in the past, but applying this framework to understanding it as quickly as the team needed to, I'm sure, sort of pushed everybody farther, faster. So, Dave -- JORDYN: Yeah, I should say that was specific to me. thoughtbot has done plenty of FinTech work, Jordyn has not. But also, to your point, Ashley, like, I would love to actually. Now I'm like, oh okay, I kind of understand where the opportunities are here. I feel more prepared now rather than, like, more daunted. ASHLEY: Well, and you have a huge network in the FinTech space. So, that was something that was hugely helpful to me was talking with other founders who have been successful in the FinTech space, or people who have exited and had a great experience, or maybe people who have exited for, you know, reasons they didn't choose. But it was so important to hear from all those different perspectives and say, okay, here's what I would want to replicate, what I would definitely want to avoid. And so, anyways, just the network that Jordyn and others had and were willing to share with me was so valuable. DAWN: I was going to quickly shout out to Dave, who was sick this morning and wasn't able to make it. We were going to have him join. He was the senior developer in this sort of product pod that you've been working with. And I'm sure he has some interesting, more technical perspective to share. He did write a blog post, I think, maybe after week four, that I'm sure has some of those insights in it for folks who might be interested in reading from a developer's perspective. Yes, this is all wonderful to hear. I am curious to know what's next for AvidFirst. ASHLEY: Yeah, continuing on. There are a couple of things to pilot. And so, that's really the next step, pilot MVP as we think about this new angle. Because we want to make sure that the solution in mind is actually the solution that's needed. And so, those are the next steps, and then capital raise and then off to the races. So, if there's anybody listening that is interested in teaming up or wants to talk or contribute, would love to have a chat. DAWN: Is there anything that we can help with, anything on your mind, more network connections? [laughs] ASHLEY: Oh, gosh, offhand, I feel like I would be over-asking at this point because you guys have been beyond helpful. I really think the framework that I have to work with going forward—the team helped build a plan for here's what to do next, here's what to do after that, and here's what to do after that—is really setting me up for success as I think about continuing this journey without the amazing team day in, day out. JORDYN: Well, you have us as a team for life now, sorry. So, anytime you need something, [laughs] you can call. VENDELA: I was going to say I hope that you stick around in our Slack channel and update us on what's going on because now we're super invested, and we definitely want to hear how you're doing. ASHLEY: Yeah, absolutely. DAWN: Vendela and Jordyn, we've got another application window happening right now about to close for the next incubator session. Who should apply? What should they expect? JORDYN: Anybody with a business idea that involves software. The earlier, the better. And a lot of people, you know, come to us and are like, "Well, I have this idea that I'm kicking around for years in my head, but I haven't done anything yet. You know, what do I have to do to apply?" And we're like, "Sounds good. Apply." And then, other folks who are a little later, you know, and they feel like maybe they've hit some doldrums with an idea that they've explored a little bit. But they need a little bit of sort of reinvigorating and, you know, like a spark to get going on it. That's also a good time. We're really sort of excited to hear everybody's ideas. And the only, you know, downside is that we get more applications than folks we can work with. And there's always, like, a lot of great stuff in there. But everyone is encouraged to apply. You know, we used to have somewhat of a, like, non-technical founder. And when we first started, that was kind of the premise was, like, if you're a non-technical founder, we'll be your technical founding team. But I think we're finding that we kind of round out any skill sets in a way. If you bring a technical background, we can help you with the sales, and the marketing, and the business strategy. And if you come with those things, we can help you with the product and the technology strategy. It's the early-stage work, and the early-stage work is the early-stage work, regardless of your background. We can help fill in those gaps. ASHLEY: Yeah, I'll just add, too, I came in with this pitch check. I'm like, I'm ready to go, you know, we just need to build this thing. And, wow, the idea has changed so much since eight weeks ago. And so, I would just say, too, like, be open to feedback, be open to where the experience takes you. Even if you do have a really well-researched idea, there's always opportunity for improvement based on what the market says. And the market is constantly changing. And customer needs are constantly changing. And so, if you're not evolving with that experience, then you're going to get left behind or build a product for no one or, you know, a product for everyone is really a product for no one also. So, being open to the team's input and process is just invaluable no matter what stage somebody is coming into this with. JORDYN: That makes me just so happy to hear. And I will add that, like, I cannot stress enough that mostly what this program is for is to help folks connect with their market. Like, we actually don't want you to listen to us. We want you to listen to your customer all day, every day. How can you make sure you're moving with those folks, evolving with them, speaking their language, addressing the pain points that they have? Because that's why you're doing this, not because of what you think alone or what we think as your product pod. It's really what the market is doing and what your customer base is doing, and thinking, and feeling. And really, the programming is sort of geared toward helping people understand how to do that work. Like, you might conceptually understand that you need to do that. As a first-time founder, I certainly, you know, I had read the blogs, man. I knew I needed to be, like, customer-centric or whatever. But, like, I didn't really actually know how to do that. And once I did talk to some folks, it was a whole other new skill set to figure out how to listen for the things that mattered in what they were saying to me, right? Translating, you know, what folks are telling you and how they talk about their life and their work into product opportunities and innovation, it's a whole skill set that I, even coming into this work, you know, as a first-time founder with the background I had, I didn't have that skill set. You know, most people sitting out there would not argue, like, of course, you need to listen to your customer and move with the market, et cetera. But the question of, like, how to operationalize that [laughs], you know, is a completely opaque thing sometimes. Even for folks who have, like, done it before somewhat, it can still remain challenging. ASHLEY: Yeah, I feel in a better position now to continue keeping pace with the market. Because if you look at FinTech, historically, there were major innovations every ten years, and then that pace changed to every couple of years, and then it changed to every one year. And now you're seeing FinTech innovation accelerated to every few months; the landscape is different. And so, the solution today may need to be different in six months, or three months, something like that. But I feel like I have the tools now to keep up with that pace of change, whereas before, I would have been left behind. So, I feel really grateful for that. Thank you. DAWN: That warms my heart. We do have a question. So, does thoughtbot help with go-to-market strategy, or is the incubator more focused on zero to MVP? JORDYN: You know, I'm full of very spicy takes. Spicy take here: you're always going to market. Zero to MVP is different than go-to-market? I'm sorry, how? So, the answer is, like, absolutely. And really, what you're doing is perennially going to the market [laughs]. You're making a go-to-market strategy. You're keeping that fresh. You're keeping it new in the same way that you're keeping your products and technology strategy fresh and new, given what you're learning and what you're hearing. So, absolutely, I would say that's actually primarily what the incubator is for [laughs], and then making sure that those strategies are aligned. So, like, one of the things that I've seen in my own work at multiple startups, not just my own, is that those things can become disconnected as your team grows because people have different backgrounds and different...they just have a different focus, right? Your head of marketing has a different focus than your head of product and has a different focus than your head of technology. And keeping all of those strategically aligned and focused on the same customer and the same problem set is a lot of the work of an early-stage startup. And that's, like, a lot of the work that we kind of help founders figure out how to do. How do you tie your go-to-market to your MVP? Like, how do those two things fit in together, right? And how do you keep them in sync? It's not merely like you do this one time and then everyone goes their separate ways [laughs], and in 18 months, you meet back again and have a conversation about it, like, [laughs] not how this works. So, I mean, absolutely. VENDELA: I would add to that, too; I think something that we talk about with all these types of projects is just...and, internally, we talk about this a lot, too, like, we kind of hate the term MVP because it's so ambiguous really. Like, what does that mean for any given product? And so, I think, to your point, Jordyn, like, the going to market and the MVP are so tied together because the whole point of an MVP is to learn something so that you can then bring it from a minimum viable product to something more than that. And we talk a lot with founders about different approaches to MVP. I think some people have maybe a narrow view of what they can be. It's this, you know, maybe slightly lower fidelity but coded custom thing. And there's lots of ways to approach it that don't fit that definition and maybe would work better as a way to experiment and learn something, and then create a new version later on. So, you know, with that first version, you can still go to market, but you're learning something, and then you're maybe building a new MVP after that. And so, making sure that that's not too precious or hard to throw away is something, I think, we tell everybody, too. DAWN: Yes, that's great. Cool. Well, I think it's about time for us to wrap up. Thank you so much, Ashley. It's always an honor to kind of watch the team work with different founders and see them sort of learning as they go and seeing the product and the opportunities evolve. And it's been really great to be able to participate a little bit more this time and chatting with you and hearing about how things are going. I'm happy to hear that there was a lot of opportunity for you to continue exploring with AvidFirst. And we'll be here, so please [laughs] come to us as much as possible. Everybody is really excited to see, you know, you and this thing be successful. So, thank you, Vendela and Jordyn, as always, for being a wonderful team. If you're interested in applying to the incubator, do it. Don't hesitate. You can always visit thoughtbot.com/incubator for more information. And thanks for tuning in. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at: tbot.io/referral. Or you can email us at: referrals@thoughtbot.com with any questions.Special Guests: Ashley Sheble, Dawn Delatte, Jordyn Bonds, and Vendela Colavecchio.Support Giant Robots Smashing Into Other Giant Robots

Dawn Delatte and Jordyn Bonds interview Ashley Sheble, the Founder of AvidFirst, about her experiences and progress in thoughtbot's Incubator Program, which aims to help founders like Ashley turn an idea into a viable product. In the third part of the Mini Incubator Series, they talk about user interviews, data analysis, and prototyping to validate ideas. They emphasize the importance of being open to user signals and adjusting their approach accordingly. They also discuss the upcoming weeks of the program and the goal of refining their story and business strategy. Just catching up? Listen to Part I and Part 2 of the Mini Incubator Series! Follow Ashley Sheble on LinkedIn. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: DAWN: Thanks, everybody, for joining. We're glad that you're here. If you've tuned in before, great, welcome back. You're probably familiar with thoughtbot; if you're not, we're a product design and development consultancy that helps make you, and your team, and your product successful. We are currently running the second session of our incubator program, which is an eight-week program that takes you through a lot of different activities and exercises to help you identify market and product opportunities, experiment with them, and ideally come up with a solution that you can move forward with. I'm Dawn. I'm a Managing Director here at thoughtbot. And I lead a team that works with very early-stage products, and founders, and companies. And I'll hand it over to Jordyn. JORDYN: I'm Jordyn Bonds, and I'm the Director of Product Strategy on Dawn's team. And I'm kind of the...I don't know what, founder in residence for the incubator trying to bring my experience as a former founder to bear for our participants, in this case, Ashley. ASHLEY: Okay, my name is Ashley Sheble. I'm the CEO and founder of AvidFirst and have been working with Jordyn and a great team in the second incubator session. So, removing all bias from the statement I'm about to say, but if anybody's thinking about applying to the next incubator, just do it. It's an amazing experience. You're going to learn so much. There are so many smart, helpful people who really care about building cool products that make a difference. And so, do it. DAWN: I love it. Thanks for the impromptu promo. JORDYN: Yeah, thank you [laughs]. It's good to hear. DAWN: Yeah, I'm excited. Cool. Well, Ashley, why don't you maybe kick us off with a little bit of a recap of these past two weeks? What have y'all been working on? ASHLEY: Yeah, so, just for a little background, in case anybody hasn't been following along, AvidFirst is a technology company aimed at simplifying college saving and spending. Our goal is really to make 529 accounts more usable broadly and then, more specifically, attractive to next-gen consumers. And for those who aren't familiar with 529 plans, that's okay because neither are about 70% of Americans. But essentially, they are college savings vehicles. They're investment accounts that allow people to contribute money. The money grows tax-free and then can be withdrawn tax-free when used for qualified education expenses. And over the past few years, the term qualified education expense has really expanded from beyond just tuition and fees to room and board on and off campus, computers, technology, supplies, apprenticeships, K through 12, like, the list is getting longer and longer. And so, our goal is just to really help simplify a really complex system and savings vehicle to make them more appealing and attractive to people. So, the past few weeks, specifically, we have been aggregating all the data from our user interviews. We've done a lot of user interviews with different stakeholders and have been taking the information and saying, okay, what do we do next? How do we validate the way we're thinking about solving this problem will actually solve the problem in the way that we think it will? And so, through lots of process mapping, brainstorming different pilot initiatives, and then now working through some of the nuances of the industry. The 529 industry, specifically, is a complex animal. I don't really know how else to explain it. It's very complex. And so, we are just navigating these complexities and looking for solutions that will truly simplify the complexity. JORDYN: I will just dig in a little bit to that analysis of the interviews that we've been conducting. That analysis kind of, like, stepped up a notch in the last week in a really fun way where we, the team, really kind of dug into the dynamics of each interview, sort of the things that we're most curious about, and have been asking and really, like, scored each interview. And then did sort of a cohort analysis, like, where are the trends with which personas? We had already had some intuitions, and we just wanted to confirm with the data that we weren't deluding ourselves about what the direction was. So, that was a really, like, I think it was a really useful exercise and kind of fun to see. And what doing that helps with is our own conviction, but then it also helps us make sure that we are honing who we're talking to going forward. Talking to folks is, like, so critical and is so not scalable. It is so time-consuming [laughs]. So, you want to make sure that you're doing it really strategically. So, it's sort of, like, every wave of interviews we do, we do a little more analysis. And it's, like, we finally got to a critical number where we felt like doing this data pass was going to be statistically significant. We had enough interviews to really focus the interviews we're going to do going forward. So, just to give a little, like, lens into how that's worked and how we've been thinking about it. DAWN: I think we ask this question often, maybe every time, but I'm interested to see how it continues to evolve. But what was something that you learned these past two weeks that really surprised you or maybe even confirmed your hunches? JORDYN: So, as often happens, when you start talking to a focus group of people who share a lot of pain points in their lives or their work, you end up with, like, a lot of trends. Like, there might be a thing you're asking them about that you're particularly focused on or curious about, and you want to focus your questions on that. But invariably, you're talking to a human being, and they're going to talk about a lot of different things. And so, early on, and when we started interviewing people at the very beginning of this project in August, you know, we were very focused on college savings and spending. But an interesting thing, like, sort of trend that came up was also how much parents care about imparting, you know, some sense of financial responsibility in their young adults [laughs]. And we were like, well, that's interesting. Okay, let's, like, keep an eye on that. Maybe that's interesting to us. And what has kind of surprised me in the last couple of weeks is how much of that has sort of solidified. This is not, like, a news flash, by the way, like I think [laughs]. This is, like, a thing. Anyone who has teenagers out there is like, duh, like, why is this shocking to you? But the way that it ties into college savings and spending, I think we found some really interesting connections and threads there that have only gotten stronger with the specific cohorts that we've been talking to. So, I think that we, at first, had started as just this sort of, like, well, that's interesting, but we'll see where it goes kind of thing. And now it's, like, become a little bit more core to how we're thinking about just broadly what folks are facing, who we're addressing. So, I guess it wasn't, like, a surprise, but, like, the deepening of that signal, you know, in the sense of signal and noise, has been, like, really interesting to us, I think. ASHLEY: There's a system thinking expert that talks about how changes in a field are rarely made by the experts in the field but rather outsiders looking in. And so, for me, that's amazing because I don't have experience as a technology founder. I'm working with others who are founders in the technology space, which is great. But it does leave some question marks for us as it relates to building some processes and doing some pilot mapping, which completely overcomable because we're able to draw on resources from within the thoughtbot organization. And then, also, just network, people within our network. Jordyn seems to know everybody. I'll be like, "Do you know somebody in North Dakota?" And she's like, "Actually, yes, my third cousin's sister lives there, and I can get her on the phone." And it's just -- JORDYN: It's my first cousin. I will tell you, it's my straight-up first cousin. ASHLEY: Well, there's always someone that Jordyn knows no matter where, it seems like, which is extremely helpful when we're trying to find experts to help us answer some questions. So, it's great to be able to work through problems in a very systematic way, using some of the strategies that thoughtbot has employed, I guess, over and over and can be applied to different industries. But it does help us find, what are the questions we still need answered? And then, who are the people that can help us answer these questions? And be very strategic about that. JORDYN: I would add to that on the networking score. I think this is one of those things that first-time founders often struggle with. They struggle with recognizing who in their network is a valuable person to talk to in the first place. And then, they struggle with making those connections because it feels like you're asking people to do stuff for you, and that doesn't always feel great. But really, your network, and where you come from, and the people you know and who care about you are one of your biggest assets going into this work. And it's important to take stock of those folks as early as you can and think about how to involve them. And often, they want to be involved. They're excited to have a way to support you and contribute their expertise or whatever else. It's actually really transformed some of my relationships, like family relationships that I didn't necessarily have as...people I just discovered in my own sort of extended family who were doing related things to me. And we're much deeper friends now because we get to talk about that stuff all the time. And before I was a founder, we just didn't really talk [laughs]. So, just think through who you know and how they might be able to help you, and chances are they really want to. It's a very useful exercise. And it doesn't have to be super transactional. It can be a real bond builder. ASHLEY: Yeah, I would say that's completely true, especially from my own experience. I don't like to ask people for help, generally. And so, asking people for their time and for their advice, I'm like, oh my gosh, why are they going to give this to me? What can I do for them? But it's really been amazing how generous people are with their knowledge, and insight, and their time. I'm attending a conference next week for the 529 industry. And there have been so many helpful, kind people who are just experts in their field, leaders in their companies and are willing to talk to me about their experiences about what challenges they see. Because ultimately, you know, when a company succeeds and helps the industry grow, everybody grows and benefits from that. So, I hadn't really looked at it that way until Jordyn really encouraged me to just be, like, just call that person or just, you know, reach out. And sure enough, they were more than willing to be helpful. DAWN: I imagine there is a sort of a bit of human factor here in that, you know, what you're giving to them is an opportunity for them to share, like, something that's, like, deeply important to them and that probably not a lot of people ask them about, even their day-to-day work. So, I imagine that can feel good, too, and maybe even sort of help them better understand [laughs], like, what it is they're doing. So, you've definitely sunk into who to talk to. What about the how? Like, what are y'all doing now to try to continue validating that this is the right opportunity and that there's a product opportunity there? ASHLEY: Yeah, so, really drilling down on those two cohorts that we mentioned a little earlier, specifically one of them, making sure that we are asking questions now related to this solution that we are thinking about, and more around their experience with similar type of products or similar type of solutions to make sure that we are thinking about building features or building process flows in a way that will integrate into the way they're used to doing things today so it doesn't seem like a new learning curve to, you know, think about adopting our product. And then, also, just making sure that we are providing value, ultimately, because we don't want to just build something just to build something that we think will work for this group of people who told us that something is hard. We want to make sure that we're actually making something that's hard much easier than it already is. JORDYN: Yeah. We've really, I mean, to build on that, we've gotten a little bit further into testing messaging, which is we think that we understand folks' problems and how they are talking about them, but we really need to validate that. And, you know, we have created some landing pages and are showing them to folks and getting their reactions. But we've also started doing a little bit of prototyping, which we hope to start showing folks soon. And this is all just...a prototype, in this case, meaning this isn't, like, a clickable app. This is just, like, sort of a static design that appears clickable [laughs], think of it like a PDF with some links in it, and just showing that to folks and saying, you know, "What would you do here? How would you respond to this?" And it's just a really great way to...it's fast. It's easy to spin one of those up and then get them in front of folks and make sure that how we're thinking about this is sort of broadly in the right direction. It's so much cheaper to find out that we're thinking about this wrongly with something like that than with an app that we spent six months building and launching, ha-ha. Now, who's done that before? Not me, no, never [laughs]. I've never wasted a year building a thing. So, it's a really fun thing to do. And sometimes you can even...it's not even, like, let's validate what we're thinking. Sometimes, it's really helpful to actually throw some curveballs in there on purpose to make sure we're invalidating the right things. So, it's really fun to be moving into that phase with what we know to be true and really getting closer to testing things out in, like, a real-world situation. ASHLEY: It's somewhat surprising, too, what people are reacting to or not reacting to. The things that we thought people would be really excited about, they're like, "Eh." And the things that we thought are just kind of, like, filler on the page, they're like, "That's awesome." So, it's really crazy to see that juxtaposition. And then, you've got some people who will be like, "Huh, that's cool." And then, you've got some people who are like, "Can I sign up right now?" And you have to say, "We'll let you know when you can, but not right now." Just the differences are pretty surprising. JORDYN: Yeah, and I'm glad you brought that up, Ashley, about, like, the stuff that you just kind of put on the page to make it look like a real page, and then people really zero in on it. There's just so much serendipity involved in this work. And part of the skill in making products is being open to the right things at the right time, right? You want to stay focused on your mission and what it is you're trying to accomplish. But you don't want to ignore, you know, if people are reacting really strongly to something that you thought was sort of ancillary, it's important to, like, take a beat and think about that. How does that fit in? Can we use that? What you want to do is find lightning that you can bottle, and if people are not feeling lightning [laughs] about the primary thing you are working on but they are about something else, that's totally okay. I mean, the recent past of successful applications in software products is littered with stories like that, where people thought they were building one thing, and they just consistently heard about this related thing from their users. And they were like, well, why don't we just invest in that? It takes a lot of courage to stare in the face of that signal, the data that you're getting from people, and let go of the things that are not working and really embrace the things that are. DAWN: This reminds me a little bit of the conversation we were having when we were together in New York last week around the focus on validating or invalidating. The conversation we were having was kind of trying to shift that away from ideas to assumptions. But this is making me think that it focuses too much on one single thing that you're trying to get an answer for, as opposed to, like you're saying, being open to sort of receiving signals about completely tangential things or things that you may have not been paying attention to before. So, that makes a lot of sense. ASHLEY: Yeah. Now I'm thinking, like, should we put even more crazy things on the page and just see what happens? Who knows? JORDYN: I think there's another aspect of this first-time founders often struggle with, which is that feeling that you shouldn't put anything on the page that you're testing that you couldn't actually do. And it's tough. It can feel a little bit like you're misleading people. But there's absolutely ethical ways to do this, where you tell people, "Hey, this is just an idea. We're just trying to get people's gut reactions to this. We have not even put pixel-to-paper here. We don't even know. We just want to get your reaction." As long as you're transparent with folks about where you're at and about not promising them things you can't actually do, I mean, obviously, if it were as easy as just promising stuff to people of what they want, we could just make a landing page that said, like, "Free bag of money. Who wants free bag of money," right? [laughs] And people would be like, "Why is the bag of money free?" [laughs] Right? And so, you really want to be careful and not necessarily do anything that is misleading. But on the other hand, there's no better way to get folks' emotional reaction than to put something together and just see how they respond to it. So, there's a lot of, like, sort of nuance to doing this. And, Dawn, to your point, the balancing act between being open and being scattered, right? That's a fine line. I've definitely been on teams before that are just, like, the new hotness every week. "Hey, there's this cool app out. Let's just immediately redesign everything to look just like that." And you're like, "Maybe? [laughs] I don't know if that's, like, the best idea." So, it's a real balancing act, but it always comes back to who you're building for and what they want and need. And if you're staying very focused on that and measuring, you know, comparing every idea anything that comes your way against those, showing it to them and getting their reaction, you can't fail. Keeping no daylight between yourself and your customer that is the surest path. DAWN: Yeah, it kind of carries through to the core thing that we're saying, which is don't focus on one thing to validate or invalidate. Be open to receiving signals from other, you know, opportunities. But that's not validating or invalidating something. That's showing you where to focus your time. And then the product experiments and feasibility research and all of that is designed to help you to get closer to validation. But, in some cases, there's a point at which you have to take a risk, right? And your customers are ultimately going to tell you over time whether or not the solution was the right one. But you get more confidence. You get closer to the right solution the more strategic you are about that process, so...oh, go ahead. ASHLEY: I think the great thing about technology, too, is it's not set in stone. You can change it. If you learn something new, you can modify what you're doing to fit what you're hearing, and I think that's so incredible. We live in a time where there are so many tools and resources out there to really be nimble. And just to Jordyn's point earlier, I think the hardest part is being willing to take in some of these signals and be like, okay, this is what they want, and being willing to move in that direction versus the path you have already designed in your head. DAWN: Yeah, we've only got a couple of weeks left in this incubator [laughs]. How are y'all feeling? What are you planning? What are you looking forward to over the next couple of weeks? ASHLEY: I can't believe that time went by so fast. I thought eight weeks felt like two years when we first started. I was like, oh, we've got so much time. We're going to do so much. We have done a lot. But the time has really flown by. So, I'm just kind of, like, now thinking about how do I make the most of the last few weeks? And just make sure that we check all the boxes that we set out to check in the beginning, and then have a plan from there in terms of continuing the work in a productive and, you know, exciting way. JORDYN: Yeah, one of the, like, sort of Northstar outcome for us in the incubator is to give the founder confidence in what they're doing and their path, the confidence in that vision, and then enough confidence to articulate it consistently to the folks they need to sort of bring along with them. So, what I'm, like, really looking forward to in the next couple of weeks is honing that story for Ashley. Like, what's your story? What's your why? What's your how? What's your when? And how to make sure that story is just easy to communicate. I mean, already, Ashley, like, up top of this exact livestream where you articulated sort of, like, what AvidFirst is doing, I think I feel better and better about that articulation given what we know. It feels really good. It feels solid. And as we're going, we're just as skeptical as anyone else, right? But we're trying to anticipate what folks...external stakeholders broadly define what their misgivings are going to be. And we're compiling a kind of list of frequently asked questions about what AvidFirst is doing, like, why 529s? Why next-gen consumers? Et cetera. Just so that that story is so internalized that, like, you can't really be taken off guard necessarily. I mean, you want to be open to new questions and new ideas. That's not what I'm saying. But just basically, like, being able to thoroughly and deeply, at the drop of a hat, to sort of pitch this to your dentist while they're cleaning your teeth, you know, like that kind of conviction and, like, the solidity of the narrative is really what we're going for in the next few weeks. And I think we're well on our way there. We have all the pieces. It's about putting it together coherently, I think, at this point. It's really exciting, though. I do feel like we're really zeroing in on a valuable lens on college saving and spending that I think the market is really ripe for, so it's exciting. DAWN: Yeah, it's been great to see all the progress. We have a comment that I just noticed. ASHLEY: Oh. DAWN: Not a question, but I wanted to call it out because it was related to what you were talking about a few minutes ago, Jordyn. Kiran said they totally agree. "We had the same epiphany/pivot this summer. We went from direct-to-consumer to an enterprise model. Try to zoom out with a systems thinking lens, and it will help with a clearer path and tell your story." JORDYN: Yeah, that's awesome. DAWN: There are no other questions from the audience. And it seems like maybe there's still a little bit of a lag. So [laughs], we can wrap up. If anybody has questions after this, feel free to comment. We'll be, you know, checking out the posts on LinkedIn and YouTube. And we can follow up there. You can always, like I said, come and follow along. Check out our thoughtbot.com incubator site. You can both apply to the next incubator session and sign up to hear from us in our weekly newsletter. We write about progress on our blog as well, so thoughtbot.com/blog. There's all kinds of ways to find us and actually talking about the work that we're doing. So, please follow along. JORDYN: Anyone out there who's wondering, am I right for the incubator? Just apply. It's really, like, nothing is too early if it's just an idea you've been kicking around that's born of your industry experience or your personal experience. The application process is really lightweight. This is not going to take you days to fill out this application. We've heard from folks that even filling out the application is the first thing they ever did with regard to the idea, helped solidify it, and solidify their thinking for them. So, just go apply. You got something? You got an idea for an app? You see a growing market out there, and you feel like it's underserved with software? Just holler at us. We'd love to hear it. Apply. It's fun [laughs]. DAWN: Yeah. Thanks, everybody, for tuning in. Thanks, Jordyn and Ashley, for participating. See you again in a couple of weeks, yeah? JORDYN: Yes. It'll be the last week, so we'll have things to say, no doubt. DAWN: Yes, tune in. It'll be a good time. All right. Thanks, everybody. AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or a development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at referrals@thoughtbot.com with any questions.Special Guests: Ashley Sheble, Dawn Delatte, and Jordyn Bonds.Support Giant Robots Smashing Into Other Giant Robots