525: Tech, Public Service, and Serendipity

Victoria Guido hosts Robbie Holmes, the founder and CEO of Holmes Consulting Group. The conversation kicks off with Robbie recounting his initial foray into the tech world at a small web hosting company named A1 Terabit.net, chosen for its alphabetical advantage in the white pages. This job was a stepping stone to a more significant role at Unisys, working for the state of New York's Department of Social Services, where Robbie inadvertently ventured into civic tech and public interest technology.

Robbie shares his career progression from supporting welfare systems in New York to becoming a technological liaison between the city and state, leading to a deeper involvement in open-source solutions. His journey through tech spaces includes developing websites, diving into the Drupal community, and eventually establishing his consulting business. Robbie emphasizes the serendipitous nature of his career path, influenced significantly by community involvement and networking rather than a planned trajectory.

Additionally, Robbie gives insights on the impact of technology in public services and his stint with the U.S. Digital Service (USDS), where he contributed to significant projects like vets.gov. Robbie promotes the value of community engagement in shaping one's career, stressing how connections and being in the right place at the right time can lead to unexpected opportunities and career pivots.

• Follow Robbie Holmes on LinkedIn, X, Facebook, Instagram, or GitHub. Check out his website at robbiethegeek.
• Follow thoughtbot on X or LinkedIn.

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 Robbie Holmes, Founder and CEO of Holmes Consulting Group. Robbie, thank you for joining me.

ROBBIE: I'm so happy to be here. It's great to talk to you, Victoria.

VICTORIA: Yes. I have known you for a long time now, but I don't know everything about you. So, I thought I would start with the question: What was your first job that you ever had?

ROBBIE: My first technical job, I ended up working for an internet web hosting company called A1 Terabit.net. And note the A1 because it came first in the white pages. It was a really small web hosting company run by a man named [SP] Maxim Avrutsky. I worked there for about six months before I submitted my resume to an online job forum. That's how old I am. And it ended up in the hands of Unisys, where I eventually worked for the state of New York.

VICTORIA: Wow [laughs]. So, what a journey that you've been on to get from starting there, and what a marketing ploy back in the day with the white pages. So, tell me a little bit more about how you went from that first job to where you are today with having your own business in consulting.

ROBBIE: Yeah, I wasn't even aware that I was jumping into the sort of civic tech space and public interest technology because the job I ended up with was working for New York State in the Department of Social Services. And welfare is federally funded and distributed to states and then states to localities. And New York City and New York State have a weird parasymbiotic relationship because over 50% of the welfare in New York State goes to the five boroughs in New York City. So, so much of my job was supporting the welfare system within the city, which was run by the human resources administration.

So, that just led to this cascade of me, like, getting invested in supporting that, and then eventually jumping over to the other side where I worked for the City of New York. And at that point, I ended up becoming sort of a technology project manager and almost a tech liaison between the city and state. And I was out in the welfare centers, helping get the job centers up to a new application called the Paperless Office System, which was a client-server app that was a wrapper around welfare.

All of that ended up leading to me finally making it to the network operation center for the City of New York, where I started replacing expensive solutions like HP OpenView with open-source solutions like Nagios and another open-source solution that provided an interface. And it really opened my eyes to the idea of open source. And I had really paid attention to a lot of open-source operating systems. So, I was kind of just a general tech nerd.

And eventually, I started building websites, and that led me to the Drupal community in New York City, which was sort of this cascade that led me to communities. And I think that's sort of a through line for my entire career is I don't really think I ever had a plan. I think my entire career has been this sort of a lucky happenstance of being prepared when an opportunity arose and sometimes being in the right place because of my connections and community.

VICTORIA: That's interesting about being involved with the people around you and seeing what problems are out there to solve and letting that lead you to where your interests lie. And then, following that, naturally led you to, like, this really long career and these really interesting, big projects and problems that you get to solve.

ROBBIE: Yeah. And I think one interesting aspect is like, I feel I spent a lot of time worried about what I was going to do and where I was going to do it. I don't have a bachelor's degree. I don't have an advanced degree. I have a high school diploma and a couple of years in college. Well, 137 credits, not the right 125 or 124 to have a bachelor's degree. I have enough credits for a couple of minors though, definitely Greek art history, I think mathematics, maybe one more. I just never got it together and actually got my degree. But that was so interesting because it was limiting to what jobs I could find.

So, I was in the tech space as an IT person and specifically doing networking. So, I was running the network operation center. I helped, like, create a whole process for how we track tickets, and how we created tickets, and how things were moved along. And, in the process, I started building websites for family and friends.

And I built a website for our network operation center, so that way we could have photos to go with our diagrams of the network. So that way, when we were troubleshooting remotely, we could actually pull up images and say, "The cable that's in port six goes off to the router. I think that port is dead. Can we move it to the port two to its right, and I'll activate it?" And that made a really interesting solution for something we weren't even aware we had, which was lack of visibility. So many of the people in the fields were newer or were trying to figure it out. And some of us had really deep knowledge of what was going on in those network rooms and hubs.

It led me to this solution of like, well, why don't we just start documenting it and making it easier for us to help when they're in the field? That led me to, like, the Drupal community because I started building sites in the Drupal CMS. And I went to, like, my first Drupal meetup in 2007, and there was, like, five of us around the table. That led to eventually me working for Sony Music and all these other things.

But the year before I found my way to the Drupal community, I probably sent out, like, 400 resumes for jobs in the tech space, didn't really get any callbacks. And then, I met the community, and I started attending events, and then eventually, I started organizing events. And then, Sony I interviewed and talked to them a couple of times. And then, a friend of mine became the boss. And she contacted me and was like, "Hey, are you in the market?" And I was like, "I don't know. Why? What's up?" And she's like, "I became Doug." And I was like, "What?" And she was like, "I'm now replacing Doug at Sony. I'm running the team." And I was like, "Yeah, I'm happy to talk."

And that was the big transition in my career from IT to sort of development and to delivery, right? Like, when it comes right down to it, is I became the manager of interactive media at Sony Music, which was really a job I landed because I was connected to the community, and running events, and getting to know everyone.

VICTORIA: Yeah. And I think it's really cool that you had this exposure early on to what you called civic tech, which we'll get into a little bit, and then you went from the community into a commercial technology space and really getting into engineering with Drupal.

ROBBIE: Yeah, it was an interesting transition because what they needed at Sony was sort of somebody who could ride the line between systems engineer, database administrator, and Drupal engineer, and also probably pre-DevOps DevOps person. So, I was responsible for all deployments and all tickets that came in. I was sort of both the technical arm of the help desk. When I joined, there was 24 websites on the Drupal platform, and when I left, there was over 200. And we upgraded it from Drupal 5 to Drupal 6 to Drupal 7 while I was there. So, I was heavily involved in all of those updates, and all those upgrades, and all of the deployments of all the new themes, and all the changes to all these sites.

So, what was great was they, I believe, if I understand it correctly, they actually created a role for me out of, like, two or three jobs because they needed a me, and they didn't have a role that existed. So, all of a sudden, they made a manager of interactive media role. And I was able to work there for two years, sort of being what I jokingly say, like, a digital janitor. I used to say that I had, like, an eight-bit key ring in a push broom. And I was always mad at your kids for trying to break my stuff.

VICTORIA: [laughs] That's so good. A digital service janitor [laughs]? The connection for me between that and where I met you in the U.S. digital service space [laughs] I feel like there's a lot of parallels between that and where your career evolved later on in life.

ROBBIE: Yeah. What's amazing is I did all this early work in my career in civic tech and didn't realize it was civic tech at the time. I just realized what I was doing was providing this huge impact and was value. You know, I spent a couple of years in the welfare centers, and I used to say all the time that the two hardest jobs in the welfare center are the person applying for welfare and the person deciding whether or not that person gets welfare. So, being a technologist and trying to help make that as simple as possible or easier and smooth the edges off of that process was really important.

And it really taught me how important technology is to delivering service. And I really never thought about it before. And then, when I was working for Phase2 technologies, I was a director of Digital Services. And I read in a blog post, I believe that was written by Mikey Dickerson, who was the original administrator for USDS, and he talked about HealthCare.gov. And he walked in the door, and he said, "How do you know HealthCare.gov is down?" And I think there was some allusion to the fact that we were like, we turn on the television and if they're yelling at us, we know it's down. And Mikey was like, "We know how to monitor things."

So, like, if you don't know Mikey Dickerson, he's the person who sort of created the web application hierarchy of needs in Google. He was an SRE. And his pyramid, like Maslow's hierarchy of needs, was all over Google when I was there. I was so impressed with the idea that, like, we aren't talking about how do we solve this problem? We're talking about knowing when there's a problem. And then, if we know there's a problem, we can put some messaging around that. We can say, like, "We're aware," right? Like if the president calls the secretary, the secretary can say, "We know it's down. We're working on it," which is building up political capital.

It's a really amazing process that I kept reading this blog post, and I was like, God, that's how I would approach it. And then, I was like, wow, I wonder if I could use my skills to help America, and very shortly submitted an application and was like, well, we'll see what happens. And about six months later, I walked in the door at the VA and was the eighth employee of the Digital Service team at the VA. That was a franchise team of the USDS model.

VICTORIA: And can you say a little bit more about what is the U.S. Digital Service and expand upon your early experience there?

ROBBIE: Yeah. So, the United States Digital Service was created after HealthCare.gov had its issues. Todd Park had convinced President Obama to reach out to get support from the private industry. And the few of the people who were there, Todd convinced to stick around and start creating a team that could support if there was this kind of issue in the future. I believe the team that was there on the ground was Mikey Dickerson, Erie Meyer, Haley Van Dyck, and Todd. And there was a few other people who came back or were very close at the beginning, including the current administrator of USDS. She has been around a long time and really helped with HealthCare.gov. It's amazing that Mina is back in government. We're very lucky to have her.

But what came out of that was what if we were able to stand up a team that was here in case agencies needed support or could vet solutions before these types of problems could exist? So, USDS was what they called the startup inside the White House that was created during the 2014 administration of President Obama. The team started that year, and I joined in May of 2016. So, I would be, like, sort of the beginning of the second team of the VA U.S. Digital Service team.

So, USDS supported this idea of tours of duty, where you're a schedule A employee, which meant you were a full-time government employee, but you were term-limited. You could do up to two years of duty and work, and then you could theoretically stick around and do two more years. That was how these roles were envisioned. I think there's lots of reasons why that was the case. But what's nice is it meant that you would come in with fresh eyes and would never become part of the entrenched IT ecosystem.

There are people that transition from USDS into government, and I think that's a huge value prop nowadays. It's something that I don't know they were thinking about when the original United States Digital Service was stood up, but it was hugely impactful. Like, I was part of the team at the VA that helped digitize the first form on vets.gov and all the work that was done. When the VA team started, there was a team that was helping with veteran benefits, and they worked on the appeals process for veteran benefits. And I joined. And there was a team that was...eventually, it became dubbed the veteran-facing tools team.

And we worked on vets.gov, which was a new front door to expose and let veterans interact with the VA digitally. And over time, all the work that went into the tools and the solutions that were built there, everything was user-researched. And all of that work eventually got brought into VA.gov in what they called a brand merger. So, we took, like, the sixth most trafficked front door of the VA and took all the modern solutioning that that was and brought it into VA.gov, the main front door. So, all of a sudden, there was an identity, a login provided on VA.gov for the first time. So big, impactful work that many people were a part of and is still ongoing today.

Surprisingly, so much of this work has now fallen under OCTO, which is the Office of the CTO in the VA. And the CTO is Charles Worthington, who was a USDSer who's the epitome of a person who goes where the work is. Charles was a Presidential Innovation Fellow who helped out in the times of HealthCare.gov and, joined USDS and did anything and everything that was necessary. He interviewed engineers. He was a product person. Charles is one of the most unique technologists and civic tech people I've ever met in my life.

But Charles, at the end of the Obama administration and in this transition, realized that the VA was in need of someone to fill the CTO role. So, he came over to become the interim CTO because one of the values of USDS is to go where the work is. And he realized, with the transition, that Marina Nitze, who was the CTO who was transitioning out, there was going to be a need for continuity. So, he came in to provide that continuity and eventually became the full-time CTO and has been there ever since.

So, he has helped shape the vision of what the VA is working towards digitally and is now...he was just named the Chief AI Officer for the agency. Charles is a great person. He has successfully, you know, shepherded the work that was being done early by some of us into what is now becoming a sort of enterprise-wide solution, and it's really impressive.

VICTORIA: I appreciate you sharing that. And, you know, I think there's a perception about working for public service or for government, state or federal agencies, that they are bureaucratic, difficult to work with, very slow. And I think that the USDS was a great example of trying to really create a massive change. And there's been this ripple effect of how the government acquires products and services to support public needs, right?

ROBBIE: Yeah, I would say there's a couple of arms of the government that were sort of modernization approaches, so you have the Presidential Innovation Fellows, which are the equivalent of, like, entrepreneurs and residents in government. And they run out of...I think they're out of the TTS, the Technology Transformation Service over at GSA, which is the General Services Administration. But the PIFs are this really interesting group of people that get a chance to go in and try to dig in and use their entrepreneurial mindset and approach to try to solve problems in government. And a lot of PIFS work in offices.

Like, Charles' early team when he first became the CTO included a lot of Presidential Innovation Fellows. It was basically like, "Hey, the VA could use some support," and these people were available and were able to be convinced to come and do this work. And then, you have the Presidential Management Fellows, which I think is a little bit more on the administration side. And then, we have 18F and USDS.

The United States Digital Service is a funded agency with an OMB. And we were created as a way to provide the government with support either by detailing people over or dropping in when there was a problem. And then, 18F is an organization that is named because the offices of GSA and TTS (Technology Transformation Service), where it's housed, are on the corner of 18th Street and F in DC. And 18F is sort of like having a technology or a digital agency for hire within the government. So, they are full-time employees of the government, sort of like USDS, except government agencies can procure the support of that 18F team, just like they would procure the support of your company. And it was a really interesting play.

They are fully cost-recoupable subcomponent of TTS, which means they have to basically make back all the money that they spend, whereas USDS is different. It's congressionally funded for what it does. But they're all similar sibling organizations that are all trying to change how government works or to bring a more modern idea or parlance into the government. I used to say to people all the time that at USDS, you know, we would set a broken bone say, and then we would come back around and say, like, "Hey, does your arm hurt anymore?" The idea being like, no. Be like, "Cool, cool. Maybe you should go to the gym, and you should eat better." And that would be, like, procurement change. That would be, like, changing for the long term.

So, all the work I was doing was building political capital so we could do better work in changing how procurement was done and then changing how the government delivered these things. So, what was awesome was, like, we used to have these fights at USDS about whether or not we were a culture change or we were firefighters. And I think the reality is once we're involved, culture changes happen. The bigger question is, are we going to be there for the long haul, or are we only there for a shorter period of time? And I think there are reasons why USDS teams had both plays. And I think it really is just two different plays for the same outcome.

VICTORIA: Yeah, that makes sense. And to pivot a little bit, I think, you know, our audience, we have clients and listeners who are founders of products that are aimed at making these, like, public service needs, or to give some examples, like, maybe they're trying to track Congressional voting patterns or contact information for different state representatives, and they're trying to navigate this space [laughs]. So, maybe you can give some advice for founders interested in selling their products to government agencies. What can they do to make it more appealing and less painful for themselves?

ROBBIE: I wouldn't consider myself a procurement expert, but at USDS, the procurement team called themselves the [SP] procurementati.

And I was a secret member of the procurementati. I often was the engineer they would call to evaluate statements of work or sometimes be on technology evaluation panels. And it was fun to be a part of that. Things that most companies don't realize is government agencies will put out things like request for information or sources sought in the government space. And this is a way for industry to influence how government tries to solve problems.

If you are trying to go after government work and you're only responding to an RFP, you're probably behind in your influence that you could have on the type of work. So, you'll see if a procurement seems to be, like, specifically focused on an approach, or a technology, or a framework, it's probably because some companies have come through and said, "I think this would probably solve your problem," and they gave examples. So, that's one way to be more connected to what's going on is to follow those types of requests.

Another is to follow the money. My wife is this amazing woman who helped write The Data Act and get it passed through government. And The Data Act is the Data and Transparency Act. And that led to her heading over to treasury and leading up a team that built USAspending.gov. So, there is a website that tracks every dollar, with some exceptions, of the funding that comes out of Congress every year. And what's great is you can track it down to where it's spent, and how it's spent, and things like that. For education purposes, I think that is a really good thing that business and growth people can focus on is try to see and target where competitors or where solutions that you've looked at have gone in the past. It's just a good set of data for you to take a look at.

The other piece is if you're creating a solution that is a delivery or a deliverable, like a SaaS solution, in order for something to be utilized in the government, it probably needs to be FedRAMP-approved, which is a process by which security approvals have been given so that government agencies have the green light to utilize your solution. So, there's tons of documentation out there about FedRAMP and the FedRAMP approval process. But that is one of those things that becomes a very big stopping point for product companies that are trying to work in the government.

The easiest way to work your way through that is to read up on it a bunch, but also find an agency that was probably willing to sponsor you getting FedRAMP approval. Most companies start working with a government agency, get an exemption for them to utilize your product, and then you get to shape what that FedRAMP process looks like. You start applying for it, and then you have to have some sort of person who's helping shepherd it for you internally in the government and accepting any issues that come along in the process. So, I guess FedRAMP approval is one that's a little complicated but would be worth looking into if you were planning on delivering a product in government.

VICTORIA: Right. And does that apply to state governments as well?

ROBBIE: So, lots of state-related and city and locality-related governments will actually adopt federal solutions or federal paradigms. So, I think in the state of California, I think FedRAMP as one of the guiding principles for accepting work into the state of California, so it's not consistent. There's not a one-to-one that every state, or every city, or every locality will pull this in. But if you are already approved to be a federal contractor, or a federal business, or a federal product, it's probably going to be easier to make your way into the local spaces also.

VICTORIA: Right. And as you said, there's plenty of resources, and tools, and everything to help you go along that journey if that's the group you're going for [laughs].

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: So, kind of bringing it back to you, like, you're saying you want those partnerships within the government. You want someone advocating for you or for your product or your service. Drawing that back to what you said earlier about community, like, how do you form a community with this group of people who are in the state, or federal government, or civic tech spaces?

ROBBIE: Yeah, I think it's an interesting problem because so much of it feels impenetrable from the outside. Most people don't even know where to start. There are organizations out there that are pretty good community connections, an example I would give is ACT-IAC. It is a public-private partnership where people from within the government, experts in their fields, and people in the private industry who are experts in their fields will be together on community boards and engaging in panels. And so, it's a really nice way to start connecting those dots.

I have no direct affiliation with ACT-IAC. But if they'd like to give me my own account, that would be great. But it is one of those organizations I've seen be successful for people trying to find their way into a community that is a little harder to find.

I think, also, so much of the community engagement happens at conferences and around...so, like, if you're in the healthcare space, this last month, you've had multiple conferences that I think were really great for people to get to know one another, you know, an example is ViVE. It just happened out in LA, which is a little more on the private sector health space, but still, government agencies were there. I know that the Department of Veterans Affairs had people there and were on panels. And then, HIMSS is another conference that takes place, and that just took place down in Miami. And in Miami, HIMSS happened and a whole bunch of other social community events took place.

So, I'm close with a thing called the Digital Services Coalition, which is 47 companies that all try to deliver good government based on the Digital Services Playbook that was created by USDS that lives at playbook.cio.gov and the way that they try to accomplish this work. And that organization, while they were in Miami, hosted a happy hour. So, there's a lot of connections that can be made once you start seeing the players and getting to know who's around. So, it's a little bit about trying to find your way to that first event, and I think that will really open up everything for you.

Within a week or two, I was at an International Women's Day event at MetroStar, which is a really great company that I've gotten a chance to spend some time with. And then, I was at an event for the Digital Services Coalition talking about open source in government. So, there's a lot of stuff out there for you to be a part of that isn't super cost-prohibitive and also doesn't take a lot once you start to open the door. You know, once you peek around that corner and you find some people, there's a lot more to be done.

VICTORIA: Yeah. And you touched on something at the end there that wants me to bring up some of the advantages you can have being a small business, a minority-owned business, or woman-owned business, or veteran-owned business, so thinking about how you can form those connections, especially if you have one of those socio and economic set-asides that you might want to consider if they're looking to work with the government as well.

ROBBIE: Yeah. Those socioeconomic set-asides include small businesses, woman-owned small business. I think it's Native and Alaskan 8(a), which is historically underrepresented and service-disabled veteran-owned. So, there are also sub-communities of associations, like there's the Digital WOSB, the digital Women-Owned Small Business alliance that was founded by Jess Morris from Pluribus Digital, and a bunch of other companies in the Digital Services Coalition. I believe she's the president of the Digital WOSB right now.

That is a sub-community of women-owned small businesses that are trying to connect and create a community that they can support one another. And that's just one example of the type of connection you can make through those types of socioeconomic set-asides. But once you have those official socioeconomic set-asides, it will allow you to get specific contracts engagements in the government that are not allowed or available for others. So, the government procurement process will have some amount of these specific socioeconomic set-asides that need to be hit. Like, 8% of all procurements need to go to this and 10% of all procurements need to go to this.

So, I think the VA is probably one of the most effective at hitting any of the socioeconomic set-asides, specifically related to service-disabled veteran-owned small businesses. So, if you happen to be a person of color and you found a business and you are female presenting, right? You may have 8(a) woman-owned small business. If you also happen to be a veteran and you're service-disabled, all of those things stack. You don't just get to have one of them. And they can be really effective in helping a business get a leg up and starting out and trying to help even the playing field for those communities.

VICTORIA: Yeah. What I really appreciated about my experience working with Pluribus Digital, and you, and people who had had that experience in the U.S. Digital Services, that there is this community and desire to help each other out and that you can have access to people who know how to move your product forward, get you the connections that you need to be competitive, and to go after the work. So, I love encouraging people to consider civic tech options. And maybe even say more about just how impactful some of it can be. And what kind of missions are you solving in these spaces?

ROBBIE: Yeah, I often try to remind people, especially those who are heading towards or considering civic tech, there are very few places in this world that you can work on something that can impact millions of people. Sure, I was lucky enough. I have tons of privilege. I worked at a lot of wacky places that have given me the access to do the type of work that I think is impactful, but very little has the kind of impact.

Like, when I was interviewed by Marina Nitze as, my last interview when I joined USDS, she sent me an email at the end of it and said like, "Everything was great. I look forward to working with you. And remember, every time you commit code into our GitHub, you'll be helping 8 million veterans." And then, she cc'd Todd Park. And Todd was the CTO of the U.S., and he responded back within a minute. Todd is one of the most busy people. It was amazing to me how fast he responded. But he was like, "Lemme tell you, as somebody who can talk on behalf of our president, our country needs you." And those kinds of things they're hard to comprehend.

And then, I joined the Digital Service team at the VA. And one of the first things that I got to support was the 10-10EZ. It's the healthcare application for veterans. And before I got there, it was a hosted PDF that we were trying to replace. And the team had been working for months to try to build a new, modern solution. What it was is it was, like, less than six submissions were happening a day because it only worked in Adobe Acrobat, I think it was 6.5 and below, and Internet Explorer 8.5 and below.

And if you think about the people that could submit utilizing that limited set of technologies, it was slowly becoming homeless veterans who were using library computers that had not been upgraded. So, there was a diminishing amount of value that it was providing. And then, on top of it, it was sort of lying to veterans. If the version of the Adobe Acrobat was out of date, or wrong, or too new, it would tell them to upgrade their browser. So, like, it was effectively not providing any value over time.

We were able to create a new version of that and that was already well on its way when I joined, but we were able to get it out the door. And it was a React frontend using a Node backend to talk to that SOAP API endpoint. Within the first week, we went from 6 submissions a day to 60 submissions a day. It's a joke, right? We were all 10x developers. We were like, "Look at us. We're killing it."

But about three years later, Matt Cutts came to a staff meeting of USDS, and he was the second administrator of the USDS. And he brought the cake that had the actual 10-10EZ form on it, and it said, "500,000." And he had checked with the analytics team, and there were over 500,000 submissions of that form, which means there are 500,000 possible veterans that now may or may not have access to healthcare benefits. Those are big problems.

All of that was done by changing out one form. It opened up the world. It opened up to a group of veterans that no one else was able to do. They would have had to go into a veteran's office, and they would have had to fill it out in paper. And some veterans just don't have the ability to do that, or don't have an address, or don't have a...so, there are so many reasons why having a digital form that worked for veterans was so important. But this one form that we digitized and we helped make modern has been submitted so many times and has helped so many veterans and their families. And that's just one example. That's just one form that we helped digitize.

But now the team, I mean, I'm back in the VA ecosystem. There's, like, 2,500 people in the general channel in the office of the CTO Slack organization. That's amazing. There's people there that are working all day, every day, trying to solve the same problems that I was trying to solve when I got here. And there's so much work being done to help veterans. But that's just one example, right? Like, at USDS, I know that the digital filing for the free version of your tax form, the IRS e-file Direct, just went live. That was something that USDS had been working on for a very long time behind the scenes. And that's going to impact everybody who submits their taxes.

These are the kind of problems that you get to work on or the scope of some of the problems if you work in these types of organizations, and that's really powerful. It's the thing that keeps drawing me back. I'm back supporting the VA again through some contracts in my business.

But it's funny, like, I was working for another agency. I was over working at DHS on an asylum project. And a friend of mine kept telling people to tell me, "Man, veterans need you. If only there was another one of you to help us over here, that would be great." And eventually, it led to me being like, well, veterans need me. I'm going to go back to the VA. And that was my second tour at USDS at the Department of Veteran Affairs. And now I'm back there again.

So, it's a very impactful place to work. There's tons of value you can provide to veterans. And, to me, it's the kind of work that keeps bringing me back. I didn't realize just how much I was a, like, impact junkie until I joined USDS, and then it really came to a head. I cannot believe how much work I've gotten to be a part of that has affected and supported those who get benefits and services from the federal government.

VICTORIA: [inaudible 33:47] impact junkie. That's funny. But yeah, no, thank you for sharing that. That's really interesting. Let me see if you could go back in time to when you first started in this journey; if you could give yourself any advice, what would you say?

ROBBIE: Yeah, I think I spent so much time being nervous about not having my degree that I was worried it was going to hinder me forever. And it's pretty amazing the career I've been able to thread together, right? Like, you know, I've hit on a few of them already.

But, like, I started with a small web hosting company, and then New York State in the Department of Social Services, then New York City in the Human Resources Administration, Sony Music, Zagat Survey, Google, Johnson & Johnson, IDT telecommunications, Phase2 technologies, where I got to work on an awful lot of problems in lots of awesome places like NBA.com, and Major League Soccer, and Bassmaster. And then, the United States Digital Service where I got to work on things supporting the Department of Veterans Affairs and the Department of Homeland Security over at ADA.gov in DOJ. I helped them out. And I worked over at USDA helping get Farmers.gov off the ground.

So, everything on my left leg, tattoo-wise, is something that changed my life from my perspective. And I have a Drupal tattoo on the back of my leg. I have a DrupalCon. So, anytime somebody said "Drupal" anywhere near a USDS person, I would magically appear because they would just be like, "Oh, Robbie has that Drupal tattoo." So, I got to work on a lot of dot govs that eventually landed or were being built in Drupal. So, I got to support a lot of work. And it meant that I got to, like, float around in government and do a lot of things that others didn't get to do.

When CISA stood up, which is the office of security inside of DHS, it's one of the newest sub-communities or subcomponents, they built DHS SchoolSafety.gov, which is a cross-MOU'd site. And I got to sit in and help at the beginning of that because of my Drupal background. But it was really fun to be the person who helped them work with the vendors and make sure that they understood what they were trying to accomplish and be a sort of voice of reason in the room.

So, I did all of that work, and then after that, I went and worked at Pluribus Digital, where I got a chance to work side by side with you. And then, that led to other things, like, I was able to apply and become the director of Digital Services and software engineering for my local county. So, I worked for Prince William County, where I bought a house during the pandemic. And then, after that contract ended, I had already started my own business. So, that's led to me having multiple individual contracts with companies and so many people. I've gotten to work on so many different things. And I feel very lucky.

If I could go back and tell myself one thing, it's just, take a breath. Everything's going to be okay. And focus on the things that matter. Focus on the things that are going to help you. Focus on community. Focus on delivering value. Everything else will work itself out. You know, I joke all the time that I'm really good at providing impact. If you can measure my life in impact and value, I would be a very rich man. If you can measure it in money, I'm doing all right, but I'm never going to be yacht Robbie, you know, but I'm going to do okay.

VICTORIA: Oh my god, yacht Robbie. That's great. So, just to recap, everything's going to be okay. You never know where it's going to take you. And don't be limited by the things that you think, you know, make you not enough. Like, there's a lot of things that you can do out there. I really like that advice.

ROBBIE: And I think one last piece is, like, community matters, if you are a part of communities and you do it genuinely, how much that will impact your career. I gave a talk from Drupal NYC to the White House and beyond. And I talked through my entire resume and how everything changed when I started doing community engagement. When I went to the Drupal community in New York City and how that led to Sony, and that led to Zagat, which led to me getting acquired by Google, like, these things all cascaded.

And then, when I moved to the DMV, I was able to join here and continue supporting communities, which allowed me to bring people into the local civic tech community from the local DC tech community. So, so many of the best USDS engineers, and designers, and product people I was able to help influence to come to government were people I met in the community or the communities I helped support. You know, I was an early revivalist of Alexandria Code and Coffee. It was a community that was started and then wavered.

And then, Sean McBeth reached out to the community and said, "Do we want to help and support getting it off the ground again?" And I immediately said, "Yes." And then, that led to my friends at BLACK CODE COLLECTIVE wanting to create a community where they could feel safe and connected and create a community of their own. And then DC Code & Coffee started. And from there, Baltimore Code & Coffee kicked off.

And it's just really nice that, like, it doesn't matter where I've been. All these things keep coming back to be a part of community and help support others. And you will be surprised at how much you get back in return. I wouldn't be the person I am today in my community. I wouldn't have my career if it wasn't for the people who started and helped shepherd me when I was starting out. And I feel like I've been trying to do the same for people for a really long time.

VICTORIA: I love that. That's what I say, too, when people ask me for advice on careers and how to grow. And my biggest piece is always to go out and meet people. And go to your community, like, look and see what's happening. Like, find people you like hanging out with and learning from. And just that should be the majority of your time probably if you're trying to figure out where to go with your career or even just, like, expand as a person sometimes [laughs].

Robbie, I was going to ask; you mentioned that you had bought a house in Virginia. One of my other warmup questions was going to be, what's your favorite thing to put on the grill?

ROBBIE: My house in Virginia definitely gets a lot of use, especially in the spring and the fall. I'm a big fan of team no extreme when it comes to temperature. But during those time periods, my grill is often fired up. My favorite is probably to make skirt steak on the grill. I'm a huge fan of tacos, especially made out of skirt steak. I'm in all day. That's one of my favorites.

I also love to smoke. I have a smoker because I'm a caricature-esque suburban dude. I'm going to live into all of the possible things I could have. But I've had a smoker for a long time, and I love making sort of poor man's burnt ends. It's one of my favorite things to make. But you got to have some time. That's the kind of thing that takes, you know, 14 hours or 16 hours, but it's really fun to take advantage of it.

A quick thing I love to make is actually smoked salmon. It takes longer to brine it than it usually does to smoke it. But it is one of the nicest things I've made on my smoker, you know, fresh pesto on a piece of salmon is pretty awesome, or everything bagel. Everything with the bagel seasoning is a pretty fun way to smoke some salmon.

VICTORIA: Wow, that sounds so good. I'm going to have to stop in next time I'm in Virginia and get some [laughs] and hang out. Do you have any questions for me?

ROBBIE: I'm excited to see where you've gone and how you've gotten here. I think this is such a cool job for you. Knowing who you are as a person and seeing you land in a company like this is really exciting. And I think you getting to be a part of this podcast, which we were joking about earlier, is I've been listening to probably since it started. I've been a big fan for a long time. So, it's cool to be here on this podcast. But it's also cool that my friend is a part of this and gets to be a part of this legacy.

I'm really excited to see where you go over time. I know my career has been changing, right? I worked in government. Before that, I did all kinds of other stuff. Nowadays I have my own business where I often joke I have sort of, like, three things I offer, which is, like, consigliere services. Wouldn't it be nice to have a Robbie on your executive team without having to pay them an executive salary?

You know, another one is like, you know, strategy and mentoring, but these are all things I know you do also, which I think is cool. But I've been working on contracts where I support companies trying to figure out how they modernize, or how their CTO can be more hands-off keyboard, or how their new director of business development can be more of a technical leader and taking on their first direct reports. So, I just enjoy all those aspects, and I just think it's something that I've watched you do in the company where we worked together.

And it's always fun to see what you're working on and getting a chance to catch up with you. I feel like you're one of those people that does a really great job of staying connected. Every once in a while, I'll get a random text message like, "Hey, how you doing?" It always makes me smile. I'm like, Victoria is a really good connector, and I feel like I am, but you're even better at it on the being proactive side. That's how this all came about, right? We caught up, and you were like, "Why don't you come on the podcast?" So, that's really exciting.

VICTORIA: Well, thank you, Robbie. Yeah, I think that's one of the great things about community is you meet people. You're like, "Oh, you're really cool. And you're doing cool stuff all the time. Like, how can I support you in your journey [laughs]? Like, what's up?"

Yeah, for me, it was hard to actually leave DC. I didn't, you know, really think about the impact of leaving behind my tech community, like, that network of people. It was pretty emotional for me, actually, especially when we finally, like, stopped doing the digital version [laughs]. And I, like, kind of gave up managing it from California, which was kind of funny anyways [laughs]. Yeah, so no, I'm grateful that we stayed in touch and that you made time to be here with us today. Is there anything else that you would like to promote?

ROBBIE: You know, just to remind you, you've done a great job of transitioning into where you are today, but anybody can do that, right? Like, before I moved to the DC area, I was in New York, and I was helping to organize JavaScript events. And I started looking at the DC area before I moved down here. And I found the DC Tech Community. And I found the Node School DC GitHub organization and reached out to the person who had ownership of it and said I wanted to help and support.

I looked at this the other day. I think I moved on May 8th, and then, like, May 11th, when I walked in the door, somebody was like, "Are you new?" And I was like, "Yeah, I just moved here." And they were like, "Oh, from where?" And I was like, "New York." And they were like, "Are you that guy who's been bugging Josh about running Node school events?" I was like, "Yeah." And like, they were planning an unconference at the end of the month. And they were like, "Would you like to run a Node school at that unconference?" Like, 27 days later.

So, it was amazing that, like, I immediately, like, fell from the New York Community where I was super connected, but I went out of my way to try to, like, see what the community looked like before I got there. And I was lucky enough to find the right people, and immediately I joked...I think I wrote a blog post that said like, "I found my new friends. By, like, going from one community to another, gave a person who was in his 40s a chance to meet new people very quickly." And it was pretty amazing, and I felt very lucky. But I did spend a little bit of energy and capital to try to figure it out because I knew it was going to be important to me.

So, I think you've done a really good job. You've helped launch and relaunch things that were going on in San Diego and becoming a part of this connection to more people. I think you and I have a very similar spirit, which is like, let's find a way to connect with humans, and we do it pretty effectively.

VICTORIA: Well, thank you. That really boosts my confidence, Robbie [laughs]. Sometimes, you show up to an event you've never been to before by yourself, and it's like a deer in headlights kind of moment. Like, oh God, what have I done [laughs]?

ROBBIE: Oh, and the last thing I need to mention is I also have a podcast. I have my podcast about film. It's called Geek on Film. I used to record it with my friend, Jon. He's a little busy right now. But I used to pitch it as a conversation show about the current films that were going on. Now, it's one lone geek's ramblings about what he just saw.

It's a great podcast for me because it gives me an opportunity to think a little more critically about film, which is one of the things that I probably have almost enough credits to get a minor in. But I absolutely love cinema and film in general. And it's given me an opportunity to connect with a lot more people about this subject and also to scratch the itch of me being able to create something around a community and around a thing I really love.

VICTORIA: That's super cool. Yeah. You're top of mind because I also like films. I'm like, what's Robbie up to? Like, what's the recommendations, you know [laughs]? Do you have a top film recommendation from the Oscars? Is that too big of a question?

ROBBIE: So, the one I will say that didn't get enough spotlight shined on it was Nimona. So, I'm a huge fan of the Spider-Man movies. I think Spider-Man Into the Spider-Verse and Across the Spider-Verse are both masterpieces. But Nimona is an animated film that was picked up by Netflix, and it is amazing.

I don't know that I laughed or cried or was more moved by a film last year. And I don't know that it gets enough credit for what it was. But it did get nominated for best-animated film, but I don't know that enough people paid attention to it. Like it may have gotten lost in the algorithm. So, if you get a chance, check out Nimona. It's one of those beautiful, little gems that, if you travel down its story, there's all these twists and turns.

It was based on a webcomic that became a graphic novel. One of the production companies picked it up, and it wasn't going to see the light of day. And then, Netflix bought its distribution rights. There's going to be a great documentary someday about, like, Inside Nimona. But I think the movie itself is really charming and moving, and I was really impressed with it. So, that was the one that got me, like, just before the Oscars this year, where I was like, this is the little animated movie that could, in my opinion. It's so charming.

VICTORIA: I will definitely have to check that out. Thank you for giving us that recommendation.

ROBBIE: Totally.

VICTORIA: Final question. I just wanted to see if you had anything to share about being an advisory board member for Gray and for Hutch Studio. Could you tell us a little bit more about that?

ROBBIE: Yeah. So, Gray Digital was founded by a friend of mine. We met through United States Digital Service. And his organization...I had been supporting him for a while and just being behind the scenes, talking to him and talking through business-related issues. And it was really nice. He offered to make me an official advisory board member. It was a great acknowledgment, and I really felt moved. There's some great people that are supporting him and have supported him. They've done really great work. Gray is out there delivering digital services in this space. And I think I was really lucky to be a part of it and to support my friend, Randall.

Hutch is different. Hutch is an organization that's kind of like if you think about it, it almost is a way to support entrepreneurs of color who are trying to make their way into the digital service delivery space. Being an advisory board member there has been really interesting because it's shaping how Hutch provides services and what their approach is to how to support these companies.

But over the last year, I've convinced the person who's running it, Stephanie, with a couple of other people, to open the door up or crack the door so we could talk directly and support the individual companies. So, it's been really great to be a Hutch advisory member to help shape how Hutch is approaching things.

But I've also been a part of, like, many interview processes. I've reviewed a lot of, like, [inaudible 48:01] who want to join the organization. And I've also created personal relationships with many of the people who are part of Hutch. And, you know, like, you know me personally, so you know I run a Day of the Dead party. We'll just party at my house every year.

I have a huge amount of affection for Mexican culture and, in general, the approach of how to remember people who are a part of your life. So, this is, like, the perfect way for me to bring people together at my house is to say, like, "Hey, my dad was awesome. What about your family? Who are your people?" What's really nice is that has given me an opportunity to host people at my house.

And I've had Hutch company owners at my house the last couple of years and the person who runs Hutch. So, it's a really great community that I look at that is trying to shape the next emergent companies that are helping deliver digital services across the government. And it's really fun to be early on in their career and help them grow.

Again, it seems silly, but it's the thing I care a lot about. How do I connect with people and provide the most value that I can? And this is a way I can provide that value to companies that may also go off and provide that value. It's a little bit of an amplifier. So, I'm a huge fan of what we've been able to accomplish and being a part of it in any way, shape, or form.

VICTORIA: Well, I think that's a really beautiful way to wrap it up.

ROBBIE: Really glad to catch up with you and be a part of this amazing podcast.

VICTORIA: Yeah, so much fun. Thank you again so much. It was great to be here with you 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. You can find me on thoughtbotsocial@vguido.

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.

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/sprint

Support Giant Robots Smashing Into Other Giant Robots