Bootstrapped Web

Brian’s product, ZipMessage, is live today on Product Hunt the same day this episode airs—Tuesday, January 11th

Does experimentation affect your business and cause more stress within your leadership team? How are the communication levels within your team? How do you reach a niche market? Jordan and Brian talk about these questions and more on this episode of Bootstrapped Web.  Jordan talks about his hangups and why his need for idea exploration is causing difficulties with his leadership team. Meanwhile, Brian is continuing to navigate the challenges of starting a new business with a niche target market. Is podcasting the answer? They also go over some interesting tools for searching for the perfect podcast, marketing to specific groups, as well as their excitement for Andrew Chen’s newest book, “The Cold Start Problem.” “I’m very much a middle sibling when it comes to management at the leadership level. It’s very collaborative.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: A new ZipMessage websiteHiring generalists or specialistsChallenging leadership team conversationsMarketing and and outreach for the podcasting communityInfluencer outreachSEO plays and search demandsAndrew Chen’s newest book release If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “I’m getting these things dialed in. It’s difficult but I think it’s finally starting to come together.” – Brian Powered By the Tweet This PluginTweet This Resources: SparkToro Podseeker “The Cold Start Problem: How to Start and Scale Network Effects” by Andrew Chen Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes. 

What does traction feel like? How do you authentically build a network? Brian and Jordan talk about marketing, website updates, and the different phases of product/market fit. Jordan dives into the different and unique ways Rally is marketing. Brian updates us on ZipMessage momentum: website updates, premium enrollment, and crossing a customer milestone. Today’s episode is all about the different ways you can build traction but also the different ways you can define traction. “If you can work directly with your audience to monetize the people who are crazy about you, you can make more money in a different model, and everyone is the most happy.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Marketing site changes at RallyGetting credit for speed and momentumNFT Projects for marketingZipMessage website updatesPersonalization for customers Creating a WordPress pluginPremium enrollment/Private or public conversationsPhases of Product/market FitWhat does traction feel like?Are customers willing to adapt for your product? If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “We did things a certain way and, if they didn’t like that, either they didn’t become a customer or they adapted. And we had plenty of customers who adapted.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes. 

When launching a new SaaS business, what comes first? What features do you focus on? How do you keep an eye on your key metrics early on? How do you handle onboarding when you’re shuffling team members’ priorities? Brian and Jordan talk all about the newest updates with ZipMessage and Rally. From experimenting with free plans, website redesigns, and preparing themselves for an influx of activity, there is a lot going on behind the scenes. Exciting things are happening but with excitement come daunting tasks, important decisions, and possible mistakes. “What we’re about to do is, we’re about to scramble people’s priorities in a challenging way.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: New activity with ZipMessageOnboarding first merchants with RallyRemembering the excitement and joy that comes from sales demosExperimenting with a free plan on ZipMessageThe differences between the free and paid planRally’s all-hands to mentally prepare for a different challenge: new prioritiesZipMessage’s website redesignThe daunting task of revamping landing pages If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “Nothing like having real customers to really drive what’s really important.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally As always, thanks for tuning in. Head here to leave a review on iTunes.

What is the difference between going to market and marketing? What mindset do you need to be in to accomplish your goals for both of these stages of business? In addition to answering these questions, Brian and Jordan dive into their marketing goals, content strategists, and updates on where they are with their Rally and ZipMessage. Jordan talks about Rally’s methodical blog posts, which will be released slowly over the next few months. Brian shares some of the new features on ZipMessage and his plans for ‘going to market.’ They also talk about how uncomfortable and rewarding the process can be. ‘Going to market’ is humbling and requires authenticity after all. “There’s a lot going on inside the company and inside the product. And ‘go to market’ is one element of that but you can’t just focus on that because there’s a lot of other things going on that we have to get right.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The difference between going to market and marketingWhat is involved when you go to marketMarketing techniques and content creatorsDifferent versions of networking If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “It’s this idea (especially in the first year) where you’ve got to be doing activities that are introducing the product to more and more new people.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  Rally ZipMessage As always, thanks for tuning in. Head here to leave a review on iTunes. 

Jordan shares some big news, 5.8 million dollars worth of news. At the feet of the news of Rally’s seed funding announcement, Brian and Jordan talk all about raising money for businesses. What are the mechanics of starting the funding journey? Which funding path should you take? What does it mean for a fund to lead a round?  Meanwhile, Brian gives updates on ZipMessage including marketing projects (comparison/competitor pages), hiring designers for website redesigns, and falling behind on content. “What we did was, we only worked with seed funds, because I wanted everyone to be focused on success at the seed stage.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Rally funding announcementsPlanning for funding and growth for RallyStrategic funding approaches and plansComparison/competitor pagesWebsite redesignsSEO content opportunities for ZipMessageHow to get the right response and the right person for the job If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “In this early stage, there is an element of creativity and strategy. I have to bring that knowledge to the project. I can’t just hand that off to someone else.” – Brian Powered By the Tweet This PluginTweet This Resources: Brian on Twitter Jordan on Twitter  ZipMessage Rally Website As always, thanks for tuning in. Head here to leave a review on iTunes.

Bootstrapped Web is no longer bootstrapped, on either side! Jordan starts off this episode with his “coming out” strategy, which all starts with his initial three-post series on Rally. He also dives into Rally updates, comparing your start-up businesses, and the importance of developing a unique view of the market. Brian takes funding from Calm Fund (formerly Earnest Capital), which has been a month in the making. He talks about the different decisions and considerations to be made when exiting Audience Ops and taking funding for ZipMessage. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “I love this [angel funding] ecosystem and how it’s been evolving.” – Brian Powered By the Tweet This PluginTweet This Here are today’s conversation points: Jordan’s “coming out” strategy for RallyBrian takes funding from Calm Fund (formerly Earnest Capital) “I have been sitting on so many secrets, it’s not healthy. It’s not healthy to be quiet and fearful. It’s not my natural state.” – Jordan Powered By the Tweet This PluginTweet This Resources Rally Blog “Your Startup is a Movement” by David Sacks Calm Fund  Brian on Twitter Jordan on Twitter  ZipMessage As always, thanks for tuning in. Head here to leave a review on iTunes. 

Some news!  Brian has sold his business, Audience Ops, to JD Graffam!  And what better way to announce this transition than to bring JD on the show!   Jordan leads the way as Brian and JD talk through how this deal came together, the process from each of their perspectives, and the successful close and transition that’s now underway. If you’re thinking about pursuing an exit from your business or thinking about acquiring one, we hope you’ll find some of our real-world experience from this deal helpful. You can read Brian’s blog post that dives deeper into the deal and thought processes that led up to the exit. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here Mentioned on today’s episode: Audience Ops JD Graffam on Twitter JD’s article, Fourteen Things That Will Keep Me from Buying Your App As always, thanks for tuning in. Head here to leave a review on iTunes. 

Introduction: Do you work with a full-service accounting and admin company? How do you create markers on your business’s path to success? What unique marketing platforms and ideas do you use? Brian and Jordan are back behind the mic, during this horrendous heatwave. Today’s topics range from admin and accounting tasks they would rather avoid, their very professional podcasting process, Rally’s current markers and goals, and Brian’s exciting marketing ideas.  If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here “Something didn’t sit right. It wasn’t ambitious enough. We need to challenge ourselves more.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: Forming a new corporation with ZipMessageThe need for full-service accounting/adminOur “professional” podcasting processListening back on episodes to help sharpen your gutRally’s current markersDo we have what we need to raise money?Working backwards from and mapping out the goal and markersHow to project numbers at this stageCreating a safe space to make mistakes, changing your mind, and getting appropriate push-back Marketing ideas and promotionThe Shipped Podcast (using ZipMessage)Testing audiences and different marketing platformsPodcast sponsorships: targeting small podcastsYouTube advertisingAlternative free trial program “Let’s not think of the worst case scenario but the realistic scenario.” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Office Engine Gusto Leave us a message here Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   As always, thanks for tuning in. Head here to leave a review on iTunes. 

After a month hiatus, Brian and Jordan are back with stories about trips, waking up in pain, and prepping for competition. They also talk about growth in terms of profitability versus milestones, the newest developments with ZipMessage, and introducing “common, everyday tools” to people outside of the SaaS community. If you have any questions, comments, or topic ideas for Bootstrapped Web, leave us a message here. “Growth as headcount as an acceptable growth metric. And the reason for that is if you’re not shooting for profitability and you’re shooting for milestones.” – Jordan Powered By the Tweet This PluginTweet This Here are today’s conversation points: The relationship between founder and VCHeadcount versus profitability as growthHiring a recruiterZipMessage goalsPrioritizing requestsSetting up new featuresOpening it up to the publicThe Shipped podcastBrian’s new technical marketerIntroduction of technology to othersNiche toolsSummit, whiteboards that do math. The easiest way to create, test, and present your logic.Taming the chaos “If profitability isn’t the goal on this path (which makes sense), what are the metrics that you’re looking at for the next 12 months or 18 months?” – Brian Powered By the Tweet This PluginTweet This Mentioned on today’s episode: Leave us a message here Rally On  ZipMessage SunriseKPI  Productize  Audience Ops ProcessKit   Carthook   As always, thanks for tuning in. Head here to leave a review on iTunes.