The Bootstrapped Founder is the home of my Twitter course Find your Following, the books Zero to Sold and The Embedded Entrepreneur, where I share how to build a business, an audience, and a path to financial independence.
You will also find the Bootstrapper’s Bookshelf, the Bootstrapped Founder Podcast, the YouTube channel, and the Bootstrapped Founder Newsletter here.
Many Heads, Not Many Hats: The Founder’s Identity Crisis
Reading Time: 8 minutesWe often joke in entrepreneurship about founders having to wear many hats. But I think that metaphor is wrong. It’s not about swapping hats. It’s about growing entirely new heads. Not just the cover of the head — the head itself. A new brain that thinks different, speaks different, prioritizes different. And somehow, these heads…
The Case Against Vendor Lock-In: Why Easy Exit Means Better Retention
Reading Time: 7 minutesSometimes software founders are a weird bunch. They’ve built their businesses on open source software and the contributions of people who’ve done a lot of work for free. They’ve benefited at great length from infrastructure and tooling built on open standards that facilitate free exchange of data and ideas. Yet when it comes to their…
The Dead Internet Theory: Are We Building Machines That Only Talk to Other Machines?
Reading Time: 5 minutesI saw something on LinkedIn the other day that stopped me mid-scroll. It was a post—clearly AI-generated, you could tell from the cadence, the slightly off phrasing, the generic inspirational tone—and underneath it were dozens of comments. Enthusiastic comments. Supportive comments. And every single one of them was also AI-generated. Bots responding to bots. A…
Marketing for Founders Who Hate Marketing
Reading Time: 7 minutesMany of the technical founders I know really don’t like marketing. And it’s not that they don’t understand it. They know how important it is to run an effective business. But they don’t really know how to do it right. They don’t know how to leverage their technical skills to make marketing easier. And they…
Vibe Coding Won’t Kill SaaS
Reading Time: 9 minutesI really want to clean up a little bit when it comes to vibe coding and software as a service businesses, because I think there’s a lot of confusion, a lot of hype, and a lot of complaints about the imminent demise of software as a service solutions. And I think it’s time that we…
How Your Data Model Shapes Your Product
Reading Time: 10 minutesMy dear friend Jack Ellis is an unending source of founder inspiration. Not only has he recently started embracing AI agentic coding—something he’s been holding back on for quite a bit. I think I’ve mentioned several times on this podcast alone how he and I seem to have quite opposing views on embracing this technology.…
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