Podcast, YouTube, Blog Dear founder, Let’s dive into a piece of entrepreneurial advice that’s highly irritating and very dangerous. Today I want to talk about the one that I get so much: “Don’t give up. Don’t ever give up. Force yourself, grind it out.” This advice is very dangerous because it builds on the founder’s capacity to struggle through challenges, but it uses this for the very wrong reasons. THE BOOTSTRAPPED FOUNDER • EPISODE 432 432: Don't Give Up... Your Assumptions 10:32 MORE...
7 days ago • 6 min read
Podcast, YouTube, Blog Dear founder, We 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. THE BOOTSTRAPPED FOUNDER • EPISODE 431 431: Many Heads, Not Many Hats: The Founder's Identity Crisis 15:18 MORE INFO Not just the cover of the head — the head itself. A new brain that thinks different, speaks different, prioritizes different. And somehow, these heads are all...
14 days ago • 10 min read
Podcast, YouTube, Blog Dear founder, Sometimes 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 own software business, they hold the opinion that you should have as much vendor lock-in as possible when it comes to your...
21 days ago • 10 min read
Podcast, YouTube, Blog Dear founder, I 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 whole conversation happening, and not a single human being was involved. But every part of that...
28 days ago • 7 min read
Podcast, YouTube, Blog Dear founder, Many 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 just feel—it's evident and obvious to them—that their time would be better spent implementing product features and technical solutions than stumbling...
about 1 month ago • 10 min read
Podcast, YouTube, Blog Dear founder, I 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 have a voice out here that is not a doomer. I’m certainly not an apologist for the SaaS movement either. But giving some realistic expectations of where we are and where the field...
about 1 month ago • 11 min read
Podcast, YouTube, Blog Dear founder, Last time I'll mention this, I promise: it's Cyber week, and I'm running my biggest sale of the year. I've slashed my Bootstrapper's Bundle by 50% - that's both my books (Zero to Sold and The Embedded Entrepreneur) as eBooks and audiobooks, plus my complete Twitter course Find Your Following. Everything I've learned about building, selling, and growing a bootstrapped business, all for $25. Normally over $150. If you've been on the fence, this is the...
about 2 months ago • 13 min read
Podcast, YouTube, Blog Dear founder, Before we dive in today: it's Black Friday week, and I'm running my biggest sale of the year. I've slashed my Bootstrapper's Bundle by 50% - that's both my books (Zero to Sold and The Embedded Entrepreneur) as eBooks and audiobooks, plus my complete Twitter course Find Your Following. Everything I've learned about building, selling, and growing a bootstrapped business, all for $25. Normally over $150. If you've been on the fence, this is the moment. Grab...
about 2 months ago • 25 min read
Podcast, YouTube, Blog Dear founder, If you had asked me a couple of years ago if I loved coding and software development, I would have given you a resounding yes. No other job had ever been as enjoyable. No other activity had ever been as rewarding as building software, writing code, building systems that do what I want them to do in ways that other people couldn’t. But if you ask me this now, I have a much more nuanced perspective. And it comes from two places: having been a software...
2 months ago • 10 min read
