Podcast, YouTube, Blog Dear founder, A couple of years ago, I tweeted that “the best tech stack is the one you already know.” To this day, this is one of my most resonating tweets. People keep bringing it back, and founders who’ve been around for a while seem to particularly agree with it. They’ve gone through the learning experience of trying new tech stacks, only to find that investing a lot of time in new technology often isn’t worth it when all you wanted to do was actually build a...
12 days ago • 8 min read
Podcast, YouTube, Blog Dear founder, As I’m building yet another software service business after having built and sold one back in 2019, I keep wrestling with a fundamental question that might sound simple but has profound implications: What do I actually own in this business? THE BOOTSTRAPPED FOUNDER • EPISODE 416 416: The Ownership Paradox: What Do You Really Control in Your Software Business? 19:12 MORE INFO And before we get to that, a word from our Sponsor, Paddle.com. They’re a great...
19 days ago • 10 min read
Podcast, YouTube, Blog Dear founder, Let’s talk about handling multiple ICPs as a solo founder. This is something I’ve been wrestling with at Podscan, and I know many of you face the same challenge: you’re building a product that could serve two, three, maybe even five different ideal customer profiles. And you’re trying to figure out how to keep them all balanced—or whether you should even try. THE BOOTSTRAPPED FOUNDER • EPISODE 415 Handling Multiple ICPs as a Solo Founder 20:14 MORE INFO...
26 days ago • 11 min read
Podcast, YouTube, Blog Dear founder, I was recently reading an article about The Great British Baking Show - or Bake Off, as we fans of this fun TV competition call it. It was written by someone who had been on the show, one of the competitors, and they were talking about how looking at the show from the inside made them realize something profound: there are no real amateurs anymore. That observation stopped me in my tracks. Even the people portrayed as Britains best amateur bakers are, in a...
about 1 month ago • 13 min read
Podcast, YouTube, Blog Dear founder, You know that moment when you realize the ground has shifted beneath your feet? I had one of those moments recently. I was watching an AI agent build out a complex feature for Podscan in about twenty minutes – something that would have taken me days to code properly just a year ago. And it hit me: the rules of the game have fundamentally changed. THE BOOTSTRAPPED FOUNDER • EPISODE 413 413: We’re Gonna Need a Bigger Moat 25:15 MORE INFO And before we get to...
about 1 month ago • 10 min read
Podcast, YouTube, Blog Dear founder, This week, I want to be as pragmatic as possible. Let’s talk about not just “AI this and AI that”, but the actual applications of generative AI that I leverage within Podscan to get my customers to see the value of the product as quickly as possible. THE BOOTSTRAPPED FOUNDER • EPISODE 412 The $0.20/Day AI System That Converts Trial Users Into Paying Customers 25:11 MORE INFO You know, it took me a long while to realize this: AI isn’t just something like a...
about 2 months ago • 27 min read
Podcast, YouTube, Blog Dear founder, I was reading Brandon Sanderson’s latest novel, Wind and Truth, when I came across a sentence that stopped me cold: “A stronger current makes for stronger fish.” That’s it. That’s what entrepreneurship is. We’re constantly encountering currents that either facilitate what we want to accomplish—the businesses we want to build, the lives we want to create—or they oppose us, trying to sweep us into dangerous waters. These currents change all the time. They...
about 2 months ago • 11 min read
Podcast, YouTube, Blog Dear founder, I think we’re at the precipice of a pretty significant change in how we build software products. Obviously, the recent ascent of vibe coding and all the agentic coding tools that we find very useful and highly effective shows a difference in how we approach building products. But there’s another change - not just in how we build, but in who these products are for. THE BOOTSTRAPPED FOUNDER • EPISODE 410 410: Building for the Age of AI Consumers 23:34 MORE...
2 months ago • 11 min read
Podcast, YouTube, Blog Dear founder, James Phoenix is an expert in agentic coding, particularly Claude code, a tool that I have been using to great effect over the last couple months. I chatted with James just a couple days ago and have implemented several of the tips that he gave me during a conversation, and I'm already almost twice as effective at using this already magically effective tool. So I don't think I can overpromise how much insight into well-structured and highly optimized...
2 months ago • 1 min read
