Podcast, YouTube, Blog Dear founder, Before we dive into this week's topic of bootstrapper constraints, a quick just-in-time mention: Next Tuesday —on the 8th of October— I'll be on a live workshop with Castos founder and CEO Craig Hewitt, where we'll talk all about effectively Building in Public. If you want to join a masterclass on building an audience around yourself and your work, this free event will be for you. In recent podcast episodes, I’ve been discussing constraints and how I deal...
11 days ago • 9 min read
Podcast, YouTube, Blog Dear founder, “I didn’t see it coming.” I had to admit that to myself a few times recently. Over the last couple of weeks, I’ve been experiencing several issues with Podscan that only came to pass because I didn’t really have any observability on my system. At least that’s what I know now. 🎧 Listen to this on my podcast. Because it always takes a while to see the bottom part of an iceberg. With Podscan, most scaling issues only show themselves in a delayed fashion; the...
18 days ago • 13 min read
Podcast, YouTube, Blog Dear founder, As a software entrepreneur wearing many hats - from coding to marketing to customer service - I’ve found AI systems to be game-changing tools in my daily work. Today, I want to share how I use these systems, particularly large language models (LLMs) like ChatGPT and Claude, to —hopefully— inspire you to benefit from similar approaches. This isn’t just about the tools themselves, but about how they’ve transformed my workflow and expanded my capabilities as...
25 days ago • 18 min read
Podcast, YouTube, Blog Dear founder, As founders, we often focus on scaling our businesses in terms of customers, revenue, or team size. But what happens when the data your business relies on scales faster than anything else? That’s the challenge I very recently faced with Podscan.fm, and it nearly brought the entire system to its knees. Nearly! If you’re building a business that deals with large volumes of external data, buckle up – this story might save you from some sleepless nights. 🎧...
about 1 month ago • 9 min read
Podcast, YouTube, Blog Dear founder, With my podcast data scanning business Podscan, I’m constantly scraping the web for terabytes of audio and metadata - but now I find myself in a wild cat-and-mouse game, trying to protect my own valuable data from aggressive AI companies doing the exact same thing. It’s a bizarre tightrope walk: I need data to be freely available, but I’m also setting up defenses against scrapers, all while wondering if I could turn these digital intruders into paying...
about 1 month ago • 5 min read
Podcast, YouTube, Blog Dear founder, Should software founders attend tech conferences? The answer is a resounding yes. If you’d asked me five years ago, I’d have completely disagreed. So today, I’ll share my journey from skepticism to enthusiasm about tech conferences — how they can be invaluable for entrepreneurs in ways that go far beyond just keeping up with the latest trends. 🎧 Listen to this on my podcast. Let’s go back in time, to before the entrepreneur in me had awoken. A couple of...
about 2 months ago • 5 min read
Podcast, YouTube, Blog Dear founder, Andrew Davies (@andjdavies) runs marketing for Paddle, the payment provider that powers several of my businesses. They also recently ran an AI launchpad accelerator, which massively impacted the trajectory of my business, Podscan. It's about time we chat more about money on the pod.Today, I get to talk to Andrew about all things payment, why a Merchant of Record is something way too few bootstrappers leverage, and what the future holds for online payments....
about 2 months ago • 1 min read
Podcast, YouTube, Blog Dear founder, Just a few years ago, I was a wholly different coder. At my best, I was breezing through documentation and writing mostly functional code. At my worst, I’d be chasing typos and strange bugs for hours, to no avail. Not once would I have thought of using AI to help me — because it didn’t exist. But things have changed. 🎧 Listen to this on my podcast. We now live in a world where software developers who don’t use AI tooling to write code are becoming extinct....
about 2 months ago • 9 min read
Podcast, YouTube, Blog Dear founder, Earlier this week, I came across a quote that resonated deeply with me: "I can accomplish anything, but I won't really be worthy until I accomplish the next big thing." This sentiment, shared in a Hacker News conversation about similarities between founders, got me thinking about the self-limiting beliefs we entrepreneurs often grapple with, especially when running solo businesses. There’s always some kind of balance to strike. Never clear-cut. Always in...
2 months ago • 4 min read