The Bootstrapped Founder

Sometimes, you have to pivot. And that's harder than it seems: old assumptions are deeply ingrained, new frontiers look scary. But right now, Podscan needs this. And today, I'll share what happened, why I'm changing direction, and where this will go. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them ou...

Ben Rometsch (@dabeeeenster.bsky.social) , the founder of Flagsmith, created a bootstrapped SaaS success story. Feature flags are transforming software deployment by decoupling releases and enhancing control. And Ben bootstrapped this deceptively simple-looking part of engineering into a significant software business.  And then there's the open-source part of all that. The Open Feature project is...

The podcasting industry is full of business opportunities. I see them every day, either as a podcaster, a listener, or someone running a SaaS in this industry. So here are the most promising ideas and problem areas in podcasting — right now. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The bl...

Pierre de Wulf (@PierreDeWulf ), the founder of Scraping Bee, transformed himself from a frustrated developer into a SaaS success story. Here's what you'll learn from this episode: 1/ 🐝 Pierre's journey began with a subpar web scraping tool, sparking the idea for Scraping Bee. Discover how he bootstrapped his company in a crowded market, emphasizing lean operations and strategic growth. 2/ 🚀 Ove...

Imagine standing at a crossroads, juggling countless possibilities yet needing to choose just one path. That's what most early-stage founders struggle with. And for me, that's picking the right course towards the ever-elusive Product-Market fit. Today, I'll share how I tackle this challenge and what I do to show my best customers the highest possible value of my product as early as possible. This...

Connor Turland (@Entrecurious) is the prototypical software entrepreneur. He found a niche from a "prior life" and is now building an AI bookkeeping SaaS. Now, many founders struggle with bookkeeping, so this is your opportunity to learn more about the pitfalls and opportunities of that field from someone who speaks both "developer" and "bookkeeper." Here's Connor and how he is employing cutting-e...

AI was supposed to do our chores while we write prose and compose symphonies. Why is it composing our music and writing our books now, while WE do the chores? As software founders, we have a special responsibility — after all, we're the ones crafting a new reality of AI empowerment. But here's the thing: an AI does not love its work. It can't. And that's a problem. Today, I'll dive into how we can...

Today, I’ll dive into the difference between a trial user and a trial abuser and what you can do to invite the former and prevent the latter. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https://thebootstrappedfounder.com/free-trial-error/ The podcast episode: https://tbf.fm/ep...

Coding with AI changes everything. It changes how we design, test, and improve our software projects. Today, I’m talking to generative AI expert James Phoenix. He’s written the book on prompt engineering and shares his hard-earned AI insights freely on the show — including a crash course in developing effectively with the Cursor IDE. Are developers just AI wranglers now? Technical managers? Will w...

YouTube is both the best and the worst source of information — because we can watch it all, but no one will tell us what's REALLY worth watching. Here's how the gatekeepers have vanished, and what has taken their place. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https://thebo...

The problem with having no boss is that there's no one to stop you from procrastinating. I'm challenged by this daily, and I have found a few ways to stay accountable. I'll share those with you today. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https://thebootstrappedfounder.c...

I want new prospects to receive the maximum possible value the moment they register for Podscan, so I treat them as customers before they even come to the page for the very first time. Here's the Podscan Dream Customer strategy — from idea to execution. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them...

Yesterday, I shrunk the size of my production database from four terabytes to just under one terabyte. Something interesting happened last weekend that made me realize I needed to change how I think about scale. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https://thebootstrapp...

When a Podscan user got a bit "too general" with their keywords, all of a sudden, my email provider stopped sending emails. Whoops. Let's talk user error and founder foresight. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out. The blog post: https://thebootstrappedfounder.com/from-overload-to-oppo...

SaaS founders are simultaneously tenants and landlords, renting the tools we need while offering our own services for subscription. It's a world where true ownership seems increasingly elusive, yet understanding its nature is crucial for building lasting value. This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, ch...

Bootstrapping is all about dealing with constraints: no money, the day job, lack of experience, and having no distribution. If you want to know how I tackle the restricted resources I am building Podscan on, this one's for you. Today, we'll dive into what drives my priorities and how they find their way into a complex platform that juggles a lot of expensive operations. This episode is sponsored b...

“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. Today, let me share my early-stage learnings about system observability in this distributed, data-centric SaaS of mine. Eve...

AI is revolutionizing the way I work as a solopreneur. So why not share exactly how I use it? You'll hear how I use AI tools for everything from coding to marketing, and how they've become my secret weapon for punching above my weight. I also get into the nitty-gritty of the challenges and limitations of AI, and how I navigate them. If you're curious about how AI can supercharge your solo business...

It started with a minor refactoring. It ended with an avalanche that almost caused an infrastructure explosion. From code to collapse — and a few weeks of frantic restoration. That's what Podscan was for the last 2 weeks. Here's why dealing with external data and its scale can be very dangerous for indie founders. This episode is sponsored by Podscan.fm The blog post: https://thebootstrappedfounde...

Welcome to the weird world of web scraping in the AI age, where founders have to protect their data from hungry AI companies but also need to collect information from all kinds of (not so) public APIs. Today, I dive into a particularly confusing situation I am in with Podscan when it comes to scraping and keeping the web free and open. This episode is sponsored by Podscan.fm The blog post: https:/...

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 bootstrap...

This week, instead of writing code, I delegated it — to AI. I've been doing this a lot lately. But does that mean I am losing my ability to code? And what about people learning how to code? Is AI serving them, or does it block them from learning the real thing? Here's what's happening in software development, if it's even worth bothering with, and what new coders should know about AI. This episode...

I gave up going to tech conferences. But that probably is an outdated opinion, particularly since as an entrepreneur, I benefit much more from hanging out with my peers. Here's what changed and why you should really consider going to these events if you're an indie founder. This episode is sponsored by Podscan.fm The blog post: https://thebootstrappedfounder.com/should-indie-hackers-go-to-tech-con...

Feeling the weight of success can be just as challenging as the climb to get there. At any point during your journey, you're confronted with having to make choices where the outcome is uncertain. I'm right in that position. So let's dive into a balancing act between the grand vision and the minutiae of running a business. This episode is sponsored by Podscan.fm The blog post: https://thebootstrapp...

@kerollmops , the technical brain behind the open-source search engine Meilisearch, joins me for a nerdy chat about all things search. I’ve been using this blazing fast tech for my own business, podscan, and kero has helped me through a few challenges over the last few weeks. I really want to dive into the economics of building a business on top of an open-source piece of software. Let's chat abou...