The Bootstrapped Founder

It's time. Solopreneurship works for a while, but it can't last forever. Not for me, not for Podscan. We need help. The blog post: https://thebootstrappedfounder.com/the-founders-first-hire-when-to-let-go-of-your-weaknesses/ The podcast episode: https://tbf.fm/episodes/389-the-founders-first-hire-when-to-let-go-of-your-weaknesses Check out Podscan, the Podcast database that transcribes every podca...

PMF is MIA without JTBD. Make sense? :D The "job to be done" sits at the core of my customer's use of my product. I need to understand it to understand them. To fathom their needs. This week, I'll share how I approach that — and why it's taken me years to get here. The blog post: https://thebootstrappedfounder.com/the-job-to-be-done-understanding-customer-value-communication/ The podcast episode:...

API docs used to be by and for developers. Now, non-technical people use AI tools to build integrations into our SaaS products. We need to rethink how we communicate with them (and the AI agents that write their code). The blog post: https://thebootstrappedfounder.com/your-api-documentation-is-not-for-developers-anymore/ The podcast episode: https://tbf.fm/episodes/your-api-documentation-is-not-fo...

This week, I'm sharing behind-the-scenes choices that allowed Podscan's growth from a small experiment to a thriving business. I'll delve into the choices I've made and how some have worked better than others. I'll explore the key decisions that have driven our success, such as selecting the right tools and technology, and utilizing AI to enhance the efficiency of our processes. Join me to learn h...

Just how much of your service should a trial user be allowed to "try"? When it costs you real money to supply your product, when and how do you apply limits so that people have to upgrade? That's my challenge this week, and I'll share a concrete example from my journey with Podscan. The blog post: https://thebootstrappedfounder.com/the-balancing-act-free-trials-value-demonstration-and-business-sus...

Podscan is profitable. Wild. A great success, a year after starting the business, and a fun opportunity to look at the options that lay before me. What will be my next milestone? What's the ultimate goal here? Well, you'll hear all about it today. The blog post: https://thebootstrappedfounder.com/podscans-profitability-milestone-whats-next/ The podcast episode: https://tbf.fm/episodes/podscans-pro...

Last week, in my hotel room just after MicroConf, I got excited about repositioning. I have had some time to think about the steps forward since then, and here's what I've come up with. This week, I dive into what I have already done, what needs to be done next, and where this is going. The blog post: https://tbf.fm/episodes/383-repositioning-podscan-from-monitoring-to-data-platform The podcast ep...

And I have a few things to say. In one of my rare directly-from-the-hotel-room-to-you episodes, I'll dive right into the many wonderful experiences of this uniquely amazing conference, and I'll share my biggest learnings with you right here. The blog post: https://thebootstrappedfounder.com/i-went-to-microconf-in-new-orleans/ The podcast episode: https://tbf.fm/episodes/382-i-went-to-microconf-in-...

The rise of AI is fundamentally changing and challenging the classic laws and principles of software development and entrepreneurship. Drawing from my experience building Podscan.fm with AI assistance, I dive into how laws like Conway's Law, Brooks' Law, and Postel's Law are being transformed in this new era of AI-assisted development, while sharing practical insights for founders and developers n...

When I talked to Anne-Laure Le Cunff earlier this week, we get into experiments and how to run them effectively. That made me think that I've been running quite a few of those recently, and here's how that has worked out for me. The blog post: https://thebootstrappedfounder.com/experiment-report-trying-new-things/ The podcast episode: https://tbf.fm/episodes/380-experiment-report-trying-new-things...

Anne-Laure Le Cunff (@neuranne) is a neuroscientist and author of the book Tiny Experiments, where she shines a scientific light on how we set goals, what experiments we should think about, and how we can deal with uncertainty in a high-stress world. We chat about goals, reprogramming your own subconscious, and how learning in public can benefit anyone on any journey. The blog post: https://theboo...

I'm not usually trying to create FOMO in other founders — I know all too well that we're busy enough with what we're building. But if you're not using chat-based AI to collaborate with (both in your business and outside of it), you're playing the game on hard mode. I'll share a few stories today of why this particular kind of virtual collaborator helps me so much in my business. The blog post: htt...

The most insidious consequence of chasing virality isn't that it makes you look foolish; it's that you're actively poisoning your precious audience. Here's what "playing the algorithm" might do to (instead of for ) your personal and professional brand. The blog post: https://thebootstrappedfounder.com/virality-is-poisonous/ The podcast episode: https://tbf.fm/episodes/377-virality-is-poisonous Che...

Justin Moore (@justinmooretfam) knows a thing or two about sponsors. He's responsible for dozens of episodes of this very podcast to be sponsored! And what he taught me, he'll teach you. I was VERY hesitant when I started looking at sponsors. I thought that would dilute my brand. Make me a sellout. But that's a self-limiting belief — and Justin will give you the tools to profitably reprogram your...

When notifications prevent you from focusing on your actual work, you know you're in trouble. Here's how I approach the balance between keeping an eye on the critical parts of the business and focusing on the deep work that needs to get done. The blog post: https://thebootstrappedfounder.com/mute-those-dings/ The podcast episode: https://tbf.fm/episodes/375-mute-those-dings Check out Podscan to ge...

Databases are hard. Making the right choices early and keeping things running smoothly even when budget pressures and customer requests start piling on — that's the hard part that many solopreneurs and indie founders struggle with. I certainly do. So here's a journey through my learnings and experiences from running SaaS offerings with sizeable —talking about terabytes of data— databases. The blog...

Sometimes, less is more. Here's how I pruned my feature backlog from 120 to 15 items. I'll share my decision-making framework; every single rule comes with examples. Time to cut down on the mental load that is having too many "ideas" in your backlog. The blog post: https://thebootstrappedfounder.com/deleting-your-backlog-a-founders-guide-to-feature-pruning/ The podcast episode: https://tbf.fm/epis...

One day, we'll all meld our minds into one, sharing our thoughts like the Borg on Star Trek. But before that, we have a few things to get done. And for us founders, that's dealing with the ever-increasing speed of technological advancement. The blog post: https://thebootstrappedfounder.com/indie-hacking-the-singularity/ The podcast episode: https://tbf.fm/episodes/372-indie-hacking-the-singularity...

Brian Sierakowski (@bsierakowski) has been busy over the last year: he started working on ChangeBot and TRMNL, and both projects are taking off. If you ever wondered what a good changelog looks like or why you might need one, this episode is for you. 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...

This week, I was super sick — to the point where all I could do was rest in bed. The businesses needed to keep running, though. And fortunately, I set them up to do just that. The blog post: https://thebootstrappedfounder.com/building-systems-that-work-while-you-dont/ The podcast episode: https://tbf.fm/episodes/370-building-systems-that-work-while-you-dont Check out Podscan to get alerts when you...

Expectations around AI tooling are changing, and software founders will be the first to either provide what people want — or perish. 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/expect-ai-tions/ The podcast episode: https://tbf.fm/episodes/369...

Johannes Jäschke is a pioneer in the intersection of technology and mental health. From a college seminar to the forefront of digital well-being, Johannes developed Hypnu, a hypnosis app that gained significant traction during the pandemic. His innovative approach offered an alternative to traditional methods, addressing insomnia and anxiety without side effects.  After successfully exiting Hypnu,...

Now that we're starting a new year, let's look ahead at the opportunities and challenges facing the software business world in 2025. 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/the-biggest-opportunity-of-2025/ The podcast episode: https://tbf...

Omar Zenhom (@TheOmarZenhom) is one of those few amazing founders who just can't stop giving back to their entrepreneurial peers, no matter how much success they might have. Recently having sold WebinarNinja, Omar still shows up every single day — on Twitter, on the $100 MBA podcast, or wherever builders and makers struggle to build and make. We talk about the exit, how to build a support network...

A new business. Raising money. Bootstrapping. Lifting. And then some. My 2024 was a year of progress, changes, and taking a few more risks than usual. Here's my 2024 year in review. 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/arvids-year-in-r...