The Bootstrapped Founder

I know you're out there. The developer who watches their colleagues enthusiastically embrace Claude Code and Cursor, having AI write entire feature sets while you proudly type every semicolon by hand. The founder who sees AI-generated code as a ticking time bomb of bugs and security vulnerabilities. The software entrepreneur who believes that real code comes from human minds, not language models.

This one's for you.

This episode of The Bootstraped Founder is sponsored by Paddle.com
You'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-friday

The...

A lot of early-stage founders have understood—mostly because more and more people are talking about their early-stage strategies—that you need to validate your ideas. You need to make an effort to figure out if the thing you're planning to do is actually reasonable to attempt. Validation is important and absolutely worth doing prior to building.

That much, many people have understood.

But here's where things get interesting. Often enough, validation looks like checking if people have the problem—checking if people have the challenge that your idea solves. And if you find people...

We're living through a fascinating moment in software development. AI coding tools can build features faster than ever before. They can scan entire codebases, spot things we might miss, and implement changes across dozens of files in seconds. It's incredible.

But there's something we need to talk about. Something that's quietly accumulating in our projects while we marvel at how quickly we can ship features.

This is called comprehension debt.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/why-ai-generated-code-hurts-your-exit/
...

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. But AI changes things. Or does it?

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-best-tech-stack-in-the-age-of-ai/
The podcast episode: https://tbf.fm/episodes/417-the-best-tech-stack-in-the-age-of-ai

Check out Podscan, the Podcast database that transcribes ever...

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?

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-ownership-paradox-what-do-you-really-control-in-your-software-business/
The podcast episode: https://tbf.fm/episodes/416-the-ownership-paradox-what-do-you-really-control-in-your-software-business

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
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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.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/handling-multiple-icps-as-a-solo-founder/
The podcast episode: https://tbf.fm/episodes/handling-multiple-icps-as-a-solo-founder

Check out Podscan, the Podcast database that transcribes every podcast ep...

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.

Not only is that changing the media landscape, it also affects what businesses are needed to serve what has replaced them.

This episode of The Bootstraped Founder is sponsored by...

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.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/were-gonna-need-a-bigger-moat/
The podcast episode: https://tbf.fm/episodes/413-we-re-gonna-need-a-bigger-moat

It took me a long while to realize this: AI isn't just something like a chatbot for my customers. AI can work behind the scenes to facilitate getting the right stuff in front of the right people for me, even just to figure out who people are and how I should talk to them. And today, I want to share exactly what I'm doing, how expensive this is to run, and how I believe this can be part of every single software as a service business out there—even if you don't have any touchpoint with artificial intelligence in th...

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 vary in strength depending on where you are in your journey. And here's the thing: they're mostly invisible until you lear...

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.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/building-for-the-age-of-ai-consumers/
The podcast episode: https://tbf.fm/episodes/410-building-for-the-age-of-ai-consumers

<...

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 agentic coding you will get from this conversation. 

This episode of The Bootstraped Founder is sponsored by Paddle.com

Today I'll be talking about a successful marketing project within my software business that turned out to be so successful that it spawned a business built on top of that business.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-podscan-ideas-vault-engineering-as-marketing/
The podcast episode: https://tbf.fm/episodes/408-the-podscan-ideas-vault-engineering-as-marketing

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid<...

Nick Groeneveld is a designer and User Experience expert who has been a valued collaborator on Podscan, my own software product. Nick works as a freelancer for a lot of companies that have no in-house design knowledge, and he's been navigating the rapid changes that AI tools like Lovable and vZero are bringing to the design world. With 10 years of professional design experience and a deep understanding of design theory, Nick brings a unique perspective on what happens when machines start creating interfaces that look surprisingly good.

We also tackle deeper questions about whether AI is making...

Today, I’ll share how I’ve been preparing Podscan (and long before that, another SaaS business) to be ready to be acquired at a moment’s notice.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/making-your-business-sellable-even-if-you-never-plan-to-sell/
The podcast episode: https://tbf.fm/episodes/406-making-your-business-sellable-even-if-you-never-plan-to-sell

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find m...

Today we’ll talk about how AI systems, particularly the ones that do all the work for us, can both massively amplify and hinder our effectiveness. The good get better, and the bad get worse. It's a problem.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-friction-paradox-why-ai-might-be-making-us-worse-at-what-we-do/
The podcast episode: https://tbf.fm/episodes/405-the-friction-paradox-why-ai-might-be-making-us-worse-at-what-we-do

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a vo...

Today we’ll talk about keeping up with an avalanche of audio data and how I built Podscan’s transcription infrastructure.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-transcription-challenge-building-infrastructure-that-scales-with-the-world/
The podcast episode: https://tbf.fm/episodes/404-the-transcription-challenge-building-infrastructure-that-scales-with-the-world

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: http...

Amar Ghose has been growing Zenmaid from idea to market leader as a non-technical founder. Zenmaid is a SaaS platform that's been helping maid service owners grow their businesses since 2013. Amar is one of those amazing founders who truly embodies the bootstrapping spirit—when his co-founder left early on at just $15k in monthly revenue, he could have easily given up. Instead, he stuck with it, and through relentless customer focus and persistence, he's built ZenMaid into a $150k per month business over the past 12 years.

What makes Amar's story particularly inspiring is that he's a non-technical fo...

Today I’ll share my insights into the podcasting universe, from a software founder perspective. There are so many untapped opportunities in a space where budgets and expectations are growing massively, so why not talk about the most challenging issues and what could be gained if they were solved.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-podcasting-infrastructure-crisis-a-2-billion-industry-built-on-digital-duct-tape/
The podcast episode: https://tbf.fm/episodes/402-a-2-billion-industry-built-on-digital-duct-tape

Check out Podscan, the Podcast database that transcribes every podcast episode out th...

Vova Feldman is the founder of Freemius, a Merchant of Record payment provider. He's been at it for a while, and it wasn't always easy. Vova shares his approach to weathering the highs and lows of entrepreneurship, how to build a team (and mis-hires), and what operating in the payment industry means for a crafty founder.

The blog post: https://thebootstrappedfounder.com/vova-feldman-mastering-entrepreneurship-in-the-payments-sector/
The podcast episode: https://tbf.fm/episodes/401-vova-feldman-mastering-entrepreneurship-in-the-payments-sector

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan...

One aspect of the AI hype we’re all dealing with right now is severely underreported. And it’s that part that I personally think has a much more substantial long-term impact than all the magical video generators and coding agents.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/the-hidden-revolutionai-is-democratizing-coding-mentorship/
The podcast episode: https://tbf.fm/episodes/400-the-hidden-revolution-ai-is-democratizing-coding-mentorship

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send...

Shane Rosenthal and Simon Hamp from the NativePHP Project have brought PHP, and with it my favorite web framework Laravel, onto Mobile devices. I love this: taking established tech and porting it into places where you wouldn’t expect. I’ll be talking to Share and Simon about how they accomplished this, and, maybe even more impressively, how they turned this into a profitable business at a very early stage.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/simon-hamp-shane-rosenthal-building-monetizing-nativephp/
The podcast episode: https://tbf.fm/epis...

When Python's dominant package manager pip was challenged by newcomer uv—which is so fast users think it's broken—it revealed a fundamental truth about first-mover advantage that every founder needs to understand. Discover why being first means building "unavoidable complexity," how smart competitors exploit this weakness, and the strategic framework for deciding whether to pioneer a market or build a better mousetrap.

The blog post: https://thebootstrappedfounder.com/the-hidden-cost-of-being-first/
The podcast episode: https://tbf.fm/episodes/the-hidden-cost-of-being-first

Check out Podscan, the Podcast database that transcribes every podcast episode out there minu...

Today’s episode represents the reality of entrepreneurship—not just the wins, but the difficult decisions and uncertainty that come with building something new. Sometimes the most valuable conversations happen when we're honest about the challenges we're facing.

The blog post: https://thebootstrappedfounder.com/when-profitability-disappears-a-podscan-reality-check/
The podcast episode: https://tbf.fm/episodes/397-when-profitability-disappears-a-podscan-reality-check

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly artic...

Jack Friks (@jackfriks) is the founder of PostBridge, a social media scheduling tool that grew from his own frustration with spending hours posting across platforms to a $18k/month business. We explore the evolution of social media toward authenticity, the challenges of building lean products as a solopreneur, and how to navigate the noise while maintaining a genuine human connection in an AI-driven world.

The blog post: https://thebootstrappedfounder.com/jack-friks-building-tools-that-empower-without-overwhelming/
The podcast episode: https://tbf.fm/episodes/396-jack-friks-building-tools-that-empower-without-overwhelming

Check out Podscan, the Podcast database that transcribes every podcast episode out...

My day-to-day coding looks very different from what it was a few years ago. Today, you'll learn about my voice-to-code workflow and how I leverage smart tools to have so much free time that I feel guilty for "not working enough." Seriously.

The blog post: https://thebootstrappedfounder.com/from-code-writer-to-code-editor-my-ai-assisted-development-workflow/
The podcast episode:  https://tbf.fm/episodes/395-from-code-writer-to-code-editor-my-ai-assisted-development-workflow

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

Y...

Taylor Otwell (@taylorotwell) didn't just create the popular open-source framework Laravel. He turned it into a highly profitable business that helps developers build profitable businesses themselves. Few other open-source devs have such a clear understanding of market needs AND developer requirements. Taylor shares his approach to monetizing freely available code, how he intentionally built an ecosystem of free and paid-for tooling, and where the Laravel journey will go.

The blog post: https://thebootstrappedfounder.com/taylor-otwell-the-quite-entrepreneurial-creator-of-laravel/
The podcast episode: https://tbf.fm/episodes/394-taylor-otwell-the-quite-entrepreneurial-creator-of-laravel

Check out Podscan, the Podcast database that transcribes...

Software-as-a-service business acquisitions are in trouble. What is responsible for a downward trend in multiples and acquisition dollar amounts? It has a lot to do with AI, but it may not be what you think.

I recently recorded an in-depth session for ​Rob Walling's SaaS Launchpad​. This module is called AI in SaaS, and I share over a dozen pitfalls, unobvious risks, and hard-earned insights from my own AI SaaS building journey. The course was already great, but... you know... ;) Use the code ARVID150 to get $150 off until June 8th.

The blog post: https://thebootstrappedfounder.com...

Ever heard of model collapse? It occurs when AI models are trained on the outputs of previous AI models. And it's not pretty.

I recently recorded an in-depth session for ​Rob Walling's SaaS Launchpad​. This module is called AI in SaaS, and I share over a dozen pitfalls, unobvious risks, and hard-earned insights from my own AI SaaS building journey. The course was already great, but... you know... ;) Use the code ARVID150 to get $150 off until June 8th.

The blog post: https://thebootstrappedfounder.com/building-ai-businesses-without-breaking-the-internet/
The podcast episode: https://tbf.fm/episodes/building-ai-businesses-without-breaking-the-internet

Second brains were all the rage a year ago. Now, it feels like we're not just externalizing our thoughts; we're training a much bigger, much less personal brain. A first brain. THE brain. Is this a good thing? Are we truly the beneficiaries here?

The blog post: https://thebootstrappedfounder.com/ai-is-flipping-our-relationship-with-technology/
The podcast episode: https://tbf.fm/episodes/391-ai-is-flipping-our-relationship-with-technology

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid<...

When I started Podscan, I wanted to go full local AI. Self-hosted, self-managed, self-serving. But that tune has changed. Here's what to think about when contemplating a local AI strategy.

The blog post: https://thebootstrappedfounder.com/when-to-choose-local-llms-vs-apis-a-founders-real-world-guide/
The podcast episode: https://tbf.fm/episodes/390-when-to-choose-local-llms-vs-apis

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

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 podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter...

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: https://tbf.fm/episodes/388-the-job-to-be-done-understanding-customer-value-communication

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://po...

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-for-developers-anymore

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my...

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 how these choices, along with important upgrades and strategic partnerships, have contributed to our achievements.

The blog post: https://thebootstrappedfounder.com/one-year-of-podscan-reflecting-on-tech-business-decisions/
The podcast episode: https://tbf.fm/episodes/386-one-year-of-podscan-reflecting-on-tech-business-decisions

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-sustainability/ 
The podcast episode: https://tbf.fm/episodes/385-the-balancing-act-free-trials-value-demonstration-and-business-sustainability 

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm

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-profitability-milestone-whats-next

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail...

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 episode: https://thebootstrappedfounder.com/repositioning-podscan-from-monitoring-to-data-platform/

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm<...

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-new-orleans

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find...

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 navigating this shifting landscape.

The blog post: https://thebootstrappedfounder.com/how-ai-changes-famous-laws-in-software-and-entrepreneurship/
The podcast episode: https://tbf.fm/episodes/381-how-ai-changes-famous-laws-in-software-and-entrepreneurship

Check out Podscan to get alerts when you're mentioned on podcasts: https...