The Bootstrapped Founder

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
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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...

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

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on...

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://thebootstrappedfounder.com/anne-laure-le-cunff-tiny-experiments/

The podcast episode: https://tbf.fm/episodes/379-anne-laure-le-cunff-tiny-experiments

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

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: https://thebootstrappedfounder.com/think-with-ai-do-with-people/
The podcast episode: https://tbf.fm/episodes/378-think-with-ai-do-with-people

Check out Podscan to...

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

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

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

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 mind to embrace alignment and value-added sponsorship relationships for whatever you do.

The blog post: https://thebootstrappedfounder.com/376-justin-moore-becoming-a-sponsor-magnet/

The podcast episode: https://tbf.fm...

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 get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on...

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 post: https://thebootstrappedfounder.com/indie-hacking-databases-at-scale/
The podcast episode: https://tbf.fm/episodes/374-indie-hacking-databases-at-scale

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

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/episodes/373-delete-your-backlog

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article...

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

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on...

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 out.

The blog post: https://thebootstrappedfounder.com/brian-sierakowski-mastering-product-communication/

The podcast episode: https://tbf.fm/episodes/317-brian-sierakowski-mastering-product-communication

Check 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're mentioned on podcasts: 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

Po...

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-expect-ai-tions

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

Yo...

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, Johannes continues to inspire with his journey through the competitive startup world, exploring how he transformed an academic idea into a practical tool that changed lives. We also examine the nuanced differences between hypnosis and meditation, shedding light on how Hy...

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.fm/episodes/367-the-biggest-opportunity-of-2025

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

...

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 as a founder, and what Arnold Schwarzenegger has to do with the AI avalanche. Enjoy!

This episode is sponsored by Paddle.com — if you're looking for a payment platform that...

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-review-2024/

The podcast episode: https://tbf.fm/episodes/365-arvids-year-in-review-2024

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

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 out.

The blog post: https://thebootstrappedfounder.com/breaking-my-own-rules/

The podcast episode: https://tbf.fm/episodes/364-breaking-my-own-rules

Check out Podscan to ge...

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 setting new standards in software development, akin to OpenTelemetry. Ben shares insights into this collaborative open-source initiative and takes you on a decade-long journey running a software agency in London, where creativity thrived, leading to the creation of a cost-effective, open-source feature f...