The Bootstrapped Founder

431: Many Heads, Not Many Hats: The Founder's Identity Crisis

We joke about founders wearing many hats, but that metaphor misses the point. It's not about swapping accessories—it's about growing entirely new heads, each with its own brain that thinks, speaks, and prioritizes differently. In this episode, I explore why the transition from consulting or agency work to software entrepreneurship is so disorienting, and why the instincts that made you successful before might be the exact things preventing success now. From the uncomfortable truth about acquisition in low-touch SaaS to the cognitive dissonance of believing in yourself while questioning everything you know, this is about what it really takes to become someone new while staying grounded in who you've always been.This episode of The Bootstraped Founder is sponsored by Paddle.comThe blog post: https://thebootstrappedfounder.com/many-heads-not-many-hats-the-founders-identity-crisis/ The podcast episode: https://tbf.fm/episodes/many-heads-not-many-hats-the-founders-identity-crisisCheck out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

430: The Case Against Vendor Lock-In: Why Easy Exit Means Better Retention

There's something strange about founders who built their entire business on open source software and open standards, then turn around and say you should lock customers in as hard as possible. I think that's a horrible practice—and counterintuitively, making it easy to leave actually makes people stay longer. Today I'm making the case for frictionless import and export, with real examples from PermanentLink and lessons from Fathom Analytics, and why informed choice beats artificial lock-in every time.This episode of The Bootstraped Founder is sponsored by Paddle.comThe blog post: https://thebootstrappedfounder.com/the-case-against-vendor-lock-in-why-easy-exit-means-better-retention/ The podcast episode: https://tbf.fm/episodes/430-the-case-against-vendor-lock-in-why-easy-exit-means-better-retention Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

429: The Dead Internet Theory: Are We Building Machines That Only Talk to Other Machines?

I spotted a LinkedIn post the other day—obviously AI-generated—with dozens of enthusiastic comments underneath. Every single one also written by AI. Bots responding to bots, a whole conversation with zero humans involved. It was both hilarious and deeply sad. This got me thinking about the dead internet theory and our role as founders in either contributing to it or pushing back against it. Today I'm exploring how we can build AI tools that augment human connection rather than replace it entirely—using AI as the means, not the end.This episode of The Bootstraped Founder is sponsored by Paddle.comThe blog post: https://thebootstrappedfounder.com/the-dead-internet-theory-are-we-building-machines-that-only-talk-to-other-machines/ The podcast episode: https://tbf.fm/episodes/the-dead-internet-theory-are-we-building-machines-that-only-talk-to-other-machines Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

428: Marketing for Founders Who Hate Marketing

Most technical founders I know understand marketing matters—they just hate doing it. They'd rather spend their time building features than fumbling through outreach and content strategies. I get it. I've been there for years. So today I'm sharing what's actually worked for me: letting machines do the heavy lifting. From programmatic SEO that turned Podscan's internal data into a signup engine, to AI-assisted customer scoring that tells me who's worth a personal conversation, to treating documentation as a discovery channel—these are systems that market your product while you focus on building it. And here's the counterintuitive part: most of the people who find you through these systems won't be your ideal customers. That's fine. They become your word-of-mouth channel instead.This episode of The Bootstraped Founder is sponsored by Paddle.comThe blog post: https://thebootstrappedfounder.com/marketing-for-founders-who-hate-marketing/ The podcast episode: https://tbf.fm/episodes/428-marketing-for-founders-who-hate-marketingCheck out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

427: Vibe Coding Won't Kill SaaS

The "vibe coding will kill SaaS" narrative is everywhere right now, and I think it's completely wrong. Yes, anyone can spin up a Lovable or Bolt.new project in an afternoon. But there's a fundamental confusion happening: people are mistaking software products for software businesses. SaaS was never really about the software — it was always about the service, the operations, the years of edge cases and integrations and customer conversations that make a product actually work. In this episode, I break down why vibe-coded solutions fall apart the moment real customers show up, why "comprehension debt" is the hidden killer of AI-built projects, and how we might need to shift our messaging to make the invisible 20% of our work visible to buyers who now think they could build everything themselves.This episode of The Bootstraped Founder is sponsored by Paddle.comYou'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-fridayThe blog post: https://thebootstrappedfounder.com/vibe-coding-wont-kill-saas/The podcast episode: https://tbf.fm/episodes/427-vibe-coding-wont-kill-saas Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fmSend me a voicemail on Podline: https://podline.fm/arvidYou'll find my weekly article on my blog: https://thebootstrappedfounder.comPodcast: https://thebootstrappedfounder.com/podcastNewsletter: https://thebootstrappedfounder.com/newsletterMy book Zero to Sold: https://zerotosold.com/My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/My course Find Your Following: https://findyourfollowing.comHere are a few tools I use. Using my affiliate links will support my work at no additional cost to you.- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw