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PODCAST

The Bootstrapped Founder

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

business entrepreneurship

All Episodes

15:18

431: Many Heads, Not Many Hats: The Founder's...

The Bootstrapped Founder ·

2026/01/09

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

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14:22

430: The Case Against Vendor Lock-In: Why Easy Exit...

The Bootstrapped Founder ·

2026/01/02

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

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12:37

429: The Dead Internet Theory: Are We Building...

The Bootstrapped Founder ·

2025/12/26

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

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18:03

428: Marketing for Founders Who Hate Marketing

The Bootstrapped Founder ·

2025/12/19

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

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18:55

427: Vibe Coding Won't Kill SaaS

The Bootstrapped Founder ·

2025/12/12

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

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22:44

426: How Your Data Model Shapes Your Product

The Bootstrapped Founder ·

2025/12/05

Jack Ellis recently shared that storing page views and custom events in separate database tables was his biggest mistake at Fathom Analytics. That got me thinking about my own data modeling decisions at Podscan—choices I made on day one that now, two years and 45 million episodes later, either enable or constrain everything I build. Today, I'm exploring how your data model doesn't just store information, it fundamentally shapes how you think about your product. From the simple decision of

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22:35

425: AI Best Practices for Bootstrappers (That...

The Bootstrapped Founder ·

2025/11/28

AI systems change constantly. Models get deprecated, APIs shift, and what works today might fail tomorrow. Instead of trying to keep up with everything, I've built my systems for permanent adaptability. That means migration patterns that let me run old and new prompts side by side, using OpenAI's hidden Flex tier to cut costs by 50%, front-loading repeated data in prompts to maximize cache savings, and implementing circuit breakers so runaway AI costs can't blow up my bill. These aren't

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18:38

424: I Never Really Loved Coding (And Only AI Made Me...

The Bootstrapped Founder ·

2025/11/21

After 20+ years as a software developer, AI coding assistants revealed a shocking truth: I never actually loved coding—I loved what code could accomplish. In this episode, I explore how transitioning from hand-crafting every line at Podscan to orchestrating AI-generated code exposed the fundamental difference between developers who cherish solving technical puzzles and entrepreneurs who prioritize shipping features that drive business value. This shift from programmer to orchestrator isn't

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17:09

423: The Marketer's Hierarchy of Needs: A Framework...

The Bootstrapped Founder ·

2025/11/14

What if your customers can't care about your advanced features because you haven't satisfied their basic needs first? Just like humans need food before philosophy, marketers need specific data in a rigid order – and understanding this hierarchy transformed how Podscan onboards customers.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:

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19:36

422: The Things Your Customers Don't Care About

The Bootstrapped Founder ·

2025/11/07

When you build a software business as a founder, you have a dream. Building. Features. APIs. UIs.But how much of that is JUST a dream, and what REALLY leads to paying customers?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/the-things-your-customers-dont-care-about/The podcast episode:

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21:59

421: Why You Should Never Start a Software Business

The Bootstrapped Founder ·

2025/10/31

The brutal truth about SaaS nobody tells you.Here’s the thing: I’m about to share all the reasons why you should never, ever start a software business. And yes, I’m fully aware that I’m talking to an audience of software founders. This is somewhat sarcastic, somewhat ironic twist on the great things about entrepreneurship. And the problems you'll face.This episode of The Bootstraped Founder is sponsored by Paddle.comYou'll find the Black Friday Guide here:

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23:25

420: AI for the Code-Writing Purist: How to Use AI...

The Bootstrapped Founder ·

2025/10/24

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.comYou'll find

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20:09

419: The Missing Piece in Your Validation Strategy

The Bootstrapped Founder ·

2025/10/17

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

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16:20

418: Why AI-Generated Code Hurts Your Exit

The Bootstrapped Founder ·

2025/10/10

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

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15:56

417: The Best Tech Stack in the Age of AI

The Bootstrapped Founder ·

2025/10/03

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

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19:12

416: The Ownership Paradox: What Do You Really...

The Bootstrapped Founder ·

2025/09/26

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

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20:14

Handling Multiple ICPs as a Solo Founder

The Bootstrapped Founder ·

2025/09/19

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

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23:08

414: The Pure Amateur is Vanishing: Why Everyone's a...

The Bootstrapped Founder ·

2025/09/12

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

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25:15

413: We’re Gonna Need a Bigger Moat

The Bootstrapped Founder ·

2025/09/05

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.comThe blog post: https://thebootstrappedfounder.com/were-gonna-need-a-bigger-moat/

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25:11

The $0.20/Day AI System That Converts Trial Users...

The Bootstrapped Founder ·

2025/08/29

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

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434 results

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