Best Bootstrapper Podcasts (2025)

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425: AI Best Practices for Bootstrappers (That Actually Save You Money) 22:35

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1d ago22:35

22:35

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 …

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424: I Never Really Loved Coding (And Only AI Made Me Realize It) 18:38

9d ago18:38

18:38

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 …

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This Hidden Lever Can Multiply Your Exit Value 5:42

10d ago5:42

5:42

Most founders underestimate this single metric — and it can dramatically change your exit. Understand this now, and it can be a powerful lever when you go to sell. What you’ll learn: • The surprising variable buyers care about most • Why two identical businesses can get wildly different offers • The counterintuitive timing mistake founders often ma…

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423: The Marketer's Hierarchy of Needs: A Framework for Understanding Customer Intelligence 17:09

16d ago17:09

17:09

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 Paddl…

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These Founders Nailed Every Mark for a High-Value Exit 8:47

17d ago8:47

8:47

Host Lexi Grant reflects on a conversation with two co-founders who were well positioned for a sale. Their business hit every mark that buyers look for — from profitability to growth — and Lexi shares exactly what made them stand out. Whether you’re thinking about selling soon or just want to build a stronger business, these four factors can help y…

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422: The Things Your Customers Don't Care About 19:36

23d ago19:36

19:36

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.com You'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-friday The blog …

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How to Handle Inbound Offers from Buyers 10:15

24d ago10:15

10:15

What happens when a buyer emails you out of the blue? Not all offers are what they seem. Learn how to spot legit interest, protect your time, and maximize your leverage when inbound offers roll in. What you’ll learn: The two types of buyer outreach—and how to tell them apart What to do (and not do) when you’re not ready to sell How to turn real inb…

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421: Why You Should Never Start a Software Business 21:59

30d ago21:59

21:59

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 …

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What Makes a Business Unsellable — And How to Fix It 10:02

1M ago10:02

10:02

It’s a question we hear all the time: “Is my business sellable?” In most cases, the answer is yes. But there are a few factors that can make selling your company harder than it should be or even impossible. In this episode of They Got Acquired, Lexi shares the four biggest reasons a company might be unsellable, and how to correct them before you’re…

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420: AI for the Code-Writing Purist: How to Use AI Without Surrendering Your Keyboard 23:25

1M ago23:25

23:25

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 …

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When’s the Right Time to Sell Your Business? 7:14

1M ago7:14

7:14

How do you know when it’s the right time to sell your business? The answer might surprise you. Lexi Grant breaks down the three real factors that determine when to sell — and why waiting for perfect market timing could actually cost you. What you'll learn: The surprising truth about market timing, and why it’s overrated How burnout can quietly dest…

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We’re Back! What You Need to Know Before Selling Your Business (Season 2 Trailer) 2:42

1M ago2:42

2:42

They Got Acquired is back! In this new season, host Lexi Grant shares insider insights every founder should know before selling a business. After years of studying M&A and publishing nearly 300 acquisition stories, Lexi breaks down what really works — and what doesn’t — when it comes to selling your company. What you'll learn this season: How to st…

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419: The Missing Piece in Your Validation Strategy 20:09

1M ago20:09

20:09

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. Th…

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418: Why AI-Generated Code Hurts Your Exit 16:20

2M ago16:20

16:20

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 …

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417: The Best Tech Stack in the Age of AI 15:56

2M ago15:56

15:56

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 Paddl…

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416: The Ownership Paradox: What Do You Really Control in Your Software Business? 19:12

2M ago19:12

19:12

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://thebootstrappedfoun…

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415: Handling Multiple ICPs as a Solo Founder 20:14

2M ago20:14

20:14

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 spon…

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414: The Pure Amateur is Vanishing: Why Everyone's a Performer Now 23:08

3M ago23:08

23:08

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. …

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413: We’re Gonna Need a Bigger Moat 25:15

3M ago25:15

25:15

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. T…

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412: The $0.20/Day AI System That Converts Trial Users Into Paying Customers 25:11

3M ago25:11

25:11

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 r…

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411: The Currents of a Founder 19:05

3M ago19:05

19:05

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 c…

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Building a $720k/yr GMV CGI Marketplace: Henning Sanden (Flipped Normals) 51:03

3M ago51:03

51:03

Welcome back to The Ramen Club Podcast, where we talk to our community members about building startups without funding. 🍜 For episode 11, I spoke to my friend and long-time Ramen Club member, Henning Sanden (founder of Flipped Normals). Henning is a Norwegian 3D artist who's worked on major movies like Pacific Rim, Venom, Alien: Covenant, Ghostbust…

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410: Building for the Age of AI Consumers 23:34

4M ago23:34

23:34

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 p…

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409: James Phoenix — Claude Code Masterclass 59:26

4M ago59:26

59:26

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 effec…

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408: The Podscan Ideas Vault: Engineering as Marketing 21:29

4M ago21:29

21:29

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/ Th…

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407: Nick Groeneveld — Exploring AI's Impact on Modern Design 49:39

4M ago49:39

49:39

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 …

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406: Making Your Business Sellable (Even If You Never Plan to Sell) 22:22

4M ago22:22

22:22

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…

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405: The Friction Paradox: Why AI Might Be Making Us Worse at What We Do 13:44

4M ago13:44

13:44

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-a…

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404: The Transcription Challenge: Building Infrastructure That Scales With The World 27:47

4M ago27:47

27:47

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://tb…

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403: Amar Ghose — From Non-Technical Founder to SaaS Innovator 44:29

5M ago44:29

44:29

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 …

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402: A $2 Billion Industry Built on Digital Duct Tape 22:58

5M ago22:58

22:58

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…

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401: Vova Feldman — Mastering Entrepreneurship in the Payments Sector 41:13

5M ago41:13

41:13

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://theb…

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400: The Hidden Revolution: AI Is Democratizing Coding Mentorship 14:31

5M ago14:31

14:31

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/th…

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399: NativePHP: How Simon Hamp & Shane Rosenthal are Building & Monetizing PHP on Mobile 50:35

5M ago50:35

50:35

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 tu…

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Top 7 Pitfalls When Using AI in Your Business: And Tips for Using AI More Effectively 1:24:43

5M ago1:24:43

1:24:43

AI is a powerful tool, but it’s not a silver bullet. Many entrepreneurs get caught up in the allure of automation and data-driven decision-making, only to realize that AI is just a technology—not a comprehensive business strategy. When used correctly, AI can streamline operations, improve efficiency, and enhance customer experiences, but overconfid…

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Mastering the 3 Conversions: A Strategy for Bootstrappers 1:22:51

5M ago1:22:51

1:22:51

Starting a business without outside funding is both challenging and rewarding—but knowing how to navigate the leap from idea to success is critical. Many entrepreneurs struggle with the transition from scrappy beginnings to sustainable growth, often focusing on the wrong milestones or failing to optimize their resources. This session, led by season…

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398: The Hidden Cost of Being First 11:54

5M ago11:54

11:54

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 framewo…

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HOW NOT TO QUIT ON A DREAM! 1:06:31

5M ago1:06:31

1:06:31

Send us a text Norman Towns on Outworking the Odds Let’s be real, success isn’t sexy at the start. Norman Towns knows that better than anyone. Before he hit the screen, he was doing all the jobs no one brags about: spinning signs on the sidewalk, washing dishes, pulling overnight security shifts. Whatever it took. In this episode, Norman keeps it r…

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397: When Profitability Disappears — A Podscan Reality Check 17:48

5M ago17:48

17:48

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-podsc…

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396: Jack Friks — Building Tools That Empower Without Overwhelming 39:17

5M ago39:17

39:17

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 ma…

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395: From Code Writer to Code Editor: My AI-Assisted Development Workflow 26:40

6M ago26:40

26:40

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-…

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394: Taylor Otwell — The (Quite Entrepreneurial) Creator of Laravel 41:55

6M ago41:55

41:55

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 freel…

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393: AI is a Threat to SaaS Multiples 23:57

6M ago23:57

23:57

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 pitfall…

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392: Building AI Businesses Without Breaking the Internet 22:48

6M ago22:48

22:48

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.…

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391: AI is Flipping Our Relationship with Technology 25:32

6M ago25:32

25:32

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 …

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390: When to Choose Local LLMs vs APIs 16:39

7M ago16:39

16:39

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…

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How to Start a Business (Even If You're Scared Sh*tless) 7:57

7M ago7:57

7:57

Send us a text Starting a small business from scratch? Learn how to launch with no money, no connections, no fluff. Ever feel like most business advice is just recycled guru nonsense or comes from people born wealthy? This episode is for the real ones—those starting small businesses without money, privilege, or fancy degrees. This episode kicks off…

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389: The Founder's First Hire: When to Let Go of Your Weaknesses 14:06

7M ago14:06

14:06

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,…

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Growing a hosting platform to $400k ARR: Elston Baretto (Tiiny Host) 52:30

7M ago52:30

52:30

After a hiatus, The Ramen Club podcast (formerly Ramen FM) is back! For episode 10, I spoke to my good friend friend and long-time Ramen Club member, Elston Baretto (founder of Tiiny Host). Tiiny Host is the simplest way to host and share your work online - uploading HTML, PHP, PDFs & Zip files (plus more soon) in seconds. Started 4 years ago, Elst…

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388: The Job To Be Done: Understanding Customer Value Communication 11:44

7M ago11:44

11:44

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-c…