The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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Rob Walling With Derrick Reimer Podcasts
Follow a tech startup on its journey from nascent idea to embryonic product, to triumphant launch. "Launch" follows Rob Walling and Derrick Reimer as they take email marketing startup Drip from the first days of inception through the agonizing months of writing code, talking to customers, and the never-ending uncertainty of whether anyone will ever use what they are building. From the honeymoon period of "green field" development to the sleepless nights of database failures, "Launch" capture ...
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Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions
27:46
27:46
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Looking back on your entrepreneurship journey, which decisions made the biggest impact? In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learning fast from failure, and building a financial cushion to take smarter risks. It’s an honest look at what worked and the choices t…
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Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again
39:39
39:39
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Are you repeating any of these mistakes in your business? In this episode, Rob Walling walks through his ‘founder regret list’, detailing 12 key mistakes from his 20-year entrepreneurial journey. In this very personal episode, he tells some stories he’s never shared publicly before. Topics we cover: (4:17) – Thinking venture capital was the only pa…
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Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves
42:28
42:28
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42:28
What if your biggest growth blocker isn’t the market, but the story you’re telling yourself? In this episode, Rob Walling welcomes back fan favorite Ruben Gamez, founder of SignWell, to debunk common bootstrapper myths. They discuss misconceptions like never needing to sell your company or market your product, and emphasize the realities of growth …
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Episode 779 | 10 Myths Most SaaS Founders Believe
44:32
44:32
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Are common SaaS myths sabotaging your success? In this episode, Rob Walling sits down with SaaS growth expert (and TinySeed Institute coach) Marc Thomas to break down ten persistent and damaging myths believed by many SaaS founders and why challenging them is key to scaling smart. Topics we cover: (4:52) – “I’m not good at marketing” is a lie (8:48…
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Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure)
39:08
39:08
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How do you price pilot projects and niche down without hedging your bets? In this episode, Rob Walling answers listener questions about pricing pilots, choosing niches, and skipping steps on his Stair Step Method of Bootstrapping. Want to get your question answered? Drop them here. Topics we cover: (3:25) – Feedback on Season 4 of TinySeed Tales (8…
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Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
28:45
28:45
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28:45
What if the traditional dream of retirement is actually a trap for entrepreneurs? In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring…
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Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit
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What’s it take to bootstrap a niche SaaS to $90M without raising a dime? In this episode, Kevin Wagstaff joins Rob Walling to share how he and his brother bootstrapped Spectora from a scrappy MVP to a $90M valuation. It’s a masterclass in finding traction in unsexy markets, building with empathy, and making smart bets like embedded payments. Topics…
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Episode 775 | A.I. Coding Tools, User Experience, Racking Your Own Servers, and More Listener Questions (with Derrick Reimer)
54:22
54:22
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54:22
What shortcuts are actually worth taking when you're building a SaaS? In this episode, Rob Walling and fan favorite Derrick Reimer delve into listener questions about startup development. They discuss the impact of AI coding tools on building minimum viable products (MVPs) and the importance of user experience (UX) with advice on balancing UX inves…
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Episode 774 | How a Non-Technical Founder Bootstrapped to Millions in Revenue
37:09
37:09
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37:09
In this episode, Rob Walling sits down with Noah Tucker, the non-technical founder behind Social Snowball, an affiliate marketing SaaS built for Shopify. Noah bootstrapped the company to $5M+ in ARR, navigating technical roadblocks, team-building hurdles, and a crumbling codebase, while leveraging bold growth tactics like influencer partnerships to…
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Episode 773 | How to Find Your Early Customer Profile (ECP)
30:15
30:15
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In this episode, Rob Walling and Maja Voje, author of Go to Market Strategist, dive into early customer profiles (ECPs) and why they matter more than ideal customer profiles (ICPs) early on. They explore practical, scrappy marketing tactics for B2B SaaS founders and share real-world advice on customer acquisition, community building, and staying au…
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Episode 772 | A Highly Effective Framework for SaaS Positioning
35:24
35:24
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How do you position your SaaS for success? In episode 772, Rob Walling talks with Anthony Pierri of Fletch about a proven approach to product positioning. They discuss key lessons from 400+ startups, focusing on workflows, competitive alternatives, and why narrowing your audience matters. Topics we cover: (6:59) – What is positioning, really? (11:1…
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Episode 771 | What Changes As You Grow, AI Agents, Patents, and More Listener Questions (with Craig Hewitt)
38:48
38:48
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Can SaaS companies survive the rise of AI Agents? In episode 771, Rob Walling is joined by Craig Hewitt to answer listener questions. They discuss the changes that happen while transitioning from a small startup to a multi-million dollar SaaS, competing against larger competitors, and maintaining startup culture as teams grow. They also share thoug…
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Episode 770 | Revenue vs. Profit, Asking for Permission, and Mike Tyson (A Rob Solo Adventure)
25:05
25:05
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Is it more important for entrepreneurs to focus on revenue or profit? In episode 770, Rob Walling goes solo to explore the relationship between revenue and profit in SaaS, and the dangers of waiting for permission. He also draws inspiration from Mike Tyson’s work ethic and George Lucas’ visionary mindset to encourage entrepreneurs to push through o…
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