Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter? In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employee…
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Your query for "Funding" returned 413 episodes.Episode 791 | TinySeed Tales s5e2: Growing Pains
In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work. Harris shares how niching down to outbound-focused agencies unlocked…
Episode 790 | From Scrappy to Scalable: Evolving Your Role as a Founder
How can you scale yourself as a founder? In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Vera, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yours…
Episode 788 | Do I Need a Co-founder? And More Listener Questions (with Derrick Reimer)
What are the real risks of AI-generated code and “vibe coding”? In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how …
Episode 787 | “We Shut Down a $1.5M Product, and Raised $10M Instead”
How do you know it’s time to move on from a product that’s growing? In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big w…
Episode 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff)
How do you really know when you’ve hit product-market fit? In this episode, Rob Walling welcomes back Kevin Wagstaff, co-founder of Spectora, to answer listener questions about early traction in Facebook groups, finding product-market fit, handling criticism, and what i…
Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit
When is the right time to sell your profitable SaaS? In this week's episode, Rob Walling talks with Pierre de Wulf, co-founder of ScrapingBee, about how they mostly bootstrapped their web scraping SaaS to $5 million ARR and an eight-figure all-cash exit. They explore the …
Episode 781 | A Founder’s Regret List: 12 Mistakes I’ll Never Make Again
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 …
Episode 780 | “I’ll Never Sell My Company” and Other Myths Founders Tell Themselves
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 t…
Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure)
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? …
