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 employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.



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Topics we cover: 




(3:12) – TinySeed returns Fund One



(9:40) – GPT-5: Upgrade or letdown?



(19:19) – Are we in an AI bubble?



(24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees



(31:06) – The bigger problem: Are startups forgetting to share the upside?



(40:05) – Lifestyle vs. Ambitious Bootstrapping




Links from the Show: 




TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd



TinySeed SaaS Accelerator - Applications are Open!



Invest in TinySeed



MicroConf



SaaS Institute



Discretion Capital 



Einar Vollset | LinkedIn



Einar Vollset (@einarvollset) | X



Tracy Osborn 



Tracy Osborn | LinkedIn



Tracy Osborn (@tracymakes) | X




If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!



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