He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex Sherman, Founder of Bluefish AI

Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months. Then retail media exploded and everything changed—he went from grinding against the current to riding a wave.After selling to Microsoft, he took 6 months off, got bored, and started Bluefish AI with the same team. This time they called Fortune 500 CMOs before building anything. His #1 advice for early-stage founders: Get on the plane. And go meet your customers. You'll be shocked by how big a difference that makes. Why You Should Listen:How to survive on 2 months of runway indefinitelyHow to validate your next startup before writing any codeWhy second-time founders often have more blind spots than first-timersKeywords:startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder00:00:00 Intro00:01:58 From management consulting dreams to startup world00:04:44 Trying to return $200K to investors after 30 days00:07:19 Pivoting through iterations to find retail media00:12:13 Finding product-market fit like a river reversing00:21:28 Microsoft acquisition with $2,000 in the bank00:24:30 Post-exit sabbatical and starting Bluefish00:35:08 Building for AI marketing with Fortune 500 design partners00:43:12 Always get on the planeSend me a message to let me know what you think!