A Product Market Fit Show | Startup Podcast for Founders He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex Sherman, Founder of Bluefish AI
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Oct 6, 2025 In this engaging discussion, Alex Sherman, Founder and CEO of Bluefish AI and former founder of PromoteIQ, shares his rollercoaster journey through the startup world. He reveals how he nearly returned $200K to investors just months in and how surviving on minimal runway taught him resilience. Alex emphasizes the power of meeting customers face-to-face, successfully pivoting to retail media, and the strategic moves that led to his company's acquisition by Microsoft. His insights on AI marketing and the unique challenges faced by second-time founders are particularly enlightening.
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Early Raise Rejected By Founder
- Alex raised about $200K for Spotfronts and realized within 30 days the idea was wrong.
- He called angels to return the money but they told him to keep it and figure it out, launching the path to PromoteIQ.
Living On Two Months Of Runway
- For about 18 months the team ran with two months of runway repeatedly while paying themselves small salaries.
- Alex reflected on being 25, paying himself $30K while peers earned six figures and feeling intense financial pressure.
Product–Market Fit Feels Like A River Flip
- Product-market fit often feels like a river reversing: you go from many no's to many yes's quickly.
- That inflection usually follows many iterative failures and requires being ready to move when timing aligns.