He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex Sherman, Founder of Bluefish AI
Description
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 indefinitely
- How to validate your next startup before writing any code
- Why second-time founders often have more blind spots than first-timers
Keywords:
startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder
00:00:00 Intro
00:01:58 From management consulting dreams to startup world
00:04:44 Trying to return $200K to investors after 30 days
00:07:19 Pivoting through iterations to find retail media
00:12:13 Finding product-market fit like a river reversing
00:21:28 Microsoft acquisition with $2,000 in the bank
00:24:30 Post-exit sabbatical and starting Bluefish
00:35:08 Building for AI marketing with Fortune 500 design partners
00:43:12 Always get on the plane
United States
