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

A Product Market Fit Show | Startup Podcast for Founders

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

Send me a message to let me know what you think!

บท

1. Intro (00:00:00)

2. From management consulting dreams to startup world (00:01:58)

3. Trying to return $200K to investors after 30 days (00:04:44)

4. Pivoting through iterations to find retail media (00:07:19)

5. Finding product-market fit like a river reversing (00:12:13)

6. Microsoft acquisition with $2,000 in the bank (00:21:28)

7. Post-exit sabbatical and starting Bluefish (00:24:30)

8. Building for AI marketing with Fortune 500 design partners (00:35:08)

9. Always get on the plane (00:43:12)