All Episodes

October 6, 2025 44 mins

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!

Mark as Played

Advertise With Us

Popular Podcasts

Las Culturistas with Matt Rogers and Bowen Yang

Las Culturistas with Matt Rogers and Bowen Yang

Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.

The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.