From Selling to Walmart to the Post-Exit Paradox: What Founders Need to Know Before Selling, with Jason Kirby

Jason Kirby started with a photography business in San Diego, built a cloud gaming company with a million users and sold it to Walmart. Now he runs Thunder, a boutique investment bank helping founders navigate capital raises, acquisitions and exits. He joins PilotWave’s Cooper and Arik Oganesian to talk about what founders get wrong about selling their companies, why traditional private equity often misses the human side of a deal and what happens when the business you've spent years building is no longer yours.

Is the highest offer always the best deal? What happens when your board stands between you and a better exit? And why do so many founders find themselves miserable after finally getting the payday they've worked toward? From earn-outs and misaligned incentives to the identity crisis that comes after an acquisition, this conversation explores why a successful exit isn't just about the money. It's about what comes next.

In this episode:

• Why where you build your company can determine who funds it
• Why traditional investment bankers don't always have founders' best interests in mind
• How earn-outs, cap tables and board decisions can turn a successful exit into a disappointment
• Why selling your company isn't always the best option
• The post-exit paradox: what happens when nobody needs you anymore
• Why founders need to build an identity beyond their business

 

 

Connect with Pilot Wave:
Website: https://www.pilotwaveholdings.com

X: https://x.com/pilotwaveai

 

Guest/s:

Jason Kirby

Thunder
https://www.thunder.vc

 

 

Host/s:

Calvin Cooper

X: https://x.com/cooper_nyc_

LinkedIn: https://www.linkedin.com/in/coopernyc

Arik Oganesian

LinkedIn: https://www.linkedin.com/in/arik-oganesian