Why Selling Your Business Is Just the Beginning: TIGER 21 Founder on Built to Sell Radio Podcast 

What happens when work becomes a choice, not a requirement? For many entrepreneurs, the answer after selling their business is more complicated than expected. 

In an episode of Built to Sell Radio podcast, TIGER 21 Founder and Chairman Michael Sonnenfeldt joins host Colin Morgan to explore what really happens after a major liquidity event, and why financial freedom often raises more questions than it answers.  

Michael, who sold two companies before the age of 43, speaks candidly about the moment he realized the skills that made him a great entrepreneur did not prepare him to be a disciplined investor. 

“On average, the skills that allowed you to be a great entrepreneur predispose you to be a mediocre investor.” —Michael Sonnenfeldt 

That insight became the foundation for TIGER 21, now a global peer membership organization for UHNW individuals who collectively manage more than $200 billion in personal assets. It began with a group of six post-sale  entrepeneurs in search of clarity has grown into a 1,600+ Member Community where wealth creators stress-test decisions, navigate complex transitions, and redefine purpose, legacy, and impact. 

In this episode, Michael offers a rare behind-the-scenes look at the emotional and financial realities of life after a sale. From the danger of overconfidence to the quiet discomfort of living off capital, the conversation is packed with raw honesty, personal anecdotes, and lessons learned through experience, not theory. 

Highlights from the podcast episode include: 

• Why the biggest post-sale investing mistake is thinking you are smarter than the market 

• The emotional challenge of wealth: how living off capital requires a new identity and mindset many entrepreneurs are not prepared for 

• How “sticker shock” hits when entrepreneurs realize a $1M business income can drop to $175k after taxes and conservative reinvestment 

• Why angel investing is rarely a wealth strategy, and often just expensive entertainment 

Whether you are preparing for an exit or already navigating your next chapter, this episode delivers the kind of insight you won’t hear anywhere else. 

Listen to the full episode now.