Built to Sell Radio Ep 487 After the Deal: How the Ultra-Wealthy Invest After Selling Their Business
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Mar 28, 2025 In this enlightening conversation, Michael Sonnenfeldt, founder of Tiger 21, shares his journey from selling two companies to guiding ultra-wealthy entrepreneurs in smart investing. He highlights the emotional challenges of wealth after exit and the importance of building a support network. Discussion includes pitfalls to avoid, the significance of character in investment groups, and the contrasting psychology of spending between self-made and inherited wealth. Sonnenfeldt emphasizes mentorship and the importance of emotional support in nurturing healthy family dynamics amid affluence.
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Life Cycle Considerations
- Consider your business's life cycle and your personal life cycle when deciding to sell.
- A young business with high upside potential may be worth keeping if you're young, while an older business might be better sold if you're nearing retirement.
Sticker Shock
- After selling, your income can decrease significantly due to taxes and lower returns on investments, a phenomenon known as sticker shock.
- Calculate potential investment income to avoid surprises and ensure it aligns with your lifestyle.
Growth as Ally and Enemy
- Understand if your business is capital-intensive or generates cash as it grows.
- Factor in the capital requirements of your business model when considering a sale.