Built to Sell Radio

Ep 487 After the Deal: How the Ultra-Wealthy Invest After Selling Their Business

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.

01:07:15

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Episode guests

Michael Sonnenfeldt

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Quick takeaways

Ultra-high-net-worth entrepreneurs often struggle to transfer entrepreneurial skills into effective investment strategies, requiring education on wealth preservation.

Many entrepreneurs face significant emotional challenges and guilt adjusting to living off their capital post-sale after realizing the impact of taxes.

Seeking mentorship and building networks are crucial for entrepreneurs to enhance their investment strategies and avoid common post-sale pitfalls.

Deep dives

The Journey of Wealth Creation and Investment

Ultra high net worth entrepreneurs often face a significant transition after selling their businesses, realizing that the skills that fueled their entrepreneurial success do not necessarily translate into effective investment strategies. Michael Sonnenfeld, who sold two companies before age 43, underscores the importance of learning wealth preservation after a liquidity event. He founded Tiger 21, a peer network for high-net-worth individuals, to share insights on responsible financial management and to avoid common post-sale pitfalls. The creation of Tiger 21 stemmed from the need to educate sellers on capital preservation, legacy planning, and emotional challenges associated with transitioning from business ownership to investment.

Intro

2min

Navigating Wealth After Success: The Birth of a Support Network

6min

Membership Criteria and Entrepreneurial Insights for High Net-Worth Individuals

3min

Navigating Growth and Transition for Entrepreneurs

26min

Navigating Business Acquisitions

14min

Wealth and Spending Psychology

11min

Navigating Wealth: The Challenges of Raising Children in Affluence

4min

Wrapping Up Insights and Encouraging Engagement

2min

What would you do with $20 million?

That’s the minimum amount required to join Tiger 21, the exclusive network where ultra-high-net-worth entrepreneurs learn how to preserve and grow their wealth.

Michael Sonnenfeldt founded Tiger 21 after selling two companies and realizing that the skills that made him a successful entrepreneur didn’t translate into smart investing. He built the group to help other entrepreneurs avoid costly post-exit mistakes.

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Built to Sell Radio

Ep 487 After the Deal: How the Ultra-Wealthy Invest After Selling Their Business

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

The Journey of Wealth Creation and Investment

Sticker Shock and Portfolio Structure

Common Investment Mistakes

The Emotional Toll of Wealth Management

The Importance of Mentorship in Entrepreneurship

Remember Everything You Learn from Podcasts