Investing Like the Ultra Wealthy Ft. Tiger 21 Founder Michael Sonnenfeldt

Michael Sonnenfeldt is the founder of TIGER 21, a community of entrepreneurs and HNW investors who collectively represent $150 billion of net worth. In this episode, they discuss the challenges around the skills of being a successful entrepreneur don’t translate to being a good investor, how to think about legacy planning, and the role alternative investments play in your portfolio.

00:00 Introduction
03:52 Michael's Background, Tiger 21's Founding
05:38 Focus on Wealth Preservation
06:17 Tiger 21 Status: 1,300 Members
07:47 Tiger 21 Structure and Reports
08:32 Net Worth Managed Range
09:54 Financial Incentives in Tiger 21
10:32 Post-Liquidity Event Challenges
11:07 Portfolio Defense Importance
13:14 Diversification Advice Ignored
15:11 Michael's Risk Management Perspective
16:28 Consequences of Disregarding Advice
17:43 Entrepreneurial vs Investor Skills
19:45 Validation After Liquidity Event
21:07 Entrepreneurs Adjusting for Investing
23:15 Wealth Creation, Overconfidence, Transition
24:28 Survivorship Bias, Importance of Humility
26:33 Learning for Better Investing
28:25 Challenges of Diversification Sweet Spot
30:06 Classic vs Entrepreneurial Investor
31:24 Market Returns and Timing Challenges
32:45 Impact of Market Fluctuations
34:02 Importance of Having an Edge
35:30 Decline in Warren Buffett's Returns
37:21 Diversification Principles, Concentration Risk
38:56 Value of Alternative Investments
40:16 Balancing Risk and Return
41:35 Pitfall: Focusing on Returns
42:20 Risk and Return for Entrepreneurs
43:43 Leveraging Entrepreneurial Skills
45:26 Drawback of Relying on Managers
47:44 Teaching Kids Delayed Gratification
49:44 Delayed Gratification in Success
51:41 Connection to Investment Success
53:34 Balancing Kids' Ambition Guidance
54:48 Risk Tolerance and Stewardship
55:57 2% Rule for Spending Inheritance
57:16 Legacy and Generational Wealth
59:05 Supportive Network Example
59:40 Tiger 21 Website Information

Connect with Michael Sonnenfeldt on LinkedIn ⁠  / michael-sonnenfeldt-84072225  
Connect with Ben Fraser on LinkedIn   / benwfraser  

Invest Like a Billionaire podcast is sponsored by Aspen Funds which focuses on macro-driven alternative investments for accredited investors.
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