If You Could Ask Just One Question
About this episode
Trevor Cummings discusses the importance of understanding how advisors invest their own money as a measure of their true beliefs and strategies.
This week's blogpost - https://bahnsen.co/4mUGiFb Trevor Cummings hosts the Thoughts On Money podcast with Brett Bonecutter to discuss a due diligence hypothetical: if you could ask an advisor or investment manager only one question, it should be “How do you invest your money?” Drawing on Nassim Taleb’s “skin in the game” idea, Trevor argues behavior and portfolio holdings reveal true beliefs more than polished pitches. He recounts meeting a Twitter-famous fund manager whose personal investments didn’t match his fund strategy, reinforcing the “eat your own cooking” rule while noting it isn’t a complete substitute for full due diligence or diversification. The conversation explores aligned incentives versus fiduciary labels, Buffett’s Goldman Sachs deal requiring executives to retain shares (“buying the jockey”), 1929-era disclosure rules on insider trading, and Trevor’s real example of a near-retiree concentrated in two stocks despite claiming high confidence. 00:00 One Question Diligence 01:40 Skin In The Game 02:48 Quitting Social Media 05:31 Fund Manager Test 09:22 Eat Your Cooking 14:34 Buffett Deal Lesson 18:35 Limits Of Skin 19:56 Peace Child Setup 20:26 Judas and the…
People in this episode
Host: Trevor Cummings
Topics covered
- due diligence
- investment strategy
- skin in the game
- aligned incentives
- fiduciary responsibility
Keywords
- Nassim Taleb
- Buffett
- Goldman Sachs
- insider trading
- portfolio holdings
Mentioned in this episode
Books & works: Thoughts On Money
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