If You Could Ask Just One Question
The One Due Diligence Question: Do You Eat Your Own Cooking?
The One Due Diligence Question: Do You Eat Your Own Cooking?
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 Gospel
21:24 Peace Child Incentives
22:21 Advisor Skin in Game
23:42 Fiduciary vs Incentives
25:09 Taleb Fund Cycle
28:35 Do You Follow Advice
31:41 1929 Insider Reporting
35:06 Eating Own Cooking
35:39 Diversification Wake Up
38:04 Due Diligence Wrap
Links mentioned in this episode:
Trevor is a Partner, Director of our Private Wealth Advisor Group, and Author of Thoughts on Money.
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