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: