If You Could Ask Just One Question

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: http://thoughtsonmoney.com http://thebahnsengroup.com