EP36 - Senile Boomer
I met a humble boomer with $100M net worth.
He is retarded. Let me explain.
They say you can't take it with you. They're wrong. You just need the right strategy.
I manage the portfolio for a man whose children think he lost his mind.
They see him as a frail patriarch, fading into dementia.
They hold meetings behind his back, whispering about him as a liability.
I dont think they understand.
This boomer is a predator playing the long game.
His "senility" is the most brilliant defensive asset I have ever witnessed.
It's a cloak of incompetence that makes everyone around him show their hand.
When you're perceived as weak, the greedy get bold.
The son-in-law "helpfully" suggests consolidating assets into a new fund he controls.
The daughter "gently" tries to get him to sign documents he "won't understand anyway."
They think they are managing a decline. They are actually failing a loyalty test.
He sits in meetings, drooling slightly.
He asks the same question three times. But he's not forgetting the answer.
Later, my phone rings.
"The son-in-law. Write him off the will from my family trust. Silently."
"My daughter's 'advisor'? Have him audited by the IRS. Anonymously."
He's not losing his empire to his heirs. He is stress-testing them to destruction.
This isn't a tragic decline. It's the most ruthless form of late-stage due diligence.
He has weaponized their perception of his weakness. And the returns have been spectacular.
You don't get to $100M just being yet another old guy who wets his diapers.
Follow me for more financial advice.
Context
If you are a lawyer dealing with family and trusts, I don't think I need to explain. Both of us probably seen the same thing and was amused by the whole thing.
Always act dumb, never appear to be too smart.
You are betting that overconfident people will show their hand prematurely.