This episode explores a parallel healthcare system that most people never see—the world where high- and ultra-high-net-worth individuals quietly step outside traditional insurance and build their own bespoke medical infrastructure. Instead of battling networks, pre-approvals, and deductibles, they self-insure, pay cash, and treat healthcare like a strategic asset rather than a reactive expense.

The discussion begins with the core decision to self-insure and what it really means to “be your own insurance company.” The hosts break down why this is only rational once you can comfortably write a seven-figure medical check without blinking, why the true threshold often sits in the $50M–$100M liquid net worth range, and how family offices carve out dedicated healthcare funds and trusts so a $3M cancer protocol never disrupts the core portfolio.

From there, the episode maps out the service stack the wealthy build on top: concierge medicine and direct primary care as the access layer, high-deductible health plans as catastrophic stop-loss and discount engines, and aggressive negotiation of cash prices that can cut hospital bills by 10–50%. Listeners learn how HSAs, Section 105 plans, HRAs, and even captive insurance companies are used to convert healthcare from an after-tax personal cost into a pre-tax, tax-advantaged, or tax-deferred spend.

The conversation then zooms out to the operational reality: family offices acting as 24/7 “health command centers,” global medical Rolodexes, executive physicals at institutions like Mayo and Cleveland Clinic, telemedicine-driven global concierge services, medical evacuations, and even private physicians on payroll traveling with the family. The episode closes on the hard question: what does it mean for equity and the future of healthcare when the ability to bypass constraints and command global excellence on demand is increasingly a function of balance sheet size?

CHAPTERS

(00:00) Constraints of US healthcare

(02:20) Self-insuring when you’re rich

(05:15) Wealth thresholds for self-insurance

(07:20) Cash pay and negotiation power

(08:59) Concierge vs direct primary care

(15:18) Catastrophic HDHP strategy

(21:54) HSAs as wealth tools

(26:08) Section 105 and HRAs

(28:05) Captive insurance for families

(30:49) Trusts, HEMS, asset protection

(32:40) Family office as health HQ

(35:20) Executive checkups and clinics

(39:03) Philanthropy and access

(40:39) Doctors on private payroll

(42:25) When insurance math flips

(48:34) Parallel systems and equity

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