Among virtually all types of risks, medical ones are perhaps the most unpredictable and challenging to insure against. Unlike life expectancy, which can be statistically modelled, an individual’s specific medical future is highly unpredictable. Treatments may vary in success, and chronic conditions might require ongoing management. This uncertainty poses a challenge in predicting the complete scope of potential medical costs. This challenge is reflected in the increasing complexity (and rising premiums) of medical policies offered by insurance companies. 

UHNWIs can afford these premiums, but making claims often entails unnecessary administrative hassle when the full costs of care can be self-insured, that is to say covered out-of-pocket when necessary.

Famous UHNWIs have generally avoided disclosing their approaches to medical insurance, most likely due to the sensitive nature of personal medical information. Nevertheless, medical self-insurance is widely recognized among well-resourced enterprises – including those led by the likes of Jeff Bezos, Warren Buffet, and Jamie Dimon – as a prudent financial decision. 

For example, in 2018, Amazon, Berkshire Hathaway, and JP Morgan, formed an alliance to take more responsibility for covering the medical costs of their respective workforces. The alliance disbanded in 2021 because it was unnecessary; the companies preferred taking more individualistic approaches tailored to their specific needs. In 2023, the Employee Benefit Research Institute reported that US companies have been self-insuring the medical risks of more than half of all the employees in the country since 2010.  Also, it is worth noting that Warren Buffett is known to be a proponent of self-insurance in general.