Minor point: I assume the author's rationale for carrying only liability insurance is that he has enough money to comfortably self-insure the risk of an at-faul

Minor point: I assume the author's rationale for carrying only liability insurance is that he has enough money to comfortably self-insure the risk of an at-fault accident. For businesses that approach makes sense - big companies self-insure most or all of their fleets, because buying third-party insurance costs more than the actuarially fair cost of risk. But those businesses also have teams of people to deal with the giant hassle that is the claims process, including dealing with the other party's (or parties') insurers, determining fault, and suing and/or negotiating a legal settlement as needed. For individuals that service is largely inseparable from risk transfer, i.e., you can really only get it through insurance. Lawyers can handle a subset of the process, but not all of it, and besides, relying on lawyers for it is probably at least as expensive as the non-risk-transfer component of insurance in expectation. In general, if someone's wealthy enough that they can effectively self-insure, even if they're completely risk-neutral, their time is probably valuable enough that they'd be better off buying insurance just to avoid having to go through the equivalent of the claims process themselves. So unless the author's rationale is wildly different than I'm thinking, in that example his insurance agent was right and he did make a stupid decision.