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For very high-net worth individuals, does it make sense to not have insurance?
Simply put, it makes sense from the moment you can afford the loss without negative consequences. For example, if your car costs $20000 and you happen to have another $20000 laying around, you can choose not to insure your car against damage. In the worst case, you can simply buy a new one. However, not insuring your car has a hidden cost: you can't long-term invest that money anymore. If your insurance costs $500 a year, and you can invest those $20000 with a return on investment of more than 2.5%, it still makes sense to invest that money while having your car insured.