$10M does get you a nice time, and you would never have to say no to any reasonable expense, but it's also definitely possible to overspend. There's some higher threshold where you really can be 'wild and crazy' and the only way to run out of money would be through bad investments.
There's a difference between always flying first class, always flying on a jetshare, and always having your plane fueled up and ready to go. Also, between driving yourself to the airport, taking a car service, having your driver take you, or having your helicopter pick you up.