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A former CEO with a high eight-figure net worth spent a recent morning searching online for cheap flights. He drives a sensible car. He wears $140 shoes, and he winces whenever he flips over the price tag on a Prada sweater. He owns a mere two houses. He knows exactly how much money he has — he can check his bank balance anytime — but it never quite feels like his. “I’m still not acclimated to being rich,” he told me. “I find even saying these words to you now a bit disturbing. It’s just not part of my identity.”
For two months, I interviewed people with extreme wealth, asking them how money had changed the way they think — how their view of the world shifted once financial constraints disappeared. How did becoming rich alter their perceptions of status, friendship, obligation, and maybe even reality itself?
I sent many requests, offering anonymity. Many said “no.” (“We’re going to pass this time,” said a rep for a well-known hedge-funder. “Not my jam,” replied a famous entrepreneur.) Even more just ignored me.
But some said “yes.” One founded a large company. Another had made millions on his own and then married into hundreds of millions more. Another multiplied his family inheritance many times over by buying into the investment firm where he worked. Another was Mark Cuban.
At first, few of them would tell me outright that wealth had changed their thinking.
