I told her about the book, an essay called Famine, Affluence, and Morality, by Peter Singer, an Australian philosopher who argued that anyone with the means to do so has a moral obligation to give to those in need.

and pathetic than a man who devotes all the hours of the waking day to the making of money for money’s sake.”

I was, on paper, almost a billionaire, depending on how you calculated it. And yet, Chris and I were still playing endless whack-a-mole. We woke up every day to hundreds of messages, and hundreds of problems. All day we’d put out fires, and the next day be greeted by hundreds more messages. Somebody wanted a huge raise. One executive was feuding wi

That panorama, which featured countless sailboats, also served as the constant reminder that “the two best days of a man’s life are the day he buys a boat and the day he sells it.” (A lesson I’d learned the hard way years earlier, after I impulsively bought my own sailboat, which promptly turned into a hole in the ocean that ate money.)

After a decade of trying all these things—crazy shopping sprees, sports cars, mansions, and ridiculously expensive boats—I came to a fundamental realization. My ultimate goal was freedom of time and freedom from worry. And, ironically, spending and tending to my expensive toys actually ate into my time and stoked my worries. It was a pyrrhic victor

Getting impressive things didn’t win me more friends. At least not the kind I wanted. In fact, it made me more insular. It made me gravitate increasingly to my old friends. My world began shrinking inward to people who knew me before the money—whose intentions I knew I could trust.

There was something else that surprised me about this big lifestyle upgrade. The thing that nobody tells you is that nobody is impressed when you drive a flashy car or show off your crazy house on Instagram. My friend Morgan Housel put it well: “People aren’t thinking: ‘Wow, I’m impressed by this person!’ They’re thinking, ‘I wish I had that house.

Chris and I were taking all of these lessons and learning how to operate dozens of businesses at once, ironically, by not operating them at all. After the meddling that I had done myself, and the million dollars flushed down the toilet, we decided on a rather simple management philosophy. We summarized it as follows: when it came to mistakes, we wo

My prying was mostly a function of habit. When you’re running a company, you have to become very opinionated about almost everything. You have to make decisions, constantly. MetaLab was my baby; the company reflected my taste and preferences and goals. But now I had to learn to hold back and bite my tongue.