Scott Galloway had a plan: sell his company, take $25 million, raise another $250 million, and become a billionaire. But then he stopped to think about it. “Why would I want back on this hamster wheel of stress?” he asked on a recent episode of his podcast, “Office Hours.”
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Chasing Money, Losing Time
Galloway, a business professor, entrepreneur and investor, said he realized the pursuit of more wealth would just cost him time, peace of mind and family moments. “I’ve been doing nothing but working for a quarter century,” he said. After hitting his personal financial target, he made a different choice: spend on what brings joy, pay people well, and give the rest away.
“I hit my number eight years ago,” he said. “And I decided there’s just no reason why I would ever need to be a billionaire.”
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“Every year I look at my number,” he explained. “Anything above that number, I do one of two things: I either spend it or I give it away.”
He added, “It feels amazing to spend money and to give it away.” He owns a plane and refuses to let money prevent him from enjoying life. When friends can’t afford to join, he covers the cost himself, saying it gives him satisfaction.
The Billionaire Trap
His shift in mindset mirrors that of Andrew Wilkinson, a Canadian entrepreneur who told his own story in the 2024 book, “Never Enough.” Wilkinson became a billionaire after building the tech conglomerate Tiny, but eventually saw the limits of wealth.
After nearly partnering with legendary investor Charlie Munger, Wilkinson said he turned it down. The thought of chasing another level of wealth no longer appealed to him.
Both Wilkinson and Galloway reached a similar conclusion. Once you have enough, more doesn’t necessarily improve your life. In fact, it can increase stress.
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Galloway recalls the fear he felt in 2008 when his first son was born during the financial crisis. “All I felt was shame and fear,” he said. “I thought, I’ve failed this kid. I don’t have enough money.” That fear stayed with him until he reached financial security.
“Happiness is not only a function of the things you have,” he said. “It’s a function of the things that you don’t have—specifically, an absence from stress.”
Talking About Money Matters
Galloway also wants to normalize open conversations about money. “This zeitgeist that you’re not supposed to talk about money is nothing but an effort by rich people to keep the poor and middle class down,” he said.
He encourages people to share information about salaries, taxes and financial tools to help each other get ahead. “Talking about it a lot gives you ideas and opportunities and can be quite cathartic,” he said.
These days, Galloway says he’s off the hamster wheel for good. He spends on joy, gives generously and says he finally feels free.
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