He made a million dollars in a year at 29 and felt miserable
The money bought freedom to do anything, but not peace, and it forced him to confront a lifetime of performing for others.
Joys of Compounding · Brent Beshore - Adventures in Permanent Equity - [Joys of Compounding, EP. 34]When Brent Beshore was 28 or 29, he made a million dollars in a year for the first time. He was on a run at what Beshore calls "one of the fast-growing companies in Missouri history," young and rich on paper, and living the plan he had chased for a decade.
That plan had been simple. Through his teens and into his 20s, Beshore, a Missouri investor who now runs a firm that buys small businesses, says he had focused maniacally on "How do you make as much money as quickly as you can?" The goal, as he puts it, was complete freedom, the ability to do whatever he wanted, whenever he wanted.
This is a story about getting exactly that and finding it empty. The money did not bring peace or joy or happiness. Beshore remembers feeling miserable at the peak of success, and asking himself if the rest of life was just endlessly growing wealth to spend it. From the outside, he looked successful. At home, he almost lost his marriage more than once, he lost friendships, and Beshore says he "went through a season of depression."
He says that time goes back to a habit he now calls the fear of man, worrying so much about what other people think that you perform for them. His 2025 annual letter says it is "the character flaw that has plagued my life." He says he learned early that people wanted performance and usefulness from him, and if he delivered, they would like him and keep him around. It was how he tried to feel safe, to matter, and to belong.
“I ran a theater and I was a character in the theater,” he says. “I lived so much of my life pretending.”
The turn came around the same time as the million dollar year. Beshore says God rescued him, and he met a group of Christians he had mocked for a decade. He began to think faith might give him what money had not. But he soon realized he had not stopped performing. He had only shifted from performing for himself to performing for God.
Now 43, Beshore says he wrote about all of this because he wants to be real. He no longer wants to act as if he knows all the answers and only talk about his wins.
Questions people ask
What does his firm, Permanent Equity, actually do?
Permanent Equity buys small, private businesses and holds them for a very long time, often decades, rather than fixing them up and selling them in a few years. It does not charge the annual management fees common in private equity, and instead gets paid only when cash is returned to investors.
What does he mean by the “fear of man”?
He means caring too much about approval, applause, and belonging that you shape your actions to please other people. In his telling, it leads to performing a role instead of being honest about who you are and what you believe.