Brent Beshore, CEO, Permanent Equity: How Winning Made me Lose

Brent Beshore made his first million at 28. Visited the White House. Got ranked 28th on the Inc. 500. Got everything he wanted.And realized he had summited the wrong mountain.In this raw conversation, Brent—CEO of Permanent Equity, a private equity firm that owns 16 companies generating $400M in revenue with zero debt—goes places most CEOs do not.He talks about weighing 252 pounds while everything he ate tasted grey. About earning a million dollars but telling his wife he didn't love her. About being an ardent atheist who made fun of Christians before everything changed.This isn't your typical CEO interview. Brent breaks down why traditional private equity is broken, how his firm operates without debt or forced exits, and why treating people well isn't just nice—it actually delivers better returns.But the real lesson?"The lie is that money will make you someone else. The truth is that money only makes you more of what you already are."If you've ever felt like you're winning the wrong game, this conversation will hit hard.TIMESTAMPS:[01:27] What is Permanent Equity?[06:43] The two stakeholders traditional PE serves—and everyone it doesn't[08:04] The portfolio: 16 companies, $400M revenue, $50M free cash flow, zero debt[10:48] "We want to be a kind, generous, long-term owner"[20:24] 28 years old: First million, Inc. 500, White House advisor, and completely hollowed out[22:47] Climbing the wrong mountain[27:36] "I don't even know what love meant when we got married"[28:05] Why he never wanted kids (and why he wishes he had five more now)[29:32] "He who has the gold makes the rules" vs. "The meek shall inherit the earth"[32:23] "Do I own the things I create? No, of course not."[37:36] Living generously: Why they give away 25% before taxes[45:25] Good reasons to sell vs. bad reasons to sell[48:37] How long-term thinking changes everything—with investors, employees, and communities[50:55] The Main Street Summit: "You belong here. You're important. You matter."[53:38] Being known vs. being loved: The safeguard against blowing up your life[54:08] Addiction, affairs, and cutting corners: What happens when you're unknown[56:50] The "Brené Brown bullsh*t" review (his favorite)[58:06] The day everything changed: Dropping the performance and being authentic[1:03:49] We're all going to anonymity—so what really matters?[1:07:04] Advice for someone climbing the wrong mountain: You're not alone[1:09:09] "Study the greats—all the greats study Jesus"GUEST: Brent Beshore CEO, Permanent Equity Columbia, MissouriHOST: Jonathan Block Founder, Stumbling Blocks PodcastLINKS: https://www.permanentequity.com/linkedin.com/in/brentbeshorehttps://www.mainstreetsummit.com/If this conversation resonated, please pass it along.