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Own The Exit

U N L O C K    E N T R E P R E N E U R I A L    F R E E D O M

Own The Exit is your quintessential guide to entrepreneurial freedom. Every entrepreneur aspires to build a prosperous business while enjoying financial and time freedom, but the reality often falls short. This podcast is your lifeline to success, providing crucial insights on preparing your business for a winning exit.

Join us as we deep dive into the world of successful exits, liberating you from active involvement and helping you realize your dreams of a fulfilling life. The power to define a triumphant exit rests solely with you, and we're here to empower your journey. 

Why Doing It Yourself Can Mean Less Money
158
Nov. 10, 2026

Why Doing It Yourself Can Mean Less Money

Is Your Rental Property Really Passive?

Buying and managing rental properties yourself often isn't the smartest way for a successful business owner to invest in real estate anymore. In this solo episode of Own The Exit, Aaron Leatherdale walks through four reasons business owners should consider group or syndicated investments instead: the rising cost of entry, the do-it-yourself math, the mental cost, and the time cost of running rentals yourself.

TAKEAWAYS
Rising insurance, property taxes, a
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Multifamily’s Boom, Crash, and the Strategy for What Comes Next
157
Oct. 27, 2026

Multifamily’s Boom, Crash, and the Strategy for What Comes Next

Multifamily real estate just went through a correction that crushed valuations, trapped overleveraged owners, and exposed the risks hidden beneath years of cheap debt. But if the worst of that reset has already happened, could the pain of the last few years be creating one of the best multifamily buying windows in nearly two decades?

In this episode of Own The Exit, Caleb and Aaron trace multifamily from the aftermath of 2008 through the cheap-money buying frenzy of COVID and into the sharp rat
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The AI Chart Every Business Owner Should See
156
Oct. 13, 2026

The AI Chart Every Business Owner Should See

Is AI a bubble, or is it still being underused? In this solo episode of Own The Exit, Aaron Leatherdale breaks down an Anthropic chart comparing what AI could theoretically do across occupations with how it's actually being used. He then shares how Oak IQ Investments uses Claude as a junior analyst, research assistant, and administrator, why every AI output still needs a human who owns it, and why he thinks keeping a human face on customer-facing work will be a competitive edge.

TAKEAWAYS
Why A
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Why Big Money Lost Its Edge (And Where It Went)
155
Sept. 29, 2026

Why Big Money Lost Its Edge (And Where It Went)

For decades, private equity was the gold standard—outperforming public markets and building massive wealth. But something quietly broke. Today, the biggest funds are underperforming, capital is getting stuck, and the old playbook isn’t working anymore.




In this episode, we break down exactly why that shift happened—and more importantly, where the real returns have moved. From understanding simple concepts like EBITDA and entry multiples to uncovering why small, “boring” businesses are now o
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Why Smart Investors Wait Years for a Check
154
Sept. 22, 2026

Why Smart Investors Wait Years for a Check

What if the best deal in your portfolio paid you absolutely nothing for three years? No cash flow. No distributions. Just silence. In this episode, we break down why that might actually be a sign you’re in the right deal—and how most investors misunderstand where real estate profits really come from.




We walk step-by-step through a 289-unit ground-up development—from raw land to a stabilized, cash-flowing asset—and uncover how value is created long before a single dollar is distributed. If
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You Think You’re Invested in Oil. But Is It the Right Way?
153
Sept. 15, 2026

You Think You’re Invested in Oil. But Is It the Right Way?

Most investors think buying stock in an oil company means they're investing in oil. But direct oil and gas investing works very differently—and understanding that distinction opens the door to an entirely different set of potential benefits and risks.




In part two with Ben Oberg of The Capitalist Network, Caleb takes a deeper look at how direct oil and gas investing works, including non-operated working interests, horizontal wells, diversification, cash flow, and the tax advantages that att
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