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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 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 outper
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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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Why High Earners Are Looking Beyond Traditional Financial Advice
152
Sept. 8, 2026

Why High Earners Are Looking Beyond Traditional Financial Advice

What happens when your income has outgrown the way you invest? In this episode of Own The Exit, Caleb and Aaron sit down with Ben Oberg of The Capitalist Network to unpack what high-income accredited investors are actually prioritizing as they move beyond traditional financial strategies and take greater ownership of their wealth.




From oil and its tax advantages to cash-flowing real estate, development deals, and institutional-grade assets, the conversation reveals why every investment doe
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This Vacant Building Became a 4X Deal
Sept. 1, 2026

This Vacant Building Became a 4X Deal

Most investors are out hunting for “good deals”… but what if the real money isn’t found—it’s created? In this episode, we take you inside a real project that sat vacant for three years and show how it was transformed into a high-performing asset with multiple income streams.




We walk through the full evolution of this building—from an outdated medical office with heavy restrictions to a thriving co-working hub, studio, and community space. This is a masterclass in seeing opportunity where o
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Why We Bought Negative Cash Flow
150
Aug. 25, 2026

Why We Bought Negative Cash Flow

Most investors are chasing cash flow and appreciation… but what if those aren’t actually where your returns come from? In this episode, we break down the real drivers behind profitable real estate investing—and why focusing on surface-level metrics can quietly cost you millions.




We walk through two real deals: one that had negative cash flow on day one but delivered massive upside, and another that looked “safe” with nearly 6% cash flow—but was actually projected to lose money. If you’ve e
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