Own The Exit

Hosted by Caleb Edwards and Aaron Leatherdale

Business Entrepreneurship

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Episodes

156

Latest episode

Oct 2026

Language

EN-US

About the show

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. Click on follow!

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October 13, 2026Episode 15612 min

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 Aaron sees AI as underused rather than overhyped, based on Anthropic's chart of theoretical capability versus observed usage How Oak IQ uses AI as a junior analyst, research assistant, and administrator Why AI-assisted work still needs a human who reviews it and takes responsibility for it Why keeping a human face on customer-facing work may become a competitive edge RESOURCES MENTIONED Anthropic: Labor Market Impacts of AI FOLLOWS Oak IQ Investments Own The Exit Aaron Investing CHAPTERS 00:00 The AI Bubble Question 00:30 The Chart: What AI Could Do vs. What It Does 04:35 How Oak IQ Uses AI Behind the Scenes 08:47 Why Every AI Output Needs a Human Owner 11:20 Will AI Replace Jobs? Keeping the Human Touch KEYWORDS AI for business owners, is AI a bubble, AI bubble, artificial intelligence and jobs, AI job displacement, blue collar jobs and AI, white collar jobs and AI, Anthropic labor market research, Claude AI for business, AI implementation for business, AI in real estate investing, AI financial model review, AI junior analyst, AI research assistant, AI investor reporting, human in the loop AI, AI slop, future of work, AI and entrepreneurship, Oak IQ Investments, Own The Exit, Aaron Leatherdale WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

September 29, 2026Episode 15528 min

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 outperforming billion-dollar deals, this episode reframes how smart investors should think about private markets going forward. TAKEAWAYS 66% of private equity returns came from cheap debt and rising prices—not operational improvement The price you pay upfront is the single biggest driver of your returns Small and mid-sized deals are outperforming large funds due to less competition and better pricing Independent sponsors create stronger alignment by only getting paid when deals succeed Diversification and disciplined selection are critical in an inefficient market with wide outcome dispersion FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The 66% Private Equity Reality 01:31 Why Private Equity Feels Confusing 05:06 Why Big Private Equity Started Failing 07:56 The Cash Flow Crisis (DPI Problem) 09:04 Where the Returns Actually Moved 12:28 The Rise of Independent Sponsors 19:49 Deleveraging & Real Cash Flow 25:30 The New Playbook for Smarter Investing KEYWORDS private equity strategy, passive investing strategies, small business acquisitions, independent sponsors, lower middle market investing, EBITDA explained, entry multiple investing, cash flow investing, leveraged buyouts, alternative investments, portfolio diversification, wealth building strategies, passive income ideas, deal sourcing, investment risk management, buy and hold business, private markets investing, financial freedom strategies, compound growth investing, disciplined investing, investment fundamentals WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

September 22, 2026Episode 15416 min

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 you’ve been chasing “mailbox money,” this episode will challenge your entire framework for evaluating investments. TAKEAWAYS Cash flow is not when money is made—it’s when it’s distributed Ground-up development creates value before income exists The profit comes from the spread between cost to build and stabilized value Entitlements can create massive value before construction even begins Timeline, cost, and quality are the biggest risks during development The operator matters more than the pro forma or underwriting model The best deals often delay gratification but maximize long-term returns FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Deal That Pays Nothing 02:19 From Dirt to Development 03:07 Entitlements & Hidden Value Creation 04:23 Understanding the Capital Stack 06:05 Where Deals Lose Money (Leaks) 08:30 Lease-Up & Stabilization 10:12 When the Value Becomes Real 11:20 Cash Flow vs. Value Creation 12:15 Who Development Is Actually For KEYWORDS real estate development, ground up construction investing, passive real estate investing, value creation real estate, real estate cash flow vs appreciation, investment strategy real estate, multifamily development, commercial real estate investing, capital stack explained, equity vs debt investing, real estate deal analysis, property development process, wealth building strategies, long term investing strategy, real estate risk management, investment portfolio diversification, financial independence investing, alternative investments, real estate underwriting, building passive income WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

September 15, 2026Episode 15320 min

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 attract high-income investors to the asset class. They also break down the risks investors need to understand, why operator selection and deal structure matter, and how collective capital can provide exposure across multiple producing wells instead of concentrating an investment in a single project. TAKEAWAYS Buying stock in an oil company isn't the same as directly owning an interest in producing oil wells. Non-operated working interests provide a different form of exposure to the asset. Horizontal drilling and diversification across multiple wells can reduce concentration and dry-well risk, although oil and gas investments still carry meaningful risks. Direct working interests can offer significant tax advantages, including deductions associated with drilling costs and a depletion allowance on qualifying production income. Operator quality, incentives, insurance, fund structure, and alignment matter significantly when evaluating an oil and gas opportunity. Oil and gas can serve a specific role within a broader portfolio through a combination of potential early cash flow, tax advantages, and direct exposure to energy production. RESOURCES MENTIONED The Capitalist Network FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Buying Oil Stocks Isn’t Investing in Oil 02:42 How Ben Discovered Direct Oil Investing 05:40 Buying Oil Stocks vs. Actually Investing in Oil 06:31 How Producing Oil Wells Generate Revenue 09:27 The Red Flags Investors Need to Recognize 11:06 How Non-Operated Working Interests Work 14:10 Tax Advantages and Investor Liability 18:59 Why Investors Are Allocating Capital to Oil KEYWORDS oil and gas investing, direct oil investing, alternative investments, accredited investor, tax advantaged investing, non operated working interest, working interest investing, horizontal drilling, oil well investing, energy investments, passive investing, alternative asset investing, portfolio diversification, tax efficient investing, high income investing, oil investment funds, passive cash flow, investment risk management, energy production, tangible assets, high net worth investing, depletion allowance WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

September 8, 2026Episode 15242 min

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 doesn't need to do the same job. They explore the difference between creating wealth and preserving it, why DIY real estate can become another full-time job, and why education may be the biggest advantage an investor can build. The goal isn't to chase a specific asset class—it's to understand your investments well enough to assess risk, recognize alignment, and act decisively when the right opportunity appears. TAKEAWAYS High income alone doesn't create durable wealth. Investors need to build a financial floor that can eventually support their lifestyle without relying entirely on earned income. Different investments can serve different purposes. Tax advantages, cash flow, growth, and capital preservation don't necessarily need to come from the same asset. Cash flow can be attractive, but investors focused on building substantial wealth may also need equity-driven opportunities designed to create value over longer time horizons. Passive access to larger, professionally managed assets can remove much of the operational burden that comes with owning and managing smaller properties yourself. Investor education creates speed and confidence. Understanding an asset, its risks, the partners, and the market can help investors evaluate opportunities without falling into analysis paralysis. RESOURCES MENTIONED The Capitalist Network FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Welcome and Introduction 02:44 Why Ben Walked Away From the Financial Advisor Industry 06:25 The Incentives Behind Traditional Financial Advice 10:12 What Accredited Investors Are Prioritizing Right Now 15:01 Building a Durable Wealth Floor 17:06 When Your Income Outgrows Your Investment Strategy 18:08 Why $9.35 Million Flowed Into One Oil Fund 22:43 Creating Wealth vs. Preserving Wealth 26:48 Stop Asking One Investment to Do Three Jobs 29:11 Why Passive Investors Can Access Bigger Assets 39:29 The Real Advantage: Becoming an Equipped Investor KEYWORDS accredited investor, alternative investments, passive investing, passive real estate investing, high income investing, durable wealth, wealth building strategies, tax advantaged investing, oil and gas investing, multifamily real estate, real estate syndication, institutional real estate, portfolio diversification, passive income, wealth preservation, financial freedom, investment education, cash flow investing, equity investing, retirement income, high net worth investing, tax efficient investing WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

September 1, 20266 min

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 others see problems—and using value creation to unlock exponential returns. TAKEAWAYS The best deals are often created—not found Vacant or “problem” properties can hold the most upside Repurposing an asset can unlock entirely new value Multiple income streams dramatically increase asset performance Amenities can drive demand even if they aren’t heavily used “Office hacking” can eliminate your own overhead while building equity FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 00:00 You Don’t Find Deals—You Create Them 00:34 The Vacant Building Nobody Wanted 01:59 Turning One Use Into Multiple Income Streams 03:15 Amenities That Attract (Even If Unused) 05:06 “Office Hacking” & Creating a 4X Asset KEYWORDS real estate value add, commercial real estate investing, office space investing, passive income strategies, real estate deal analysis, property repurposing, multiple income streams real estate, coworking space business, value creation real estate, investment property strategy, creative real estate investing, building passive income, real estate entrepreneurship, asset repositioning, commercial property investing, wealth building strategies, alternative investments, real estate development ideas, income producing assets, financial independence investing WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

August 25, 2026Episode 15024 min

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 ever relied on pro formas or been tempted by steady income alone, this episode will completely reframe how you evaluate deals. TAKEAWAYS Cash flow and appreciation are outputs—not true sources of return There are only two real sources of yield: macro market and value drivers Relying solely on market conditions is a dangerous long-term strategy The best deals combine favorable market timing with strong value creation Negative cash flow deals can outperform when value drivers are strong “Safe” cash-flowing deals can still lose money due to poor basis and structure Understanding the value creation spectrum gives you control over outcomes Buying at the right basis is one of the most critical factors in investing FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Cash Flow Is Misunderstood 03:07 The Two Sources of Yield Explained 06:13 Market Cycles & Buying Opportunities 09:00 The Value Creation Spectrum 12:11 Case Study: Negative Cash Flow Deal 15:01 Repositioning & Value Creation Results 18:08 Case Study: 6% Cash Flow Deal 21:00 Why the “Safe” Deal Lost Money 22:40 The Truth About “Safe” Investments KEYWORDS real estate investing strategy, passive income investing, multifamily investing, value add real estate, real estate cash flow myths, investment risk analysis, IRR explained, real estate deal analysis, property investing strategies, commercial real estate investing, passive wealth building, investment fundamentals, real estate market cycles, forced appreciation, real estate underwriting, capital stack risk, real estate returns explained, wealth building strategies, alternative investments, financial independence investing WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

August 18, 2026Episode 14916 min

You Have $3M… But You’re Stuck

Most people are chasing the wrong number—and it’s keeping them stuck. In this episode, Caleb breaks down the difference between building a “pile” of money versus creating a “pipe” that actually pays you. Because having millions on paper means nothing if your income disappears the moment you stop working. After a life-altering moment with his son, Caleb realized that financial freedom isn’t about net worth—it’s about whether money shows up when you can’t. This episode will challenge everything you’ve been taught about investing, retirement, and what it really means to be secure. TAKEAWAYS Why net worth alone can leave you financially trapped The critical difference between a “pile” and a “pipe” How traditional investing creates slow self-liquidation The simple “flip” that changes your entire financial strategy How to calculate your real monthly freedom number How to start shifting toward income-producing investments FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Lie of Net Worth 02:04 Why the “Pile” Fails 04:15 Introducing the “Pipe” Concept 06:25 Why Passive Income at 65 Is Broken 08:13 Income-First Investing Strategy 13:36 Define Your Monthly Number KEYWORDS passive income strategy, cash flow investing, real estate investing for beginners, financial freedom strategy, income producing assets, build passive income streams, wealth building strategy, escape the rat race, retirement income planning, cash flow vs net worth, financial independence plan, investing for entrepreneurs, passive investing ideas, real estate cash flow, alternative investments, monthly income investing, portfolio diversification strategy, wealth mindset shift, financial security planning, income first investing WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

August 11, 2026Episode 14816 min

The Alternative Investment Trinity

Too many investors expect one investment to deliver massive cash flow, explosive growth, and huge tax savings all at once. But that's not how sophisticated portfolios are built—and it's one of the biggest reasons investors end up chasing disappointing deals. In this episode of Own The Exit, Caleb shares the framework he uses to build his own alternative investment portfolio. Learn why every investment should have a specific job, how the Alternative Investment Trinity works, and why combining real estate, oil and gas, and private credit can create a more resilient portfolio built for long-term wealth. TAKEAWAYS Why expecting one deal to do everything is a costly investing mistake. How sophisticated investors build portfolios instead of chasing individual deals. The three objectives every investment portfolio should optimize for: income, growth, and taxes. Why diversification is about assigning specific jobs—not owning more assets. The importance of using uncorrelated assets to improve portfolio resilience. How specialists outperform "jack-of-all-trades" investments over time. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 – Why One Investment Can't Do Everything 01:02 – The Three Jobs Every Portfolio Must Accomplish 04:32 – The Alternative Investment Trinity Explained 05:23 – Real Estate, Oil & Gas, and Private Credit Roles 14:44 – Building a Portfolio That Lasts 15:52 – Stop Chasing Deals. Build a Strategy. KEYWORDS alternative investments, passive investing, private credit, multifamily investing, oil and gas investing, passive income, wealth building, accredited investor, investment portfolio, portfolio diversification, tax strategies, commercial real estate, private markets, financial freedom, cash flow investing, alternative assets, investment strategy, portfolio management, durable wealth, high income investing, real estate syndication, long-term investing WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments! If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a smarter investment portfolio. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

August 4, 2026Episode 14710 min

How You Make (or lose) Money In Real Estate

Every real estate investment produces returns from one of two places: the market or your ability to create value. The problem? Too many investors unknowingly rely on forces they can't control—and when the market shifts, their entire investment thesis can collapse. In this episode of Own The Exit, Caleb breaks down the two sources of yield in commercial real estate and explains why the most successful investors focus on creating returns instead of hoping for them. Learn how understanding this simple framework can help you evaluate opportunities, manage risk, and invest with greater confidence through every market cycle. TAKEAWAYS Understand the two primary sources of investment returns in commercial real estate. Why betting solely on market appreciation creates unnecessary risk. How value creation gives investors greater control over outcomes. Lessons learned from the real estate correction of 2022–2023. Why interest rates and cap rates dramatically impact investment performance. How disciplined underwriting protects investors during market downturns. The importance of buying deals that work without relying on market appreciation. How experienced operators create value regardless of market conditions. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Investment Bet Most People Never Realize They're Making 02:33 The Difference Between Market Yield and Value Creation 03:24 What the 2022 Real Estate Correction Taught Investors 06:04 How to Build Returns You Can Actually Control 08:19 The One Question Every Investor Should Ask Before Investing 08:47 The Framework for Smarter Investing in Any Market KEYWORDS commercial real estate, passive investing, passive income, multifamily investing, real estate investing, value investing, cap rates, interest rates, investment strategy, accredited investor, private real estate, investment risk, cash flow investing, market cycles, portfolio diversification, value creation, underwriting, commercial property, wealth building, recession investing, alternative investments, financial freedom WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠ , dive into our enriching content on ⁠YouTube⁠ , and explore ⁠our website⁠ to learn how intelligent passive investing can help you build durable wealth. If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone looking to become a more disciplined investor. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or your preferred podcast platform.