Own The Exit

Hosted by Caleb Edwards and Aaron Leatherdale

Business Entrepreneurship

Website RSS feed LinkedIn Instagram YouTube

Episodes

150

Latest episode

Aug 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!

Listen to episodes

60 recent

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.

July 28, 2026Episode 14613 min

The Wealth Building Framework I Actually Use

Making more money doesn't automatically make you wealthy. In fact, many entrepreneurs and high-income earners unknowingly stay trapped in the middle-class wealth cycle because they're focused on increasing income instead of building assets that generate lasting financial freedom. In this episode of Own The Exit, Caleb breaks down the Durable Wealth Flywheel—a framework designed to help business owners transform earned income into passive income, tax-efficient investments, and long-term wealth. Learn why raising your income ceiling isn't enough, how to raise your financial floor, and why true wealth begins when your passive income exceeds your active income. TAKEAWAYS Why income and wealth are completely different financial metrics. The biggest mistake successful business owners make after increasing income. How to build a stronger financial floor before expanding your ceiling. The three asset categories that create durable wealth. How private credit can generate consistent passive cash flow. Why multifamily real estate provides long-term growth. How tax-advantaged investments can reduce earned income taxes. Understanding the Durable Wealth Flywheel strategy. Why buying businesses becomes more powerful after building passive income. The moment every entrepreneur should strive for: "The Flip." FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Income Isn't Wealth 02:16 Why You Must Raise Your Financial Floor 03:48 The Three Asset Classes That Build Durable Wealth 06:14 The Durable Wealth Flywheel Explained 10:46 The Flip: When Passive Income Takes Over 12:29 How to Truly Own Your Exit KEYWORDS passive investing, passive income, durable wealth, wealth building, business owner, entrepreneur, alternative investments, private credit, multifamily real estate, oil and gas investing, tax strategies, accredited investor, financial freedom, cash flow investing, generational wealth, asset allocation, wealth mindset, income vs wealth, business acquisitions, passive cash flow, portfolio diversification, 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 lasting wealth through smarter investing. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or your favorite podcast platform.

July 21, 2026Episode 14511 min

The 3 Questions To Ask Before You Exit

If you have a major liquidity event on the horizon — whether it’s selling a business, exiting a real estate portfolio, or preparing for a large capital event — what you do next matters more than most people realize. In this solo episode of Own The Exit, Aaron breaks down the three critical questions every entrepreneur and investor needs to answer before deploying capital after an exit. From tax strategy and investment timelines to understanding your competitive advantage as an investor, this episode gives a practical framework for navigating wealth transitions with confidence. TAKEAWAYS The 3 essential questions to ask before deploying capital Why liquidity events create both opportunity and risk How business owners should think about replacing income after an exit The importance of tax planning before a sale closes Why investing in familiar asset classes reduces risk How passive real estate investing can replace active management headaches Real-world examples of investors transitioning into passive income RESOURCES MENTIONED Oak IQ Investments FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 00:00 The 3 Questions Every Seller Must Answer 01:10 Question #1 02:05 Question #2 03:41 Question #3 05:57 Real Estate Investor Case Study: Jeff 07:39 Multifamily Investor Case Study: Fred 09:04 Business Exit Case Study 11:00 Planning Your Next Move After A Liquidity Event KEYWORDS liquidity event, business exit strategy, passive real estate investing, 1031 exchange, wealth preservation, entrepreneur investing, passive income strategies, business sale planning, real estate portfolio exit, accredited investor strategies, alternative investments, multifamily investing, tax efficient investing, capital deployment, real estate syndication, investment diversification, generational wealth, financial freedom, investment strategy, private investments, business owner wealth planning, passive cash flow 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 preparing for a major financial transition. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

July 14, 2026Episode 14418 min

The Business That Puts Your Investment Capital on Steroids

What if the same investment deals you’re already participating in could also become a business that pays you? In this episode of Own The Exit, Caleb and Aaron break down the capital aggregation strategy — a wealth-building model that allows investors to pool capital through their own fund structure and earn not only from their personal investments, but also from the activity of raising and aggregating capital. They explain how accredited investors are leveraging fund structures to access larger private deals, negotiate better terms, and invest alongside institutional players that most individuals would never normally have access to. This episode is a deep dive into how the ultra-wealthy scale investment returns by controlling access and capital flow. TAKEAWAYS What the capital aggregation model actually is How investors can make money beyond their own invested capital Why pooled capital creates access to better deals and terms The difference between investing individually vs through a fund Why accredited investors have a unique advantage in private markets How fund structures allow investors to participate alongside institutions The importance of compliance and securities attorneys The 3 things needed to successfully launch a fund strategy RESOURCES MENTIONED Become a Fund Manger → Multiplier University Free Trial Check out our deals → Oak IQ Investments FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Strategy That Pays You To Invest 03:41 How Capital Aggregation Actually Works 06:31 Why Fund Managers Can Earn Massive Upside 08:47 Investor A vs Investor B Explained 11:20 Avoiding Bad Deals & Building Trust 13:00 The 3 Things You Need To Launch A Fund 15:01 How Multiplier University Helps Fund Managers Scale 17:00 Investing Alongside Institutional Capital KEYWORDS capital aggregation, private equity investing, accredited investor, passive investing, private real estate investing, fund management, investment fund strategy, capital raising, alternative investments, wealth building strategies, private deals, passive income investing, investment syndication, private markets, real estate syndication, institutional investing, entrepreneur investing, private capital, fund structures, cash flow investing, high net worth investing, private alternative investments 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 another entrepreneur or investor looking to scale their wealth beyond traditional investing. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

July 7, 2026Episode 14314 min

The Number One Variable in Real Estate Investing

What actually causes real estate deals to fail? In this solo episode of Own The Exit, Caleb breaks down the single most important variable in real estate investing — and it’s probably not what most investors think. It’s not the market. It’s not the operator. It’s not even the debt itself. It’s time. Using examples from the 2008 housing crisis, today’s commercial real estate debt environment, and decades of market cycles, Caleb explains why the structure of a deal determines whether investors survive long enough to let the thesis play out. He also walks through the three key questions every passive investor should ask before investing in a syndication or private real estate deal. TAKEAWAYS Why time is the most overlooked variable in real estate investing How bad deal structures create forced losses What 2008 taught investors about leverage and survivability Why floating rate debt has hurt so many syndications The difference between market risk and forced selling risk How great operators structure deals conservatively The 3 questions every passive investor should ask before investing Why reserves and runway matter more than flashy returns FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Hidden Variable Behind Every Failed Deal 02:26 What 145 Years Of Real Estate Data Reveals 05:23 Why Commercial Real Estate Is Under Pressure 07:05 Debt, Market Risk & The Importance Of Time 10:29 How Great Operators Structure Deals Differently 11:54 The 3 Questions Every Passive Investor Must Ask 13:53 Why Time Determines Wealth In Real Estate KEYWORDS real estate investing, passive real estate investing, real estate syndication, commercial real estate, multifamily investing, real estate market cycles, floating rate debt, real estate risk management, investment structure, passive income investing, real estate leverage, investment underwriting, private real estate deals, accredited investor education, wealth preservation, conservative investing, real estate debt strategy, long term investing, market volatility, private alternative investments, operator risk, real estate cash flow 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 another investor looking to better understand risk, structure, and long-term wealth creation in real estate. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

June 30, 2026Episode 14232 min

The Golden Cage of Entrepreneurship with Morgan Keim

What if the life you built for success quietly became a trap? In this episode of Own The Exit, Caleb and Aaron sit down with alternative investment strategist Morgan Keim to unpack the difference between income and true ownership. Morgan shares his journey from raising hundreds of millions in venture capital-backed food tech to building passive income and investor freedom through multifamily real estate and alternative assets. The conversation dives into burnout, dependency, passive income, conservative underwriting, workforce housing, and the emerging world of niche alternative investments — from tequila barrels to film bridge lending. More importantly, it explores the deeper question many entrepreneurs eventually face: “What kind of life am I actually building?” TAKEAWAYS Why high income does not automatically equal freedom The hidden dependency problem many entrepreneurs face How passive income changes the way founders think and operate Why workforce housing became Morgan’s investment focus The importance of stable, supply-constrained markets How niche alternative investments create differentiated opportunities Why critical thinking matters more than hype in investing How ultra-wealthy investors use alternative assets differently RESOURCES MENTIONED Ocean Ridge Capital FOLLOWS Oak IQ Investments Own The Exit Aaron Investing Caleb Investing Morgan Keim CHAPTERS 00:00 The Wake-Up Call Behind Venture Success 02:33 From Income To Ownership 05:06 The Golden Cage Entrepreneurs Build 08:00 What Passive Income Actually Changes 12:28 Why Cleveland Outperformed Sexy Markets 16:43 Finding Investment Edges In Overlooked Niches 21:32 The Alternative Asset Opportunities Most Investors Never See 27:02 Building Access To Off-The-Wall Investments 31:40 Morgan’s Mission With Ocean Ridge Capital KEYWORDS passive income, entrepreneur burnout, alternative investments, multifamily investing, workforce housing, financial freedom, venture capital, passive cash flow, accredited investor strategies, private investing, wealth building, real estate investing, investment diversification, conservative underwriting, private alternatives, founder mindset, cash flow investing, passive wealth, entrepreneurial investing, supply constrained markets, financial independence, alternative asset 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!

June 23, 2026Episode 14116 min

The Oil and Gas Strategy High-Income Earners Are Using Instead of Stocks

If you’re a high-income earner still trying to solve your tax problem with stocks and index funds, you may be using the wrong tool entirely. In this episode of Own The Exit, Caleb and Aaron break down why oil and gas investing has become one of the most powerful tax strategies used by high-income entrepreneurs, business owners, surgeons, attorneys, and executives. They explain how intangible drilling costs (IDCs) work, why private oil and gas funds can dramatically outperform public energy ETFs from a tax-efficiency standpoint, and the exact framework they use to reduce risk while maximizing cash flow and deductions. TAKEAWAYS Why stocks and brokerage accounts don’t solve active income tax problems How oil and gas tax deductions have existed since 1954 What intangible drilling costs (IDCs) are and how they work How accredited investors can offset W-2 income through oil and gas investing The difference between public energy ETFs and private oil funds Why diversification matters even within oil and gas investing The framework Caleb uses to evaluate oil and gas opportunities How private energy investments can create strong cash flow alongside tax advantages RESOURCES MENTIONED IRS Publication on Intangible Drilling Costs FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Oil & Gas Is A Tax Strategy 02:21 How The Tax Math Actually Works 04:21 The Framework Caleb Uses To Reduce Risk 06:48 The Importance Of GP vs LP Structures 08:33 Aaron’s Perspective As A Real Estate Investor 12:28 Why Public Energy ETFs Miss The Biggest Benefits 13:36 The Oil & Gas Tax Calculator Explained KEYWORDS oil and gas investing, tax strategies for high income earners, passive income investing, intangible drilling costs, IDC tax deductions, accredited investor opportunities, alternative investments, private oil funds, oil and gas tax benefits, W-2 tax reduction, private investing strategies, energy investing, tax efficient investing, cash flow investments, private equity alternatives, wealth preservation, entrepreneur investing, investment diversification, high net worth investing, tax write offs, passive cash flow, private alternative investments 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 another entrepreneur or high-income earner looking to reduce taxes and build long-term wealth. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!

June 16, 2026Episode 1409 min

Concerned About The Economy? Here’s What The Media Didn’t Share!

Mainstream headlines are designed to grab attention, not necessarily tell the whole story. In this episode, we break down what the latest jobs report really says and why smart investors should care more about trends than fear-driven narratives. Despite constant warnings about recession, inflation, AI, tariffs, and consumer confidence, the labor market continues to show strength. We unpack the revisions hidden beneath the headlines and explain why strong employment remains the foundation behind real estate and alternative investments. TAKEAWAYS The initial jobs report is only a first draft—revisions matter. The economy averaged 188,000 jobs per month over the last three months. Leading indicators should be monitored but kept in perspective. Strong employment supports housing, retail, healthcare, storage, and industrial assets. Smart investors focus on long-term trends instead of media-driven fear. Good underwriting matters regardless of economic conditions. Negative headlines attract attention, but facts create clarity. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Headlines Mislead Investors 00:38 Breaking Down The May Jobs Report 02:16 The Real Story Behind 188,000 Jobs Per Month 03:33 The Media Finds Fear In Good News 03:54 Understanding The Employment Trends Index 06:24 The First Domino In The Economy 06:48 Why Strong Data Doesn't Replace Good Underwriting KEYWORDS jobs report, labor market, employment trends, economic outlook, recession fears, real estate investing, passive income, alternative investments, market trends, inflation concerns, investor mindset, wealth building, economic indicators, job growth, financial literacy, commercial real estate, underwriting, media bias, investment strategy, 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 stable future. Listen to all episodes on ⁠Spotify⁠ , ⁠Apple Podcasts⁠ , or any preferred podcast platform!