Own The Exit

Caleb Edwards and Aaron Leatherdale

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!

  1. 4d ago

    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!

  2. Sep 1

    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 foundVacant or “problem” properties can hold the most upsideRepurposing an asset can unlock entirely new valueMultiple income streams dramatically increase asset performanceAmenities 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!

  3. Aug 25

    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 returnThere are only two real sources of yield: macro market and value driversRelying solely on market conditions is a dangerous long-term strategyThe best deals combine favorable market timing with strong value creationNegative cash flow deals can outperform when value drivers are strong“Safe” cash-flowing deals can still lose money due to poor basis and structureUnderstanding the value creation spectrum gives you control over outcomesBuying 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!

  4. Aug 18

    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 trappedThe critical difference between a “pile” and a “pipe”How traditional investing creates slow self-liquidationThe simple “flip” that changes your entire financial strategyHow to calculate your real monthly freedom numberHow 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!

  5. Aug 11

    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!

  6. Aug 4

    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.

  7. Jul 28

    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.

  8. Jul 21

    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 capitalWhy liquidity events create both opportunity and riskHow business owners should think about replacing income after an exitThe importance of tax planning before a sale closesWhy investing in familiar asset classes reduces riskHow passive real estate investing can replace active management headachesReal-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!

4.9
out of 5
87 Ratings

About

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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