Own The Exit

Caleb Edwards and Aaron Leatherdale
  • 4.9 (87)
  • Entrepreneurship
  • Updated Weekly

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. 5d ago

    Your Biggest Investment Isn’t in the Market. It’s In Your Tax Return with Chris Miller

    What if the biggest leak in your wealth isn’t your investments—but your taxes? In this episode, we sit down with a tax strategist who’s spent decades helping high earners and business owners stop overpaying the IRS. The reality? Most entrepreneurs are so focused on growing revenue that they completely ignore the one line item quietly draining millions over a lifetime—taxes. This conversation breaks down how proactive tax strategy can legally reduce your burden by 25–30%, why most CPAs aren’t built for this level of planning, and how to start thinking about your tax bill like your biggest opportunity—not your biggest obligation. TAKEAWAYS Taxes are the single largest expense for high-income earnersMost business owners focus on revenue instead of taxable incomeTraditional CPAs are reactive—not proactiveStrategic tax planning can reduce your bill by 25–30%Bonus depreciation and alternative structures unlock massive savingsSimple strategies like income shifting are often overlookedReinvesting saved tax dollars accelerates wealth buildingFear of the IRS keeps people stuck overpayingTax strategy should align with your long-term exit plan RESOURCES MENTIONED One Atlanta Tax Solutions FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ Chris Miller CHAPTERS 00:00 Why Taxes Are Your Biggest Expense 03:24 The 2008 Wake-Up Call That Changed Everything 07:22 Why Business Owners Miss This Completely 10:12 Breaking Down Bonus Depreciation 15:01 Why Trusting Your CPA Is Costing You 20:24 Real Examples of Tax Savings 23:14 Simple vs. Advanced Tax Strategies 29:11 Avoidance vs. Evasion (What’s Legal) 36:50 Taxes vs. Business Valuation KEYWORDS tax strategies, tax reduction, high income earners, business owner taxes, passive income strategies, bonus depreciation, cost segregation, tax planning, wealth building strategies, financial freedom, reduce taxable income, tax saving tips, investment tax strategies, entrepreneur finances, tax optimization, capital gains strategies, income shifting, tax mitigation, business exit planning, wealth preservation 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!

    50 min

  2. May 19

    Does Your Portfolio Match Your Brain?

    What if the biggest edge in your portfolio isn’t your capital—but the way you think? In this episode of Own The Exit, Caleb challenges entrepreneurs and business owners to rethink how they invest after building wealth. Once the cash starts stacking up, too many founders abandon the exact mindset that made them successful and default to generic financial advice that was never built for operators. From Alex Hormozi’s wake-up moment to Caleb’s own journey through entrepreneurship, family adversity, and private market investing, this episode explores why entrepreneurs often thrive when they invest like owners—not spectators. If you’ve built wealth through business, this conversation will help you align your portfolio with the mind that created it. TAKEAWAYS Why entrepreneurs should invest differently than the average personHow to align your portfolio with your natural strengthsThe difference between ownership investing and spectator investingWhy private markets often make intuitive sense for operatorsThree practical questions to guide your next investment move FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Does Your Portfolio Match Your Brain? 02:16 The Hormozi Wake-Up Call 06:31 Why Entrepreneurs Should Invest Differently 08:47 Investing Like an Owner 09:55 A Personal Wake-Up Call 11:20 Why Real Estate Made Sense 14:44 Three Questions Every Entrepreneur Must Ask 17:34 Your Next Sensible Step 19:16 Build a Portfolio Like You Built Your Business KEYWORDS entrepreneur investing, business owner wealth, private equity, real estate investing, wealth strategy, portfolio diversification, ownership mindset, passive income, alternative investments, business acquisition, private markets, investment strategy, wealth building, cash flow investing, accredited investor, multifamily investing, commercial real estate, operator mindset, financial freedom, wealth stewardship, portfolio strategy 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 a business owner ready to invest like an owner. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

    20 min

  3. May 12

    The Real Estate Structure Wealthy Investors Use That Nobody Explains

    There’s a reason wealthy investors continue to compound in real estate while most people stay stuck on the sidelines—and it has nothing to do with how much money they have. It comes down to understanding a structure that almost nobody explains. In this episode, we break down the real estate syndication model—the exact vehicle institutions, family offices, and high-level investors use to access large-scale multifamily deals without becoming landlords. You’ll learn how the structure works, the roles involved, and why this model creates a completely different investing experience than traditional real estate. TAKEAWAYS The real barrier to large-scale real estate investing isn’t money—it’s access to the right structureReal estate syndications allow investors to participate in institutional-quality deals without becoming operatorsThe GP-LP model creates a clean division where professionals handle execution and investors provide capitalPassive investing in syndications is fundamentally different from owning and managing rental propertiesThe “advisor gap” is why most qualified investors never see these opportunities FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Intro: The Structure Nobody Explains 00:57 Why Scale Requires a Different Model 01:59 How Real Estate Syndications Work 03:33 GP vs LP Roles Explained 04:52 The Advisor Gap & Why You’ve Never Seen This 05:34 Why Most Investors Stay in Public Markets KEYWORDS real estate syndication, passive real estate investing, accredited investor opportunities, multifamily investing strategy, institutional real estate, private real estate deals, wealth building strategies, passive income real estate, alternative investments, real estate deal structure, general partner vs limited partner, investment diversification strategies, financial independence planning, high net worth investing, private market investing, real estate portfolio growth, cash flowing assets, long term wealth building, real estate education, investment strategy explained 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!

    7 min

  4. May 5

    Turn Financial Goals Into a Real Investment Plan

    What separates people who talk about building wealth from those who actually do it? A real plan backed by action. In this episode of Own The Exit, Aaron breaks down how financial goals only become real when they’re attached to a clear investment strategy. Too many people stay stuck in uncertainty—waiting for the perfect market, perfect timing, or perfect deal. But wealth is rarely built through hesitation. It’s built through intentional action and consistent execution. From buying his very first house with no prior experience to helping oversee nearly $300 million in real estate assets, Aaron shares how clarity comes through movement, not overthinking. If you’ve been sitting on the sidelines, this episode will help you start turning your financial vision into an actual investment plan. TAKEAWAYS Why financial goals need a defined investment roadmapHow action creates momentum and confidenceThe hidden cost of waiting for perfect timingWhy uncertainty should not stop wealth buildingHow small steps can compound into long-term success FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 00:00 From First Deal to Real Wealth 00:33 Why Goals Without Action Fail 01:24 Building Your Investment Mindset 03:41 Stop Waiting for Perfect Timing 04:32 Push Through Fear and Take Action 05:08 Start Your Investment Plan Today KEYWORDS financial goals, investment plan, real estate investing, passive income, wealth building, financial freedom, investment strategy, market timing, investor mindset, passive wealth, entrepreneurship, business owner investing, long term wealth, action plan, financial roadmap, real estate portfolio, passive investing, wealth strategy, investment confidence, wealth growth 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 ready to turn goals into real wealth. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

    5 min

  5. Apr 28

    What Makes Oil So Tax Efficient

    Why do sophisticated investors keep coming back to oil and gas—even in a world pushing clean energy? In this solo episode, Caleb breaks down the real reasons high-income earners are leveraging oil and gas investments to reduce taxes, generate fast cash flow, and hedge against inflation. From powerful IRS deductions to strategic fund structures, this episode reveals how the right investment can transform your entire financial picture—not just your returns. TAKEAWAYS How oil & gas investments can offset earned income—not just passive incomeWhy 70–80% of drilling costs can be deducted in year oneThe power of depletion allowance and tax-free cash flowHow investors generate cash flow within 1–2 quartersThe difference between PDP funds and new drilling programsWhy horizontal drilling significantly reduces riskHow to structure investments for maximum tax efficiency (GP vs LP)Why oil & gas acts as a hedge during inflationary cyclesThe importance of diversification across operators and fundsWhy separating investment strategy from personal ideology matters FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why investors choose oil & gas 01:50 Depletion allowance & tax-free income 03:52 Real return example breakdown 04:53 How to invest in oil & gas 05:13 PDP funds (existing production strategy) 06:50 Investing alongside major operators 07:50 Pro tips: diversification strategy 08:55 Investor classification (GP vs LP) 09:50 Portfolio construction & alternatives 11:30 Oil demand vs clean energy narrative 13:45 How to get started KEYWORDS oil and gas investing, tax strategies for high income earners, passive income ideas, alternative investments, accredited investor strategies, tax reduction investments, cash flow investments, inflation hedge assets, private equity investing, energy sector investing, portfolio diversification strategies, wealth building strategies, tax efficient investing, drilling investment opportunities, income producing assets, high net worth investing, financial independence strategies, passive wealth building, private market investments, long term wealth strategies 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!

    14 min

  6. Apr 21

    The 75% Rule for Building Your Business With Young Han

    What if business isn’t about genius — but mechanics? In this episode, we sit down with Young Han — a serial entrepreneur building 20 cash-flowing businesses in five years. After a midlife reset, moving his family to small-town Texas, and walking away from the Silicon Valley grind, Young reverse engineered a repeatable system for building companies. His thesis? 75% of every business is the same — and most founders fail because they underestimate the volume of execution required to win. This conversation dives deep into incubators, acquisitions, culture design, mechanical execution, capital efficiency, and why most entrepreneurs accidentally build themselves a job instead of freedom. TAKEAWAYS 75% of every business operates on the same core pillars: marketing, operations, finance, delivery, and systems.Volume of execution is drastically underestimated by most founders.You must manually master inputs before you automate outputs.Overcomplication kills more businesses than competition.Business valuation can be engineered by adjusting pricing, profit, and positioning.If you don’t move yourself out of the way, you become the growth bottleneck.Time boxing and auditing your inputs is the fastest path to time freedom. RESOURCES MENTIONED Straight from the Gut – Jack Welch FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ Young Han CHAPTERS 00:00 – The 75% Rule of Business 04:12 – Building an Incubator Flywheel 06:58 – Cash Flow Businesses as Capital Engines 10:48 – Buying Broken Businesses 15:22 – Volume Solves Most Problems 17:05 – Manual First, Automation Later 24:09 – The 3 Core Fundamentals of Investing 28:06 – Should You Even Own a Business? 32:42 – The Key Man Bottleneck 44:34 – Advice to His Younger Self 47:55 – Time Boxing for Freedom KEYWORDS entrepreneurship systems, business incubator model, small business acquisitions, buying cash flowing businesses, operational efficiency, mechanical business building, founder bottleneck, time freedom strategy, financial freedom for entrepreneurs, private equity mindset, recurring revenue businesses, scaling service businesses, business automation strategy, acquisition entrepreneurship, volume based marketing, cash flow investing, valuation engineering, culture design in business, high performance entrepreneurship, exit strategy planning 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!

    52 min

  7. Apr 14

    Private Equity Real Estate: 3 Filters to Find the Right Deal (and Skip the Landmines)

    Private equity real estate sounds simple: buy well, improve income, cut expenses, increase value. But a great deal and a terrible deal can look identical inside a polished pitch deck. In this episode, Caleb breaks down the three filters every serious investor must use before wiring capital. If you're a business owner evaluating private equity real estate opportunities, this framework will help you separate high-quality sponsors and durable deals from hype-driven landmines. TAKEAWAYS Filter the sponsor before you filter the deal.Track record, alignment, and communication reveal operator quality.Underwrite survival first — upside second.A deal that only works in a perfect world is not a deal.Downside plans matter more than optimistic projections.Understand where you sit in the capital stack.Structure and terms can protect you even when markets shift. RESOURCES MENTIONED Multiplier University – 7 Day Free Trial FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 – Why “Great Deals” Can Mislead You 02:10 – Filter #1: Sponsor Quality & Alignment 07:22 – Filter #2: Fundamentals & Survival Plan 11:56 – Filter #3: Structure & Capital Stack 15:35 – The 3 Filter Recap 16:26 – The Leverage Play for Entrepreneurs KEYWORDS private equity real estate, sponsor vetting, real estate capital stack, preferred return explained, downside risk mitigation, underwriting fundamentals, deal structure analysis, accredited investor strategy, passive real estate investing, net operating income growth, commercial real estate investing, multifamily investing strategy, operator alignment, real estate waterfall structure, investment due diligence checklist, business owner investing, private placement investing, real estate sponsor evaluation, capital preservation strategy, real estate risk management 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!

    18 min

  8. Apr 7

    Oil Market 2026: The Supply Crisis No One Is Talking About

    What happens when 20% of the world’s oil supply suddenly gets trapped behind one geopolitical choke point? In this episode of Own The Exit, we break down the oil market crisis that most headlines are still calling “fear” — but the real story is far more serious. This isn’t just a sentiment-driven spike. This is a structural supply disruption with real economic consequences. From tanker shutdowns in the Strait of Hormuz to emergency reserve depletion and the looming “oil cliff,” we unpack what’s really happening, what it means for inflation, recession risk, and where the biggest opportunities may emerge in U.S. energy markets. TAKEAWAYS Why this oil spike is driven by physical supply constraints, not fearHow tanker insurance shutdowns froze global oil movementWhy strategic reserves only buy temporary timeThe significance of mid-April as a market inflection pointHow the Permian Basin and Atlantic producers benefitWhat this means for inflation, recession risk, and wealth transfer FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Strait Shutdown Changes Everything 01:27 Why This Is Not Fear Pricing 03:13 Why Headlines Are Missing The Real Problem 04:49 The Years of Underinvestment 06:31 The Oil Cliff Explained 07:05 Crisis Creates Opportunity 09:21 Three Scenarios Ahead 11:18 Why Energy Security Still Matters KEYWORDS oil crisis, supply shock, energy markets, inflation risk, recession outlook, commodity investing, geopolitical risk, tanker disruption, strategic reserves, WTI crude, energy investing, passive wealth, macroeconomics, market volatility, supply chain risk, oil prices, global recession, Permian Basin, wealth preservation, inflation hedge 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!

    13 min
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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!

Information

  • Creator
    Caleb Edwards and Aaron Leatherdale
  • Years Active
    2023 - 2026
  • Episodes
    138
  • Rating
    Explicit
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit

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