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. 1D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. MAR 31

    Which Real Estate Role Should You Be In?

    You’re not too busy for real estate. You’re just stuck in the wrong role. In this episode, Caleb breaks down the mindset shift that every high-performing entrepreneur needs to unlock wealth through real estate—without adding another inbox to your life. Learn why “passive” income isn’t really passive, how to find your best-fit investing role, and the scalable structures that let you buy your time back while still owning the asset. This is for business owners who want the cash flow and tax benefits—without becoming a landlord. TAKEAWAYS Why time isn't the real barrier to real estate investingThe key difference between operators and capital partnersHow role-market fit determines your ideal real estate seatThe burden of mental load—even with outsourced laborWhat syndications and turnkey deals actually offer busy entrepreneurs FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 – The problem with doing it all 01:08 – Time isn't the issue—your role is 03:07 – The tax no one talks about 04:15 – The real divide: operator vs capital 05:18 – How to determine your best-fit investing role 06:14 – What capital partners actually do 07:39 – Syndications explained for entrepreneurs 09:04 – Turnkey real estate: pros and pitfalls 10:29 – Why your time scarcity creates leverage 11:03 – The only seat that scales KEYWORDS passive income, real estate investing, syndication deals, turnkey properties, capital partner, role market fit, operator vs owner, time freedom, business owner investing, real estate portfolio, entrepreneur wealth, scalable investing, cash flow, tax benefits, mental load, high net worth investing, real estate strategy, financial independence, ownership mindset, real estate freedom, exit strategy, busy professionals 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!

    12 min

  7. MAR 24

    Boost the Valuation of Your Business With Insights From Erik Wiklendt

    How much is your business actually worth? Eric Wiklendt has helped over 100 business owners sell, scale, and structure exits that don’t just look good on paper—but actually close. In this episode, Eric breaks down the biggest misconceptions owners have about valuations, how buyers really think, and why most sellers screw up the story behind their numbers. This is required listening for any founder who thinks “I’ll just sell when I’m ready.” Eric walks through real-world deals, unpacks the math behind multiples, and reveals what every buyer looks for—and what makes them walk away. TAKEAWAYS Why the multiple you want might not matterThe difference between price and value in a buyer’s eyesHow to prep your financials for serious exit conversationsReal examples of valuation mistakes owners makeThe exit story every buyer wants to hear RESOURCES MENTIONED Connect with Eric Wiklendt on LinkedIn FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 02:11 – Eric’s Backstory: Coaching 100+ Exits 05:34 – Why Multiples Are Misunderstood 08:19 – “Five Times What?” 11:27 – What Buyers Are *Really* Buying 14:02 – When EBITDA Isn’t the Whole Story 18:45 – Real Deal Breakdown: Why It Failed 21:10 – Numbers vs. Narrative in an Exit 24:39 – The One Question to Ask Every Seller KEYWORDS business valuation, how to value your business, sell your company, multiples, EBITDA, business exit, private equity, business acquisition, M&A strategy, how buyers think, business storytelling, financial due diligence, exit planning, business broker tips, company valuation, business for sale prep, founder strategy, sell-side advisor, selling a company, what buyers want 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!

    37 min

  8. MAR 17

    Private Equity: Why It’s Confusing and How to Finally Understand It

    If you’ve ever heard someone say, “I invest in private equity,” and thought… okay, but what does that actually mean? You’re not alone. Private equity is one of the broadest terms in investing — so broad that even successful entrepreneurs feel intimidated asking questions. In this episode, we demystify private equity in simple terms and give you a practical on-ramp. You’ll learn why entrepreneurs have an unfair advantage in private markets, why real estate is the simplest gateway into private equity mechanics, and how the real leverage comes from becoming the access point — not just the investor. TAKEAWAYS Private equity is a category, not a single investment type.Entrepreneurs have a built-in advantage because they understand revenue, expenses, and people.Private markets are driven by fundamentals more than public perception.Multifamily real estate is one of the simplest ways to understand private equity mechanics.Increasing NOI increases property value — even without market tailwinds.Single asset SPVs allow entrepreneurs to pool capital legally and strategically.The ultimate leverage play is becoming the access point to deals. RESOURCES MENTIONED Multiplier University – 7 Day Free Trial FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 – Why Private Equity Feels Intimidating 02:35 – Private Equity Is a Category, Not a Thing 05:04 – The 3 Core Business Fundamentals 08:45 – Why Real Estate Is the Simplest On-Ramp 10:48 – How NOI Drives Value 13:58 – The Power Move: Become the Access Point 15:55 – Rod’s $2.4M Case Study 19:12 – Why I created Multiplier University 21:05 - The 3 Final Takeaways KEYWORDS private equity explained, how private equity works, single asset SPV, special purpose vehicle investing, private markets investing, entrepreneur investing strategy, multifamily real estate investing, net operating income explained, cap rate formula, passive income for business owners, accredited investor strategy, commercial real estate private equity, investment fund structure, pooling capital legally, private equity for entrepreneurs, real estate value add strategy, building wealth outside your business, alternative investments, capital raising strategy, investment vehicle structure 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!

    22 min
See All (135)

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
    135
  • Rating
    Explicit
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit