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. 2D AGO

    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

  2. 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

  3. 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

  4. 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

  5. MAR 10

    Boomers Are Ready to Sell. Will You Buy In?

    We're standing at the edge of the greatest wealth transfer in U.S. history — $15 trillion in private business assets are about to change hands as Baby Boomers retire. In this episode, Caleb and Aaron break down what that means for investors, entrepreneurs, and anyone looking to stake their claim in the future economy. From multifamily real estate and oil & gas to hard money lending and boring service businesses, this episode lays out a thesis-driven playbook for how to capitalize on the massive shift already in motion. If you're not positioning yourself now, you're going to miss one of the biggest opportunities of our lifetime. TAKEAWAYS $15 trillion in private business assets are set to change hands as Boomers retireYou need a clear investing thesis and strategy to capitalize on the shiftMultifamily is stable, predictable, and resilient for long-term investorsPrivate debt offers double-digit returns and asset-backed securityOil and gas assets are aging and primed for reinvestment“Boring” service businesses can be rolled up for serious equity exitsTech and AI are replacing people — own the tools, not just the labor RESOURCES MENTIONED Oak IQ Investments Buy Then Build by Walker Deibel FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 01:02 – The Baby Boomer Asset Dump 03:24 – Multifamily as a Business 04:49 – The Boring Biz Buy-Up 06:28 – Oak IQ’s Three-Pronged Thesis 07:34 – Oil & Gas Wealth Transfer 08:44 – Private Debt = Passive Power 10:56 – The Bridge Loan Collapse 13:02 – How to Define Your Wealth Thesis 15:45 – Rolling Up Service Businesses 17:23 – Robots Are Taking Over Jobs 20:41 – Action Steps to Own the Exit KEYWORDS baby boomer wealth transfer, boring business rollup, private equity strategy, passive investing, multifamily investment, hard money loans, oil and gas investing, bridge loans real estate, asset-backed lending, business buying, private debt funds, real estate cash flow, $15 trillion wealth shift, retirement asset sales, service business acquisitions, real estate thesis, investing strategy, financial independence, wealth building, buy and build, alternative investments, Oak IQ strategy, rollup exit, AI-proof businesses 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!

    24 min

  6. MAR 3

    7 Rules to Streamline Your Marketing

    Most founders are their best salesperson and their only marketer. But if sales stall when you take a break—you don’t have a marketing engine. You have a grind cycle. In this power-packed solo episode, Caleb reveals the 7 non-negotiables for building a marketing system that works without you. These aren’t hacks or theory—this is the rhythm to run if you want pipeline, profit, and peace. TAKEAWAYS The 7 rules that make your marketing scale without your constant involvementHow to create an offer that attracts, qualifies, and closes buyersWhy a 45-minute weekly review beats a pretty dashboardThe simple weekly rhythm that builds momentum and protects marginWhy creative output—not just ad spend—drives cost-per-lead down RESOURCES MENTIONED Business Made Simple by Donald Miller Scribe AI FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Do You Have a System or Just Hustle? 01:08 - Marketing as the Engine of Your Business 02:07 - Rule 1: Customer & Pain Map 03:41 - Rule 2: Offer Before Product 05:40 - Rule 3: Message-Channel Fit 07:22 - Rule 4: What to Measure Weekly 08:30 - Rule 5: Build a Creative Engine 10:12 - Rule 6: Capture and Follow-Up Speed 11:37 - Rule 7: Budget and Roles That Scale 13:36 - The Weekly Rhythm to Scale Without You KEYWORDS scalable marketing, lead generation systems, owner-independent marketing, creative engine, business made simple, conversion optimization, marketing automation, sales systems, pipeline growth, digital marketing strategy, customer acquisition cost, value-based offer, follow-up strategy, speed to lead, small business growth, entrepreneur playbook, delegation, marketing rhythm, building brand authority, business exits 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

  7. FEB 24

    Proven 4 Step Framework to Boost Sales Momentum With Marc Daniels

    Marc Daniels built and sold one of the first computer mail-order businesses in the U.S., helped scale a company to a $941M exit, and has coached hundreds of entrepreneurs to build real, profitable companies. But he says most business owners are focused on the wrong things. In this episode, Marc drops a proven framework to turn chaos into clarity—four quarterly projects that eliminate waste, ride trends, and drive exponential growth. This isn’t theory. From losing everything in a head-on collision to scaling SaaS and manufacturing companies globally, Marc’s execution-first mindset will challenge how you structure your weeks, quarters, and even your exit strategy. TAKEAWAYS Why yearly planning fails—and what to do insteadThe 4-part “SWOT-dle” framework that builds actual momentumHow to spot business trends early and ride them to revenueWhy your biggest obstacle is usually not what you thinkPractical execution hacks for owners with zero bandwidth RESOURCES MENTIONED Buy Back Your Time - Dan Martell Marc Daniels Website & Readiness Assessment FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ Marc Daniels CHAPTERS 00:00 The 4 Things That Move the Needle 01:06 Marc Daniels’ Story: From Car Crash to Coach 07:05 Launching a Business with a $250 Ad 13:12 The Power of Trend-Driven Strategy 16:33 How to Spot Trends Early 21:14 Why Your Quarterly Projects Fail 26:14 Why Cash Flow Plans Always Fall Short 29:28 Forecast vs. Strategy 34:03 The Real First Step: Customer Acquisition 37:41 How to Build Recurring Revenue in Any Industry 41:05 What Marc Wishes He Knew at 19 44:02 Take Marc’s Readiness Assessment KEYWORDS business execution, strategic planning, business trends, recurring revenue, buy back your time, quarterly strategy, business coaching, entrepreneur mindset, scaling businesses, business operations, exit planning, passive income, SaaS strategy, startup growth, business forecasting, leadership habits, financial freedom, legacy building, revenue growth, time management, team delegation 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!

    46 min

  8. FEB 17

    What Buyers See That You Don't

    80% of businesses that go to market will NEVER sell. In this duo episode, Caleb and Aaron get brutally honest about what makes your business unsellable—even if it’s profitable. They break down the silent killer of most exits: key man risk. If your company depends on you, you don’t own a business—you own a job. And jobs don’t sell for 8 figures. TAKEAWAYS Why private equity passes on profitable businessesThe hidden trap of “owner dependency” and how it discounts your valuationWhy your success might be masking a fragile companyHow systems, leadership, and ego collide in your exit strategyThe first step to making your business sellable this week FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Why 80% of Businesses Don’t Sell 01:25 - Owner Dependency Is Killing Your Exit 05:57 - Building a Job vs. Building a Business 08:28 - Fragile Companies Hide Behind Great Founders 12:15 - What Buyers REALLY Look For 17:46 - Leadership Can’t Be Systemized (But It Can Be Taught) 22:06 - Start Here: Document Everything 25:47 - Hiring Before It Hurts 29:03 - Buffett’s “Wonderfully Simple” Test 32:00 - The Boring Business Exit Blueprint KEYWORDS business exits, private equity, selling a business, business valuation, owner dependency, key man risk, systems and processes, leadership development, scalable business model, SOPs, team building, entrepreneur mindset, ego in business, business strategy, operational risk, business transferability, business growth, exit planning, business readiness, recurring revenue 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!

    33 min
See All (131)

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
    131
  • Rating
    Clean
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit