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. 6D AGO

    If You're Still Holding On, You're Losing Money

    Would your business survive without you—or would it collapse? In this solo episode, Aaron breaks down the leadership traps that make entrepreneurs tighten their grip but silently destroy your company’s exit potential. This one’s a masterclass in ego-checking, team-building, and future-proofing your business value. If you're a founder, owner, or leader who wants freedom *and* a high-valuation exit, don’t wait until you’re burnt out to make changes. Learn how to build an exit-ready team now—so your company thrives whether you’re in the room or not. TAKEAWAYS Why ego and owner-dependence sabotage your exit valueThe importance of replacing yourself early in the company journeyHow loyalty-based hiring can hold you backWhat a truly exit-ready team looks likeThe “business appraisal” mindset you need todayWhy documenting every role, process, and system is essential RESOURCES MENTIONED Buy Back Your Time by Dan Martell FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 00:31 - Four Gaps That Kill Exit Value 02:34 - Replace Yourself Early 05:42 - Why Loyalty Isn’t Enough 07:04 - Team Buy-In vs. Leader Worship 08:30 - The Exit Readiness Test 09:55 - Defining Your Personal Exit Strategy 11:22 - Final Recap & Action Steps KEYWORDS exit planning, team building strategies, leadership gaps, business valuation, founder ego, scalable business systems, loyalty hiring risks, exit readiness, documented processes, buy back your time, owner dependence, succession planning, replacing yourself, scalable team structure, delegating leadership, team mission alignment, hiring strategy, team roles clarity, entrepreneur exit strategy, passive business ownership, scaling without burnout 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

  2. 12/23/2025

    Don’t Just Make Money, Build Wealth with Alan Franks

    Most business owners are great at making money—but wealth? That's a whole different game. In this powerful conversation, Caleb sits down with Alan Franks, a financial advisor who actually *gets it*. No cookie-cutter plans. No commission traps. Just real strategies that help entrepreneurs turn active income into lasting legacy. They unpack what it really means to reach "critical mass" in your wealth, how to leverage tax law like the wealthy do, and why so many financial advisors are failing their clients. If you're a high performer looking to reduce taxes, create true passive income, and build a legacy that lasts beyond your lifetime, this episode is for you. TAKEAWAYS The difference between building income and building wealthWhy most financial advisors aren’t incentivized to help entrepreneurs winThree types of taxes to plan for: income, capital gains, and estateThe power of defined benefit plans for business ownersWhy securities-backed lines of credit might be your secret weaponHow to think in terms of opportunity cost instead of “either-or” RESOURCES MENTIONED Empowered Money by Alan Franks Who Not How by Dan Sullivan & Benjamin Hardy The Psychology of Money by Morgan Housel FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ Alan Franks CHAPTERS 00:00 Why Income ≠ Wealth 01:08 Alan’s Entrepreneurial Backstory 04:15 Redefining Legacy 06:14 Multi-generational Mindset 09:21 Critical Mass & Financial Planning 12:17 The Three Types of Taxes 16:42 Defined Benefit Plans & Tax Deductions 19:07 Estate Planning for Business Owners 24:43 Opportunity Cost vs Either-Or Thinking 30:00 Real Estate, Crypto, Stocks—Do All Three? 33:52 Leveraging Lines of Credit Strategically 40:48 The Risk Side of Leverage 45:18 Syndications & Market Realities 47:02 Exit Round: Alan's Book Recs & Passive Income Strategy KEYWORDS financial planning for business owners, tax mitigation strategies, real estate syndications, legacy planning, securities backed lines of credit, opportunity cost, passive income strategy, defined benefit plan, income vs wealth, building generational wealth, multi-generational planning, estate tax reduction, capital gains planning, alternative investments, financial freedom strategy, high net worth planning, critical mass wealth, good debt vs bad debt, entrepreneur finances, holistic financial plan, investing diversification, cash flow strategies, line of credit 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!

    58 min

  3. 12/16/2025

    AI Won’t Replace You But This Will

    Artificial Intelligence is no longer a future concept—it’s here, and it’s reshaping how real estate, business, and asset management operate. In this solo episode, Aaron Leatherdale breaks down how he’s using AI inside a multi-entity real estate investment firm, what “super agents” are, and why embracing change is the only way forward. He shares real-life examples of GPT Enterprise integrations, the risk of job loss for non-adopters, and why being “too excited” about AI is just as dangerous as being afraid of it. Whether you're overwhelmed by the AI wave or eager to implement, this is your playbook for intelligent action in a changing world. TAKEAWAYS AI is a tool—how you train it determines the value“Super Agents” are AI systems integrated with all business dataAI won’t replace everyone, but it will replace someoneThe real threat is not using AI at allYou must assign a team member to manage AI implementationAdmin and white-collar jobs are at highest riskSlower adopters will struggle to surviveAI lets you scale by reducing inefficiencies FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 03:01 - How API automation works with ChatGPT 05:23 - AI is like email in the '90s 07:09 - White-collar jobs in danger 09:01 - Who stays and who goes in the AI era 10:46 - AI is neutral—it’s about who uses it KEYWORDS artificial intelligence, real estate investing, AI automation, GPT enterprise, white collar jobs, business efficiency, private equity, passive investing, financial independence, job security, ChatGPT, real estate tech, future of work, entrepreneurial strategy, asset management, business systems, automation tools, AI implementation, productivity, wealth building, AI vs humans, scalable business models, GPT projects, real estate automation 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

  4. 12/09/2025

    7 Silent Killers of Business Growth

    Are you stuck grinding in your business but still feeling broke, burned out, or boxed in? In this solo episode, Caleb reveals the seven silent killers of business growth—and what to do about them before the year ends. This is not theory. These are the exact patterns we’ve seen destroy good businesses with great people—until they fixed these core mistakes. If you want next year to look different than this year, start here. TAKEAWAYS Why chasing revenue without profit is killing your growthThe #1 mindset shift to escape the bottleneck trapHow to audit your tasks using the Buy Back principleWhy systems must come before hiringThe danger of survival-mode thinkingHow to extract gold through Dream Client InterviewsWhat your exit scorecard really is—and how to use it RESOURCES MENTIONED Buy Back Your Time by Dan Martell FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 01:41 - Mistake 1: Chasing Revenue Over Profit 02:30 - Mistake 2: Hiring Without Systems 02:58 - Mistake 3: Ignoring Market Shifts 03:41 - Mistake 4: Doing Everything Yourself 04:49 - Mistake 5: Thinking Short-Term 05:32 - Mistake 6: Assuming You Know Your Customer 06:36 - Mistake 7: No End Game or Exit Plan 07:46 - How to Use This Playbook KEYWORDS entrepreneur mistakes, business growth, profit margins, buy back your time, hiring systems, scaling a business, passive income, business strategy, exit strategy, business audit, task delegation, dream client interview, entrepreneurship traps, business bottleneck, long-term vision, operational systems, founder burnout, business leadership, business owner freedom, scaling smart, reverse engineering goals, small business scaling, time freedom, automate and delegate 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!

    9 min

  5. 12/02/2025

    The Truth About Financial Advisors with Richard McWhorter

    What does it take to earn the trust of billionaires? In this episode, Beverly Hills-based wealth advisor Richard McWhorter reveals how he serves ultra-high-net-worth clients across sports, entertainment, and business. From navigating conflicts of interest in big firms to creating truly tailored financial strategies, Richard shares what sets apart the advisors who only “sell” from those who truly advise. We dive into the psychology of wealth, how the ultra-rich think differently about risk, the economic trends shaping future investments, and why critical thinking—not hype—is the most valuable skill in money management. TAKEAWAYS The key difference between selling vs. advising clientsHow ultra-wealthy clients approach risk and wealth preservationWhy big firms often limit truly creative financial strategiesThe role of trust and unbiased opinions in wealth managementHow to critically think about economic trends and investment data RESOURCES MENTIONED SRM Private Wealth FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ Richard McWhorter CHAPTERS 00:00 Selling vs. advising: the big difference 02:28 Richard’s journey into wealth management 05:12 Breaking free from big-firm conflicts of interest 08:23 How ultra-wealthy clients build and maintain trust 11:15 The role of creative strategies beyond traditional products 15:10 Understanding client psychology and behavior 19:12 Economic realities: tariffs, interest rates, and inflation 25:36 Why energy and infrastructure matter in future investments 30:45 Critical thinking vs. chasing hype 36:40 The Exit Round: Richard’s personal lessons 40:20 Where to find Richard McWhorter online KEYWORDS how billionaires manage wealth, ultra high net worth investing, private wealth management strategies, financial advisor vs fiduciary, creative wealth preservation tactics, economic trends 2025, tariffs and inflation impact, interest rate strategy for investors, energy and infrastructure investments, risk management for the ultra-rich, alternative investments beyond stocks, wealth psychology and decision making, unbiased financial advising, long-term wealth planning strategies, building trust with high-net-worth clients WANT TO LEARN MORE? Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover 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!

    41 min

  6. 11/25/2025

    3 GPT Prompts That Boost Valuation

    If I told you the fastest way to increase your company's valuation wasn’t about selling more, raising prices, or landing new clients—but about keeping more of the money you already make—would you believe me? In this episode, Caleb reveals a simple 3-step system powered by ChatGPT that can cut up to 25% of your monthly expenses without layoffs. These are the exact prompts Caleb has used in his own companies and seen other founders deploy with game-changing results. You’ll walk away with practical AI tools that can instantly boost profitability, free up cashflow, and increase your exit multiple—all without sacrificing growth. TAKEAWAYS Why profit is the real driver of valuation (not revenue)The 3-step GPT expense-cutting systemHow to uncover redundant or outdated contracts instantlyThe exact CFO-level GPT prompt that cuts 25% of expensesReal-world examples of founders saving $19K–$42K instantlyHow to reinvest savings into growth levers that multiply your exit RESOURCES MENTIONED Try ChatGPT here → ChatGPT FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Why Profit Beats Revenue 01:25 - $19K Savings in One Hour 02:19 - Step 1: Categorize Expenses 03:41 - Step 2: The GPT CFO Audit 05:31 - Step 3: Implement & Negotiate 06:48 - Real-World Case Studies 07:22 - Caleb’s Challenge to You KEYWORDS AI in business, GPT prompts, cut costs with AI, business profitability, enterprise valuation, Own The Exit, Caleb OAKIQ, expense reduction strategies, ChatGPT for entrepreneurs 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!

    8 min

  7. 11/18/2025

    Smart Oil and Gas Investment Tips with Courtney Moeller

    She grew up riding pump jacks in West Texas and now she’s helping high-income professionals slash their tax bills and grow serious cash flow through strategic oil and gas investments. In this episode, Courtney Moeller joins us to break down the truth behind working interest, the real risks (and myths), and why this overlooked asset class might be the greatest wealth hack nobody's talking about. This is not your dad’s oil investing. Courtney reveals how to invest alongside billion-dollar operators, minimize dry-well risk, and structure deals that not only cash flow fast but also give investors massive year-one tax benefits. Whether you’re a W-2 earner, business owner, or pro looking for tax efficiency—this one’s for you. TAKEAWAYS Oil and gas offers unique tax advantages unmatched by most other assetsWhy horizontal wells drastically reduce dry-hole riskThe myth of EVs replacing oil and what most investors get wrongHow to vet oil and gas operators like a proReturns you should expect from smart oil dealsThe timeline for return of capital and cash flow accelerationWhy demand from AI and data centers is fueling energy investment urgency RESOURCES MENTIONED Oil and Gas Report Courtney’s Website FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Courtney’s wild oilfield background 04:22 - Why now is the window to invest 06:48 - EV myths and the truth about energy demand 09:04 - Vetting oil and gas operators 13:10 - Why oil beats real estate on taxes 17:00 - What dry wells really cost you 21:14 - How Courtney structures her deals 23:31 - Return timelines and cash flow expectations 28:03 - 85% K1 loss? Yep. 30:45 - Freedom, family, and oil wealth KEYWORDS oil and gas investing, passive income, tax advantages, W2 tax strategy, working interest, cash flow, horizontal drilling, high income earners, accredited investors, financial independence, energy investing, inflation hedge, generational wealth, investment diversification, tax deferral, royalty income, depletion allowance, Permian Basin, offsetting earned income, energy sector, real asset investing, alternative investments, AI energy demand, Bitcoin mining and oil 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. 11/11/2025

    The Real Asset Gold Rush Is On

    In this solo episode of Own The Exit, Caleb sounds the alarm on the biggest economic shift of our lifetime: the AI revolution. If you're still building your wealth using the same assumptions from 10—or even 5—years ago, you're already behind. AI is not coming; it's here, and it's rewriting every rule of business, investing, and financial security. From job replacement at massive scale to algorithmic trading destroying diversification, Caleb breaks down why traditional investment models are failing and what smart entrepreneurs must do to stay ahead. This is your wake-up call: start owning assets AI can’t replicate, or risk losing it all. TAKEAWAYS AI will eliminate millions of jobs—including white-collar roles—within yearsPublic markets are more correlated and fragile than everThe old 60/40 portfolio model is officially deadTrue diversification requires owning hard, productive assetsSmart investors are using AI inside their business—but storing wealth outside of AI’s reach RESOURCES MENTIONED OakIQ.com FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ Caleb Investing⁠ CHAPTERS 02:00 AI Disrupting Jobs: Scary Stats You Need to Know 05:30 Market Fragility & the End of Diversification 08:30 What It Means for Entrepreneurs 10:00 Real Assets That AI Can’t Replace 12:00 The Creepy (But Real) Future of AI in Homes 13:30 The Wealth Strategy That Still Wins KEYWORDS AI investing, job automation, financial fortress, passive income, 60/40 portfolio, real estate investing, own the exit, OakIQ, AI and wealth, smart investing strategies, diversified assets, AI risk, asset protection 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!

    15 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 - 2025
  • Episodes
    117
  • Rating
    Clean
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit

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