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

    Is a Recession Coming?

    Ray Dalio says we’re heading for a debt spiral. Apollo Global predicts the biggest boom in U.S. history. Who’s right? It doesn’t matter—if you’re positioned correctly. In this dynamic duo episode, Caleb and Aaron break down how everyday investors can take control of their financial future, no matter what headlines scream. Learn why diversification is broken, how ultra-wealthy investors are allocating capital (hint: it's not where your financial advisor told you), and the PRIME framework for making strategic moves through chaos. This one is for anyone who’s serious about escaping Wall Street dogma and actually owning their exit. TAKEAWAYS Recession doesn’t destroy wealth—it redistributes itWall Street "diversification" no longer protects youThe ultra-wealthy are holding cash for opportunity—not fearHard assets and private equity outperform public markets long-termTrusting your portfolio to a salaried advisor is riskyUse the P.R.I.M.E. framework: Pause, Review, Identify, Move, Evaluate FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 – Ray Dalio vs. Apollo Global: Who’s Right? 01:45 – Why You Can’t Rely on Predictions 03:58 – Recessions Don’t Destroy Wealth — They Move It 06:12 – Why “Diversification” No Longer Works 09:40 – How the Ultra-Wealthy Are Actually Allocating Capital 13:32 – What Tiger 21 Investors Are Doing with Their Portfolios 17:50 – Why Your Financial Advisor May Be Misleading You 20:28 – The PRIME Framework: Pause. Review. Identify. Move. Evaluate. 26:43 – Final Thoughts: Own Your Exit, Own Your Wealth KEYWORDS Ray Dalio, Apollo Global, Tiger 21, investing in a recession, private equity, alternative investments, PRIME framework, hard assets, portfolio strategy, financial freedom, OakIQ, Own The Exit 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!

    34 min

  2. OCT 14

    How to Outwork 95% of People

    In a world obsessed with shortcuts and hacks, the real edge isn’t just working smarter—it’s working smarter AND harder. In this solo episode, Caleb breaks down why skill stacking, deep focus, and relentless consistency are the ultimate cheat codes to success in business, investing, and life. From Elon Musk to Michael Jordan, from Cal Newport to Alex Hormozi, Caleb reveals what separates the people who quietly win long term from those who burn out chasing the next shiny thing. By the end of this episode, you’ll know how to outwork 95% of the competition without burning yourself out. TAKEAWAYS Why the “work smarter, not harder” mantra is incompleteHow deep focus multiplies your productivityThe power of stacking complementary skills for leverageWhy consistency beats talent in the long gameHow to create compounding results without burnout FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The real cheat code: smarter + harder work 00:29 Why shortcuts don’t create long-term success 01:08 Lessons from Elon Musk and Michael Jordan 02:16 What “working harder” actually means 03:07 Deep focus vs shallow busyness 04:32 Skill stacking for leverage (Alex Hormozi example) 06:17 Why complementary skills multiply results 07:41 Relentless consistency: the MrBeast effect 09:04 Outlasting the competition without burnout KEYWORDS work smarter and harder, deep work productivity, skill stacking for entrepreneurs, how to stay consistent, Alex Hormozi business lessons, Cal Newport deep work, MrBeast success secrets, how to outwork competition, consistency beats talent, productivity without burnout, how to focus deeply, skill leverage in business, discipline vs motivation, building compounding results, business growth mindset 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!

    10 min

  3. OCT 7

    Define Rich for Yourself

    In this special solo episode of Own The Exit, Caleb honors the late Charlie Kirk by unpacking what it truly means to be wealthy. It’s not just about building businesses or chasing dollar signs—it's about becoming the kind of person who can handle prosperity without losing their soul in the process. From character-first wealth building to defining what “rich” really means for you, this is an emotionally honest and highly practical breakdown of how legacy, values, and financial literacy intersect to build not just success, but significance. TAKEAWAYS Wealth without character leads to internal povertyYou can be rich in money but bankrupt in your soulLegacy matters more than lifestyleDefine your personal version of “rich”Financial literacy is a non-negotiable superpowerDon’t glorify hustle—build systems that give freedomCompounding interest works both ways—use it wiselySacrifice distractions, not your family or integrityEnough is better than endlessly chasing more FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Why wealth without character is hollow 01:22 - Honoring Charlie Kirk beyond politics 02:16 - The power of becoming before earning 03:09 - Legacy vs. success sequence 04:32 - Charlie’s formula for material wealth 05:08 - Most people don’t want the grind 06:10 - Sacrificing distractions, not values 07:26 - The real prize: time & freedom 08:13 - Defining “rich” with critical mass 09:04 - Why financial literacy changes lives 10:54 - Business smarts start with money smarts 11:35 - Hustle isn’t the only path to wealth 12:45 - Solving real problems at your scale 13:19 - Summary: 6 powerful wealth lessons KEYWORDS financial freedom, character development, generational wealth, business systems, legacy building, passive income, financial literacy, compounding interest, critical mass, values-based investing, wealth without burnout, intentional living, entrepreneurship, time freedom, defining rich, success sequence, hustle culture, purpose-driven wealth, internal poverty, building legacy, charlie kirk 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!

    16 min

  4. SEP 30

    Does Money Really Buy Happiness?

    Can money really buy happiness—or does it just magnify who you already are? In this deeply thought-provoking episode, Caleb and Aaron unpack the famous Harvard happiness study that claims happiness plateaus at $85,000 a year, share real-world stories from high-net-worth individuals, and discuss why money is only a tool—not the ultimate answer. They explore why happiness is an internal choice, how money removes obstacles but doesn’t create meaning, and why your “why” matters more than any dollar amount. If you’re building with the end in mind, this conversation will challenge how you view wealth, freedom, and fulfillment. TAKEAWAYS The $85,000-a-year happiness plateau explainedWhy money magnifies who you already areHow income can remove obstacles but not create fulfillmentThe deeper “why” behind pursuing financial freedomHow to build both wealth and internal happiness FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Can money really buy happiness? 00:19 Breaking down the Harvard $85,000 happiness study 02:14 Why happiness plateaus after basic needs are met 04:32 The fleeting joy of material upgrades 06:57 Money as a magnifier of who you already are 09:43 Stories of wealthy people still unfulfilled 12:56 Happiness as a choice, not a dollar amount 15:22 The deeper “so that” behind pursuing passive income 18:45 Two conflicting studies on income and happiness 21:38 Building internal happiness alongside external wealth 24:17 Final thoughts: Money, meaning, and freedom KEYWORDS does money buy happiness, $85,000 happiness study, income vs happiness research, money and life satisfaction, wealth and fulfillment, financial freedom mindset, money as a tool not the goal, removing obstacles with money, how income affects happiness, why happiness is internal, money mindset shifts, wealth psychology for entrepreneurs, freedom vs fortune, building a meaningful business, financial freedom vs life purpose 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!

    27 min

  5. SEP 23

    3 Ways to Exit Your Business

    What does it truly mean to “own your exit”? In this solo episode, Aaron breaks down the three ways entrepreneurs can approach their business exit strategy—whether it’s selling for a huge payday, staying on to scale with new resources, or never exiting at all but gaining freedom within the business you’ve built. You’ll learn why the right exit isn’t one-size-fits-all, how to think strategically about your future, and why beginning with the end in mind is the only way to truly own your journey as an entrepreneur. TAKEAWAYS The three main types of business exits every entrepreneur should considerWhy selling your business isn’t always the ultimate goalHow staying on after a capital event can unlock new levels of growthWhy freedom within your business might be the best exit of allThe importance of thinking 2–5 years ahead to truly “own your exit” RESOURCES MENTIONED Oak IQ Investments FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ CHAPTERS 00:00 Why owning your exit starts with the end in mind 00:23 The myth of the one-size-fits-all “big exit” 01:42 Exit #1: Selling and walking away 03:05 Exit #2: Selling but staying to scale 05:03 A story of growth through staying on post-sale 07:22 Exit #3: Never exiting, but freeing yourself within the business 09:20 Choosing the right exit for your life 10:24 Think 2–5 years ahead to own your exit 11:49 Final thoughts: Make the business serve you KEYWORDS business exit strategy, selling a business, entrepreneurial freedom, business ownership, scaling a company, staying after a sale, passive ownership, exit planning, Oak IQ Investments, Own The Exit podcast 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. SEP 16

    How Value Exchange Creates Wealth with Rick Pino

    How do you build true financial freedom without trading time for money? In this powerful conversation, Rick Pino reveals how entrepreneurs can escape the grind by focusing on value exchange, serving instead of selling, and leveraging digital products to scale income beyond limits. From his early days as a worship leader to building multi-million-dollar businesses and now teaching others to monetize their expertise online, Rick shares timeless principles for creating wealth, time freedom, and impact. TAKEAWAYS Why selling is serving, not takingThe Jewish wealth principle of value exchangeHow to disconnect your time from your dollarWhy digital products are the fastest wealth path in 2025The Be → Do → Have framework for success RESOURCES MENTIONED Rick Pino Official Site FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ Rick Pino CHAPTERS 00:00 The Jewish wealth principle: value exchange 02:00 Rick Pino’s entrepreneurial journey 05:00 Balancing faith, purpose, and profit 09:15 Solving problems vs. selling products 13:20 Sales as service: shifting your mindset 17:40 Digital products: the fastest wealth path 23:08 Be → Do → Have: the success framework 30:00 Taking ownership and self-agency 36:14 Building businesses that create time freedom 40:00 Exit Round questions with Rick Pino KEYWORDS digital entrepreneurship strategies, how to build wealth without trading time, value exchange principle, selling as serving mindset, creating scalable digital products, how to monetize your expertise online, financial freedom for entrepreneurs, business mindset shifts, be do have framework for success, solving problems to create wealth, online business models 2025, scalable income strategies, disconnecting time from money, how to create passive income with digital products, faith and entrepreneurship balance 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

  7. SEP 9

    What 100 Episodes Taught Us!

    We’ve officially hit 100 episodes of Own the Exit! In this milestone conversation, Caleb and Aaron reflect on the lessons learned from two years of weekly episodes, highlight unforgettable guest moments, and—for the first time ever—answer the same Exit Round questions they’ve asked every guest. From how to build with the end in mind, to why your business shouldn’t become your prison, to the importance of stacking skills and planning your freedom, this episode is a candid and inspiring look behind the scenes of the journey so far. TAKEAWAYS How and why Own the Exit was createdThe biggest lessons learned from the incredible guests hosted on the showWhy most entrepreneurs accidentally build a cage instead of freedomThe myth of “selling your soul” to your businessThe five Exit Round questions every entrepreneur should ask themselves FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Celebrating 100 episodes of Own the Exit 01:08 Why we started this podcast 02:33 The theme of building with the end in mind 04:15 What we learned from 100 guests 06:31 The winding, non-linear entrepreneurial journey 07:56 The most powerful guest lessons 09:16 Why your business shouldn’t be your prison 11:06 Answering The Exit Round for the first time 18:06 What we’d tell our younger selves 20:05 How we create freedom through business 23:18 Why you need a plan and an exit strategy 24:11 Thank you for 100 episodes! KEYWORDS entrepreneurship lessons from 100 episodes, how to build a business with the end in mind, business exit strategy planning, how to create financial freedom through business, time freedom for entrepreneurs, scaling a business sustainably, avoiding entrepreneurial burnout, business planning and goal setting, why most entrepreneurs fail to exit, how to make your business run without you, exit strategy for small business owners, building a sellable business, lessons from top entrepreneurs, creating passive income while scaling, avoiding the business owner trap 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!

    25 min

  8. SEP 2

    We’ve Made Our Mark on the Inc 5000 List!

    We hit #336 on the Inc. 5000 list. That’s top 0.001% out of 32 million businesses in America. But what happens after the balloons drop, the champagne's gone, and the party’s over? In this episode, Caleb and Aaron pull back the curtain on the hard truths behind fast growth—and why it nearly broke their business. This episode is not a humblebrag—it’s a warning. Rapid growth sounds sexy until you're managing burnout, cashflow crunches, and five-year hold assets with delayed returns. Tune in as the team shares what it *really* means to scale intelligently, and how they're building a company that will last decades, not just make headlines. TAKEAWAYS Why fast growth can be a hidden liability The real reason most businesses fail (hint: it’s not revenue) How to avoid burning out your team while scaling The difference between a ‘grow-at-all-costs’ mindset and strategic growth Why infrastructure matters more than another sale How Oak IQ became the 10th fastest growing real estate firm in the U.S. RESOURCES MENTIONED Inc. 5000 List FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 - Growth vs. Sustainability 01:00 - Oak IQ Makes the Inc. 5000 03:00 - Hidden Costs of Scaling Fast 06:00 - Profit, Cashflow, and Burnout 09:00 - The Strategic Growth Mindset 12:00 - Why Every Asset is Its Own Business 16:00 - Lessons for Long-Term Wealth KEYWORDS Inc 5000, fast growth, strategic growth, business scaling, real estate investing, Oak IQ, cashflow management, private equity, sustainability in business, entrepreneur lessons 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!

    19 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
    107
  • Rating
    Clean
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit