Own The Exit

Caleb Edwards and Aaron Leatherdale
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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. 3 DAYS AGO

    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

  2. 30 SEPT

    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

  3. 23 SEPT

    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

  4. 16 SEPT

    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

  5. 9 SEPT

    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

  6. 2 SEPT

    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

  7. 26 AUG

    Why Debt Beats Cash When Inflation is High

    Inflation isn’t slowing down—and if you’re holding cash, you’re losing wealth every day. In this solo episode, Aaron explains how to make inflation work for you instead of against you by leveraging debt and owning hard assets that appreciate while the dollar loses value. You’ll learn why “cash is king” is a dangerous myth in an inflationary economy, how debt can actually be a wealth-building strategy, and why hard assets like real estate can protect you from the silent thief of inflation. TAKEAWAYS Why inflation compounds over time and erodes buying power.How debt becomes cheaper in real dollars over the years.The dangers of hoarding cash during inflationary cycles.Why hard assets like real estate outpace inflation.Three actionable steps to hedge against inflation. RESOURCES MENTIONED Own The Exit Resources FOLLOWS ⁠Oak IQ Investments⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠ CHAPTERS 00:00 How inflation erodes your wealth 00:38 Why inflation compounds year after year 01:42 Wages vs. inflation 03:07 Riding the inflation wave with hard assets 05:24 Why debt is king in an inflationary economy 06:48 The danger of hoarding cash 07:48 Three steps to hedge against inflation 09:24 Summary: make inflation work for you KEYWORDS inflation strategy, how to hedge against inflation, debt vs cash, real estate as inflation hedge, why debt is good during inflation, how inflation compounds, wealth building strategies, hard assets vs cash, inflation survival guide, owning rental properties, inflation and mortgage debt, passive income from real estate, economic inflation planning, financial freedom during inflation, 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 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

  8. 19 AUG

    How to Escape Your Own Business

    In this episode, Caleb delivers a blueprint for real entrepreneurial freedom. This isn’t about quitting your business—it's about building one that doesn’t require you to be on the clock. If your income dies the moment you unplug, you're not truly free. Caleb walks you through the mindset shift from operator to architect, how to calculate your personal freedom number, and the exact systems that turn hustle into leverage. This is the episode every overworked founder needs to hear—because freedom doesn’t come from more effort, it comes from better design. TAKEAWAYS Operators grind; owners build systems that scale.Freedom starts with a personal “freedom number”—not random income goals.Stacking income streams is essential: active, passive, and leveraged.Document, automate, and delegate through operational, financial, and people systems.Define what “exit” means for you—and reverse engineer it one system at a time. RESOURCES MENTIONED ⁠OakIQ.com⁠ FOLLOWS ⁠⁠⁠Oak IQ Investments⁠⁠⁠ ⁠⁠Own The Exit⁠⁠ ⁠⁠Caleb Investing⁠⁠ CHAPTERS 0:40 What Real Ownership Means 1:08 Operators Grind. Owners Build. 2:06 Start Delegating Today 2:30 Define Your Freedom Number 3:03 Stack Income Streams 4:00 The 3 Critical Systems 4:35 The Exit Blueprint Recap 5:02 Your First Small Step KEYWORDS entrepreneurial freedom, exit strategy, business systems, leveraged income, passive income, freedom number, operator to owner, business automation, founder mindset, exit blueprint, cashflow systems, real estate investing, build a business that runs without you, 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!

    6 min
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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
    105
  • Rating
    Clean
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit