Own The Exit

Caleb Edwards and Aaron Leatherdale
  • 4.9 (88)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY
Own The Exit

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

    What I Wish I Knew at 25...

    What if everything you've been taught about money, success, and business is keeping you from the real win? In this solo episode, Caleb Edwards drops 10 brutally honest lessons forged through two decades of entrepreneurship, fatherhood, and faith—including losing half his net worth while his son fought for his life. These aren’t recycled Instagram soundbites. They’re hard-won truths from someone who’s walked through fire. Caleb talks about trading cash flow for ownership, why a poverty mindset survives even in six-figure earners, and why presence is more powerful than any paycheck. If you’re a high-performer who’s realizing that hustle isn’t the same as freedom—this is your episode. These 10 principles will help you shift from just stacking income to actually living out legacy. TAKEAWAYS Cash flow creates income, but ownership creates legacy.Time—not money—is the real measure of freedom.The middle-class mindset is fear wrapped in respectability.Money should serve you, not master you.Your business isn’t a business if it can’t run without you.Your kids care more about your presence than your net worth.Responsibility pulls men out of passivity.If you lose your mission, you lose everything.Therapy is good—but purpose is better.Faith, family, and freedom are the only metrics that matter long-term. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ Caleb Investing⁠ CHAPTERS 0:00 10 Lessons That Would’ve Saved Me 15 Years 1:06 Cash Flow Is Cool. Ownership Is King 2:14 Time Is the Most Expensive Asset 3:03 Networks: Gold Mine or Time Suck 3:47 The Middle-Class Mindset Is a Trap 4:32 Money Problems Are Often Lens Problems 5:02 Entrepreneurs Who Can’t Step Away Are Employees 5:30 The Goal Isn’t Rich. It’s Free. 6:00 Presence > Paychecks 6:24 Men Need Responsibility More Than Therapy 6:56 Legacy: Faith, Family, Capitalism KEYWORDS entrepreneur lessons learned, freedom over income, ownership vs cashflow, mindset of the wealthy, Caleb Edwards podcast, how to build generational wealth, time freedom entrepreneur, fatherhood and business, business exit advice, purpose over hustle, middle class mindset trap, passive income vs ownership, faith and capitalism, 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!

    8 min

  2. JUN 24

    Should You Scale Your Business at All Costs?

    What if the push to grow fast is the very thing that’s sabotaging your freedom? In this episode, Caleb and Aaron pull the curtain back on why the “scale at all costs” mentality is killing more businesses than it’s helping. They challenge the glorification of hyper-growth and unpack the hidden dangers of rushing success without foundation. From managing cash flow to managing your mind, this episode is a raw, real look at what sustainable entrepreneurship actually looks like. You’ll hear lessons about long-game thinking, avoiding the focus trap, and why patience—not hype—is your most underrated growth strategy. If you’re tired of building things that break under pressure, this conversation will help you slow down and scale smart. TAKEAWAYS Fast growth without foundation leads to collapse.Every big push must be followed by intentional recovery.Patience isn’t passive—it’s the secret to compounding momentum.Cash flow problems—not bad ideas—kill most businesses.Being consistently focused beats being constantly busy.Scale what’s working instead of chasing what’s new.Don’t keep restarting—save your progress and build from it. RESOURCES MENTIONED Rich Dad Poor Dad by Robert Kiyosaki FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ ⁠⁠⁠⁠Aaron Investing⁠⁠ Caleb Investing⁠ CHAPTERS 0:00 The Myth of Scale-at-All-Costs 1:45 The Price of Building Without Foundations 3:03 Smart Growth Is Slower (and Stronger) 5:12 Sprints and Recovery: How to Avoid Burnout 7:45 Entrepreneurs Don’t Rest—But Should 9:21 Patience: The Real Superpower 11:48 Consistency > Hype 13:23 Operations Matter More Than Vision Alone 15:14 Cash Flow: The #1 Business Killer 18:17 Why You Must Pay Yourself First 19:42 Focus: The Entrepreneur’s Trap 20:37 Hormozi’s Growth Curve Breakdown 24:41 Donkey Kong and Business Lessons 26:20 Beat the Boss. Save the Progress. KEYWORDS smart business growth, scale a business sustainably, avoid burnout entrepreneurship, how to manage cash flow, founder mindset shift, business scaling strategy, patient entrepreneurship, entrepreneur focus trap, Alex Hormozi business curve, informed optimism business, cash flow vs profit, consistent business growth, how to avoid startup failure, own the exit podcast, Caleb Edwards, Aaron Leatherdale business 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 who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

    27 min

  3. JUN 17

    Simple 3 Step Sequence to Safeguarding Your Wealth

    Everyone wants passive income—but almost no one talks about how to earn the right to have it. In this candid solo episode, Aaron Leatherdale breaks down the three-step wealth-building framework that every investor and entrepreneur must understand before they jump into alternative deals, syndications, or passive strategies. Aaron flips the script on internet gurus and get-rich-quick investors by showing why you shouldn't skip active income. He walks through how to build your primary engine, secure your financial base like Fort Knox, and then scale real wealth through passive vehicles—at the right time and in the right order. This is the anti-hype playbook for anyone who wants to play the long game and actually own their exit. TAKEAWAYS Active income is the foundation of real wealth.You need cash reserves before you start investing.Passive income only works if you earned capital to invest.Skipping steps leads to instability and burnout.Alternative investments are a multiplier—not a shortcut.The wealth game is long-term and sequence matters.Freedom comes when your passive income equals your expenses.Every dollar from step one can fuel steps two and three if done right. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ ⁠⁠⁠⁠Aaron Investing⁠⁠ CHAPTERS 0:00 Why Your Job Isn't Wealth 0:24 The Dangerous Rush to Passive Income 1:45 Step One: Maximize Active Income 5:01 Step Two: Build Fort Knox (Cash Reserves) 7:24 Step Three: Invest to Multiply 9:46 Passive Income vs. Income Replacement 12:00 How Much Do You Need to Make $100k in Passive? 14:25 Why Aaron Still Works Actively 16:15 The 20-Year Wealth Snowball KEYWORDS wealth building strategy, passive income vs active income, financial freedom plan, alternative investments explained, how to replace active income, cash reserves importance, private equity investing, multifamily real estate cash flow, step-by-step wealth system, Dave Ramsey for entrepreneurs, Oak IQ wealth plan, investing in syndications, long-term financial planning, business owner investing strategy 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!

    17 min

  4. JUN 10

    Your Business Still Owning You???

    Most entrepreneurs aren’t building freedom—they’re building a high-paid trap. In this brutally honest solo episode, Caleb Edwards delivers a wake-up call for founders stuck in hustle cycles and glorified self-employment. If your business can’t survive 30 days without you, you don’t own a business—you own a job with more stress and better branding. Caleb unpacks the critical difference between being the operator and being the owner—and lays out the three shifts every serious entrepreneur must make to unlock real leverage. You’ll walk away from this episode with a new lens on time, income, systems, and what freedom actually costs. If you’ve built income but not margin, you’re still on the clock. It's time to build the business that works without you. TAKEAWAYS If your business dies without you, you built a job, not freedom.Real ownership is measured by margin, not revenue.Leverage means your income grows even when you're not working.Freedom comes from systems, not hustle.You must shift from operator to architect.Time, energy, and autonomy are just as important as profit.Legacy is built by what you live, not just what you leave. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit  Caleb Investing⁠ CHAPTERS 0:00 Would Your Business Survive Without You? 0:46 Hustle Culture Is a Trap 2:45 Revenue Isn’t Freedom 3:07 Why Most Entrepreneurs Lack Leverage 4:33 The Real Question: Are You Free? 5:30 From Operator to Architect: The Ownership Shift 6:32 Three Moves to Unlock Real Ownership 7:33 The Moment That Changed Everything 9:10 Rebuild Your Systems, Reclaim Your Time KEYWORDS entrepreneur ownership shift, time freedom business, passive income for founders, business that runs without you, operator vs owner mindset, how to build business systems, entrepreneurial leverage, stop trading time for money, margin over hustle, building legacy not just revenue, freedom through automation, business philosophy for founders, Caleb Edwards podcast, 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!

    9 min

  5. JUN 3

    Dr. Ruth Mannschreck’s 5 Part Framework to Work Less and Make More

    In this powerful episode of Own the Exit, Caleb sits down with Dr. Ruth Mannschreck—a dentist-turned-coach who slashed her practice hours from five days to two… and grew revenue beyond the original mark. What started as a personal crisis with her daughter’s health turned into a wake-up call: redesign life and business on your terms—or burn out trying. Ruth unpacks the 5-part framework that helped her do it—and now helps other business owners do the same. Whether you’re running a dental practice, a consulting firm, or a real estate portfolio, these principles are industry-agnostic and exit-proof. From building bulletproof systems to empowering teams, redefining leadership, and installing values-driven culture—this episode is a blueprint for owning more time, more freedom, and ultimately, your exit. TAKEAWAYS You don’t need more hours—you need better systems.Your team will rise to the level you empower them to.Documenting the emotional journey of a customer changes everything.Hiring for values is more powerful than hiring for skills.Culture must be visible in behavior, not just on the wall.Leadership isn’t about control—it’s about clarity and trust.Working fewer hours can grow your revenue if you redesign right.A business that runs without you is the most valuable one to sell. RESOURCES MENTIONED Unreasonable Hospitality by Will Guidara FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ Caleb Investing⁠ Ruth Mannschreck workfewerhours.com CHAPTERS 0:41 Ruth’s Origin Story: Crisis Forced the Shift 3:03 Scaling Back to Scale Revenue 5:25 How to Build a Team That Protects You 7:44 The Doctor Next Door and Coaching Begins 9:22 Step One: Systematize Everything 12:23 Systems Should Include Emotion 14:20 Communication Systems That Prevent Silos 19:06 Step Three: High-Performance Team Building 21:26 Ruth’s Hiring and Roleplay Techniques 26:01 Step Four: Core Values Must Become Behavior 28:28 Culture in Action: The Chick-fil-A Effect 30:52 Step Five: Leadership That Creates Ownership 33:13 Why This Makes Your Business More Sellable 34:55 The Exit Round: Favorite Book + Passive Income 36:57 Ruth’s Advice to Her Younger Self 38:15 Ruth’s Plan for Scalable Impact 39:06 Connect with Ruth: workfewerhours.com KEYWORDS work fewer hours, high performance team, systematizing your business, exit strategy, business culture examples, leadership in modern teams, how to scale without burnout, business that runs without you, values-based hiring, communication in scaling businesses, SOP creation, passive income for service providers, Dr. Ruth Mannschreck, own the exit podcast, sellable business framework 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!

    40 min

  6. MAY 27

    How the Philosophy of Perception Relates to Value

    What do the wealthiest entrepreneurs have in common? It’s not just grit or capital—it’s how they think. In this solo episode, Caleb Edwards dives deep into why the most powerful business moves aren't tactical—they're philosophical. He unpacks the three principles that separate struggling operators from strategic visionaries: perception, scarcity, and belief. You’ll hear how Solomon’s 2.2 trillion-dollar wisdom still applies to modern founders, why behavior always follows belief (in your clients, your team, and yourself), and how most entrepreneurs are solving the wrong problem. If you’ve built something meaningful but feel stuck, this episode is your call to pivot from hustle to mastery. TAKEAWAYS People don’t buy what’s real—they buy what they believe is valuable.Scarcity is a filter that sharpens focus, not a flaw to fix.Behavior always follows belief—change belief, change outcomes.Your real product is the transformation your client thinks they’re buying.Wisdom isn’t abstract—it’s the foundation of generational wealth.Economic decisions are value judgments, not just transactions.More offers dilute power; clarity compounds it.You’ll never outperform your core beliefs. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ Caleb Investing⁠ CHAPTERS 0:00 The Secret Billionaires Have in Common 2:19 Solomon’s Wisdom: Business Begins in Belief 4:30 Business Is Philosophy + Economics 6:41 Why Perceived Value Always Wins 9:05 Oak IQ’s Real Offer (And Yours) 11:29 Scarcity Is the Ultimate Clarifier 13:53 From Hustle to Legacy: Caleb’s Turning Point 15:59 Behavior Follows Belief: Clients, Teams, and You 18:24 Journal This: Your Money Beliefs Matter 20:30 The Entrepreneur’s Triple Question: Truth, Scarcity, and Value KEYWORDS philosophy in business, perceived value vs real value, scarcity mindset, business clarity, entrepreneur beliefs, Thomas Sowell economics, how to scale a business, behavior follows belief, Solomon wisdom business, passive investing mindset, Oak IQ Investments, real estate investor mindset, high net worth strategy, exit strategy business, legacy-focused entrepreneurship 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

  7. MAY 20

    Fast Lane to Success: Execute, Iterate, Dominate

    In this episode of Own the Exit, Caleb Edwards delivers a powerful lesson on why speed of execution is the defining factor in business success. He breaks down the difference between iteration and ideation, explaining why launching quickly and improving along the way beats waiting for perfection every time. Caleb shares real-world examples from his own journey, including how his investment firm became a leader simply by moving faster than the competition. He also unpacks the psychology behind customer decisions, explaining why reducing “time to value” is the key to market dominance. If you’ve been sitting on an idea, waiting for the perfect moment—this episode is your wake-up call. TAKEAWAYS Done is better than perfect—perfection kills momentum.Speed of execution is the ultimate competitive advantage.Market feedback is the only way to truly refine your idea.The first to market wins—but only if they improve the fastest.Customer loyalty comes from continuous improvement and over-delivering.Time to value matters—faster results mean higher perceived value.Businesses that execute fast, iterate often, and improve consistently will dominate. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ Caleb Investing⁠ CHAPTERS 0:00 Done Is Better Than Perfect 0:36 Why Money Follows Speed 1:42 The Real Value of Fast Execution 2:38 How Oak IQ Beat the Market 3:28 Iteration > Ideation 4:33 Optimize Time to Value 5:24 Pizza, Xanax, and Speed Economics 6:25 Upgrade Existing Clients First 7:11 The 6-Part Chain Reaction to Exit KEYWORDS business execution, speed over perfection, competitive advantage, iteration vs ideation, time to value, customer experience, scaling a business, entrepreneurship, business growth, over-delivering, startup strategy, launching fast, market feedback, business psychology, 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

  8. MAY 13

    8 Loopholes You Haven’t Heard Of

    Most business owners and high-income earners focus on making money—but few master the art of keeping it. In this episode of On The Exit, Caleb and Aaron expose the biggest tax-saving strategies that the wealthy use to legally reduce their tax burden and build lasting wealth. From cost segregation in real estate to oil and gas investments, these are the tools that can save you six or seven figures over time. If you’re tired of giving away too much to Uncle Sam, listen in as we break down the eight advanced tax strategies that can help you maximize deductions, invest smarter, and legally keep more of what you earn. TAKEAWAYS The top 1% don’t just make more—they keep more.Taxes are the biggest wealth killer for high earners.The tax code is full of legal ways to reduce what you owe.Cost segregation accelerates real estate depreciation.Opportunity zones allow tax-free investment growth.Oil and gas investments provide huge tax deductions.1031 exchanges defer capital gains tax.The right CPA can save you millions over time. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ ⁠⁠⁠⁠Aaron Investing⁠⁠ Caleb Investing⁠ CHAPTERS 00:00 Why Entrepreneurs Overpay in Taxes 02:35 The IRS Tax Code is a Playbook 04:57 8 Advanced Tax Strategies You Need 07:03 How Cost Segregation Saves Millions 09:03 The Power of Opportunity Zones 11:25 Why Oil & Gas Investments Are Tax Gold 13:44 1031 Exchanges: Deferring Taxes the Smart Way 16:07 The Risks & Rewards of Tax Planning 18:25 Don’t Get Stuck on One Strategy 20:42 How to Offset Taxes With Smart Investing 22:48 Free Masterclass on Advanced Tax Strategies Coming Soon KEYWORDS tax-saving strategies, tax loopholes, cost segregation, real estate investing, 1031 exchange, oil and gas investment, passive income, tax deductions, high-income earners, wealth-building, tax code secrets, opportunity zones, CPA tax advice, advanced tax strategies, reducing tax burden EPISODE 83 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
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4.9
out of 5
88 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
    91
  • Rating
    Clean
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit

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