Own The Exit

Caleb Edwards and Aaron Leatherdale

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. HÁ 1 DIA

    Should You Stack Businesses or Master One?

    In this episode, Caleb and Aaron unpack a question every high-performer eventually faces: is stacking ventures strategic—or self-sabotage? With honesty and depth, they explore how personal capacity, fear of failure, and shiny object syndrome quietly erode momentum. This is the episode that challenges the lie that more equals better. Learn how to recognize when it's time to build another thing—and when you're just escaping the hard part of what you've already started. You’ll walk away with a clearer lens on the entrepreneurial growth curve, the real purpose of “overlap,” and why consolidation often creates more leverage than expansion. This one will hit home for any founder juggling too much and growing too little. TAKEAWAYS You don’t need another business.Most people quit before the growth starts.Execution matters more than ideas.One solid business can do it all.Focus creates overflow—not burnout.Stop using new ventures to escape the hard.Overlap is leverage when it’s intentional.Shiny objects steal real progress. RESOURCES MENTIONED Rich Dad Poor Dad by Robert Kiyosaki FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ ⁠⁠⁠⁠Aaron Investing⁠⁠ Caleb Investing⁠ CHAPTERS 0:13 Losing Yourself in the Build 0:27 Should You Build One Business or Ten? 2:44 Why Balance Is an Enigma 5:11 Execution Always Beats the Idea 7:32 The Entrepreneurial Growth Curve 9:49 Why You Keep Starting Over 11:50 Are You Willing to Stay Committed? 14:02 Creating Overlap Not Chaos 16:17 The Overflow Principle Explained 18:31 You’re Not Elon Musk 20:47 Shiny Objects Steal Your Time 22:56 Stop Chasing the Rush 25:12 Walmart, Amazon, and Singular Focus KEYWORDS stacking businesses, focus vs diversification, entrepreneurial growth curve, shiny object syndrome, when to scale a business, how to build leverage, startup execution strategy, private equity podcast, business consolidation tips, founder burnout, overlapping businesses, Gary Vee quotes, Alex Hormozi mindset, self-agency entrepreneurship, how to push through business plateau 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!

    26min
  2. 22 DE JUL.

    How Hailey Bieber Made $1 Billion Fast

    In this solo episode, Caleb reverse-engineers how Hailey Bieber pulled off a $1B exit with Rode—her skincare brand—less than three years after launch. And no, it’s not because she was a celebrity. It’s because she executed a flawless five-part playbook that every entrepreneur should be studying right now. From viral engineering to timing the exit at peak momentum, Caleb lays out each billion-dollar principle in a way that makes them simple to copy and paste into your next venture. If you're building a fund, a product, or an empire—this is your cheat code. TAKEAWAYS Build where founder-market fit is authentic and obvious.Start with a narrow product focus before expanding.Engineer virality and scarcity—don’t just hope for it.Build a medium moat (audience) before retail or channel expansion.Exit when you have momentum—not when you’re burned out. RESOURCES MENTIONED MultiplierU.com OakIQ.com FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 0:48 Hailey Bieber’s $1B Exit 1:07 Founder-Market Fit vs. Product-Market Fit 2:12 Why Personal Credibility Matters 3:13 The Origin Story of Multiplier U 4:14 Find the Right Audience Obsession 4:24 Start Narrow, Scale Broad 5:30 Engineering Virality 6:41 Build a Medium Moat First 7:25 Exit at the Peak, Not the Bottom 8:41 The 5-Step Copy/Paste Exit Formula KEYWORDS hailey bieber business, rode skincare exit, billion dollar startup, founder market fit, celebrity brands, exit strategy, brand virality, ecommerce playbook, high margin products, building a brand, multiplier u, own the exit podcast, Caleb OAKIQ, startup growth, how to scale a company 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!

    10min
  3. 15 DE JUL.

    Why Rich People Answer DMs with Justin Freishtat

    If you think your product matters more than your personal brand, think again. In this episode, Justin Freishtat reveals how he went from door-to-door food sales to building an $87 million business, exiting, and raising capital for major funds—all by mastering the art of leverage and visibility. From bootstrapping Heartland Foods to crafting cash-flowing digital businesses, Justin breaks down how brand authority, DM outreach, and knowing your role inside a business create unfair advantages. Whether you’re stuck trying to scale, unsure how to attract high-net-worth investors, or just sick of hiding behind your company logo, Justin’s story proves that execution beats excuses, every time. This one’s a tactical goldmine for anyone ready to build real freedom with speed. TAKEAWAYS People don’t follow companies—they follow people.Build your personal brand before you build your funnel.You can outwork everyone and still lose if your vehicle is wrong.DM outreach beats ads when you do it right.Partnerships win if everyone sticks to their strengths.You don’t need more leads—you need more reps.Build short money and long money at the same time. RESOURCES MENTIONED Rich Dad Poor Dad by Robert Kiyosaki FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ ⁠⁠⁠⁠Aaron Investing⁠⁠ Caleb Investing⁠ Justin Freishtat CHAPTERS 0:00 You Will Lose Money—Play Anyway 1:20 From Door Knocking to $87M Exit 4:30 How Sales Taught Me Everything 7:00 Why Most Business Partnerships Fail 9:20 The DM Outreach Blueprint 15:00 Building a Brand that Prints Money 19:30 From Food Trucks to Private Equity 24:00 Personal Brand > Company Brand 29:00 If It’s Not Working, Pivot Not Quit KEYWORDS Justin Freishtat, door to door sales success, brand authority tactics, how to raise capital, social media growth strategies, business partnerships, digital marketing agency model, personal brand vs business brand, DM outreach strategies, passive income tips, short money vs long money, forced innovation story, scaling with partners, no contract business model, Heartland Foods 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!

    37min
  4. 8 DE JUL.

    15 Fundamentals to Lead Like a Boss

    Most successful entrepreneurs assume they're just one strategy away from the next level—but that assumption might be what’s holding them back. In this solo episode, Caleb Edwards strips away the noise and delivers a raw, no-BS breakdown of the 15 non-negotiable fundamentals every wealth-builder needs to revisit, master, and repeat. This is not a “how to hustle harder” episode. It’s a straight shot of clarity for anyone who’s crushed it in business, yet knows something’s missing in the personal discipline game. If you're time-poor but outcome-obsessed, this episode is your wake-up call. Caleb hits everything from energy management to personal finance, public speaking to fitness—reminding us that no level of success exempts you from the basics. The real exit is earned in the shadows of daily mastery. TAKEAWAYS What got you here won’t get you there.First impressions shape big opportunities.Real listeners win more trust and deals.Clear writing means clear thinking.Your energy is more important than your time.Sleep, food, and fitness drive success.Discipline creates freedom, not restriction.Personal finances make or break your exit. RESOURCES MENTIONED The Power of Full Engagement by Jim Loehr FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit ⁠ Caleb Investing⁠ CHAPTERS 0:00 Why Winning Stops Working 1:05 Mastering First Impressions and Conversations 3:10 Speak and Write with Authority 5:10 Build a Body That Builds Wealth 7:20 Multiply Energy and Money 9:05 Stay Dangerous with Learning 10:00 Protect Focus and Rest 11:10 Fix Your Personal Finances KEYWORDS entrepreneur fundamentals, wealth habits, energy management, personal finance discipline, public speaking for entrepreneurs, high performer routines, how to own the exit, passive investing mindset, Caleb Edwards podcast, business exit strategy, investor success habits, high income earner mistakes, clear writing for deals, investor health habits, entrepreneurial burnout EPISODE 91 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!

    12min
  5. 1 DE JUL.

    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!

    8min
  6. 24 DE JUN.

    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!

    27min
  7. 17 DE JUN.

    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!

    17min
  8. 10 DE JUN.

    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!

    9min
4,9
de 5
88 avaliações

Sobre

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!