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. 4d ago

    The Business That Puts Your Investment Capital on Steroids

    What if the same investment deals you’re already participating in could also become a business that pays you? In this episode of Own The Exit, Caleb and Aaron break down the capital aggregation strategy — a wealth-building model that allows investors to pool capital through their own fund structure and earn not only from their personal investments, but also from the activity of raising and aggregating capital. They explain how accredited investors are leveraging fund structures to access larger private deals, negotiate better terms, and invest alongside institutional players that most individuals would never normally have access to. This episode is a deep dive into how the ultra-wealthy scale investment returns by controlling access and capital flow. TAKEAWAYS What the capital aggregation model actually isHow investors can make money beyond their own invested capitalWhy pooled capital creates access to better deals and termsThe difference between investing individually vs through a fundWhy accredited investors have a unique advantage in private marketsHow fund structures allow investors to participate alongside institutionsThe importance of compliance and securities attorneysThe 3 things needed to successfully launch a fund strategy RESOURCES MENTIONED Become a Fund Manger → Multiplier University Free Trial Check out our deals → Oak IQ Investments FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Strategy That Pays You To Invest 03:41 How Capital Aggregation Actually Works 06:31 Why Fund Managers Can Earn Massive Upside 08:47 Investor A vs Investor B Explained 11:20 Avoiding Bad Deals & Building Trust 13:00 The 3 Things You Need To Launch A Fund 15:01 How Multiplier University Helps Fund Managers Scale 17:00 Investing Alongside Institutional Capital KEYWORDS capital aggregation, private equity investing, accredited investor, passive investing, private real estate investing, fund management, investment fund strategy, capital raising, alternative investments, wealth building strategies, private deals, passive income investing, investment syndication, private markets, real estate syndication, institutional investing, entrepreneur investing, private capital, fund structures, cash flow investing, high net worth investing, private alternative investments 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 another entrepreneur or investor looking to scale their wealth beyond traditional investing. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

  2. Jul 7

    The Number One Variable in Real Estate Investing

    What actually causes real estate deals to fail? In this solo episode of Own The Exit, Caleb breaks down the single most important variable in real estate investing — and it’s probably not what most investors think. It’s not the market. It’s not the operator. It’s not even the debt itself. It’s time. Using examples from the 2008 housing crisis, today’s commercial real estate debt environment, and decades of market cycles, Caleb explains why the structure of a deal determines whether investors survive long enough to let the thesis play out. He also walks through the three key questions every passive investor should ask before investing in a syndication or private real estate deal. TAKEAWAYS Why time is the most overlooked variable in real estate investingHow bad deal structures create forced lossesWhat 2008 taught investors about leverage and survivabilityWhy floating rate debt has hurt so many syndicationsThe difference between market risk and forced selling riskHow great operators structure deals conservativelyThe 3 questions every passive investor should ask before investingWhy reserves and runway matter more than flashy returns FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 The Hidden Variable Behind Every Failed Deal 02:26 What 145 Years Of Real Estate Data Reveals 05:23 Why Commercial Real Estate Is Under Pressure 07:05 Debt, Market Risk & The Importance Of Time 10:29 How Great Operators Structure Deals Differently 11:54 The 3 Questions Every Passive Investor Must Ask 13:53 Why Time Determines Wealth In Real Estate KEYWORDS real estate investing, passive real estate investing, real estate syndication, commercial real estate, multifamily investing, real estate market cycles, floating rate debt, real estate risk management, investment structure, passive income investing, real estate leverage, investment underwriting, private real estate deals, accredited investor education, wealth preservation, conservative investing, real estate debt strategy, long term investing, market volatility, private alternative investments, operator risk, real estate cash flow 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 another investor looking to better understand risk, structure, and long-term wealth creation in real estate. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

  3. Jun 30

    The Golden Cage of Entrepreneurship with Morgan Keim

    What if the life you built for success quietly became a trap? In this episode of Own The Exit, Caleb and Aaron sit down with alternative investment strategist Morgan Keim to unpack the difference between income and true ownership. Morgan shares his journey from raising hundreds of millions in venture capital-backed food tech to building passive income and investor freedom through multifamily real estate and alternative assets. The conversation dives into burnout, dependency, passive income, conservative underwriting, workforce housing, and the emerging world of niche alternative investments — from tequila barrels to film bridge lending. More importantly, it explores the deeper question many entrepreneurs eventually face: “What kind of life am I actually building?” TAKEAWAYS Why high income does not automatically equal freedomThe hidden dependency problem many entrepreneurs faceHow passive income changes the way founders think and operateWhy workforce housing became Morgan’s investment focusThe importance of stable, supply-constrained marketsHow niche alternative investments create differentiated opportunitiesWhy critical thinking matters more than hype in investingHow ultra-wealthy investors use alternative assets differently RESOURCES MENTIONED Ocean Ridge Capital FOLLOWS Oak IQ Investments Own The Exit Aaron Investing Caleb Investing Morgan Keim CHAPTERS 00:00 The Wake-Up Call Behind Venture Success 02:33 From Income To Ownership 05:06 The Golden Cage Entrepreneurs Build 08:00 What Passive Income Actually Changes 12:28 Why Cleveland Outperformed Sexy Markets 16:43 Finding Investment Edges In Overlooked Niches 21:32 The Alternative Asset Opportunities Most Investors Never See 27:02 Building Access To Off-The-Wall Investments 31:40 Morgan’s Mission With Ocean Ridge Capital KEYWORDS passive income, entrepreneur burnout, alternative investments, multifamily investing, workforce housing, financial freedom, venture capital, passive cash flow, accredited investor strategies, private investing, wealth building, real estate investing, investment diversification, conservative underwriting, private alternatives, founder mindset, cash flow investing, passive wealth, entrepreneurial investing, supply constrained markets, financial independence, alternative asset 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!

  4. Jun 23

    The Oil and Gas Strategy High-Income Earners Are Using Instead of Stocks

    If you’re a high-income earner still trying to solve your tax problem with stocks and index funds, you may be using the wrong tool entirely. In this episode of Own The Exit, Caleb and Aaron break down why oil and gas investing has become one of the most powerful tax strategies used by high-income entrepreneurs, business owners, surgeons, attorneys, and executives. They explain how intangible drilling costs (IDCs) work, why private oil and gas funds can dramatically outperform public energy ETFs from a tax-efficiency standpoint, and the exact framework they use to reduce risk while maximizing cash flow and deductions. TAKEAWAYS Why stocks and brokerage accounts don’t solve active income tax problemsHow oil and gas tax deductions have existed since 1954What intangible drilling costs (IDCs) are and how they workHow accredited investors can offset W-2 income through oil and gas investingThe difference between public energy ETFs and private oil fundsWhy diversification matters even within oil and gas investingThe framework Caleb uses to evaluate oil and gas opportunitiesHow private energy investments can create strong cash flow alongside tax advantages RESOURCES MENTIONED IRS Publication on Intangible Drilling Costs FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Oil & Gas Is A Tax Strategy 02:21 How The Tax Math Actually Works 04:21 The Framework Caleb Uses To Reduce Risk 06:48 The Importance Of GP vs LP Structures 08:33 Aaron’s Perspective As A Real Estate Investor 12:28 Why Public Energy ETFs Miss The Biggest Benefits 13:36 The Oil & Gas Tax Calculator Explained KEYWORDS oil and gas investing, tax strategies for high income earners, passive income investing, intangible drilling costs, IDC tax deductions, accredited investor opportunities, alternative investments, private oil funds, oil and gas tax benefits, W-2 tax reduction, private investing strategies, energy investing, tax efficient investing, cash flow investments, private equity alternatives, wealth preservation, entrepreneur investing, investment diversification, high net worth investing, tax write offs, passive cash flow, private alternative investments 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 another entrepreneur or high-income earner looking to reduce taxes and build long-term wealth. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

  5. Jun 16

    Concerned About The Economy? Here’s What The Media Didn’t Share!

    Mainstream headlines are designed to grab attention, not necessarily tell the whole story. In this episode, we break down what the latest jobs report really says and why smart investors should care more about trends than fear-driven narratives. Despite constant warnings about recession, inflation, AI, tariffs, and consumer confidence, the labor market continues to show strength. We unpack the revisions hidden beneath the headlines and explain why strong employment remains the foundation behind real estate and alternative investments. TAKEAWAYS The initial jobs report is only a first draft—revisions matter.The economy averaged 188,000 jobs per month over the last three months.Leading indicators should be monitored but kept in perspective.Strong employment supports housing, retail, healthcare, storage, and industrial assets.Smart investors focus on long-term trends instead of media-driven fear.Good underwriting matters regardless of economic conditions.Negative headlines attract attention, but facts create clarity. FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Headlines Mislead Investors 00:38 Breaking Down The May Jobs Report 02:16 The Real Story Behind 188,000 Jobs Per Month 03:33 The Media Finds Fear In Good News 03:54 Understanding The Employment Trends Index 06:24 The First Domino In The Economy 06:48 Why Strong Data Doesn't Replace Good Underwriting KEYWORDS jobs report, labor market, employment trends, economic outlook, recession fears, real estate investing, passive income, alternative investments, market trends, inflation concerns, investor mindset, wealth building, economic indicators, job growth, financial literacy, commercial real estate, underwriting, media bias, investment strategy, long term 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!

  6. Jun 9

    Baby Boomers Are Retiring at 10,000 Per Day. Here's the Angle Nobody's Taking

    Baby boomers are retiring at a rate of nearly 10,000 per day, and over the next decade, an estimated $15 trillion in business equity will change hands. Most people are focused on buying “boring businesses” during this massive wealth transfer — but what if the bigger opportunity is somewhere else entirely? In this episode of Own The Exit, Caleb and Aaron break down the hidden opportunity behind the silver tsunami: becoming the trusted bridge between exiting business owners and private investment opportunities. They unpack why buying businesses is becoming increasingly competitive, how private fund management works, and why entrepreneurs are uniquely positioned to capitalize on the next phase of wealth creation. TAKEAWAYS Why the “buy boring businesses” trend is getting overcrowded The real opportunity behind the $15 trillion wealth transfer How exiting entrepreneurs think about investing differently Why private funds can create leverage and long-term wealth The 3 filters entrepreneurs use to evaluate investments How collective capital creates stronger investment opportunities Why trust and credibility matter more than financial complexity RESOURCES MENTIONED Rich Dad Poor Dad Multiplier University Free Trial FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Aaron Investing⁠ ⁠Caleb Investing⁠ CHAPTERS 00:00 Why Buying Businesses Became Popular 01:20 The Hidden Opportunity Behind The Trend 05:18 Why Buying Businesses Is Getting Harder 08:28 The Biggest Problem Entrepreneurs Face After Selling 10:12 Why Entrepreneurs Prefer Tangible Investments 13:02 The Entrepreneur Investor Framework 15:07 Launching A Private Investment Fund 17:34 How Fund Managers Make Money 19:42 What A Fund Actually Is 21:32 The Best Way To Capitalize On The Silver Tsunami KEYWORDS baby boomer retirement, silver tsunami, wealth transfer, private equity investing, private investment funds, passive income strategies, entrepreneur investing, business acquisitions, boring businesses, alternative investments, passive real estate investing, accredited investors, generational wealth, private capital, investment opportunities, real estate syndication, business exits, legacy wealth, cash flow investing, entrepreneurial investing, investor mindset, wealth building strategies 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!

  7. Jun 2

    The Math Behind Multifamily Syndications Most Investors Never See

    In Part 2 of this deep dive, we go beyond the surface and break down the actual math behind multifamily syndications—what the returns really look like, how the tax advantages work, and why most investors completely miss the bigger picture. This episode walks through the two layers of return, how high-income earners can leverage tax efficiency to dramatically improve outcomes, and a five-point framework to properly vet a deal before ever wiring capital. If you’ve ever wondered what separates sophisticated investors from everyone else, this is it. TAKEAWAYS Multifamily investments generate both cash flow and back-end equity returns Preferred returns typically range from 6–8% before profit splits Cost segregation and depreciation can create powerful tax advantages Accredited investors unlock access to institutional-quality opportunities Operator track record matters more than the deal itself Market selection directly impacts long-term performance Debt structure can make or break a deal in volatile markets Understanding the PPM is critical to evaluating risk Alignment of interest ensures operators have skin in the game Passive investing requires upfront diligence—not blind trust FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ CHAPTERS CHAPTERS 00:00 Intro: What This Episode Covers 00:44 The Two Layers of Return 02:15 How the Tax Advantage Works 04:07 Who Qualifies to Invest 05:14 The 5-Point Deal Vetting Framework 08:07 What Passive Investing Really Means KEYWORDS multifamily syndication, passive real estate investing, accredited investor strategies, real estate cash flow, IRR explained, cost segregation benefits, real estate tax advantages, passive income strategies, alternative investments, private equity real estate, investment deal analysis, real estate underwriting basics, wealth building strategies, high income investing, portfolio diversification, investment risk management, real estate deal vetting, capital gains strategy, financial independence planning, income producing assets 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. May 26

    Your Biggest Investment Isn’t in the Market. It’s In Your Tax Return with Chris Miller

    What if the biggest leak in your wealth isn’t your investments—but your taxes? In this episode, we sit down with a tax strategist who’s spent decades helping high earners and business owners stop overpaying the IRS. The reality? Most entrepreneurs are so focused on growing revenue that they completely ignore the one line item quietly draining millions over a lifetime—taxes. This conversation breaks down how proactive tax strategy can legally reduce your burden by 25–30%, why most CPAs aren’t built for this level of planning, and how to start thinking about your tax bill like your biggest opportunity—not your biggest obligation. TAKEAWAYS Taxes are the single largest expense for high-income earnersMost business owners focus on revenue instead of taxable incomeTraditional CPAs are reactive—not proactiveStrategic tax planning can reduce your bill by 25–30%Bonus depreciation and alternative structures unlock massive savingsSimple strategies like income shifting are often overlookedReinvesting saved tax dollars accelerates wealth buildingFear of the IRS keeps people stuck overpayingTax strategy should align with your long-term exit plan RESOURCES MENTIONED One Atlanta Tax Solutions FOLLOWS ⁠⁠Oak IQ Investments⁠⁠ ⁠Own The Exit⁠ ⁠Caleb Investing⁠ Chris Miller CHAPTERS 00:00 Why Taxes Are Your Biggest Expense 03:24 The 2008 Wake-Up Call That Changed Everything 07:22 Why Business Owners Miss This Completely 10:12 Breaking Down Bonus Depreciation 15:01 Why Trusting Your CPA Is Costing You 20:24 Real Examples of Tax Savings 23:14 Simple vs. Advanced Tax Strategies 29:11 Avoidance vs. Evasion (What’s Legal) 36:50 Taxes vs. Business Valuation KEYWORDS tax strategies, tax reduction, high income earners, business owner taxes, passive income strategies, bonus depreciation, cost segregation, tax planning, wealth building strategies, financial freedom, reduce taxable income, tax saving tips, investment tax strategies, entrepreneur finances, tax optimization, capital gains strategies, income shifting, tax mitigation, business exit planning, wealth preservation 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!

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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 - 2026
  • Episodes
    145
  • Rating
    Explicit
  • Copyright
    © Caleb Edwards and Aaron Leatherdale
  • Show Website
    Own The Exit