Own The Exit

Hosted by Caleb Edwards and Aaron Leatherdale

Business Entrepreneurship

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Episodes

141

Latest episode

Jun 2026

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EN-US

About the show

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!

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June 30, 2026Episode 14232 min

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?”TAKEAWAYSWhy 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 differentlyRESOURCES MENTIONEDOcean Ridge CapitalFOLLOWSOak IQ InvestmentsOwn The ExitAaron InvestingCaleb InvestingMorgan Keim CHAPTERS00:00 The Wake-Up Call Behind Venture Success02:33 From Income To Ownership05:06 The Golden Cage Entrepreneurs Build08:00 What Passive Income Actually Changes12:28 Why Cleveland Outperformed Sexy Markets16:43 Finding Investment Edges In Overlooked Niches21:32 The Alternative Asset Opportunities Most Investors Never See27:02 Building Access To Off-The-Wall Investments31:40 Morgan’s Mission With Ocean Ridge CapitalKEYWORDSpassive 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 investingWANT 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!

June 23, 2026Episode 14116 min

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.TAKEAWAYSWhy 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 advantagesRESOURCES MENTIONEDIRS Publication on Intangible Drilling CostsFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 Why Oil & Gas Is A Tax Strategy02:21 How The Tax Math Actually Works04:21 The Framework Caleb Uses To Reduce Risk06:48 The Importance Of GP vs LP Structures08:33 Aaron’s Perspective As A Real Estate Investor12:28 Why Public Energy ETFs Miss The Biggest Benefits13:36 The Oil & Gas Tax Calculator ExplainedKEYWORDSoil 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 investmentsWANT 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!

June 16, 2026Episode 1409 min

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.TAKEAWAYSThe 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.FOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 Why Headlines Mislead Investors00:38 Breaking Down The May Jobs Report02:16 The Real Story Behind 188,000 Jobs Per Month03:33 The Media Finds Fear In Good News03:54 Understanding The Employment Trends Index06:24 The First Domino In The Economy06:48 Why Strong Data Doesn't Replace Good UnderwritingKEYWORDSjobs 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 investingWANT 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!

June 9, 2026Episode 13923 min

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 complexityRESOURCES MENTIONEDRich Dad Poor DadMultiplier University Free TrialFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 Why Buying Businesses Became Popular01:20 The Hidden Opportunity Behind The Trend05:18 Why Buying Businesses Is Getting Harder08:28 The Biggest Problem Entrepreneurs Face After Selling10:12 Why Entrepreneurs Prefer Tangible Investments13:02 The Entrepreneur Investor Framework15:07 Launching A Private Investment Fund17:34 How Fund Managers Make Money19:42 What A Fund Actually Is21:32 The Best Way To Capitalize On The Silver TsunamiKEYWORDSbaby 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 strategiesWANT 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!

June 2, 2026Episode 1389 min

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 trustFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERSCHAPTERS00:00 Intro: What This Episode Covers00:44 The Two Layers of Return02:15 How the Tax Advantage Works04:07 Who Qualifies to Invest05:14 The 5-Point Deal Vetting Framework08:07 What Passive Investing Really MeansKEYWORDSmultifamily 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 assetsWANT 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!

May 26, 2026Episode 13750 min

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.TAKEAWAYSTaxes 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 planRESOURCES MENTIONEDOne Atlanta Tax SolutionsFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠Chris MillerCHAPTERS00:00 Why Taxes Are Your Biggest Expense03:24 The 2008 Wake-Up Call That Changed Everything07:22 Why Business Owners Miss This Completely10:12 Breaking Down Bonus Depreciation15:01 Why Trusting Your CPA Is Costing You20:24 Real Examples of Tax Savings23:14 Simple vs. Advanced Tax Strategies29:11 Avoidance vs. Evasion (What’s Legal)36:50 Taxes vs. Business ValuationKEYWORDStax 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 preservationWANT 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!

May 19, 2026Episode 13620 min

Does Your Portfolio Match Your Brain?

What if the biggest edge in your portfolio isn’t your capital—but the way you think?In this episode of Own The Exit, Caleb challenges entrepreneurs and business owners to rethink how they invest after building wealth. Once the cash starts stacking up, too many founders abandon the exact mindset that made them successful and default to generic financial advice that was never built for operators.From Alex Hormozi’s wake-up moment to Caleb’s own journey through entrepreneurship, family adversity, and private market investing, this episode explores why entrepreneurs often thrive when they invest like owners—not spectators. If you’ve built wealth through business, this conversation will help you align your portfolio with the mind that created it.TAKEAWAYSWhy entrepreneurs should invest differently than the average personHow to align your portfolio with your natural strengthsThe difference between ownership investing and spectator investingWhy private markets often make intuitive sense for operatorsThree practical questions to guide your next investment moveFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 Does Your Portfolio Match Your Brain?02:16 The Hormozi Wake-Up Call06:31 Why Entrepreneurs Should Invest Differently08:47 Investing Like an Owner09:55 A Personal Wake-Up Call11:20 Why Real Estate Made Sense14:44 Three Questions Every Entrepreneur Must Ask17:34 Your Next Sensible Step19:16 Build a Portfolio Like You Built Your BusinessKEYWORDSentrepreneur investing, business owner wealth, private equity, real estate investing, wealth strategy, portfolio diversification, ownership mindset, passive income, alternative investments, business acquisition, private markets, investment strategy, wealth building, cash flow investing, accredited investor, multifamily investing, commercial real estate, operator mindset, financial freedom, wealth stewardship, portfolio strategyWANT 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 a business owner ready to invest like an owner. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

May 12, 2026Episode 1356 min

The Real Estate Structure Wealthy Investors Use That Nobody Explains

There’s a reason wealthy investors continue to compound in real estate while most people stay stuck on the sidelines—and it has nothing to do with how much money they have. It comes down to understanding a structure that almost nobody explains.In this episode, we break down the real estate syndication model—the exact vehicle institutions, family offices, and high-level investors use to access large-scale multifamily deals without becoming landlords. You’ll learn how the structure works, the roles involved, and why this model creates a completely different investing experience than traditional real estate.TAKEAWAYSThe real barrier to large-scale real estate investing isn’t money—it’s access to the right structureReal estate syndications allow investors to participate in institutional-quality deals without becoming operatorsThe GP-LP model creates a clean division where professionals handle execution and investors provide capitalPassive investing in syndications is fundamentally different from owning and managing rental propertiesThe “advisor gap” is why most qualified investors never see these opportunitiesFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 Intro: The Structure Nobody Explains00:57 Why Scale Requires a Different Model01:59 How Real Estate Syndications Work03:33 GP vs LP Roles Explained04:52 The Advisor Gap & Why You’ve Never Seen This05:34 Why Most Investors Stay in Public MarketsKEYWORDSreal estate syndication, passive real estate investing, accredited investor opportunities, multifamily investing strategy, institutional real estate, private real estate deals, wealth building strategies, passive income real estate, alternative investments, real estate deal structure, general partner vs limited partner, investment diversification strategies, financial independence planning, high net worth investing, private market investing, real estate portfolio growth, cash flowing assets, long term wealth building, real estate education, investment strategy explainedWANT 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!

May 5, 2026Episode 1335 min

Turn Financial Goals Into a Real Investment Plan

What separates people who talk about building wealth from those who actually do it? A real plan backed by action.In this episode of Own The Exit, Aaron breaks down how financial goals only become real when they’re attached to a clear investment strategy. Too many people stay stuck in uncertainty—waiting for the perfect market, perfect timing, or perfect deal. But wealth is rarely built through hesitation. It’s built through intentional action and consistent execution.From buying his very first house with no prior experience to helping oversee nearly $300 million in real estate assets, Aaron shares how clarity comes through movement, not overthinking. If you’ve been sitting on the sidelines, this episode will help you start turning your financial vision into an actual investment plan.TAKEAWAYSWhy financial goals need a defined investment roadmapHow action creates momentum and confidenceThe hidden cost of waiting for perfect timingWhy uncertainty should not stop wealth buildingHow small steps can compound into long-term successFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠CHAPTERS00:00 From First Deal to Real Wealth00:33 Why Goals Without Action Fail01:24 Building Your Investment Mindset03:41 Stop Waiting for Perfect Timing04:32 Push Through Fear and Take Action05:08 Start Your Investment Plan TodayKEYWORDSfinancial goals, investment plan, real estate investing, passive income, wealth building, financial freedom, investment strategy, market timing, investor mindset, passive wealth, entrepreneurship, business owner investing, long term wealth, action plan, financial roadmap, real estate portfolio, passive investing, wealth strategy, investment confidence, wealth growthWANT 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 ready to turn goals into real wealth. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

April 28, 2026Episode 13314 min

What Makes Oil So Tax Efficient

Why do sophisticated investors keep coming back to oil and gas—even in a world pushing clean energy?In this solo episode, Caleb breaks down the real reasons high-income earners are leveraging oil and gas investments to reduce taxes, generate fast cash flow, and hedge against inflation. From powerful IRS deductions to strategic fund structures, this episode reveals how the right investment can transform your entire financial picture—not just your returns.TAKEAWAYSHow oil & gas investments can offset earned income—not just passive incomeWhy 70–80% of drilling costs can be deducted in year oneThe power of depletion allowance and tax-free cash flowHow investors generate cash flow within 1–2 quartersThe difference between PDP funds and new drilling programsWhy horizontal drilling significantly reduces riskHow to structure investments for maximum tax efficiency (GP vs LP)Why oil & gas acts as a hedge during inflationary cyclesThe importance of diversification across operators and fundsWhy separating investment strategy from personal ideology mattersFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 Why investors choose oil & gas01:50 Depletion allowance & tax-free income03:52 Real return example breakdown04:53 How to invest in oil & gas05:13 PDP funds (existing production strategy)06:50 Investing alongside major operators07:50 Pro tips: diversification strategy08:55 Investor classification (GP vs LP)09:50 Portfolio construction & alternatives11:30 Oil demand vs clean energy narrative13:45 How to get startedKEYWORDSoil and gas investing, tax strategies for high income earners, passive income ideas, alternative investments, accredited investor strategies, tax reduction investments, cash flow investments, inflation hedge assets, private equity investing, energy sector investing, portfolio diversification strategies, wealth building strategies, tax efficient investing, drilling investment opportunities, income producing assets, high net worth investing, financial independence strategies, passive wealth building, private market investments, long term wealth strategiesWANT 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!