Own The Exit

What does it take to earn the trust of billionaires? In this episode, Beverly Hills-based wealth advisor Richard McWhorter reveals how he serves ultra-high-net-worth clients across sports, entertainment, and business. From navigating conflicts of interest in big firms to creating truly tailored financial strategies, Richard shares what sets apart the advisors who only “sell” from those who truly advise.We dive into the psychology of wealth, how the ultra-rich think differently about risk, the economic trends shaping future investments, and why critical thinking—not hype—is the most valuable skill in money management.TAKEAWAYSThe key difference between selling vs. advising clientsHow ultra-wealthy clients approach risk and wealth preservationWhy big firms often limit truly creative financial strategiesThe role of trust and unbiased opinions in wealth managementHow to critically think about economic trends and investment dataRESOURCES MENTIONEDSRM Private WealthFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠Richard McWhorterCHAPTERS00:00 Selling vs. advising: the big difference02:28 Richard’s journey into wealth management05:12 Breaking free from big-firm conflicts of interest08:23 How ultra-wealthy clients build and maintain trust11:15 The role of creative strategies beyond traditional products15:10 Understanding client psychology and behavior19:12 Economic realities: tariffs, interest rates, and inflation25:36 Why energy and infrastructure matter in future investments30:45 Critical thinking vs. chasing hype36:40 The Exit Round: Richard’s personal lessons40:20 Where to find Richard McWhorter onlineKEYWORDShow billionaires manage wealth, ultra high net worth investing, private wealth management strategies, financial advisor vs fiduciary, creative wealth preservation tactics, economic trends 2025, tariffs and inflation impact, interest rate strategy for investors, energy and infrastructure investments, risk management for the ultra-rich, alternative investments beyond stocks, wealth psychology and decision making, unbiased financial advising, long-term wealth planning strategies, building trust with high-net-worth clientsWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

If I told you the fastest way to increase your company's valuation wasn’t about selling more, raising prices, or landing new clients—but about keeping more of the money you already make—would you believe me? In this episode, Caleb reveals a simple 3-step system powered by ChatGPT that can cut up to 25% of your monthly expenses without layoffs.These are the exact prompts Caleb has used in his own companies and seen other founders deploy with game-changing results. You’ll walk away with practical AI tools that can instantly boost profitability, free up cashflow, and increase your exit multiple—all without sacrificing growth.TAKEAWAYSWhy profit is the real driver of valuation (not revenue)The 3-step GPT expense-cutting systemHow to uncover redundant or outdated contracts instantlyThe exact CFO-level GPT prompt that cuts 25% of expensesReal-world examples of founders saving $19K–$42K instantlyHow to reinvest savings into growth levers that multiply your exitRESOURCES MENTIONEDTry ChatGPT here → ChatGPTFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 - Why Profit Beats Revenue01:25 - $19K Savings in One Hour02:19 - Step 1: Categorize Expenses03:41 - Step 2: The GPT CFO Audit05:31 - Step 3: Implement & Negotiate06:48 - Real-World Case Studies07:22 - Caleb’s Challenge to YouKEYWORDSAI in business, GPT prompts, cut costs with AI, business profitability, enterprise valuation, Own The Exit, Caleb OAKIQ, expense reduction strategies, ChatGPT for entrepreneursWANT 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!

She grew up riding pump jacks in West Texas and now she’s helping high-income professionals slash their tax bills and grow serious cash flow through strategic oil and gas investments. In this episode, Courtney Moeller joins us to break down the truth behind working interest, the real risks (and myths), and why this overlooked asset class might be the greatest wealth hack nobody's talking about.This is not your dad’s oil investing. Courtney reveals how to invest alongside billion-dollar operators, minimize dry-well risk, and structure deals that not only cash flow fast but also give investors massive year-one tax benefits. Whether you’re a W-2 earner, business owner, or pro looking for tax efficiency—this one’s for you.TAKEAWAYSOil and gas offers unique tax advantages unmatched by most other assetsWhy horizontal wells drastically reduce dry-hole riskThe myth of EVs replacing oil and what most investors get wrongHow to vet oil and gas operators like a proReturns you should expect from smart oil dealsThe timeline for return of capital and cash flow accelerationWhy demand from AI and data centers is fueling energy investment urgencyRESOURCES MENTIONEDOil and Gas ReportCourtney’s WebsiteFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 - Courtney’s wild oilfield background04:22 - Why now is the window to invest06:48 - EV myths and the truth about energy demand09:04 - Vetting oil and gas operators13:10 - Why oil beats real estate on taxes17:00 - What dry wells really cost you21:14 - How Courtney structures her deals23:31 - Return timelines and cash flow expectations28:03 - 85% K1 loss? Yep.30:45 - Freedom, family, and oil wealthKEYWORDSoil and gas investing, passive income, tax advantages, W2 tax strategy, working interest, cash flow, horizontal drilling, high income earners, accredited investors, financial independence, energy investing, inflation hedge, generational wealth, investment diversification, tax deferral, royalty income, depletion allowance, Permian Basin, offsetting earned income, energy sector, real asset investing, alternative investments, AI energy demand, Bitcoin mining and oilWANT 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!

In this solo episode of Own The Exit, Caleb sounds the alarm on the biggest economic shift of our lifetime: the AI revolution. If you're still building your wealth using the same assumptions from 10—or even 5—years ago, you're already behind. AI is not coming; it's here, and it's rewriting every rule of business, investing, and financial security.From job replacement at massive scale to algorithmic trading destroying diversification, Caleb breaks down why traditional investment models are failing and what smart entrepreneurs must do to stay ahead. This is your wake-up call: start owning assets AI can’t replicate, or risk losing it all.TAKEAWAYSAI will eliminate millions of jobs—including white-collar roles—within yearsPublic markets are more correlated and fragile than everThe old 60/40 portfolio model is officially deadTrue diversification requires owning hard, productive assetsSmart investors are using AI inside their business—but storing wealth outside of AI’s reachRESOURCES MENTIONEDOakIQ.comFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠Caleb Investing⁠CHAPTERS02:00 AI Disrupting Jobs: Scary Stats You Need to Know05:30 Market Fragility & the End of Diversification08:30 What It Means for Entrepreneurs10:00 Real Assets That AI Can’t Replace12:00 The Creepy (But Real) Future of AI in Homes13:30 The Wealth Strategy That Still WinsKEYWORDSAI investing, job automation, financial fortress, passive income, 60/40 portfolio, real estate investing, own the exit, OakIQ, AI and wealth, smart investing strategies, diversified assets, AI risk, asset protectionWANT 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!

What if your property's WiFi could be a wealth-building machine? In this episode, we sit down with Bill Douglas, CEO of Optic Wise and co-author of *Peak Property Performance*, to unpack how real estate owners are boosting NOI by owning their digital infrastructure.Bill shares how he turned a 299-unit property from $15 to over $800 in NOI per unit annually—without touching the physical building. If you think "bulk internet" is the move, this episode will flip that script.TAKEAWAYS Why bulk internet deals often sabotage long-term NOI How owning your digital infrastructure increases valuation The importance of being AI-ready even if you're not AI-active The hidden operating savings from unified networks How data ownership enhances retention, security, and profitability Why most real estate tech investments fail—and how to avoid itRESOURCES MENTIONEDPeak Property PerformanceOptic WiseFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 – Why WiFi Is a Wealth Lever01:39 – Coral Snake Bite That Changed Everything03:03 – Turning Around a 14-Year-Old Company05:03 – The “Insane Bet” That Paid Off08:06 – Why Real Estate Is Tech-Phobic12:05 – Bulk Internet is a Trap15:35 – The Real Cost of ‘Free’ Networks20:58 – Smart Tech & Tenant Experience24:05 – Sentiment Analysis & AI Living Units28:53 – Building AI-Ready Properties33:05 – $824/Unit Case Study Breakdown37:15 – Exit Round: Books, Advice, StrategyKEYWORDSreal estate tech, commercial real estate, multifamily investing, NOI increase, passive income, digital infrastructure, AI in real estate, bulk internet, property technology, smart apartments, building automation, asset valuation, submetering, opex savings, smart locks, passive real estate, real estate investing, infrastructure ROI, future of real estate, property management techWANT 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!

Entrepreneurs see opportunities everywhere—but which ones are actually yours to solve right now? In this solo episode, Aaron breaks down how to beat shiny object syndrome, protect your cashflow, and scale faster by saying “no” more often.From Warren Buffett’s “say no” philosophy to Jeff Bezos’s one-way vs. two-way doors, and a simple six-filter decision framework, you’ll learn a practical way to decide what to pursue—and what to ignore—so you can build one business fully before chasing the next.TAKEAWAYSWhy most businesses fail (cashflow, not demand) and how overcommitment accelerates itThe “stay in your lane” rule for foundersGolden rule: don’t add a new line until your current one runs without you for 4+ weeksBezos’s one-way vs. two-way doors: when to experiment vs. when to prove firstSix filters: Strategic Fit, Reversibility, Resources, Impact vs. Effort, Circle of Competence, Hell-Yes TestRESOURCES MENTIONEDAtomic Habits — James ClearFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠CHAPTERS00:00 – Why Saying “No” Builds Wealth01:04 – The Hidden Cost of Shiny Objects02:52 – Buffett, Bezos & The Filters05:23 – The Golden Rule for Adding Lines06:48 – Munger, James Clear & Final FocusKEYWORDSshiny object syndrome, founder focus, strategic filters, one-way doors, cashflow risk, core competency, Warren Buffett, Jeff Bezos, Charlie Munger, Atomic Habits, 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!

Ray Dalio says we’re heading for a debt spiral. Apollo Global predicts the biggest boom in U.S. history. Who’s right? It doesn’t matter—if you’re positioned correctly. In this dynamic duo episode, Caleb and Aaron break down how everyday investors can take control of their financial future, no matter what headlines scream.Learn why diversification is broken, how ultra-wealthy investors are allocating capital (hint: it's not where your financial advisor told you), and the PRIME framework for making strategic moves through chaos. This one is for anyone who’s serious about escaping Wall Street dogma and actually owning their exit.TAKEAWAYSRecession doesn’t destroy wealth—it redistributes itWall Street "diversification" no longer protects youThe ultra-wealthy are holding cash for opportunity—not fearHard assets and private equity outperform public markets long-termTrusting your portfolio to a salaried advisor is riskyUse the P.R.I.M.E. framework: Pause, Review, Identify, Move, EvaluateFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 – Ray Dalio vs. Apollo Global: Who’s Right?01:45 – Why You Can’t Rely on Predictions03:58 – Recessions Don’t Destroy Wealth — They Move It06:12 – Why “Diversification” No Longer Works09:40 – How the Ultra-Wealthy Are Actually Allocating Capital13:32 – What Tiger 21 Investors Are Doing with Their Portfolios17:50 – Why Your Financial Advisor May Be Misleading You20:28 – The PRIME Framework: Pause. Review. Identify. Move. Evaluate.26:43 – Final Thoughts: Own Your Exit, Own Your WealthKEYWORDSRay Dalio, Apollo Global, Tiger 21, investing in a recession, private equity, alternative investments, PRIME framework, hard assets, portfolio strategy, financial freedom, OakIQ, Own The ExitWANT 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!

In a world obsessed with shortcuts and hacks, the real edge isn’t just working smarter—it’s working smarter AND harder. In this solo episode, Caleb breaks down why skill stacking, deep focus, and relentless consistency are the ultimate cheat codes to success in business, investing, and life.From Elon Musk to Michael Jordan, from Cal Newport to Alex Hormozi, Caleb reveals what separates the people who quietly win long term from those who burn out chasing the next shiny thing. By the end of this episode, you’ll know how to outwork 95% of the competition without burning yourself out.TAKEAWAYSWhy the “work smarter, not harder” mantra is incompleteHow deep focus multiplies your productivityThe power of stacking complementary skills for leverageWhy consistency beats talent in the long gameHow to create compounding results without burnoutFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 The real cheat code: smarter + harder work00:29 Why shortcuts don’t create long-term success01:08 Lessons from Elon Musk and Michael Jordan02:16 What “working harder” actually means03:07 Deep focus vs shallow busyness04:32 Skill stacking for leverage (Alex Hormozi example)06:17 Why complementary skills multiply results07:41 Relentless consistency: the MrBeast effect09:04 Outlasting the competition without burnoutKEYWORDSwork smarter and harder, deep work productivity, skill stacking for entrepreneurs, how to stay consistent, Alex Hormozi business lessons, Cal Newport deep work, MrBeast success secrets, how to outwork competition, consistency beats talent, productivity without burnout, how to focus deeply, skill leverage in business, discipline vs motivation, building compounding results, business growth mindsetWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

In this special solo episode of Own The Exit, Caleb honors the late Charlie Kirk by unpacking what it truly means to be wealthy. It’s not just about building businesses or chasing dollar signs—it's about becoming the kind of person who can handle prosperity without losing their soul in the process.From character-first wealth building to defining what “rich” really means for you, this is an emotionally honest and highly practical breakdown of how legacy, values, and financial literacy intersect to build not just success, but significance.TAKEAWAYSWealth without character leads to internal povertyYou can be rich in money but bankrupt in your soulLegacy matters more than lifestyleDefine your personal version of “rich”Financial literacy is a non-negotiable superpowerDon’t glorify hustle—build systems that give freedomCompounding interest works both ways—use it wiselySacrifice distractions, not your family or integrityEnough is better than endlessly chasing moreFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS00:00 - Why wealth without character is hollow01:22 - Honoring Charlie Kirk beyond politics02:16 - The power of becoming before earning03:09 - Legacy vs. success sequence04:32 - Charlie’s formula for material wealth05:08 - Most people don’t want the grind06:10 - Sacrificing distractions, not values07:26 - The real prize: time & freedom08:13 - Defining “rich” with critical mass09:04 - Why financial literacy changes lives10:54 - Business smarts start with money smarts11:35 - Hustle isn’t the only path to wealth12:45 - Solving real problems at your scale13:19 - Summary: 6 powerful wealth lessonsKEYWORDSfinancial freedom, character development, generational wealth, business systems, legacy building, passive income, financial literacy, compounding interest, critical mass, values-based investing, wealth without burnout, intentional living, entrepreneurship, time freedom, defining rich, success sequence, hustle culture, purpose-driven wealth, internal poverty, building legacy, charlie kirkWANT 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!

Can money really buy happiness—or does it just magnify who you already are? In this deeply thought-provoking episode, Caleb and Aaron unpack the famous Harvard happiness study that claims happiness plateaus at $85,000 a year, share real-world stories from high-net-worth individuals, and discuss why money is only a tool—not the ultimate answer.They explore why happiness is an internal choice, how money removes obstacles but doesn’t create meaning, and why your “why” matters more than any dollar amount. If you’re building with the end in mind, this conversation will challenge how you view wealth, freedom, and fulfillment.TAKEAWAYSThe $85,000-a-year happiness plateau explainedWhy money magnifies who you already areHow income can remove obstacles but not create fulfillmentThe deeper “why” behind pursuing financial freedomHow to build both wealth and internal happinessFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 Can money really buy happiness?00:19 Breaking down the Harvard $85,000 happiness study02:14 Why happiness plateaus after basic needs are met04:32 The fleeting joy of material upgrades06:57 Money as a magnifier of who you already are09:43 Stories of wealthy people still unfulfilled12:56 Happiness as a choice, not a dollar amount15:22 The deeper “so that” behind pursuing passive income18:45 Two conflicting studies on income and happiness21:38 Building internal happiness alongside external wealth24:17 Final thoughts: Money, meaning, and freedomKEYWORDSdoes money buy happiness, $85,000 happiness study, income vs happiness research, money and life satisfaction, wealth and fulfillment, financial freedom mindset, money as a tool not the goal, removing obstacles with money, how income affects happiness, why happiness is internal, money mindset shifts, wealth psychology for entrepreneurs, freedom vs fortune, building a meaningful business, financial freedom vs life purposeWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

What does it truly mean to “own your exit”? In this solo episode, Aaron breaks down the three ways entrepreneurs can approach their business exit strategy—whether it’s selling for a huge payday, staying on to scale with new resources, or never exiting at all but gaining freedom within the business you’ve built.You’ll learn why the right exit isn’t one-size-fits-all, how to think strategically about your future, and why beginning with the end in mind is the only way to truly own your journey as an entrepreneur.TAKEAWAYSThe three main types of business exits every entrepreneur should considerWhy selling your business isn’t always the ultimate goalHow staying on after a capital event can unlock new levels of growthWhy freedom within your business might be the best exit of allThe importance of thinking 2–5 years ahead to truly “own your exit”RESOURCES MENTIONEDOak IQ InvestmentsFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠CHAPTERS00:00 Why owning your exit starts with the end in mind00:23 The myth of the one-size-fits-all “big exit”01:42 Exit #1: Selling and walking away03:05 Exit #2: Selling but staying to scale05:03 A story of growth through staying on post-sale07:22 Exit #3: Never exiting, but freeing yourself within the business09:20 Choosing the right exit for your life10:24 Think 2–5 years ahead to own your exit11:49 Final thoughts: Make the business serve youKEYWORDSbusiness exit strategy, selling a business, entrepreneurial freedom, business ownership, scaling a company, staying after a sale, passive ownership, exit planning, Oak IQ Investments, Own The Exit podcastWANT 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!

How do you build true financial freedom without trading time for money? In this powerful conversation, Rick Pino reveals how entrepreneurs can escape the grind by focusing on value exchange, serving instead of selling, and leveraging digital products to scale income beyond limits.From his early days as a worship leader to building multi-million-dollar businesses and now teaching others to monetize their expertise online, Rick shares timeless principles for creating wealth, time freedom, and impact.TAKEAWAYSWhy selling is serving, not takingThe Jewish wealth principle of value exchangeHow to disconnect your time from your dollarWhy digital products are the fastest wealth path in 2025The Be → Do → Have framework for successRESOURCES MENTIONEDRick Pino Official SiteFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠Rick PinoCHAPTERS00:00 The Jewish wealth principle: value exchange02:00 Rick Pino’s entrepreneurial journey05:00 Balancing faith, purpose, and profit09:15 Solving problems vs. selling products13:20 Sales as service: shifting your mindset17:40 Digital products: the fastest wealth path23:08 Be → Do → Have: the success framework30:00 Taking ownership and self-agency36:14 Building businesses that create time freedom40:00 Exit Round questions with Rick PinoKEYWORDSdigital entrepreneurship strategies, how to build wealth without trading time, value exchange principle, selling as serving mindset, creating scalable digital products, how to monetize your expertise online, financial freedom for entrepreneurs, business mindset shifts, be do have framework for success, solving problems to create wealth, online business models 2025, scalable income strategies, disconnecting time from money, how to create passive income with digital products, faith and entrepreneurship balanceWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

We’ve officially hit 100 episodes of Own the Exit! In this milestone conversation, Caleb and Aaron reflect on the lessons learned from two years of weekly episodes, highlight unforgettable guest moments, and—for the first time ever—answer the same Exit Round questions they’ve asked every guest.From how to build with the end in mind, to why your business shouldn’t become your prison, to the importance of stacking skills and planning your freedom, this episode is a candid and inspiring look behind the scenes of the journey so far.TAKEAWAYSHow and why Own the Exit was createdThe biggest lessons learned from the incredible guests hosted on the showWhy most entrepreneurs accidentally build a cage instead of freedomThe myth of “selling your soul” to your businessThe five Exit Round questions every entrepreneur should ask themselvesFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 Celebrating 100 episodes of Own the Exit01:08 Why we started this podcast02:33 The theme of building with the end in mind04:15 What we learned from 100 guests06:31 The winding, non-linear entrepreneurial journey07:56 The most powerful guest lessons09:16 Why your business shouldn’t be your prison11:06 Answering The Exit Round for the first time18:06 What we’d tell our younger selves20:05 How we create freedom through business23:18 Why you need a plan and an exit strategy24:11 Thank you for 100 episodes!KEYWORDSentrepreneurship lessons from 100 episodes, how to build a business with the end in mind, business exit strategy planning, how to create financial freedom through business, time freedom for entrepreneurs, scaling a business sustainably, avoiding entrepreneurial burnout, business planning and goal setting, why most entrepreneurs fail to exit, how to make your business run without you, exit strategy for small business owners, building a sellable business, lessons from top entrepreneurs, creating passive income while scaling, avoiding the business owner trapWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

We hit #336 on the Inc. 5000 list. That’s top 0.001% out of 32 million businesses in America. But what happens after the balloons drop, the champagne's gone, and the party’s over? In this episode, Caleb and Aaron pull back the curtain on the hard truths behind fast growth—and why it nearly broke their business.This episode is not a humblebrag—it’s a warning. Rapid growth sounds sexy until you're managing burnout, cashflow crunches, and five-year hold assets with delayed returns. Tune in as the team shares what it *really* means to scale intelligently, and how they're building a company that will last decades, not just make headlines.TAKEAWAYS Why fast growth can be a hidden liability The real reason most businesses fail (hint: it’s not revenue) How to avoid burning out your team while scaling The difference between a ‘grow-at-all-costs’ mindset and strategic growth Why infrastructure matters more than another sale How Oak IQ became the 10th fastest growing real estate firm in the U.S.RESOURCES MENTIONEDInc. 5000 ListFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS00:00 - Growth vs. Sustainability01:00 - Oak IQ Makes the Inc. 500003:00 - Hidden Costs of Scaling Fast06:00 - Profit, Cashflow, and Burnout09:00 - The Strategic Growth Mindset12:00 - Why Every Asset is Its Own Business16:00 - Lessons for Long-Term WealthKEYWORDSInc 5000, fast growth, strategic growth, business scaling, real estate investing, Oak IQ, cashflow management, private equity, sustainability in business, entrepreneur lessonsWANT 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!

Inflation isn’t slowing down—and if you’re holding cash, you’re losing wealth every day. In this solo episode, Aaron explains how to make inflation work for you instead of against you by leveraging debt and owning hard assets that appreciate while the dollar loses value.You’ll learn why “cash is king” is a dangerous myth in an inflationary economy, how debt can actually be a wealth-building strategy, and why hard assets like real estate can protect you from the silent thief of inflation.TAKEAWAYSWhy inflation compounds over time and erodes buying power.How debt becomes cheaper in real dollars over the years.The dangers of hoarding cash during inflationary cycles.Why hard assets like real estate outpace inflation.Three actionable steps to hedge against inflation.RESOURCES MENTIONEDOwn The Exit ResourcesFOLLOWS⁠Oak IQ Investments⁠⁠Own The Exit⁠⁠Aaron Investing⁠⁠CHAPTERS00:00 How inflation erodes your wealth00:38 Why inflation compounds year after year01:42 Wages vs. inflation03:07 Riding the inflation wave with hard assets05:24 Why debt is king in an inflationary economy06:48 The danger of hoarding cash07:48 Three steps to hedge against inflation09:24 Summary: make inflation work for youKEYWORDSinflation strategy, how to hedge against inflation, debt vs cash, real estate as inflation hedge, why debt is good during inflation, how inflation compounds, wealth building strategies, hard assets vs cash, inflation survival guide, owning rental properties, inflation and mortgage debt, passive income from real estate, economic inflation planning, financial freedom during inflation, Oak IQ Investments, Own The Exit podcastWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to discover how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

In this episode, Caleb delivers a blueprint for real entrepreneurial freedom. This isn’t about quitting your business—it's about building one that doesn’t require you to be on the clock. If your income dies the moment you unplug, you're not truly free.Caleb walks you through the mindset shift from operator to architect, how to calculate your personal freedom number, and the exact systems that turn hustle into leverage. This is the episode every overworked founder needs to hear—because freedom doesn’t come from more effort, it comes from better design.TAKEAWAYSOperators grind; owners build systems that scale.Freedom starts with a personal “freedom number”—not random income goals.Stacking income streams is essential: active, passive, and leveraged.Document, automate, and delegate through operational, financial, and people systems.Define what “exit” means for you—and reverse engineer it one system at a time.RESOURCES MENTIONED⁠OakIQ.com⁠FOLLOWS⁠⁠⁠Oak IQ Investments⁠⁠⁠⁠⁠Own The Exit⁠⁠⁠⁠Caleb Investing⁠⁠CHAPTERS0:40 What Real Ownership Means1:08 Operators Grind. Owners Build.2:06 Start Delegating Today2:30 Define Your Freedom Number3:03 Stack Income Streams4:00 The 3 Critical Systems4:35 The Exit Blueprint Recap5:02 Your First Small StepKEYWORDSentrepreneurial freedom, exit strategy, business systems, leveraged income, passive income, freedom number, operator to owner, business automation, founder mindset, exit blueprint, cashflow systems, real estate investing, build a business that runs without you, own the exit podcast,WANT TO LEARN MORE?Join us on ⁠⁠LinkedIn⁠⁠, dive into our enriching content on ⁠⁠YouTube⁠⁠, and explore ⁠⁠our website⁠⁠ to unravel how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone who wants to build a stable future. Listen to all episodes on ⁠⁠Spotify⁠⁠, ⁠⁠Apple Podcasts⁠⁠, or any preferred podcast platform!

This episode is a punch in the face to every sales myth you’ve ever believed. Caleb sits down with Benjamin Dennehy, famously branded the UK’s Most Hated Sales Trainer, to dismantle the fake confidence, emotional attachment, and lack of process plaguing modern sales teams. If you want to stop losing deals—and your dignity—this one’s a must-listen.Benjamin goes deep into the psychology of selling, why being liked is killing your close rate, and how most entrepreneurs unknowingly train their teams to be manipulated by buyers. Brutal honesty meets elite strategy in this hilarious, no-holds-barred conversation.TAKEAWAYSMost salespeople are emotionally attached to outcomes—and it’s killing their performance.Your prospects are following a process designed to deceive and plunder you.If you don't control the sales process, you’re being controlled by it.Order takers aren’t salespeople. Learn the difference or lose money.Sales must be structured, controlled, and disqualifying—not winged.RESOURCES MENTIONEDBenjamin Dennehy Official SiteFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠Benjamin DennehyCHAPTERS1:24 Why He Calls Himself “Most Hated”5:06 Emotional Weakness in Sales9:43 Why Most Hires Are Sales Fails14:35 Sales Isn’t a Numbers Game21:29 The Prospect Matrix Exposed30:02 How to Sell Without Being Used37:14 Proof His System Actually Works45:09 His Wild Exit Strategy48:07 Benjamin’s One Big Lesson51:08 Free Gift for ListenersKEYWORDSsales training, sales psychology, emotional selling, sales process, disqualifying prospects, high ticket sales, sales team management, Benjamin Dennehy, own the exit podcast, how to close deals, sales strategy, sales mindset, sales objections, elite sales tactics, business to business salesWANT 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!

In this solo, Caleb uncovers the under-the-radar investment opportunity no one’s talking about—because they’re all distracted by AI. But here’s the twist: the AI revolution isn’t just about tech stocks. It’s about energy—and the power it takes to run this new world.With staggering stats on global energy demand and hard truths about renewable scalability, Caleb makes the case for why oil and gas—yes, really—are poised for asymmetric returns. This episode is for investors who see past the headlines and follow smart money to where the real cash will be made.TAKEAWAYSTraining and running AI models requires massive electricity output.Renewables can’t scale fast enough to meet the exploding demand.Oil and gas remain the backbone of global energy, despite ESG hype.Upstream oil investment is declining while demand keeps rising.This creates a rare window for asymmetric returns in hard energy assets.RESOURCES MENTIONEDOakIQ.comFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS1:36 AI’s Hidden Energy Cost3:11 Why Renewables Can’t Keep Up4:55 Global Energy Investment Trends6:03 Demand Surges, Supply Shrinks7:13 Oil & Gas: The Contrarian Play8:11 Own the Engine, Not Just the ExitKEYWORDSAI energy demand, oil and gas investing, upstream oil, passive cash flow, hard assets, electricity crisis, smart money, ESG vs. returns, contrarian investing, own the exit, Caleb OAKIQWANT 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!

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.TAKEAWAYSYou 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 MENTIONEDRich Dad Poor Dad by Robert KiyosakiFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit ⁠⁠⁠⁠⁠Aaron Investing⁠⁠Caleb Investing⁠CHAPTERS0:13 Losing Yourself in the Build0:27 Should You Build One Business or Ten?2:44 Why Balance Is an Enigma5:11 Execution Always Beats the Idea7:32 The Entrepreneurial Growth Curve9:49 Why You Keep Starting Over11:50 Are You Willing to Stay Committed?14:02 Creating Overlap Not Chaos16:17 The Overflow Principle Explained18:31 You’re Not Elon Musk20:47 Shiny Objects Steal Your Time22:56 Stop Chasing the Rush25:12 Walmart, Amazon, and Singular FocusKEYWORDSstacking 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 plateauWANT 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!

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.TAKEAWAYSBuild 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 MENTIONEDMultiplierU.comOakIQ.comFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Caleb Investing⁠CHAPTERS0:48 Hailey Bieber’s $1B Exit1:07 Founder-Market Fit vs. Product-Market Fit2:12 Why Personal Credibility Matters3:13 The Origin Story of Multiplier U4:14 Find the Right Audience Obsession4:24 Start Narrow, Scale Broad5:30 Engineering Virality6:41 Build a Medium Moat First7:25 Exit at the Peak, Not the Bottom8:41 The 5-Step Copy/Paste Exit FormulaKEYWORDShailey 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 companyWANT 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!