The Journey (w/ Leo Young)

Leo Young
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The Journey with Leo Young brings unfiltered, high-impact conversations with entrepreneurs, investors, and operators who built success the hard way. Leo is a former Tesla top performer and private equity acquisitions pro who now leads Cornell Communities, revitalizing affordable housing nationwide. He breaks down the mindsets, failures, and strategies behind wealth building, disciplined investing, leadership, and scaling real businesses through real execution. Expect raw stories, sharp insights, and tactics you can use to level up.

  1. FEB 7

    How to Raise Private Money for Real Estate Deals (w/ Jay Conner) [TJP Ep29]

    In this episode of The Journey, Leo sits down with Jay Conner, real estate investor and nationally recognized expert on raising private money without banks. Jay explains how he replaced traditional financing with private lenders, the mindset shift required to raise capital ethically, and why trust matters more than interest rates. The conversation breaks down private money fundamentals, common mistakes investors make, and how to build a reliable capital network that works in any market. If you want to understand how serious investors fund deals consistently, even when banks tighten lending, this episode is a must listen. Key topics covered How Jay moved from bank loans to 100 percent private moneyHow to attract private lenders without pitching or pressureThe framework Jay uses to educate and onboard lendersThe mindset required to raise capital with confidenceCommon mistakes investors make with private moneyWhy private funding creates speed, certainty, and leverage Timestamps 00:00 Intro 02:00 Jay’s background and early investing journey 05:00 The deal that changed his approach to financing 08:00 What private money really is 12:00 How Jay raised capital from private lenders 16:00 Educating lenders instead of pitching 20:00 Structuring win win relationships 24:00 Common private money mistakes 28:00 Protecting trust and credibility 32:00 Scaling faster without banks 36:00 Why private money works in any market 40:00 Final advice and takeaways Free resources from Jay Download Jay’s free book Where to Get the Money Now and learn how to raise unlimited private money without relying on banks. Free guide: https://www.jayconner.com/MoneyGuide Free book with shipping and handling: https://www.jayconner.com/Book Connect with Jay Conner Website: https://www.jayconner.com LinkedIn: https://www.linkedin.com/in/privatemoneyauthority/ YouTube: https://www.youtube.com/@raisingprivatemoneyrealestate Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young Instagram: https://www.instagram.com/leoyoungrealestate Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call Support the show If this episode brought you value, follow, rate, and share the podcast so more people can discover it. Disclaimer This podcast is for educational purposes only and is not financial, legal, or tax advice.

    42 min

  2. JAN 26

    When Leads Destroy Value (w/ Mark Osborne) [TJP Ep28]

    In this episode of The Journey, Leo sits down with Mark Osborne, a real estate investor and operator focused on building durable businesses through discipline, fundamentals, and long term thinking. Mark shares how his investing approach has evolved across multiple market cycles, why fundamentals matter more than hype, and how operators can avoid common mistakes that stall growth. The conversation explores decision making under uncertainty, risk management, and what it takes to stay consistent when markets shift and capital becomes harder to access. This episode offers a grounded perspective for investors who want sustainable growth, clear thinking, and real execution instead of shortcuts. Key topics covered Building durable real estate businessesWhy discipline matters more than market timingOperating through changing market cyclesBalancing growth with risk managementWhy fundamentals outlast hypeTrust, reputation, and long term relationshipsLessons from both easy and difficult markets Timestamps 00:00 Intro 02:00 Mark’s background and investing journey 05:00 Early lessons that shaped his approach 08:00 Market cycles and investor psychology 12:00 Risk management and downside protection 16:00 Common investor mistakes 20:00 Scaling responsibly 24:00 Decision making under uncertainty 28:00 Building trust and credibility 32:00 Discipline, patience, and consistency 36:00 Advice for today’s market 40:00 How to connect with Mark42:00 Final thoughts Free resource from Mark Download a free copy of the #1 best selling book on disciplined decision making, long term thinking, and building durable wealth through every market cycle.https://modernrevenuestrategies.com/freedownload Connect with Mark Osborne Website: https://modernrevenuestrategies.com LinkedIn: https://www.linkedin.com/in/remarkablemark/ Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young Instagram: https://www.instagram.com/leoyoungrealestate Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call Support the show If this episode brought you value, follow, rate, and share the podcast so more people can discover conversations like this. Disclaimer This podcast is for educational purposes only. It is not financial, legal, or tax advice.

    46 min

  3. 12/20/2025

    From $120M Defense Programs to Passive Income (w/ Flint Jamison) [TJP Ep27]

    In this episode of The Journey, Leo sits down with Flint Jamison, aerospace engineer turned full-time real estate investor and founder of Vestus Capital. After a decade managing multimillion-dollar aircraft programs at Boeing, Flint realized that climbing the corporate ladder would never give him the freedom he wanted. He took the engineering mindset he mastered in aerospace and applied it to underwriting, systems, and building passive income through multifamily real estate. Flint shares the exact frameworks he used to transition out of his W2 job, the mistakes passive investors must avoid, and how to evaluate operators, deals, and risk with clarity. This conversation goes deep into identity shifts, family pressures, burnout, entrepreneurship, and the courage required to reinvent your life. If you’re an engineer, a W2 professional, or anyone considering a major pivot, Flint’s story and systems will help you see the path forward. 👉 Highlights You Will Learn in This Episode ✈️ How Flint went from aerospace engineering to real estate 🔥 The burnout moment that pushed him to rethink his career 🧠 Why engineers succeed in underwriting and due diligence 📉 The biggest mistakes passive investors make 👤 Why the operator matters more than the deal 💡 The mindset shift that helped him leave corporate 🏢 How he built Vestus Capital and began raising capital 🔎 The framework he uses to vet sponsors and investments ⏳ How he bought back his time and redesigned his lifestyle 👨‍👩‍👧 Navigating identity, family expectations, and career transitions 📈 Advice for W2 professionals starting their investing journey //Timestamps// 00:00 Intro 01:10 Flint’s early career in aerospace 03:00 Managing multimillion-dollar aircraft programs 05:20 Burnout and the turning point 07:00 First exposure to passive investing 08:30 The engineering mindset applied to real estate 10:10 Mistakes most passive investors overlook 12:40 Why operator quality drives everything 15:00 The moment Flint knew he could leave corporate 17:30 Identity shift and family dynamics 19:40 Building Vestus Capital 21:00 His system for vetting deals and sponsors 23:10 How he built trust while raising capital 25:30 Buying back time and pursuing freedom 27:00 Advice for W2 professionals 29:30 The frameworks he wishes he knew earlier 32:00 How to connect with Flint 🤝 Connect with Flint Website: vestuscapital.com LinkedIn: linkedin.com/in/flintjamison 👋 Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young Instagram: https://www.instagram.com/leoyoungrealestate Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call ⚠️ Disclaimer This podcast is for educational purposes only. It is not financial, legal, or tax advice. Always consult licensed professionals before making investment or business decisions. 👍 Support the Show If this episode brought you value, please follow, rate, and share the podcast so more people can discover conversations like this.

    45 min

  4. 12/13/2025

    Why Your Business Feels Chaotic (w/ Caleb Christopher) [TJP Ep26]

    In this episode of The Journey, Leo talks with Caleb Christopher, founder of Creative TC and DOSGuard. Caleb is a former corrections officer and cybersecurity specialist who now handles more than 50 creative finance transactions a month. He applies engineering-level thinking and risk management to real estate, operations, and systems that scale. Most people think creative finance is shady or guru-driven. Caleb treats it as a risk problem that needs structure, incentives, and ethics. He built a remote first operations company using talent in South Africa, created an insurance product for due on sale risk, and developed TABLE, a values-based operating system for his team. This episode is packed with insights on entrepreneurship, stress, partnerships, culture, hiring, risk, and building companies that last. What You Will Learn How Caleb went from corrections officer to IT to cybersecurity to creative finance The accidental landlord story that started everything Why creative finance is a risk management discipline How he built a remote first team in South Africa The near bankruptcy moment that changed his leadership How TABLE values guide every decision How to hire for judgment Why founders need to say no How he launched a title company built for scale Why AI amplifies both good and bad decisions Timestamps 00:00 Intro01:00 Real estate marketing hot takes02:00 Toxic positivity and guru culture03:20 Career path to risk management04:30 Discovering real estate and creative finance08:30 Building Creative TC10:30 Why he avoids hiring from mentorship groups11:20 Reputation and protecting your name12:00 The stress of payroll and uncertainty13:30 High judgment employees16:20 Strong opinions and attracting the right people17:10 Learning to say no18:00 Founder brain vs team stability20:40 Compensation, structure, culture22:00 The TABLE values24:50 Adopting AI responsibly26:10 Raising capital27:20 Why title companies are underrated31:20 Partnership experiences38:00 Key man insurance40:00 Ethical dealmaking42:50 Connect with Caleb45:00 The question he wants every founder to ask One Smart Move Before You Dive Into Creative Finance If you are exploring creative finance, raising capital, or building a business with real risk involved, do not guess. Visit my site to learn practical frameworks for evaluating deals, managing risk, and protecting your investors. Connect with Caleb Learn more at calebchristopher.io and follow @fcalebchristopher on Instagram and Facebook. Website: calebchristopher.ioInstagram: instagram.com/fcalebchristopherFacebook: facebook.com/FCalebChristopher Connect with Leo LinkedIn: linkedin.com/in/leo-youngInstagram: instagram.com/leoyoungrealestateInvest with us: tidycal.com/leoyoungrealestate/investor-alignment-call Disclaimer This podcast is for educational purposes only. It is not financial, legal, or tax advice. Consult licensed professionals before making decisions. If you enjoyed this episode, follow, rate, and share the podcast.

    44 min

  5. 12/06/2025

    What No One Tells You About Buying a Franchise (w/ Giuseppe Grammatico) [TJP Ep25]

    Leo sits down with Giuseppe Grammatico, franchise consultant, entrepreneur and author of Franchise Freedom. After helping more than a thousand people assess whether they should leave their W2 and become business owners, Giuseppe has built a proven framework for evaluating risk, opportunity and personal fit. He explains why so many people feel overwhelmed when exploring business ownership, how franchise lists send people in the wrong direction, and why the real starting point is clarity about your lifestyle, goals and the role you want to play. Giuseppe breaks down how to evaluate opportunities without emotion, what franchisors actually look for, and how to narrow thousands of options into a few that truly align with your life. Whether you are exploring franchising, real estate, or any form of entrepreneurship, this conversation gives you a clearer way to think about ownership, risk and long term decision making. What you will learn: Why most people want to start a business but do not know where to beginThe common mistakes new entrepreneurs make when researching franchisesHow to define your ideal business model before reviewing brandsLifestyle fit vs trend chasingWhat franchisors look for in qualified candidatesWhy your daily role matters more than the industryThe differences between home based, retail and full buildout modelsWhen franchising is not the right pathHow to review opportunities with clarity instead of overwhelm⏱️ Timestamps 00:00 Introduction and Giuseppe’s background 05:00 Why people feel stuck when exploring business ownership 10:00 How to define your ideal business before looking at brands 15:00 Lifestyle fit and understanding the owner role 20:00 What franchisors look for in qualified candidates 25:00 Startup timelines and common business models 30:00 When franchising may not be the right fit 👇 One Smart Move Before You Explore Business Ownership (from Giuseppe) If you are thinking about franchising or leaving your W2 to start a business, do not guess your way through it. Download my free book to learn how to evaluate opportunities, reduce risk, and choose a model that fits your goals and lifestyle. 📘 Free Book: https://ggthefranchiseguide.com/book/ 🎥 More Education: https://www.youtube.com/@ggthefranchiseguide Connect with Giuseppe Facebook: https://www.facebook.com/GGTheFranchiseGuide Instagram: https://www.instagram.com/ggthefranchiseguide Twitter: https://twitter.com/ggfranchguide YouTube: https://www.youtube.com/@ggthefranchiseguide Spotify Podcast: https://open.spotify.com/show/13LTN5UzA57w2dTB4iV0fm LinkedIn: https://www.linkedin.com/company/gg-the-franchise-guide Apple Podcast: https://podcasts.apple.com/us/podcast/franchise-freedom/id1499864638 TikTok: https://tiktok.com/@ggthefranchiseguide Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young Instagram: https://www.instagram.com/leoyoungrealestate Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-callDisclaimer This episode is for educational and entertainment purposes only. Nothing here is financial, legal or tax advice. Always consult your own licensed professionals before making decisions.

    43 min

  6. 11/28/2025

    How a Ranch Kid Became the Cowboy Who Built 600 Units (w/ Joe Rinderknecht) [TJP Ep24]

    From ranch kid to 600+ units — this is the story of grit, resilience, and rebuilding after tragedy.In this episode, Leo sits down with Joe Rinderknecht, co-founder of Cowboy Capital and Upgrade Partners Capital. Joe grew up ranching in rural Idaho before breaking generational expectations and building a real estate portfolio of more than 600 multifamily units across the Midwest and Texas. Joe shares how tragedy reshaped his life, how he rebuilt from nothing, the brutal value-add deal that nearly took him out, and the mindset that carried him through the darkest seasons. This is one of the most raw and inspiring stories we’ve had on the show. What you’ll learn in this episode:• How Joe went from ranch life to multifamily ownership• The mindset shift that helped him overcome generational limitations• How one tragic accident changed his life forever• The value-add project that nearly broke him• How he manages stress, burnout, and family life• Why execution matters more than perfect decision-making• How he built a lean, highly effective real estate team• The mission behind Tiny’s Tribe and how he helps families in crisis Connect with Joe:Website & Newsletter: www.cowboycapital.usFree eBook: https://offer.fundraisecapital.co/free-ebook/YouTube: https://www.youtube.com/channel/UC2fHkPIsNqOAwifn7jbG5SwLinkedIn: https://www.linkedin.com/in/joerinderknecht/ Connect with Leo:LinkedIn: https://www.linkedin.com/in/leo-young/Instagram: https://www.instagram.com/leoyoungrealestate/Investor Call: https://tidycal.com/leoyoungrealestate/investor-alignment-call Disclaimer:This episode is for educational and entertainment purposes only. Nothing shared is financial, legal, or tax advice. Always consult licensed professionals before making investment decisions.

    46 min

  7. 11/22/2025

    The Mindset Behind Managing $2.5B in Client Assets (w/ Andrew Kahner) [TJP Ep23)

    In this episode, Leo sits down with Andrew Kahner, Managing Director and Private Wealth Advisor at UBS Wealth Management and co-founder of Connor Segal Partners. With nearly 20 years of experience advising entrepreneurs, executives and high net worth families, Andrew leads one of New York’s top advisory teams, managing more than $2.5 billion in client assets. Andrew breaks down UBS’s Liquidity / Longevity / Legacy framework and how his 12 person team helps clients turn income and business success into durable, multi generational wealth. Through simple analogies and real world examples, he explains what actually goes into building, protecting and transferring wealth at scale. This episode explores how ultra successful families think about risk, why timing the market usually fails, and how to prepare early for liquidity events so you do not leave millions on the table in taxes or inefficient structures. 👉 Highlights you will learn in this episode: 💰 How Andrew’s team manages $2.5B for entrepreneurs, executives and families 🧱 The UBS Liquidity / Longevity / Legacy framework and how to apply it 🧮 The core questions he asks every client about budget, goals and liabilities 📉 Why trying to time the market destroys more wealth than downturns ⏱️ How bear markets actually behave and why 2 to 3 years of liquidity matters 🏦 Public vs private markets and why illiquidity can be a benefit 🧠 How family offices and ultra wealthy clients think differently 🏛️ When and why to set up a family office based on tax and estate rules 👥 How Andrew built a 12 person advisory team and hires for culture ⚖️ Balancing an elite career with family and personal life 🚀 Why founders should call years before a liquidity eventIf you want to learn how serious wealth creators think about liquidity, risk and legacy, and how to turn income or a future exit into long term financial freedom, this episode is essential. //Timestamps// 00:27 - Helping successful professionals turn income into lasting wealth 01:44 - Team approach to client support 02:11 - Framework for internal liquidity and planning 03:51 - Bespoke investment strategy08:38 - Importance of understanding budgets and spending 10:56 - Common mistake: trying to time the market 13:03 - Liquidity bucket strategy 18:41 - Long-term investment thinking for family offices 23:20 - Tax and estate planning considerations for wealthier individuals 32:38 - Types of clients: founders and corporate executives 🤝 CONNECT WITH ANDREWWebsite: http://www.ubs.com/fa/andrewkahner 👋 CONNECT WITH LEO1) LinkedIn: https://www.linkedin.com/in/leo-young/2) Instagram: https://www.instagram.com/leoyoungrealestate/3) Want to invest with us? https://tidycal.com/leoyoungrealestate/investor-alignment-call ⚠️ Disclaimer:Nothing in this episode or description is financial, legal or tax advice. All opinions are for educational and entertainment purposes only and do not represent the views of UBS or any other institution. Please consult your own financial, legal and tax professionals before making any investment or planning decisions. 🔥 Subscribe for more conversations on real estate, AI and entrepreneurship. 👍 Like this episode if Andrew's story gave you new ways to think about wealth, and drop your thoughts or questions in the comments. #RealEstateInvesting #ArtificialIntelligence #Entrepreneurship #WealthManagement #FinancialFreedom

    37 min

  8. 11/07/2025

    The Secret Framework Behind AI-Powered Real Estate (w/ Georgy Marrero) [TJP Ep22]

    In this episode, Georgy Marrero shares how he’s bridging the gap between AI and commercial real estate. Georgy is the founder of Equis Capital, where he’s led over 20 acquisitions across 750+ units in multifamily, senior housing, industrial, and land. Before becoming an investor, Georgy was an engineering leader at Meta’s AI Labs and Amazon Alexa, and he holds a U.S. patent in real-time computer vision. Through his fractional CTO studio, NoomShot, Georgy now helps real estate and service businesses integrate production-grade AI tools into their operations, a space often overlooked by traditional tech talent. 👉 Highlights you’ll learn in this episode: 🏗️ How Georgy transitioned from Meta engineer to a real estate investor 📘 The lesson from Rich Dad, Poor Dad that shaped his mindset about time and money 💡 Why multifamily remains a timeless investment class and how he expanded into senior housing and industrial assets 🌍 How he’s introducing multifamily concepts to the Dominican Republic ⚙️ The systems and structure behind Equis Capital’s deal flow and operations 🤖 How to apply AI frameworks to real estate, operations, and business workflows 🧠 Why most AI implementations fail and how to fix it with adoption and training 💬 The four-step process for automating tasks the right way without overengineering 🔥 How startup principles and AI thinking are reshaping commercial real estate If you’re interested in AI, real estate investing, or scaling a business through smarter systems, this episode breaks down how both worlds collide and how to use AI to buy back your time. //Timestamps// 00:00 Intro 00:30 Georgy’s background and transition from Meta to real estate 01:46 How Rich Dad, Poor Dad changed his view on time vs. money 03:46 Raising capital and building trust through experience 05:59 What Equis Capital invests in and how they structure deals 07:14 How Equis expanded into senior housing and industrial assets 08:04 Why there’s no multifamily concept in the Dominican Republic 09:31 The mission behind bringing U.S.-style multifamily to the DR 10:37 How Equis manages operations, deal sourcing, and capital 12:41 Building systems and SOPs to manage multiple projects 13:52 Why operations is the most important part of any real estate deal 16:09 Where AI fits into acquisitions, financing, and operations 17:58 Building an AI underwriting tool for real estate 18:44 Why AI training is more valuable than new AI tools 19:38 How to decide what to automate, delegate, or eliminate 20:47 The four-step framework for documentation and automation 24:13 Why quality control and human oversight still matter in AI 25:29 How AI can manage inbound and outbound leads in real estate 26:39 The 80/20 of automation for real estate operators 28:15 Why simplicity beats overengineering 30:03 The real reason most AI initiatives fail: adoption and culture 32:29 Training teams and integrating AI into daily workflows 34:51 The startup grind vs. real estate investing 37:19 How to build teams and structure incentives in real estate 41:59 The advice Georgy would give his younger self 42:14 Who Equis and NoomShot are looking to partner with 43:27 How to connect with Georgy Marrero 🤝 CONNECT WITH GEORGYWebsite: https://equis.capitalLinkedIn: https://linkedin.com/in/georgymarreroInstagram: https://instagram.com/georgymh 👋 CONNECT WITH LEO 1) LinkedIn: https://www.linkedin.com/in/leo-young/ 2) Instagram: https://www.instagram.com/leoyoungrealestate/ 3) Want to invest with us? https://tidycal.com/leoyoungrealestate/investor-alignment-call Disclaimer:The information shared in this episode is for educational and informational purposes only. It should not be considered legal, financial, or investment advice. Always consult with a qualified professional before making any real estate or investment decisions. The views and opinions expressed by the guests are their own and do not necessarily reflect those of the host or production team.

    44 min
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The Journey with Leo Young brings unfiltered, high-impact conversations with entrepreneurs, investors, and operators who built success the hard way. Leo is a former Tesla top performer and private equity acquisitions pro who now leads Cornell Communities, revitalizing affordable housing nationwide. He breaks down the mindsets, failures, and strategies behind wealth building, disciplined investing, leadership, and scaling real businesses through real execution. Expect raw stories, sharp insights, and tactics you can use to level up.

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