The Journey (with Leo Young)

Leo Young
  • 5.0 (13)
  • Entrepreneurship

The Journey with Leo Young features transparent conversations with entrepreneurs, investors, and operators about what it really takes to build wealth, lead teams, and scale real businesses. Leo is the founder of Cornell Communities, a real estate investment firm revitalizing manufactured housing communities nationwide. Before that, he was a top performer at Tesla and worked in private equity acquisitions. This podcast goes beyond surface-level success stories to unpack the decisions, failures, mindset shifts, and operating lessons behind the journey.

  1. 3d ago

    From Negative Net Worth to Location Freedom: Building Businesses That Run Without You (w/ Adrienne Green) [TJP Ep54]

    In this episode of The Journey, Leo sits down with Adrienne Green, founder of Workergenics and Investaway, who went from negative net worth and a high school math teaching career to building two remote companies, selling a real estate agent team, and traveling the world full time with her husband and three kids. She is calling in from Lima, Peru. She did not stumble into this life. She designed it through five-year vision mapping, monthly family finance meetings, and a relentless focus on putting the right systems and people in place so her time would never be the bottleneck. This episode is part operations masterclass, part life design blueprint, and part honest conversation about what it actually takes to build a business that runs without you. 👉 What you'll learn: 🌎 How she designed a location-independent life and pulled it off with three young kids 📊 The three financial statements every family should be running quarterly 🤖 How 50 transactions in six months changed her entire view on virtual assistants 🌏 Hiring, vetting, and retaining VAs from the Philippines the right way 💸 How to structure bonuses and compensation so your team actually stays 🧹 Why building lean systems in thin margins makes you more profitable when you scale 🎯 The one mindset shift that turned every expense into a question about ROI // Timestamps // 00:00 From Negative Net Worth to Entrepreneurial Success 04:53 The Journey to Location Freedom 10:53 Building a Virtual Assistant Business 15:03 Navigating the Challenges of Hiring VAs 23:16 Developing Mid to High-Level Talent 24:09 Navigating Team Dynamics and Cultural Challenges 26:48 Finding the Right Fit: The Bus Analogy 28:55 Extreme Ownership in Leadership 33:25 Budgeting for Talent: ROI Considerations 37:30 Compensation Structures and Incentives 40:34 Training and Development for Virtual Assistants 43:26 Lessons Learned: Ramping Up with Virtual Teams 44:54 Connecting with Adrienne Green: Opportunities for Collaboration 👇 From Adrienne: If you feel like you don't have enough time or freedom, start here. 📋 Free Time + Freedom Starter Pack: letsgo.adriennegreen.com/timefreedomstarter  🤝 Connect with Adrienne Green Website: adriennegreen.com Workergenix: workergenix.com Instagram: instagram.com/arealgreen YouTube: youtube.com/@ARealGreen LinkedIn: linkedin.com/in/arealgreen Facebook: facebook.com/ARealGreen123 Podcast: The Freedom Blueprint on Spotify and Apple Podcasts 👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call  👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Entrepreneurship #VirtualAssistants #LocationIndependent #RemoteWork #TheJourneyPodcast #LeoYoung #AdrienneGreen #Workergenics #Investaway #RealEstateInvesting #LifeDesign #WorkLifeBalance #FamilyFinance #ScalingABusiness

  2. Sep 26

    Retired at 43 from $115,000 in debt: how he engineered an early retirement plan (w/ Daniel Rogers) [TJP Ep53]

    In this episode of The Journey, Leo sits down with Daniel Rodgers, a two-time Google Manager of the Year who retired at 43 after starting his career with over $100,000 in student loan debt and $15,000 in credit card debt. His book Escape the Clock won the 2025 American Writing Award for Best Personal Finance Book. Daniel did not stumble into financial independence. He built a program, tracked every decision in a spreadsheet, and ran it for 20 years until the math said he was done. No guru framework. No lottery ticket. Just a system that he now gives away for free. This episode is a masterclass in how ordinary people escape ordinary outcomes. 👉 What you'll learn: 📊 How a spreadsheet built in debt became a retirement program at 43 💳 The financial landmines hitting Gen Z harder than any generation before 🏠 Buy vs. rent: how to make the right call based on your actual numbers 🧠 Why hitting a retirement number is not enough without cash flow 📉 Withdrawal strategy vs. cash flow strategy: the hybrid that actually works ⏰ The golden handcuffs moment: a hospital visit that finally made him quit 🔄 Why paying off your mortgage early is not always the right move 📚 The two books on money psychology that changed how he thinks // Timestamps // 00:00 Introduction to Financial Independence 03:41 The Journey to Financial Freedom 08:01 Pivotal Moments in Career and Life 14:09 Navigating Housing Decisions 19:25 Redefining the American Dream 24:01 The Psychology of Financial Independence 31:02 Building a Balanced Financial Portfolio 37:14 Lightning Round: Insights and Reflections 👇 From Daniel: Everything you need to start building your program is in one place. 🔗 Free planner, newsletter, book, and time with Dan: escapetheclock.com  🤝 Connect with Daniel Rodgershttp://www.escapetheclock.com/subscribe  👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call 👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #PersonalFinance #EarlyRetirement #FinancialIndependence #FIRE #TheJourneyPodcast #LeoYoung #DanielRodgers #EscapeTheClock #WealthBuilding #MoneyMindset #RetirementPlanning #CashFlow #Google #DebtFree

  3. Sep 23

    $300M Litigation Attorney on How to Protect Your Business Legally (w/ Parag Amin) [TJP Ep52]

    In this episode of The Journey, Leo sits down with Parag Amin, trial attorney, founder of one of Southern California's most decorated litigation firms, and Amazon bestselling author of The Entrepreneur's Legal Playbook. He has saved and recovered over $300 million for his clients, been recognized as a Rising Star by Super Lawyers for 10 consecutive years, and received the LA Times Legal Visionary Award for 2026. He built all of it from his bedroom in a townhouse, with no clients, no office, and no backup plan. This episode covers what it actually takes to survive your worst season as a founder, why the legal wrapper around your business matters more than most owners realize, and why the story behind the book starts with his father. 👉 What you'll learn: ⏱️ The 30,000 days framework and why time is the only asset that matters 📄 Practicing law from a townhouse bedroom and scaling to 14 staff 🦠 Losing money every month during COVID and choosing to stay anyway ⚖️ Contingency vs. hourly cases and how the wrong mix almost killed the firm 🧠 Why better questions get better results in law and in business 📖 The story behind The Entrepreneur's Legal Playbook and why his father is the reason it exists 🔍 Arbitration clauses: when to fight them and when to let it go 💡 The one belief he wishes he had challenged much earlier in life // Timestamps // 00:00 Introduction 00:31 Why you only get 30,000 days 02:21 From document review to starting a law firm 05:51 Learning to litigate when someone's throwing bricks at you 08:44 What makes a top trial attorney 10:40 Raising kids while running a business 13:31 The COVID crisis and deciding whether to quit 17:49 The turnaround plan and rebalancing the client mix 22:42 Personal brand and systems as growth drivers 25:25 His father's story and why he wrote the book 28:03 Key lessons from The Entrepreneur's Legal Playbook 31:45 When to settle vs. go to trial 36:17 Lightning round 40:10 What his father thinks of what he's built 41:03 How to connect with Parag 👇 From Parag: If you are a business owner who wants to protect what you are building, start here. 📖 The Entrepreneur's Legal Playbook: Navigating the Pitfalls That Can Destroy Your Business: available on Amazon 🤝 Connect with Parag Amin Instagram: @paragaminesq  Linkedin: Parag L. Amin Youtube: Parag L. Amin Website: www.paragaminesq.com  👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call  👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Entrepreneurship #LegalAdvice #TrialAttorney #BusinessOwner #TheJourneyPodcast #LeoYoung #ParagAmin #EntrepreneursLegalPlaybook #Litigation #COVID #Resilience #PersonalBrand #SmallBusiness #Founders

  4. Sep 12

    How Everyday Investors Can Access US Real Estate Through Private Equity (w/ August Biniaz) [TJP Ep51]

    In this episode of The Journey, Leo sits down with August Biniaz, co-founder and CIO of CPI Capital, a cross-border private equity firm that has closed over $225 million in multifamily and build-to-rent assets across the US Sun Belt. Their mandate from day one: give Canadians access to US real estate through their retirement accounts, something almost no one else had figured out how to do. August grew up in Iran, where real estate was the only hedge against hyperinflation. He got his license in his twenties, did fix and flips, built custom homes, ran a construction company, and eventually realized the ceiling was too low. Private equity had no ceiling. So he built one. This episode is part deal structure deep dive, part cross-border investing masterclass, and part founder story about betting on a market nobody else was serving. 👉 What you'll learn: 🏗️ From fix and flips to custom homes to a $225M private equity firm 🇨🇦 Why Canadians are underserved when it comes to US real estate exposure 🏦 How CPI structured a cross-border fund that files US taxes on behalf of Canadian investors 📊 Multifamily vs. build-to-rent: risk profiles, return targets, and when each makes sense 🤝 How he found his co-founders including why his wife became the best investor relations person in the room 💡 The Alex Hormozi framework that convinced him to stop home building and go bigger 📉 Why rent control in Canada is bad for consumers not just investors 🎯 The one thing he would do differently: stop chasing shiny objects sooner // Timestamps // 00:00 Navigating the Turbulent Real Estate Landscape 03:42 The Emotional Side of Investing 06:48 The Evolution of CPI Capital 11:52 Understanding the Multifamily Market 20:27 Cross-Border Investment Challenges 28:04 Comparing Canadian and US Real Estate 36:17 The Development vs. Value-Add Debate 41:00 Lessons Learned and Future Focus 🤝 Connect with August Biniaz Website: cpicapital.com linkedin.com/in/augustbiniaz instagram.com/cpicapital x.com/CPI_Capital youtube.com/@realestateinvestingdemystified   👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call 👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice.  All investments carry risk. Consult licensed professionals before making investment decisions. #RealEstateInvesting #PrivateEquity #Multifamily #BuildToRent #CrossBorderInvesting #TheJourneyPodcast #LeoYoung #AugustBiniaz #CPICapital #CanadianInvestors #PassiveInvesting #Syndication #SunBelt #WealthBuilding

  5. Sep 5

    How His Company Grew From $3.5M to $30M in 2 Years (w/ Damon Flowers) [TJP Ep50]

    In this episode of The Journey, Leo sits down with Damon Flowers, serial entrepreneur, founder of Modern Operators, and a 22 year student of business who scaled an e-commerce company from $3.5 million to $30 million in two years, built a training company from zero to $12 million, and spent the same two decades studying why founders keep getting in their own way. His conclusion: the chaos most founders experience on the outside is almost always rooted in something unresolved on the inside. And the businesses that win are the ones that stop outsourcing their core to a stack of disconnected tools and start building an operational engine that runs without the owner in the room. This episode goes deep on what modern operations actually means and why growth is the last thing you should be focused on. 👉 What you'll learn: ⚙️ The five stages of business and why growth is stage five not stage one 🧠 Why founders are the biggest bottleneck in their own company 🤖 How to deploy agentic AI across your entire team not just yourself 🗂️ What a company OS is and why Notion plus good structure changes everything 📊 The difference between systematizing for scale and systematizing for exit 🚢 The crew and the boat: the ownership culture framework that actually sticks 🔁 Why most businesses are not set up for growth before they try to grow 💡 What Damon changed his mind on after 20 years of building // Timestamps // 00:00 Introduction to Agentic AI and Business Transformation 02:58 The Evolution of Business Operations 05:28 The Five Stages of Business Growth 11:16 Building a Solid Foundation for Growth 16:56 Leveraging AI in Business Operations 22:28 Creating a Culture of Ownership and Empowerment 27:43 Mindset Shifts for Business Owners 33:34 The Importance of Organizational Structure 39:11 Final Thoughts and Advice for Entrepreneurs 👇 From Damon: If you're a founder in the $2M to $30M range and stuck in the day-to-day, reach out directly. 💼 LinkedIn: linkedin.com/in/damonflowers 💼 LinkedIn (Mark): linkedin.com/in/mark-malian 📺 YouTube: How to Build a Company That Runs Without You: youtube.com/watch?v=7iCPDcIsyeU 💬 Community: reddit.com/r/ModernOperators 🌐 Newsletter: modernoperators.com/archive  👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call 👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Entrepreneurship #Operations #ModernOperators #AIForBusiness #SystemsThinking #TheJourneyPodcast #LeoYoung #DamonFlowers #ScalingABusiness #CompanyOS #AgenticAI #FounderMindset #BusinessSystems #Delegation

  6. Aug 29

    How to Build a Business That Runs Without You, from a Top Leadership Consultant and Author (w/ Liz Weber) [TJP Ep49]

    In this episode of The Journey, Leo sits down with Liz Weber, a leadership consultant with over 30 years of experience, author of more than 10 books, and one of fewer than 100 people in the country holding both a Certified Speaking Professional and Certified Management Consultant designation. She is ranked in the top 30 global gurus on leadership alongside John Maxwell and Simon Sinek. Her take: most leadership problems are not complicated. They are just misdiagnosed. Liz works with business owners, C-suite executives, and boards of directors on strategic planning, org structure, and talent development. In this episode she gets specific about what is actually breaking down inside growing companies and what to do about it. 👉 What you'll learn: 🧠 Why helping your team too often trains them to stop thinking for themselves 📋 The delegation and decision ladder that tells everyone what they own 🗂️ How to use vision, mission, and values as management tools not just wall decor 📣 The one question that forces accountability without confrontation 🔁 Why most leaders implement before they track and how that derails growth 👥 How to have the necessary conversations without dreading them 📐 How to structure an org chart before you have the headcount to fill it 🎯 The 12 month challenge that will change how your business runs // Timestamps // 00:00 Navigating Overwhelm in Leadership 10:06 The Journey to Consulting and Leadership 22:11 The Fundamentals of Business Success 22:57 Navigating Leadership Challenges 27:52 Implementing Effective Business Structures 32:25 Delegation and Accountability in Leadership 36:10 Setting Expectations and Performance Management 42:54 Future-Proofing Your Business Leadership 🤝 Connect with Liz Weber Website: www.WBSLLC.com  linkedin.com/in/lizwebercmc/  👋 Connect with Leo   linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call  👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Leadership #BusinessGrowth #Entrepreneurship #TeamBuilding #TheJourneyPodcast #LeoYoung #LizWeber #StrategicPlanning #Delegation #CompanyCulture #Accountability #SmallBusiness #ScalingUp #ManagementConsulting

  7. Aug 22

    How this Former Pro-Baseball Player Built and Sold His $800m Financial Advisory Practice to His Employees (w/ Jack Oujo) [TJP Ep 48]

    In this episode of The Journey, Leo sits down with Jack Oujo, CPA, CFP, and founder of one of the nation's largest tax-focused wealth management firms. He spent eight years as a professional baseball umpire, reached Triple-A, and was named the top umpiring prospect in the minor leagues. The MLB said no. He had a pregnant wife, no money, and had to start over from scratch. What followed was a career most advisors would not believe is possible: an $800 million practice built entirely on referrals, never a single paid client, 15 employees, and an exit to two people he mentored from within. This episode is about reinvention, trust, and what it actually takes to build something that outlasts you. 👉 What you'll learn: ⚾ Eight years in the minor leagues, a pregnant wife, and a release that changed everything 📚 CPA, CFP, master's in taxation, and two kids, all done in three and a half years while working full time 🤝 How to build an $800 million practice without spending a dollar on marketing 💼 Why combining accounting and wealth management was an open field nobody else wanted 👥 Hiring for character over credentials and building a culture people refuse to leave 📋 The quantified bonus system that made performance self-policing 🚪 Firing the bottom tier of clients and what happened next 📖 Too Smart to Be an Umpire: the book that connects all the dots //Timestamps// 00:00 The Journey of Jack Ojo: From Umpire to Entrepreneur 02:59 Lessons in Business Transition and Exit Strategies 05:50 The Importance of Mentorship and Seeking Help 08:35 Building a Wealth Management Firm: Insights and Strategies 11:33 Creating Trust and Client Relationships in Business 14:27 The Art of Umpiring: Skills and Lessons Learned 17:20 The Bonds of Sports: Community and Connection 22:46 The Power of Networking 23:26 Transitioning Careers: From Baseball to Wealth Management 24:33 Building a Boutique Firm: Client Selection and Culture 26:02 Employee Development and Company Culture 28:05 Transparency in Business: Sharing Numbers with Employees 29:41 Best Business Decisions: Slow Growth and Staffing 32:08 Hiring the Right People: Character Over Credentials 34:46 Creating a Positive Work Environment 35:39 Attracting Talent: The Role of Referrals 37:59 Focusing on Growth: Systems and Planning 40:49 Reflections on Business Decisions and Personal Growth 42:34 The Journey of Writing: Lessons from 'Too Smart to Be an Umpire' 🤝 Connect with Jack Oujo https://toosmarttobeanumpire.com/ https://www.linkedin.com/in/jack-oujo-cpa-cfp-ms-tax-97906810/  👋 Connect with Leo linkedin.com/in/leo-young i nstagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call 👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Entrepreneurship #WealthManagement #Baseball #Reinvention #TheJourneyPodcast #LeoYoung #JackOujo #TaxPlanning #BusinessExit #Referrals #CompanyCulture #SmallBusiness #FinancialAdvisor #TooSmartToBeAnUmpire

  8. Aug 15

    How He Built a 3,000+ Car Rental Company and Turned Down Venture Capital (w/ Rei Vardi) [TJP Ep47]

    In this episode of The Journey, Leo sits down with Rei Vardi, founder of Eon, a national EV sharing platform with over 3,000 vehicles in 50 cities across the US. He started with one Tesla outside a college dorm, survived COVID with $500 in his bank account, slept in a van outside Silicon Valley pitching investors, watched two co-founders walk out at the worst possible moments, and never took a single dollar from venture capital. He almost lost the business five times in eight years. He built it anyway. This episode is about judgment, resilience, and what it actually takes to build something real without a safety net. 👉 What you'll learn: 🚗 Starting a national EV platform with one Tesla and no money 🏕️ Sleeping in a van in Silicon Valley to chase a term sheet 💸 Surviving COVID with $500 in the bank 🤝 Two co-founders who walked at the worst possible moments and what he did next 🚫 Why walking away from VC funding was the best decision he never planned 📈 Zero ads, zero funding, and 3,000 vehicles: how SEO and word of mouth built the fleet 🧠 Why good judgment is worth more than productive output at any level 🛠️ What it looks like to build an operations business the right way from day one // Timestamps // 00:00 The Journey of Ray Vardi: From Dorm Room to National EV Platform 04:14 The Importance of Decision-Making in Leadership 08:49 From College to Entrepreneurship: The Birth of Eon 17:09 Overcoming Challenges: The Struggles of Building a Business 20:16 Facing Adversity: The Entrepreneurial Journey 24:43 The Art of Asking for Help 27:57 Valuing Your Business: Lessons Learned 32:37 Scaling Challenges in the Mobility Industry 36:18 Embracing Failure as a Path to Success 38:10 Finding Joy in the Entrepreneurial Process 38:58 Future Vision: Building a Frictionless Experience 👇 From Rei: Try it the next time you travel. 📲 Download the Eon Rides app: eonrides.com 🤝 Connect with Rei Vardi https://www.linkedin.com/in/reivardi/ https://www.linkedin.com/company/eonrides/ https://www.eonrides.com/ 👋 Connect with Leo linkedin.com/in/leo-young instagram.com/leoyoungrealestate Invest with us: tidycal.com/leoyoungrealestate/investor-alignment-call 👍 If this episode brought you value, follow, rate, and share. ⚠️ Disclaimer: This podcast is for educational purposes only. Not financial, legal, or tax advice. All investments carry risk. Consult licensed professionals before making investment decisions. #Entrepreneurship #Startups #EVSharing #Tesla #BootstrappedFounder #TheJourneyPodcast #LeoYoung #ReiVardi #Eon #NoVC #Resilience #Founder #BuildingWithoutFunding #StartupLife

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The Journey with Leo Young features transparent conversations with entrepreneurs, investors, and operators about what it really takes to build wealth, lead teams, and scale real businesses. Leo is the founder of Cornell Communities, a real estate investment firm revitalizing manufactured housing communities nationwide. Before that, he was a top performer at Tesla and worked in private equity acquisitions. This podcast goes beyond surface-level success stories to unpack the decisions, failures, mindset shifts, and operating lessons behind the journey.

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