The Journey (with Leo Young)

Personal Growth, Executive Coaching, and Global Brand Building (w/ Robert White) [TJP Ep36]

In this episode of The Journey, Leo sits down with Robert White, leadership expert, executive mentor, and founder of two global leadership development companies that have trained more than 1.4 million people across four continents. Robert shares the story behind building massive training organizations, living and working across Asia for over two decades, and why he ultimately chose to focus on mentoring individuals instead of scaling organizations. He explains the belief systems that quietly shape our behavior, the hidden mindset that holds many high achievers back, and why personal responsibility is the foundation of real leadership. The conversation explores entrepreneurship, human potential, cultural awareness in global business, and the principles Robert discovered after studying thousands of high performers. If you are a founder, leader, or entrepreneur looking to grow both your business and yourself, this episode offers timeless insights from someone who has spent 50 years studying human transformation. Key topics covered * The belief that silently limits high achievers: “I am not enough” * How Robert built leadership programs that trained 1.4 million people * Lessons from building companies across the United States and Asia * Why awareness is the most important leadership skill * The difference between guilt and shame across cultures * Growing a company almost entirely through referrals * The mindset shift that helped Robert triple his income after personal growth training * Why entrepreneurs must learn quickly from what works and what fails * The eight principles that separate high performers from everyone else * How commitment drives success even when everything else breaks down Timestamps 00:00 Introduction to Robert White 00:54 The belief that drives many high achievers 04:58 Why we search for evidence to confirm our beliefs 07:44 Robert’s early business and turning point at age 27 10:37 Discovering personal development training 12:41 Rapid business growth after mindset changes 13:52 Founding leadership training companies 15:15 Why learning from reality matters in business 17:10 Moving to Japan and building a global company 20:23 Early struggles starting a business abroad 23:04 Growing a company through referrals 25:31 Culture, belief, and commitment inside organizations 27:57 The eight principles behind high performers 30:30 Focus and disciplined personal change 32:52 Cultural differences in global leadership 35:15 Why even coaches need coaches 38:39 Lessons from living abroad and returning home 40:13 How to connect with Robert 🤝 Connect with Robert White Website: https://extraordinarypeople.com [https://extraordinarypeople.com/] 👋 Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young [https://www.linkedin.com/in/leo-young] Instagram: https://www.instagram.com/leoyoungrealestate [https://www.instagram.com/leoyoungrealestate] Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call [https://tidycal.com/leoyoungrealestate/investor-alignment-call] 👍 Support the Show If this episode brought you value, please 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. Always consult licensed professionals before making investment or business decisions. #LeadershipDevelopment #EntrepreneurMindset #PersonalGrowth #ExecutiveLeadership #BusinessStrategy #FounderJourney #MindsetMatters #TheJourneyPodcast #LeoYoung

Building a Real Estate Portfolio from Scratch: 30 Years in Flipping, Development, and Multifamily (w/ Adriana Barrerro) [TJP Ep35]

In this episode of The Journey, Leo sits down with Adriana Barrero, co founder of Elan Equity and a seasoned real estate operator with nearly three decades of experience across residential, development, multifamily, and commercial real estate. Adriana shares her journey from immigrating to the United States with 300 dollars to building and redeveloping properties in Austin’s urban core. She explains how resilience, pivoting through adversity, and long term thinking shaped her approach to investing. The conversation dives into underwriting discipline, sponsor vetting, conservative projections, and why values matter more than marketing decks. If you are an investor who cares about durability, integrity, and protecting capital through market cycles, this episode offers hard earned perspective from someone who has taken deals full cycle. Key topics covered * Why pivoting is the most important skill in business and investing * From immigrant beginnings to full cycle multifamily operator * Lessons learned from flipping, wholesaling, and ground up development * Why multifamily fits the “basic necessity” investing thesis * Red flags in underwriting and overly optimistic projections * How cap rates really impact long term outcomes * The importance of sponsor background checks and due diligence * Why “conservative” is often misused in investment decks * Values, honesty, and protecting investor capital * Thinking in probabilities instead of promises Timestamps 00:01 Adriana’s background and introduction 00:44 Biggest lesson learned this year 03:51 Immigrating with 300 dollars and building from scratch 06:11 Moving internationally and discovering real estate 08:14 First unexpected real estate win 10:40 Transition from residential to multifamily 14:54 Hard lessons from development projects 18:00 Pivoting and problem solving in real estate 20:26 Entering commercial real estate 22:17 How Adriana underwrites deals 28:11 Vetting sponsors and background checks 30:51 Most important trait in an operator 32:21 Why “conservative” is often misused 34:30 Proving doubters wrong 🤝 Connect with Adriana Barrero LinkedIn: https://www.linkedin.com/in/adriana-barrero/ [https://www.linkedin.com/in/adriana-barrero/]  Facebook: https://www.facebook.com/adriana.barrero.193648 [https://www.facebook.com/adriana.barrero.193648]  Website: http://elanequity.com [http://elanequity.com] Email: Adriana@ElanEquity.com [Adriana@ElanEquity.com]  Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young [https://www.linkedin.com/in/leo-young] Instagram: https://www.instagram.com/leoyoungrealestate [https://www.instagram.com/leoyoungrealestate] Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call [https://tidycal.com/leoyoungrealestate/investor-alignment-call] Support the show If this episode brought you value, follow, rate, and share the podcast so more investors can discover conversations like this. Disclaimer This podcast is for educational purposes only. It is not financial, legal, or tax advice. Always consult licensed professionals before making investment decisions.

How Business Owners Can Hire Better: Behavioral Data, Role Fit, & the Cost of Bad Hires (w/ Tiffany Slowinski) [TJP Ep34]

In this episode of The Journey, Leo sits down with Tiffany Slawinski, founder of Team Spark Advisors, Culture Index expert, and former VP of Sales who has overseen more than 200 markets. With a background in psychology and years of leadership experience, Tiffany helps CEOs and founders put the right people in the right seats so their businesses can grow without unnecessary friction. Tiffany shares why most business problems are actually people problems, how behavioral data changes hiring decisions, and the hidden cost of keeping the wrong person in the wrong role. The conversation dives into leadership blind spots, cultural fit, hiring mistakes, and why doubling down on strengths creates stronger companies than obsessing over weaknesses. If you are a founder, CEO, or business owner struggling with hiring, turnover, or team alignment, this episode will change how you think about building your organization. Key topics covered * Why people, not marketing or strategy, are usually the growth bottleneck * How Culture Index measures work related behavioral traits * The real cost of a bad hire and employee turnover * Why likability in interviews can be misleading * Hiring for the dominant function of a role * The difference between autonomy, social ability, and detail orientation * When to adapt a role versus when to replace the person * Why stress and misalignment create long term business risk * How founders can double down on strengths instead of fixing weaknesses * Building teams that allow visionaries to stay visionary Timestamps 00:00 Why most business problems are people problems 01:09 Tiffany’s biggest lesson this year 03:02 What Culture Index is and how it works 04:15 Tiffany’s journey from psychology to business leadership 07:58 Building the right role before hiring 12:48 Why interviews can be misleading 15:03 Can personality traits change over time 17:08 Right person, right seat philosophy 19:35 Why business owners struggle with hiring 23:06 Common hiring mistakes founders make 25:38 Is this only for large companies 30:30 Tiffany’s turning point with Culture Index 32:40 Measuring ROI of hiring correctly 35:16 The hidden cost of stress and misalignment 36:53 Hard but necessary leadership questions 38:28 Playing to strengths versus fixing weaknesses 41:07 How to connect with Tiffany Connect with Tiffany Slowinski LinkedIn: https://www.linkedin.com/in/tiffanyslowinski/ Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young [https://www.linkedin.com/in/leo-young] Instagram: https://www.instagram.com/leoyoungrealestate [https://www.instagram.com/leoyoungrealestate] Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call [https://tidycal.com/leoyoungrealestate/investor-alignment-call] Support the show If this episode brought you value, follow, rate, and share the podcast so more founders can discover these conversations. Disclaimer This podcast is for educational purposes only. It is not financial, legal, or tax advice. Always consult licensed professionals before making business decisions

How he Built a Profitable Startup: Raising Capital, Hiring Offshore & Keeping Control (w/ Nathan Gwilliam) [TJP Ep33]

In this episode of The Journey, Leo sits down with Nathan Gwilliam, serial entrepreneur and founder behind multiple digital companies, including the platform behind one of the most visited adoption websites in the world. Nathan shares how he started his first company as a college student in the late 90s, grew it into a global platform over 24 years, and eventually exited before launching several new ventures. His latest company, PodUp, was built after experiencing firsthand how complex and fragmented the podcasting ecosystem had become. What started as a challenge while publishing daily content turned into the idea for an all-in-one platform designed to help creators launch, grow, and monetize podcasts more efficiently. The conversation explores entrepreneurship, raising capital, building global teams, and why profitability should always be a founder’s north star. Nathan also shares lessons from scaling multiple companies, how referrals drive both fundraising and growth, and why decisive action matters more than perfect decisions. If you are a founder, creator, or entrepreneur looking to build scalable digital businesses, this episode offers practical insights from someone who has repeatedly built, sold, and rebuilt companies from the ground up. Key topics covered * How Nathan built and sold one of the largest adoption platforms online * The challenge that led him to create an all-in-one podcasting platform * Russell Brunson’s challenge to publish every day for a year * Turning podcast content into millions in new company value * Why raising capital can feel like giving up control * The importance of referrals when raising investment capital * Why founders should focus on profitability early * Building global teams and scaling operations in India * The importance of hiring A players and building strong systems * Why indecision can be worse than making the wrong decision Timestamps 00:00 Introduction to Nathan Gwilliam 00:52 Nathan’s early entrepreneurial journey 02:00 Building adoption.com and the mission behind it 03:30 The idea behind PodUp and solving podcasting complexity 04:21 Russell Brunson’s challenge to publish daily 06:20 The reality of producing daily content 08:27 Turning a podcast into a new software company 09:35 Raising capital and why Nathan dislikes fundraising 11:44 How referrals helped raise millions in investment 12:46 Lessons from selling previous companies 14:05 Avoiding bad investor terms 15:55 Why founders must prioritize profitability 17:41 Building a global team in India 19:07 Breaking misconceptions about international talent 22:16 The importance of hiring the right leaders 24:55 Building systems and processes that scale 27:42 Why content builds trust with customers 29:31 Nathan’s most important lesson from entrepreneurship 30:38 Why indecision can be worse than failure 31:21 The power of testing and iteration in business 33:28 How to connect with Nathan 🤝 Connect with Nathan Gwilliam https://www.linkedin.com/in/nathangwilliam [https://www.linkedin.com/in/nathangwilliam] https://www.instagram.com/nathangwilliam/?hl=en [https://www.instagram.com/nathangwilliam/?hl=en] https://www.facebook.com/nathangwilliam/ [https://www.facebook.com/nathangwilliam/] https://x.com/NathanGwilliam [https://x.com/NathanGwilliam] 👋 Connect with Leo https://www.linkedin.com/in/leo-young [https://www.linkedin.com/in/leo-young] https://www.instagram.com/leoyoungrealestate [https://www.instagram.com/leoyoungrealestate] Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call [https://tidycal.com/leoyoungrealestate/investor-alignment-call] 👍 Support the Show If this episode brought you value, please follow, like, 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. Always consult licensed professionals before making investment or business decisions.

How VCs Evaluate Startups: Founders, Data, Market Size & Early-Stage Investing (w/ Matt Ober) [TJP Ep32]

In this episode of The Journey, Leo sits down with Matt Ober, short term rental operator, investor, and founder of a fast growing hospitality portfolio built on data driven investing and systems based operations. Matt explains how he approaches short term rentals as a business, not a side hustle. He breaks down how underwriting, market selection, automation, and guest experience work together to drive consistent cash flow, even in competitive markets. This conversation goes beyond Airbnb basics and into how professional operators think about risk, scalability, and long term sustainability. If you are interested in short term rentals, hospitality investing, or building systems that remove you from day to day operations, this episode offers practical insights you can apply immediately. Key topics covered * How Matt evaluates short term rental markets before buying * The data points that matter most when underwriting STR deals * How systems and automation reduce operational stress * Why guest experience directly impacts revenue and reviews * Common mistakes new STR investors make when scaling too fast * How Matt thinks about risk management in hospitality investing * The difference between owning a rental and running a rental business * Building teams and processes that scale without burnout Timestamps 00:00 Intro 02:00 Matt’s background and entry into short term rentals 05:00 Why STRs should be treated like a business 08:00 Market selection and underwriting fundamentals 12:00 Data, pricing, and demand drivers 16:00 Systems, automation, and operational efficiency 20:00 Guest experience and brand differentiation 24:00 Scaling responsibly and avoiding common pitfalls 28:00 Managing risk and market shifts 32:00 Long term strategy for STR investing 36:00 Advice for investors entering short term rentals 40:00 How to connect with Matt42:00 Final thoughts and takeaways Connect with Matt Ober Website: https://www.socialleverage.com [https://www.socialleverage.com] LinkedIn: https://www.linkedin.com/in/obermattj [https://www.linkedin.com/in/obermattj] X: https://x.com/obermattj?s=21 [https://x.com/obermattj?s=21] Connect with Leo LinkedIn: https://www.linkedin.com/in/leo-young [https://www.linkedin.com/in/leo-young] Instagram: https://www.instagram.com/leoyoungrealestate [https://www.instagram.com/leoyoungrealestate] Invest with us: https://tidycal.com/leoyoungrealestate/investor-alignment-call [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. Always consult licensed professionals before making investment or business decisions.