Investing To Win

Garret Wong
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

Hey there, audience! This is the Investing to WIN podcast, the show dedicated to inspiring budding entrepreneurs and business owners to live balanced, fulfilled lives. Our guests share their personal journeys, struggles, adversity and success stories. If you're a person that is working too hard, thinking of change or looking towards a future goal, you've come to the right place! This show is committed to offering honest conversations to discuss common sense strategies and professional guidance to achieving success and fulfillment. Your host is Garret Wong; an Ex-Scientist turned Serial Entrepreneur who, while growing up saw his father and mother run 4 businesses simultaneously while still being able to travel. But when his father passed away at the early age of 59, just before he was ready to retire, Garret's path and perspective of "success" was changed forever. In addition to his other businesses he brings decades of experience in buying, renovating, and managing rental properties for investors across the world. Thanks for being here and get ready to Invest to Win!! https://garretwong.com/

  1. Investing Smarter with AI: Wall Street Veteran Eric Chu on Building Wealth, Avoiding Emotion, and the Future of Fintech

    2d ago

    Investing Smarter with AI: Wall Street Veteran Eric Chu on Building Wealth, Avoiding Emotion, and the Future of Fintech

    Investing Smarter with AI: Wall Street Veteran Eric Chu on Building Wealth, Avoiding Emotion, and the Future of Fintech In this episode of *Investing to Win*, host **Garret Wong** sits down with Eric Chu to dive into: - Smarter Investing for Everyday People Using AI-Powered Tools - The Rise of AI Data Centers as an Investment Opportunity - Lessons from Wall Street: How Retail Investors Can Compete with Institutions …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary In this episode of Investing to Win, host Garret Wong sits down with Eric Chu, a Wall Street veteran with over 15 years of experience spanning hedge funds, investment banking, and data center development. Eric shares how his front-row seat to the 2008 financial crisis and the COVID-19 market disruption shaped his investing philosophy — and ultimately led him to co-found Trade Desk Securities, a next-generation fintech platform designed to help everyday investors build smarter, more disciplined portfolios. Eric breaks down the three most important lessons every investor needs to internalize: remove emotion from decision-making, build a well-diversified portfolio, and stop trying to time the market. Drawing on his years as an institutional analyst and operator, he explains why individual investors actually have a critical edge over institutions — a longer investment horizon — and how to leverage that advantage through discipline, tools, and a clear plan. The conversation is grounded, practical, and refreshingly free of jargon. The episode also dives deep into Trade Desk Securities' flagship AI-powered engine, Prism, which is designed to help self-directed investors monitor risk, execute thematic trades, and build recurring investment habits — without being overwhelmed by thousands of tickers, complex tools, or conflicting signals. Eric explains how the platform was built specifically for busy working professionals: lawyers, accountants, pharmaceutical executives, and other high-income earners who want to invest intelligently but don't have hours to devote to research every week. Toward the end of the conversation, Garret and Eric explore the intersection of AI and data center infrastructure as an investment category — from how to gain exposure through ETFs to the environmental concerns around power and water consumption. Eric closes with a memorable golf analogy: you don't have to shoot for eagles to win — just avoid the double bogeys. For investors at any level, this episode is a masterclass in disciplined, long-term thinking. --- ## 🎯 Key Takeaways • Control your emotions first — Fear and greed are the number one enemy of both retail and institutional investors; the best returns come from discipline, not reaction. • Diversify intentionally — Spreading risk across sectors, asset classes, and geographies is not optional; it is the foundation of a resilient portfolio. • Stop trying to time the market — Chasing rallies and panic-selling during downturns are the mistakes even professional investors make most often. • Use your long investment horizon as a weapon — Individual investors can hold positions for 5–15 years; institutional investors often can't, which creates real opportunities for patient retail investors. • Leverage AI tools for productivity, not shortcuts — Platforms like Prism can cut research time dramatically, but investors still need to review outputs critically rather than treating AI as a black box. • Managing risk is as important as finding great ideas — As Eric's golf analogy explains, avoiding the big losses matters just as much as picking the winners. --- ## 🧠 Topics Covered • The emotional psychology of investing and why emotion is every investor's biggest risk • How retail investors can realistically compete with institutional money managers • The long investment horizon advantage that individual investors hold over hedge funds • How Trade Desk Securities and its Prism AI engine were built to serve busy working professionals • Paper trading as an essential first step for new investors building good habits • The role of ETFs in gaining diversified exposure to AI and data center infrastructure • Why AI-powered financial tools need regulatory guardrails — and how Trade Desk implements them • Data center development: from 4 kilowatts per rack to gigawatt-scale AI infrastructure • Environmental sustainability in data center design — liquid cooling, closed-loop systems, and innovation • What has changed in markets over the last decade: faster information, algorithmic trading, and democratized AI tools --- ## 🔍 SEO Keywords investing for beginners, AI investing tools, Wall Street insider advice, retail investor tips, Trade Desk Securities, fintech platform, data center investment, AI infrastructure stocks, portfolio diversification, how to avoid market timing, institutional vs retail investors, paper trading for beginners, Eric Chu, long-term investing strategy, Prism AI engine, ETF investing, algorithmic trading, financial technology, Investing to Win podcast, emotion in investing --- ## ⏱️ Timestamps [00:00:02] – Introduction: Eric Chu's Wall Street Roots and What Investing Banks Taught Him About Becoming a Founder [00:01:11] – The Top 3 Investing Lessons Eric Would Tell His Younger Self [00:03:05] – Why Market Timing Is So Tempting — And Why It Almost Always Fails [00:04:43] – The Individual Investor's Hidden Advantage Over Wall Street Institutions [00:07:39] – Eric Chu's Full Career Story: From NYU Business School to Hedge Funds, Data Centers, and Fintech [00:10:05] – Why COVID Changed Everything — And How Trade Desk Securities Was Born [00:11:32] – Navigating Two Market Crises: Lessons from 2008 and COVID for Every Investor [00:13:47] – Operator Turned Advisor: How Trade Desk's Unique Background Creates Real Client Value [00:15:34] – Why Trade Desk Was Built: Serving the Busy Professional Who Wants to Invest But Doesn't Have Time [00:19:57] – How Trade Desk Bridges Retail Investing and Institutional Investment Banking in One Platform [00:22:59] – AI Before ChatGPT: How Trade Desk Built Prism and Why Regulatory Guardrails Matter [00:24:13] – Why Fintech Regulation Is a Feature, Not a Bug — And the Barrier It Creates for Bad Actors [00:26:02] – Data Centers, AI Infrastructure, and the NIMBY Problem: A Candid Look at Power and Resources [00:29:32] – Innovative Cooling Solutions and Why the Data Center Industry Is in the First Inning [00:30:58] – How to Invest in AI Infrastructure Without Picking Individual Stocks [00:32:54] – The Real Risk of AI Investment Tools: How to Use Them Without Being Misled [00:36:07] – Inside Trade Desk: KPIs, User Behavior, and Predicting Churn Before It Happens [00:38:53] – A Beginner's First 30 Days: The Case for Paper Trading Before Risking Real Money [00:41:21] – What Eric Believes About Markets Now That He Didn't Believe 10 Years Ago [00:44:12] – Defining Success and Winning in Investing: Eric's Golf Analogy That Every Investor Needs to Hear In his final answer --- ## 👤 About Eric Chu Eric Chu is a Wall Street veteran with more than 15 years of experience across hedge funds, investment banking, and institutional-grade data center development. He earned his MBA from NYU Stern School of Business and went on to work across both the buy side and sell side of finance, including positions at a $2 billion AUM hedge fund during the 2008 financial crisis and as a telecommunications and data center research analyst at a major investment bank. Eric later served as President of the Data Center Infrastructure Group at a publicly listed data center operator, overseeing greenfield and brownfield development projects and deploying over half a billion dollars in capital through a major private equity joint venture across Asia. He is the co-founder and CEO of Trade Desk Securities, a U.S. registered broker-dealer and FINRA member that provides retail investors, high-net-worth individuals, and institutional clients with a technology-forward investment platform powered by AI — including its proprietary Prism engine for portfolio monitoring and risk analysis. --- ## 🔗 Episode Links & Resources • Guest Website: https://www.tradesk.co/ • LinkedIn: https://www.linkedin.com/in/eric-chu-cfa-7159567/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    47 min
  2. AI for Small Business: How to Delegate Smarter, Avoid Costly Mistakes, and Build Real AI Employees

    Jun 23

    AI for Small Business: How to Delegate Smarter, Avoid Costly Mistakes, and Build Real AI Employees

    AI for Small Business: How to Delegate Smarter, Avoid Costly Mistakes, and Build Real AI Employees In this episode of *Investing to Win*, host **Garret Wong** sits down to dive into: - Practical AI Implementation for Small Business Owners - Building and Managing AI Employees and Workflows - AI Risk Management, Security, and Human Oversight …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary In this solo episode, host Garret Wong breaks down one of the biggest misconceptions surrounding artificial intelligence: AI will not save your business—but proper delegation might. Rather than treating AI as a magical solution, Garret explains how business owners can use AI as a practical support tool to reduce repetitive work, improve communication, and create more time for high-value decisions. Drawing from his own experience building AI-powered systems and his personal AI assistant "Jarvis," Garret walks listeners through the specific business functions where AI performs exceptionally well. From email drafting and meeting summaries to SOP creation, research, documentation, and workflow automation, he demonstrates how entrepreneurs can use AI to increase consistency, improve follow-through, and eliminate operational bottlenecks. The episode also explores the risks of over-relying on AI. Garret discusses hallucinations, privacy concerns, data security, operational failures, and the importance of maintaining a "human-in-the-loop" approach. He shares real-world examples of how AI systems can create costly mistakes when given too much authority without oversight. Whether you're considering your first AI-powered workflow or exploring the idea of AI employees within your company, this episode provides a practical framework for evaluating opportunities, reducing risk, and implementing AI responsibly. Listeners will walk away with actionable strategies for identifying the right tasks to automate while keeping critical business decisions firmly in human hands. --- ## 🎯 Key Takeaways • Treat AI as a thinking and communication assistant, not a decision-maker • Use AI to automate repeatable tasks while reserving transformational work for humans • Create SOPs, documentation, and training materials from existing business processes • Maintain human oversight when AI impacts customers, finances, or operations • Build AI workflows around narrow responsibilities instead of broad objectives • Evaluate AI opportunities using frequency, time cost, risk, clarity, and verification --- ## 🧠 Topics Covered • AI implementation strategies for small businesses • Delegation versus automation in entrepreneurship • Building AI employees and workflow automation • Human-in-the-loop AI management • AI-generated content and communication systems • Business process documentation and SOP creation • AI security, privacy, and data protection • Research and decision support using AI • Common AI implementation mistakes • Scaling operations with AI-assisted workflows --- ## 🔍 SEO Keywords AI for business, Small business AI, AI automation, AI employees, Business systems, Workflow automation, Artificial intelligence, Entrepreneurship, Business operations, AI implementation, AI productivity, Business delegation, Human in the loop AI, AI workflows, Process automation, SOP creation, AI tools for entrepreneurs, Business efficiency, Operational excellence, Garret Wong --- ## ⏱️ Timestamps [00:00:00] – Why AI Won’t Save Your Business Without Better Delegation [00:02:22] – Understanding What AI Does Well and Where It Falls Short [00:04:48] – Using AI for Communication, Email Drafting, and Business Writing [00:07:06] – Creating Better AI Outputs by Training Systems to Sound Like You [00:08:09] – Summarizing Meetings, Organizing Information, and Improving Follow-Up [00:09:34] – Turning Everyday Conversations into SOPs, Checklists, and Training Systems [00:12:01] – Leveraging AI for Research, Market Analysis, and Business Intelligence [00:14:29] – The Dark Side of AI: Hallucinations, Errors, and Business Risk [00:16:50] – Why Human Oversight Is Essential in Every AI Workflow [00:19:14] – AI Loops, Operational Failures, and the Importance of Monitoring [00:21:32] – Garbage In, Garbage Out: Improving AI Through Better Inputs [00:24:01] – Building Reliable AI Systems with Guardrails and Documentation [00:26:12] – What a True AI Employee Actually Looks Like [00:28:34] – Security, Privacy, Access Control, and Protecting Sensitive Information [00:31:01] – Creating Specialized AI Skills Instead of One Massive AI Assistant [00:33:24] – The Five Decision Filters for Choosing AI Automation Opportunities [00:35:00] – Using AI to Launch and Scale a New Business [00:35:51] – Final Lessons on Responsible AI Adoption for Entrepreneurs --- ## 👤 About Garret Wong Garret Wong is an entrepreneur, investor, property management executive, and technology strategist specializing in business systems, operational efficiency, and AI implementation. As the host of the Investing To Win Podcast, Garret works with founders, investors, and business leaders to explore practical strategies for growth. Through his work building AI-powered workflows and business automation systems, he helps companies improve productivity while maintaining strong operational controls and human oversight. --- ## 🔗 Episode Links & Resources • Website: https://garretwong.com/ • LinkedIn: https://www.linkedin.com/in/garret-wong-33197913/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    37 min
  3. Entrepreneur Mental Health: Finding Balance, Preventing Burnout & Building Real Success with Kenyada Meadows

    Jun 16

    Entrepreneur Mental Health: Finding Balance, Preventing Burnout & Building Real Success with Kenyada Meadows

    Entrepreneur Mental Health: Finding Balance, Preventing Burnout & Building Real Success with Kenyada Meadows In this episode of *Investing to Win*, host **Garret Wong** sits down with Kenyada Meadows to dive into: - Entrepreneur Mental Health and Balance - Burnout Prevention for Business Owners - Personal Fulfillment, Success, and Leadership …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/QAstJPsDGoI&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary Many entrepreneurs spend years chasing growth, success, and financial freedom, only to discover that the very businesses they built are consuming their time, relationships, and well-being. In this episode, Garret Wong sits down with executive coach, entrepreneur, and author Kenyada Meadows to explore the hidden mental and emotional challenges faced by high-performing business owners. Drawing on more than 25 years of leadership experience in corporate finance, banking, and executive management, Kenyada shares why burnout is often rooted in misaligned priorities rather than workload alone. He explains how entrepreneurs can better understand their motivations, redefine success, and create healthier relationships with work, family, and themselves. The conversation dives into the realities of entrepreneurship, including the immigrant mindset, resilience, contentment versus happiness, and why many entrepreneurs struggle to achieve true balance. Kenyada also shares practical strategies around journaling, therapy, meditation, self-awareness, and building routines that support long-term success. Whether you're scaling a business, managing a growing team, or simply feeling overwhelmed by competing priorities, this episode offers a powerful framework for creating a more sustainable and fulfilling entrepreneurial life. --- ## 🎯 Key Takeaways • Reevaluate whether your work aligns with your personal values and goals. • Build success around contentment and fulfillment rather than constant achievement. • Protect your mental health through intentional reflection, therapy, or journaling. • Create routines that adapt to life's changing seasons instead of seeking perfect balance. • Listen to diverse perspectives when making important personal and business decisions. • Invest in coaching and mentorship to accelerate growth and avoid costly mistakes. --- ## 🧠 Topics Covered • Entrepreneur burnout and mental health • Finding work-life balance as a business owner • The immigrant mindset and entrepreneurial resilience • Happiness versus contentment in business and life • Executive coaching and leadership development • The role of therapy and mental wellness for entrepreneurs • Building sustainable success without sacrificing relationships • Strategic thinking, journaling, and self-reflection • Personal growth and emotional intelligence • Defining success beyond money and business performance --- ## 🔍 SEO Keywords Entrepreneur Mental Health, Entrepreneur Burnout, Business Owner Wellness, Executive Coaching, Leadership Development, Entrepreneur Mindset, Work Life Balance, Personal Growth, Mental Health for Entrepreneurs, Business Success, Founder Mental Health, Executive Leadership, Self Awareness, Productivity, Entrepreneur Coaching, Business Coaching, The New Alpha, Kenyada Meadows, Emotional Intelligence, Entrepreneur Lifestyle --- ## ⏱️ Timestamps [00:00:00] – Entrepreneur Burnout: Why Working Harder Doesn't Always Create Better Results [00:01:44] – Are Entrepreneurs Born or Made? Exploring Nature, Nurture, and Opportunity [00:04:03] – The Immigrant Mindset, Work Ethic, and Building Resilience Through Adversity [00:07:15] – Meet Kenyada Meadows: From Corporate Finance Leadership to Executive Coaching [00:10:19] – Why Entrepreneurs Struggle to Balance Business Success and Family Life [00:13:17] – Can Entrepreneurs Ever Be Truly Happy? Contentment, Gratitude, and Fulfillment [00:16:07] – Measuring Mental Health Through Physical Health, Energy, and Daily Habits [00:18:45] – Handling Criticism, Feedback, and Expectations From Family and Friends [00:23:10] – The Executive Parent Company and Kenyada's Coaching Framework [00:26:17] – Why Coaching, Mentorship, and Therapy Accelerate Personal Growth [00:29:17] – The Power of Verbalizing Problems and Creating Space for Clear Thinking [00:31:46] – Strategic Walks, Journaling, and Developing Self-Awareness as an Entrepreneur [00:34:27] – Building Daily Routines That Support Balance, Health, and Performance [00:39:43] – Defining Success: Relationships, Legacy, and Sustainable Achievement [00:42:42] – Final Thoughts on Entrepreneurship, Mental Health, and Living Intentionally --- ## 👤 About Kenyada Meadows Kenyada Meadows is the Founder of The Executive Parent Company, an executive coach, entrepreneur, and author of The New Alpha. With more than 25 years of experience in corporate finance, banking, and executive leadership—including senior roles at some of the world's largest financial institutions—he helps entrepreneurs, executives, and business owners create greater balance, fulfillment, and sustainable success. His work focuses on leadership development, mental wellness, personal growth, and helping high performers align their professional achievements with meaningful lives. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/QAstJPsDGoI&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • LinkedIn: https://www.linkedin.com/in/kenyadameadowscpaciacfe/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    45 min
  4. Multifamily Investing in a High-Rate Environment with Michael Pouliot | Margin of Safety, Operations & AI

    Jun 9

    Multifamily Investing in a High-Rate Environment with Michael Pouliot | Margin of Safety, Operations & AI

    Multifamily Investing in a High-Rate Environment with Michael Pouliot | Margin of Safety, Operations & AI In this episode of *Investing to Win*, host **Garret Wong** sits down with Michael Pouliot to dive into: - Multifamily investing and operations during rising interest rate environments - Building resilient real estate portfolios through operational excellence - Using AI and technology to improve property management performance …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/7lE4dfglhmU&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary In this episode of Investing to Win, Garret Wong sits down with Michael Pouliot, Co-Founder and CIO of Carbon Residential, to discuss what is really happening in multifamily real estate as investors navigate higher interest rates, refinancing challenges, and changing market conditions. Drawing on his experience at JPMorgan and Merrill Lynch, Michael explains why many multifamily operators are struggling today and how assumptions around debt, cap rates, and rent growth have impacted returns. Michael shares his journey from the fixed-income desks of Wall Street to becoming a fourth-generation real estate entrepreneur focused on workforce housing. He discusses the lessons learned from buying his first investment property, why he chose real estate over traditional finance, and how his family’s real estate background shaped his investment philosophy. The conversation dives deep into Carbon Residential’s unique investment strategy, including its focus on family-oriented workforce housing, top-rated school districts, long-term resident retention, and operational efficiency. Michael explains why multifamily should be viewed as an operating business rather than simply a financial asset and how superior operations create downside protection for investors. Garret and Michael also explore the growing role of AI in property management, from leasing and collections to resident renewals and operational workflows. Michael shares how technology is helping his team improve resident experiences while creating greater efficiency across their portfolio, offering listeners practical insights into the future of real estate investing and management. --- ## 🎯 Key Takeaways • Understand how rising interest rates have created refinancing challenges across multifamily real estate • Focus on operational excellence to improve NOI and protect investor returns • Invest in properties that align with long-term tenant needs and retention • Leverage AI to streamline leasing, collections, and resident communications • Prioritize strong school districts and family-oriented housing when evaluating workforce housing opportunities • Treat multifamily real estate as an operating business, not just a financial investment --- ## 🧠 Topics Covered • Multifamily investing in a high-interest-rate market • Refinancing risk and debt structure challenges • Cap rates, leverage, and value-add investing • Michael Pouliot's transition from Wall Street to real estate • Workforce housing investment strategies • Vertical integration versus third-party property management • Family-focused multifamily communities • Property management operational efficiency • AI applications in real estate and leasing • Long-term wealth creation through real estate ownership --- ## 🔍 SEO Keywords multifamily investing, multifamily real estate, workforce housing, real estate investing, property management, Michael Pouliot, Carbon Residential, real estate operations, commercial real estate, apartment investing, AI in real estate, vertical integration, cash flow investing, interest rates, refinancing risk, cap rates, real estate syndication, passive investing, wealth building, investing to win --- ## ⏱️ Timestamps [00:00:00] – Multifamily Investing Challenges in Today's High Interest Rate Environment [00:01:14] – Understanding Current Multifamily Loan Rates and Government-Backed Financing Programs [00:04:00] – Comparing Today's Interest Rates to the Low-Rate Era of 2020–2021 [00:04:54] – Meet Michael Pouliot: From Wall Street Fixed Income to Multifamily Real Estate [00:06:25] – Managing Institutional Fixed Income Portfolios at JPMorgan and Merrill Lynch [00:08:44] – Why Michael Chose Real Estate Over a Traditional Finance Career [00:12:22] – Buying the First Investment Property and Building Early Real Estate Wealth [00:15:06] – Lessons from Real Estate Investing During and After Market Downturns [00:16:52] – How Rising Rates Impact Multifamily Cash Flow, Valuations, and Refinancing [00:20:11] – Syndicators, Market Cycles, and the Risks of Aggressive Multifamily Investing [00:24:23] – Carbon Residential's Investment Philosophy and Margin of Safety Approach [00:25:25] – Why School Districts Drive Housing Demand and Resident Retention [00:27:27] – Creating Long-Term Tenant Communities Through Family-Oriented Housing [00:31:22] – The Benefits of Investing in Older Multifamily Assets [00:31:50] – Building a Vertically Integrated Multifamily Real Estate Company [00:34:48] – Property Management Efficiency, Staffing, and Operational Performance [00:39:13] – AI in Property Management: Leasing, Renewals, Collections, and Operations [00:44:24] – Why Real Estate Remains a Relationship and People Business [00:45:07] – How Carbon Residential Creates Investor Value Through Operations [00:47:33] – Technology, AI, and the Future of Property Management [00:48:21] – Defining Success, Family, Legacy, and Winning in Life [00:50:02] – Episode Wrap-Up and Final Thoughts --- ## 👤 About Michael Pouliot Michael Pouliot is the Co-Founder and Chief Investment Officer of Carbon Residential, a vertically integrated private equity real estate firm focused on workforce housing throughout the Southeastern United States. Prior to founding Carbon Residential, Michael built his career at JPMorgan and Merrill Lynch, where he managed fixed-income portfolios for ultra-high-net-worth clients, foundations, and institutions. Today, he combines institutional finance expertise with hands-on operational management to acquire, improve, and operate multifamily communities that provide quality housing for middle-income families. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/7lE4dfglhmU&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • Guest Website: https://www.investwithcarbon.com/ • LinkedIn: https://www.linkedin.com/in/michael-pouliot/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    52 min
  5. Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood

    Jun 2

    Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood

    Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood In this episode of *Investing to Win*, host **Garret Wong** sits down with Andy Ellwood to dive into: - Entrepreneurial resilience and startup survival - Leadership, networking, and fundraising in high-growth startups - Building mission-driven companies that solve meaningful problems …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/JiPWC1Cbh7Y&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary Andy Ellwood has experienced the highest highs and lowest lows of entrepreneurship. After helping scale multiple successful startups, including Waze, which was acquired by Google, Andy launched Basket, a grocery technology company focused on helping families save money. The company appeared to be on a strong trajectory until tragedy struck when its largest investor and board chairman unexpectedly died in a plane crash, taking with him a critical funding commitment that the company depended on for survival. In this episode, Andy shares the emotional and operational challenges that followed, including missed payroll, difficult conversations with employees, emergency fundraising, and ultimately shutting the company down. He explains the lessons he learned about succession planning, investor concentration risk, leadership under pressure, and why founders must continuously expand their networks rather than relying on a small circle of supporters. The conversation also explores Andy's philosophy that founders should fall in love with solving a problem rather than becoming attached to a particular company or product. This mindset eventually led him to launch Stretch, a grocery intelligence platform helping consumers compare prices across retailers and combat rising food costs. Listeners will walk away with practical insights on startup resilience, attracting A-players, building optionality in life and business, fundraising strategy, leadership during uncertainty, and the importance of creating businesses that solve real-world problems. --- ## 🎯 Key Takeaways • Never stop expanding your network, even when existing relationships seem secure • Prepare contingency plans for investors, executives, and key team members • Fall in love with solving the problem, not the solution you've built • Use failure scenarios to identify risks before they become reality • Attract A-players by connecting them to a meaningful mission • Create more optionality in life and business to increase long-term success --- ## 🧠 Topics Covered • Startup survival after losing a lead investor • Fundraising lessons and investor concentration risk • Leadership during crisis and uncertainty • Building and scaling venture-backed startups • The acquisition journeys of Waze and other startups • Networking and relationship capital • Mission-driven entrepreneurship • Grocery technology and consumer savings • Recruiting and retaining A-player talent • Defining wealth through optionality --- ## 🔍 SEO Keywords Entrepreneurship, Startup Founder, Startup Failure, Business Resilience, Fundraising, Venture Capital, Leadership, Andy Ellwood, Startup Lessons, Waze, Google Acquisition, Business Growth, Networking, Relationship Capital, Food Technology, Grocery Industry, Food Inflation, Mission-Driven Business, A Players, Founder Mindset, Optionality, Startup Strategy --- ## ⏱️ Timestamps [00:00:00] – The Tragic Loss of a Lead Investor and the Startup Crisis That Followed [00:02:34] – Three Hard Lessons Learned from Losing Critical Funding Overnight [00:05:42] – Why Founders Must Fall in Love with the Problem, Not the Product [00:09:20] – Succession Planning, Risk Management, and Preparing for Failure [00:10:39] – The Tombstone Exercise: Imagining How Your Company Could Die [00:13:36] – Andy Ellwood's Entrepreneurial Origins and First Business at Age Twelve [00:16:06] – Learning Sales Through Lawn Care and Life Insurance [00:17:55] – Selling Private Jets for Warren Buffett and Lessons from Billionaires [00:20:15] – Why Relationships Matter More Than Networking [00:23:33] – Startup Success, Waze, and the Road to Building Basket [00:25:22] – Creating Basket and Solving Grocery Price Transparency [00:27:02] – Why a Promising Startup Ultimately Failed [00:27:35] – Introducing Stretch and the Future of Grocery Intelligence [00:30:01] – Recovering from Failure and Starting Again as a Founder [00:31:17] – Food Insecurity, Consumer Behavior, and Grocery Inflation [00:34:26] – Market Research, Customer Insights, and Startup Validation [00:35:18] – AI, Agentic Commerce, and Building for the Future [00:37:45] – Recruiting, Motivating, and Retaining A-Player Talent [00:41:11] – Why Mission Matters More Than Compensation [00:45:14] – Defining Success, Wealth, and the Power of Optionality [00:48:31] – Final Thoughts and Closing Remarks --- ## 👤 About Andy Ellwood Andy Ellwood is the founder and CEO of Stretch, a grocery intelligence platform helping consumers make smarter grocery shopping decisions. He previously helped scale Waze during its growth journey prior to its acquisition by Google and has built multiple venture-backed startups throughout his career. His expertise spans startup growth, fundraising, leadership, consumer technology, and mission-driven entrepreneurship. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/JiPWC1Cbh7Y&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • Guest Website: https://stretchgroceries.com/ • LinkedIn: https://www.linkedin.com/in/andyellwood/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    51 min
  6. Raising Capital in Real Estate: Syndications, Private Equity & Avoiding Bad Deals with John Azar

    May 26

    Raising Capital in Real Estate: Syndications, Private Equity & Avoiding Bad Deals with John Azar

    Raising Capital in Real Estate: Syndications, Private Equity & Avoiding Bad Deals with John Azar In this episode of *Investing to Win*, host **Garret Wong** sits down with John Azar to dive into: - Real estate syndication and raising capital - Private equity investing in commercial real estate - Risk management, underwriting, and operator due diligence …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/Mrc-ck8CzQw&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary In this episode of the Investing to Win podcast, Garret Wong sits down with commercial real estate investor and private equity operator John Azar to unpack the realities of raising capital in today’s uncertain economic environment. From syndications and GP structures to underwriting and investor trust, John explains what separates experienced operators from inexperienced “gurus” chasing quick money. He shares why raising capital is only one piece of the equation — and why deployment, asset management, and operator experience ultimately determine success. John also walks listeners through his journey from investment banking and structured finance to building multifamily portfolios and launching Peak 15 Capital. Along the way, he discusses surviving the 2008 financial crisis, navigating the volatility of 2021–2023, and the lessons learned from seeing inexperienced syndicators lose investor money during overheated market cycles. His perspective offers a grounded, experience-driven approach to commercial real estate investing that prioritizes patience, underwriting discipline, and long-term reputation over hype. The conversation dives deep into private equity structures, GP and LP relationships, preferred equity, cash flow strategies, and why underwriting the people behind a deal matters just as much as underwriting the asset itself. John also explains how his firm evaluates sponsors, why conservative assumptions matter more than optimism, and how institutional investors are approaching real estate today. Garret and John close the episode by discussing mentorship, failure, reputation, and the importance of learning through experience. Whether you are an aspiring syndicator, passive investor, or seasoned operator, this episode delivers a practical and honest look at what it really takes to succeed in commercial real estate and private equity. --- ## 🎯 Key Takeaways • Understand that raising capital is only effective when paired with strong deployment and asset management strategies • Learn why operator credibility, reputation, and track record matter more than flashy marketing • Discover how experienced investors evaluate both deals and the people behind them • Recognize the dangers of inexperienced syndicators during overheated market cycles • Apply conservative underwriting and stress testing to protect investments during uncertainty • Embrace failure as part of the learning process in business and investing --- ## 🧠 Topics Covered • Real estate syndications explained • GP vs LP investment structures • Accredited investors and SEC regulations • Commercial real estate private equity strategies • Multifamily investing and operator risk • Preferred equity and capital stack structures • Underwriting and due diligence best practices • Lessons from the 2008 financial crisis • Institutional investor behavior in today’s market • Building long-term reputation and investor trust --- ## 🔍 SEO Keywords real estate syndication, raising capital, commercial real estate, private equity, multifamily investing, GP equity, LP investing, accredited investors, underwriting deals, investor relations, passive investing, real estate investing, cash flow investing, private equity real estate, institutional investors, asset management, syndication investing, commercial property investing, entrepreneurship, Peak 15 Capital --- ## ⏱️ Timestamps [00:00:00] – Why Raising Capital Is the Lifeblood of Real Estate Investing [00:02:09] – What a Real Estate Syndication Actually Is Explained Simply [00:05:26] – The Dangers of Inexperienced Syndicators and Fake Gurus [00:11:46] – John Azar’s Background in Investment Banking and Commercial Real Estate [00:16:09] – Lessons Learned From Surviving Multiple Real Estate Market Cycles [00:19:02] – Why Failure Is Essential for Success in Business and Investing [00:20:20] – What Private Equity Means in Commercial Real Estate [00:22:36] – How Peak 15 Capital Evaluates Deals and Sponsors [00:25:02] – What GP Equity Firms Actually Look for in Real Estate Operators [00:28:43] – The Importance of Underwriting the People Behind the Deal [00:31:49] – The Truth About Cash Flow and Liquidity for Syndicators [00:35:19] – Why Car Wash Investments Outperformed Multifamily Cash Flow [00:37:50] – Dry Powder, Institutional Investors, and Market Caution [00:40:52] – Asset Classes, Self Storage, and Alternative Commercial Real Estate Plays [00:43:03] – Predictions for Commercial Real Estate Over the Next 12 to 24 Months [00:46:30] – Advice for Young Real Estate Investors Entering the Industry [00:48:30] – Launching Peak 15 Capital Institute and Educational Platforms [00:50:25] – Defining Success, Reputation, and Winning in Business --- ## 👤 About John Azar John Azar is the founder of Peak 15 Capital, a commercial real estate private equity firm focused on GP equity, multifamily investments, and strategic partnerships with operators and developers. With a background in investment banking, structured finance, and commercial real estate syndication, John has transacted thousands of multifamily units and worked with institutional investors across the United States. His expertise includes underwriting, capital raising, asset management, and navigating complex market cycles through disciplined investment strategies. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/Mrc-ck8CzQw&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • Guest Website: https://www.peak15cap.com/ • LinkedIn: https://www.linkedin.com/in/jalalazar/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    54 min
  7. Blockchain Investing for Family Offices: Stablecoins, Tokenization, and the Next Financial Infrastructure

    May 19

    Blockchain Investing for Family Offices: Stablecoins, Tokenization, and the Next Financial Infrastructure

    Blockchain Investing for Family Offices: Stablecoins, Tokenization, and the Next Financial Infrastructure In this episode of *Investing to Win*, host **Garret Wong** sits down with Mitchell Mechigian to dive into: - Blockchain as the next-generation financial infrastructure (not just “crypto price speculation”) - How family offices should allocate to blockchain and venture: diversification early, concentration later - Stablecoins and tokenization as real-world breakout use cases (and where crypto is overfunded vs underfunded) …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/T9J6e1KjqdI&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary Mitchell Mechigian reframes crypto as something far more practical than a price bet: a modernization of the financial system’s underlying rails. He explains why blockchain is best understood as “financial infrastructure” that can make money more digital-first, programmable, and efficient, especially across borders where legacy systems still feel paper-based, slow, and friction-heavy. Instead of focusing on headlines, he emphasizes the boring but powerful categories: payments, remittances, stablecoins, and tokenization. The conversation also gets tactical for investors, particularly family offices. Mitchell breaks down how Fifth Era thinks about venture allocation: diversify heavily at the earliest stages (including fund-of-funds exposure across hundreds of underlying companies), then become more concentrated as companies mature and diligence becomes easier with clearer product, revenue, and exit paths. He shares how their strategy has evolved across early, mid, and late-stage opportunities, including investments connected to major players in the space. Garret and Mitchell also clarify common confusion around crypto vs blockchain. Mitchell lays out clean definitions, explaining how stablecoins work, how permissioned blockchains differ from permissionless networks like Ethereum, and why major institutions are choosing open-source rails even when launching regulated, whitelisted products. He argues that stablecoins have already become a quiet but massive payments layer, and he contextualizes blockchain’s development arc by comparing it to the internet’s decades-long build phase. Finally, the episode expands into AI and its overlap with blockchain, including how agents might transact using digital-first money and why “censorship resistance” matters in a world increasingly dependent on centralized infrastructure. Mitchell closes by sharing his personal definition of success: control of your time, freedom of schedule, and the ability to be present for the people and priorities that matter most. --- ## 🎯 Key Takeaways • Reframe crypto as financial infrastructure that upgrades how money moves, settles, and clears globally • Use diversification at the earliest stages of venture, then shift to concentration as companies mature • Understand stablecoins as a major real-world use case: digital dollars on blockchain rails • Distinguish permissionless networks (ex: Ethereum) from permissioned products (ex: whitelisted tokenized funds) • Recognize where crypto has been overfunded (protocol infrastructure) and where it is underfunded (applications) • Define success as time autonomy: control your schedule and priorities, not just financial outcomes --- ## 🧠 Topics Covered • Blockchain vs crypto vs stablecoins: practical definitions for investors • Cross-border payments, remittances, and why legacy finance is still “analog” • Family office portfolio construction and venture allocation to digital assets • Early-stage diversification via fund-of-funds vs later-stage concentrated bets • Tokenization of real-world assets and institutional adoption (ex: money market funds) • Stablecoin market structure: issuers, reserves, and dollar pegs • Overfunded protocol layers vs underfunded application layers in crypto venture • AI investing cycles, valuation euphoria, and early-stage GP selection strategy • Censorship resistance: financial systems, geopolitics, and dependence on centralized platforms • Remote firm operations, performance culture, and relationship-driven investing --- ## 🔍 SEO Keywords • blockchain investing • crypto venture capital • family office investing • stablecoins • tokenization • financial infrastructure • digital assets • cross-border payments • remittances • permissioned blockchain • permissionless blockchain • Ethereum • Bitcoin • Tether • Circle • BlackRock tokenization • Securitize • venture fund of funds • crypto applications • AI and blockchain --- ## ⏱️ Timestamps [00:00:01] – Crypto is not a price bet: why blockchain is the next financial infrastructure layer [00:02:37] – How to convince a “boring compounding” family office to allocate to blockchain venture [00:04:11] – Early-stage diversification strategy: fund-of-funds exposure across hundreds of companies [00:05:15] – When to concentrate: moving from early-stage spray-and-pray to late-stage diligence and conviction [00:07:05] – Blockchain vs crypto vs NFTs: simple definitions and what actually matters for investors [00:08:12] – Stablecoins explained: how digital dollars work, who issues them, and why they stay pegged [00:09:34] – Permissioned vs permissionless: tokenized funds, KYC/AML whitelisting, and institutional rails [00:11:43] – Mitchell’s background: from Morgan Stanley to LSE research to building Fifth Era [00:16:25] – What Wall Street teaches you about markets: liquidity, scale, and why settlement is still outdated [00:20:43] – Does blockchain deserve a seat at the table: adoption signals, ETFs, and stablecoins as a breakout use case [00:25:12] – What is overfunded vs underfunded in crypto: protocol infrastructure vs the application layer [00:28:20] – AI meets blockchain: why agents may transact on-chain and where the overlap is headed [00:30:05] – Censorship resistance and geopolitical risk: what happens when infrastructure can “turn you off” [00:33:08] – Investing in AI in a euphoric market: diversify early, avoid hype, and focus on long-term edge [00:36:31] – Fifth Era Partners overview: founders, team footprint, regulatory setup, and global LP base [00:40:35] – Remote work in investing: relationship-driven execution without a traditional bricks-and-mortar office [00:43:55] – Hiring and culture: when remote works, when it breaks, and why in-person time still matters [00:47:31] – Defining success and winning: time freedom, autonomy, and living without an alarm clock --- ## 👤 About Mitchell Mechigian Mitchell Mechigian is a Partner at Fifth Era Partners, a venture investment firm focused on blockchain and digital assets. With a background in mathematics and experience at Morgan Stanley in capital markets and investment banking, he later pursued research at the London School of Economics focused on cryptocurrencies and the global financial system. At Fifth Era, Mitchell leads direct investments across the mid-to-late stages, with a focus on foundational financial infrastructure themes like stablecoins, tokenization, payments, and institutional adoption. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/T9J6e1KjqdI&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • Guest Website: https://www.fifthera.com • LinkedIn: https://www.linkedin.com/in/mitch-mechigian-b42b3572/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    50 min
  8. Leaving Corporate America: How Chris Wilson Built a 13-Location Business After a Career Pivot

    May 12

    Leaving Corporate America: How Chris Wilson Built a 13-Location Business After a Career Pivot

    Leaving Corporate America: How Chris Wilson Built a 13-Location Business After a Career Pivot In this episode of *Investing to Win*, host **Garret Wong** sits down with Christopher Wilson to dive into: - Corporate career transitions into entrepreneurship - Building and scaling a franchise business - Financial freedom, retirement planning, and legacy building …and the powerful lessons entrepreneurs, investors, and operators can use to level up their business, leadership, and thinking. 🎥 **Prefer watching the conversation? The full video is available on YouTube:** https://youtu.be/q7P3hyaOTUg&list=UULFRs3SSmwVFbR2QEjIDqU0Ug This creates a richer experience with facial expressions, visuals, and deeper engagement. Whether you're a business owner, investor, operator, or someone exploring new pathways to financial freedom, this episode delivers practical, no-fluff insights you can take action on immediately. --- ## 🔥 Episode Summary After spending 14 years inside one of the world’s largest pharmaceutical companies, Chris Wilson found himself exhausted by constant mergers, acquisitions, and corporate restructuring. When a severance package was offered, he used it as an opportunity to finally pursue the entrepreneurial path he had always envisioned. In this episode, Chris shares how he transitioned from corporate America into business ownership by acquiring an H&R Block franchise and eventually growing it into a 13-location operation across North Carolina and Virginia. Chris explains why entrepreneurship was always part of his DNA, growing up in a family of business owners and learning firsthand what it meant to work for yourself. He opens up about the emotional and financial realities of leaving a stable corporate paycheck behind, how transferable corporate skills became essential to scaling his business, and why buying an existing business can be far less risky than starting from scratch. Garret and Chris also dive deep into leadership, systems, franchising, acquisitions, and the importance of working on a business rather than inside it. Chris shares lessons learned from acquiring accounting firms, building teams, and managing large-scale operations while maintaining personal freedom and flexibility. The conversation also explores retirement planning and financial literacy, particularly within underserved communities. Chris discusses the inspiration behind his book on making retirement savings last a lifetime and why he believes entrepreneurship, ownership, and financial education are key tools for building generational wealth and long-term freedom. --- ## 🎯 Key Takeaways • Use corporate experience as a foundation for entrepreneurship • Buy existing cash-flowing businesses instead of starting from scratch • Build systems and teams that allow you to work on the business, not in it • Learn leadership and management skills before making the leap • Understand the long-term impact of retirement and financial planning decisions • Pursue entrepreneurship for freedom, flexibility, and ownership of your future --- ## 🧠 Topics Covered • Leaving corporate America after mergers and acquisitions • Transitioning from pharmaceuticals into entrepreneurship • Buying and scaling an H&R Block franchise • Building multi-location businesses and leadership teams • Working on the business vs. working in the business • Franchise growth through acquisitions and organic expansion • Financial literacy and retirement planning • Entrepreneurship mindset and decision-making frameworks • The importance of transferable corporate skills • Creating financial freedom and generational legacy --- ## 🔍 SEO Keywords entrepreneurship, leaving corporate america, franchise business, H&R Block franchise, career pivot, business acquisitions, mergers and acquisitions, financial freedom, retirement planning, business ownership, entrepreneur mindset, corporate burnout, small business growth, franchising, financial literacy, generational wealth, leadership, business systems, the e myth, investing to win podcast --- ## ⏱️ Timestamps [00:00:00] – Introduction and Chris Wilson’s Corporate Career Pivot [00:00:22] – Life Inside a Global Pharmaceutical Company During Constant Mergers [00:01:13] – Starting a Business Before Leaving Corporate America [00:02:11] – Why Chris Chose an H&R Block Franchise Model [00:03:24] – When the Financial Services Strategy Suddenly Changed [00:04:21] – Garret Wong’s Own Transition From Science to Entrepreneurship [00:05:21] – The Desire for Freedom That Drives Entrepreneurs [00:06:31] – Transferable Corporate Skills That Help Entrepreneurs Scale [00:07:27] – Defining Personal Freedom and Entrepreneurial Success [00:08:16] – Growing Up Around Family Businesses and Entrepreneurship [00:09:16] – Early Career Experience in Oil, Pharmaceuticals, and Technology [00:10:41] – Returning to North Carolina and Finding the Right Environment [00:11:06] – Learning Computer Programming and Accounting Before Entrepreneurship [00:12:44] – Protecting Retirement Savings While Starting a Business [00:13:46] – Knowing When It’s Time to Leave Corporate America [00:15:26] – Managing Fear, Risk, and Family Concerns During Career Transitions [00:16:21] – The Emotional Relief of Leaving Corporate Stress Behind [00:17:34] – Buying an Existing Business Instead of Starting From Scratch [00:18:29] – The First Big Entrepreneurial Reality Check [00:19:20] – Why Chris Never Wanted to Leave the Franchise System [00:20:06] – Opportunities to Buy Businesses From Retiring Owners [00:21:01] – Challenges Chris Expected Versus Reality After Leaving Corporate [00:22:18] – Running a Franchise as a Side Business Before Going All In [00:22:39] – Scaling From One Location to 13 Stores [00:24:28] – Lessons From Acquiring Franchise and Accounting Businesses [00:26:11] – Using the E-Myth Philosophy to Build Systems and Teams [00:27:08] – Working on the Business Instead of Inside the Business [00:28:24] – What Tax Clients Revealed About Retirement Planning Mistakes [00:29:38] – Why Chris Wrote a Book on Financial Foundations and Retirement [00:30:15] – Adapting After H&R Block Sold Its Financial Services Division [00:31:24] – Choosing to Stay and Grow in the Tax Industry [00:32:55] – The Hidden Stress of Corporate Life [00:33:26] – A Framework for Evaluating Entrepreneurship Before Taking the Leap [00:35:37] – Why Team Building and Leadership Skills Matter [00:36:13] – Learning Management Skills on the Corporate Dime [00:36:42] – Entrepreneurship Doesn’t Require a Revolutionary Idea [00:37:52] – Lessons From Tommy Hilfiger on Learning Through Experience [00:39:21] – Defining Success, Freedom, and Legacy [00:40:52] – Final Thoughts and Closing Conversation --- ## 👤 About Chris Wilson Chris Wilson is an entrepreneur, franchise owner, and financial education advocate with more than two decades of experience building and scaling businesses. After spending 14 years in the pharmaceutical industry with GSK and other major corporations, Chris transitioned into entrepreneurship through an H&R Block franchise acquisition. Today, he operates 13 locations across North Carolina and Virginia, owns additional businesses in tax and real estate, and focuses on helping individuals strengthen their financial foundations and prepare for long-term financial security. --- ## 🔗 Episode Links & Resources • 🎥 **Watch the YouTube version:** https://youtu.be/q7P3hyaOTUg&list=UULFRs3SSmwVFbR2QEjIDqU0Ug • LinkedIn: https://www.linkedin.com/in/chris-wilson-b117819/ • Guest Website: https://www.hrblock.com/ --- ## 📘 Recommended by Garret **Get Garret’s bestselling book *The Property Playbook*: https://a.co/d/3Ww0si0** Build wealth without burnout using the systems that scaled over $1B in managed assets. --- ## 🌐 Stay Connected **Join the My First Keys Community:** https://my-first-keys.mn.co/landing/ Weekly landlord education, walkthroughs, systems & support. **Follow**

    43 min
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5
out of 5
2 Ratings

About

Hey there, audience! This is the Investing to WIN podcast, the show dedicated to inspiring budding entrepreneurs and business owners to live balanced, fulfilled lives. Our guests share their personal journeys, struggles, adversity and success stories. If you're a person that is working too hard, thinking of change or looking towards a future goal, you've come to the right place! This show is committed to offering honest conversations to discuss common sense strategies and professional guidance to achieving success and fulfillment. Your host is Garret Wong; an Ex-Scientist turned Serial Entrepreneur who, while growing up saw his father and mother run 4 businesses simultaneously while still being able to travel. But when his father passed away at the early age of 59, just before he was ready to retire, Garret's path and perspective of "success" was changed forever. In addition to his other businesses he brings decades of experience in buying, renovating, and managing rental properties for investors across the world. Thanks for being here and get ready to Invest to Win!! https://garretwong.com/

Information

  • Creator
    Garret Wong
  • Years Active
    2023 - 2026
  • Episodes
    153
  • Rating
    Explicit
  • Copyright
    © https://garretwong.com/investing-to-win/
  • Show Website
    Investing To Win