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. Jul 21

    Franchise Royalties Explained: What You're Really Paying For

    Franchise Royalties Explained: What You're Really Paying For In this episode of *Investing to Win*, host **Garret Wong** sits down with Giuseppe Grammatico to dive into: - Understanding franchise royalties and fees - The step-by-step process of choosing the right franchise fit - The economics of owning a franchise long-term …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 Most people hear the word "franchise" and picture fast food — but as franchise consultant Giuseppe explains in this episode, a franchise is really just a system: a plug-and-play structure for running a business that removes the guesswork of building a brand, a CRM, and a customer base from scratch. Giuseppe walks through why the "widget" almost doesn't matter — what matters is demand in your local market and your willingness to follow a proven system. The conversation dives deep into the topic every prospective franchisee gets stuck on: royalties. Giuseppe reframes the question from "how much is this costing me" to "what am I getting for this fee" — coaching, marketing infrastructure, purchasing power, and ongoing support that would otherwise take years to build alone. He explains how royalty structures vary widely across the roughly 4,000 franchise brands in the U.S. — flat fees versus sliding scales, and why reading the Franchise Disclosure Document (FDD) line by line is essential before building a pro forma. Giuseppe also shares his own path into franchising: growing up in his family's Italian restaurant in New Jersey, a grueling five-hour daily commute working on Wall Street, and eventually building two franchise territories in New Jersey before pivoting during the 2008 downturn into healthcare-adjacent building services. That real-world experience — buying, operating, and eventually selling his own franchise — now informs how he coaches families through the entire process: getting finances in order, defining the "ideal business" before ever looking at a brand, navigating the application and discovery day process, and understanding what happens after the agreement is signed. The episode closes with a candid look at the back half of franchise ownership: what it actually takes to sell a franchise, why resale multiples can run three to five times earnings (or higher for proven brands), and the pitfalls of franchisees who leave their brand to "go it alone" without realizing how much marketing, purchasing power, and support they're walking away from. Giuseppe ties it all back to his own definition of success — not financial freedom, but time freedom — built by designing a business and a calendar around never missing his kids' games. --- ## 🎯 Key Takeaways • Evaluate a franchise royalty by asking what support, coaching, and infrastructure it funds • Read the Franchise Disclosure Document (FDD) closely • Get your finances and liquidity in order before you ever start comparing franchise brands • Define your "ideal business" first rather than starting with a specific brand or industry. • Buying into a franchise gives immediate access to systems, marketing, and training • Understand the resale and exit picture early --- ## 🧠 Topics Covered • How franchise royalties are structured and what they actually pay for • Reading and understanding a Franchise Disclosure Document (FDD) • Comparing franchise ownership to running an independent startup • Giuseppe's path from a family-owned Italian restaurant to Wall Street to franchise ownership • Choosing a recession-resistant, low-overhead franchise business model • Buying a second franchise territory and understanding territory fees • The full process of selecting, applying for, and opening a franchise • Franchise marketing support, KPIs, and lead-to-close ratios • Exit strategy, resale multiples, and transferring a franchise • The risks of leaving a franchise brand to operate independently • How a free franchise consulting service works --- ## 🔍 SEO Keywords franchise ownership, franchise royalty fees, how to buy a franchise, franchise consultant, franchise disclosure document, FDD, franchise vs startup, buying a franchise business, franchise territory fee, home service franchise, B2B franchise, franchise exit strategy, selling a franchise, franchise resale multiple, franchise marketing support, franchise coaching, small business ownership, entrepreneurship podcast, time freedom, franchise investment --- ## ⏱️ Timestamps [00:00:00] – Introduction: Why Franchising Isn't Just Fast Food Garret opens by challenging the assumption that franchising means fast food, and Giuseppe explains why a franchise is really a repeatable system anyone can execute — regardless of the "widget." [00:00:59] – What Franchise Royalties Actually Pay For Giuseppe reframes the royalty conversation: instead of asking how much it costs, franchisees should ask exactly what support and infrastructure that fee is funding. [00:02:45] – A Personal Story: Weighing a Tim Hortons Franchise Garret shares his family's own experience considering a Tim Hortons franchise and asks whether a royalty should really be counted as a straight expense against profit. [00:05:35] – Giuseppe's Background: From a Family Restaurant to Wall Street Giuseppe walks through growing up in his parents' 40-year Italian restaurant, his early career on Wall Street, and the grueling five-hour daily commute that pushed him toward entrepreneurship. [00:07:28] – Discovering Franchising and Buying His First Territory A chance conversation with a franchise coach opens Giuseppe's eyes to franchising beyond fast food, leading him to purchase his first territory in 2007. [00:10:47] – What Restaurant Experience Teaches About Running a Business Garret and Giuseppe compare notes on how working in a restaurant builds a work ethic and adaptability that most other jobs never demand. [00:11:45] – Choosing a Recession-Resistant, Low-Overhead Franchise Giuseppe details the specific criteria he used to select his first franchise: no storefront, minimal staff, and an investment kept under $200,000. [00:15:09] – Expanding Into a Second Territory in Northern New Jersey After building central New Jersey for over a decade, Giuseppe explains how he expanded into a neighboring territory rather than buying a competing brand. [00:18:58] – Territory Fees Explained Giuseppe breaks down the difference between a franchise fee and a territory fee, and how expansion pricing works for non-brick-and-mortar businesses. [00:20:26] – The Full Process: From Choosing a Franchise to Opening Your Doors A step-by-step walkthrough of how a prospective franchisee should approach the search — starting with finances, not with brands. [00:23:10] – Location, Staffing, and State Availability Considerations Giuseppe covers how geography, staffing models (W-2 vs. contractor), and state-by-state registration affect which franchises are even available to a buyer. [00:25:17] – What Franchisors Look for in an Applicant The conversation turns to how franchisors vet candidates and what transferable skills matter more than direct industry experience. [00:26:14] – The Application, Discovery Day, and Getting Approved Giuseppe explains the typical multi-call process, franchisee validation calls, and what happens at a discovery day. [00:28:29] – Opening a Brick-and-Mortar Location: Site Selection to Launch For physical locations, Giuseppe outlines the timeline from site selection and traffic studies through pre-opening marketing and staffing. [00:30:59] – How Franchise Marketing Support Actually Works A deep dive into how digital marketing, lead generation, and call centers are handled for franchisees in home-service and B2B brands. [00:35:50] – Fast-Tracking Revenue With Built-In Systems and Training Giuseppe explains why franchisees can be cash-flowing within three months, thanks to day-one access to CRM, marketing assets, and operational training. [00:38:13] – Why Franchising Trains You to Work On the Business, Not In It Garret connects the conversation to the classic "E-Myth" idea, and Giuseppe explains how franchise systems push owners into an oversight role early. [00:39:22] – Why Industry Experience Can Actually Work Against a Franchise Applicant Giuseppe shares a candid, contrarian take on why franchisors are sometimes wary of applicants who already have hands-on experience in that trade. [00:40:35] – Franchise Exit Strategy and Resale Multiples The discussion shifts to how franchise businesses are valued and sold, and why brand history can support a stronger resale multiple. [00:42:02] – How Franchise Transfers and Resales Actually Work Giuseppe explains the transfer fee process, the franchisor's role in vetting a buyer, and why franchise resales rarely go through a broker. [00:43:54] – The Risk of Leaving a Franchise to Go Independent Garret and Giuseppe discuss why franchisees who drop their brand to operate solo often underestimate what they're giving up in marketing and purchasing power. [00:48:14] – When Support Gaps Cause Franchisees to Struggle A closer look at why some franchise experiences go poorly — often due to inconsistent support rather than the franchise model itself. [00:49:02] – How Giuseppe's Free Franchise Consulting Service Works Giuseppe explains how his no-cost matchmaking service works, who...

    Franchise Royalties Explained: What You're Really Paying For

  2. Jul 14

    Manufactured Housing Investing: Why Mobile Home Parks Outperform Through Every Market Cycle | Ali

    Manufactured Housing Investing: Why Mobile Home Parks Outperform Through Every Market Cycle | Ali In this episode of *Investing to Win*, host **Garret Wong** sits down with Nasir Ali to dive into: - Manufactured Housing Investing - Building Wealth Through Commercial Real Estate and Mobile Home Parks - Passive Investing, Underwriting, and Creating Recession-Resistant Cash Flow …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 Manufactured housing has quietly become one of the strongest-performing real estate asset classes, yet many investors still overlook its long-term potential. In this episode of Investing to WIN, Garret Wong sits down with commercial real estate expert Ali, whose family has been involved in real estate investing for eight generations and manufactured housing for more than four decades. Ali shares how growing up in the family business shaped his investment philosophy and why he believes mobile home communities offer one of the most resilient opportunities available today. Throughout the conversation, Ali explains how his experience underwriting large commercial portfolios—including managing valuations for more than 1,600 assets in Saudi Arabia—reinforced the importance of disciplined analysis, creative problem solving, and buying assets based on strong fundamentals. He discusses why manufactured housing consistently outperformed during the 2008 financial crisis, the pandemic, and other economic downturns, highlighting the unique advantages of owning land while residents own their homes. Listeners will also gain practical insight into evaluating manufactured housing communities, avoiding common acquisition mistakes, understanding infrastructure risks, and recognizing why experienced operators have a significant competitive advantage. Ali shares several personal stories about acquiring distressed businesses with creative financing, turning around underperforming assets, and building multiple income streams through strategic real estate investing. Whether you're an experienced investor looking to diversify or someone exploring passive investment opportunities, this episode provides a detailed look into an asset class that combines stable cash flow, long-term appreciation, and the growing demand for affordable housing. Garret and Ali also discuss leadership, succession planning, and why creating value for investors, residents, and communities is the foundation of sustainable success. --- ## 🎯 Key Takeaways • Understand why manufactured housing has historically outperformed during economic downturns. • Learn how disciplined underwriting reduces investment risk and improves long-term returns. • Discover the advantages of owning land while residents own their homes. • Recognize the operational mistakes investors make when purchasing manufactured housing communities. • Explore creative financing strategies that helped build wealth with limited capital. • Build a long-term investment mindset focused on resilience, affordability, and sustainable growth. --- ## 🧠 Topics Covered • Manufactured housing investing fundamentals • Why mobile home parks are recession-resistant • Commercial real estate underwriting and valuation • Lessons from evaluating over 1,600 commercial properties • Investing during the 2008 financial crisis • Common mistakes when buying manufactured housing communities • Infrastructure due diligence and operational management • Creative financing and acquiring distressed assets • Passive investing through real estate funds • Leadership, succession planning, and building generational wealth --- ## 🔍 SEO Keywords Manufactured housing investing, Mobile home park investing, Affordable housing, Commercial real estate, Passive real estate investing, Real estate syndication, Real estate fund, Underwriting commercial real estate, Mobile home communities, Manufactured housing communities, Cash flow investing, Recession-resistant investments, Real estate investing podcast, Creative financing, Seller financing, Real estate due diligence, Commercial property investing, Accredited investors, Rise360 Ventures, Investing to WIN Podcast --- ## ⏱️ Timestamps [00:00:00] – Introduction to Ali's Real Estate Journey and Early Career [00:03:07] – Growing Up in a Family of Entrepreneurs [00:04:36] – Underwriting 1,600 Commercial Properties in Saudi Arabia [00:07:52] – Investing Through the 2008 Financial Crisis [00:11:58] – Why Manufactured Housing Became the Family's Core Investment Strategy [00:14:45] – Manufactured Housing During Economic Downturns [00:17:08] – The Business Model Behind Mobile Home Parks [00:20:29] – Managing Expenses, Rent Control, and Operating Challenges [00:22:38] – Why Experienced Operators Have a Competitive Advantage [00:23:55] – Biggest Mistakes Investors Make When Buying Mobile Home Parks [00:28:10] – How to Get Started Without Significant Capital [00:31:53] – Building Wealth Through Creative Deals [00:37:14] – Should You Build or Buy a Manufactured Housing Community? [00:39:25] – Inside Rise360 Ventures [00:41:56] – Manufactured Housing Funds vs Traditional Syndications [00:44:44] – Who Can Invest and What Makes Rise360 Different [00:48:22] – Defining Success Beyond Financial Wealth [00:50:54] – Final Thoughts and Closing Remarks --- ## 👤 About Nasir Ali Nasir Ali is a commercial real estate investor, entrepreneur, and manufactured housing specialist with more than 45 years of experience in the industry. Coming from an eighth-generation commercial real estate family and a second-generation manufactured housing business, Ali has built his career around underwriting, acquisitions, operations, and long-term wealth creation. He has led major international valuation projects, including managing the appraisal and strategic analysis of more than 1,600 commercial properties for one of Saudi Arabia's largest organizations. Today, Ali serves as a leader at Rise360 Ventures, where he helps accredited investors access professionally managed manufactured housing investments while focusing on affordable housing, operational excellence, and long-term passive income. His expertise spans commercial underwriting, creative financing, distressed asset acquisitions, and building recession-resistant investment portfolios. --- ## 🔗 Episode Links & Resources • Guest Website: https://rise360ventures.com/ • LinkedIn: https://www.linkedin.com/company/rise360ventures/ --- ## 📘 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**

    Manufactured Housing Investing: Why Mobile Home Parks Outperform Through Every Market Cycle | Ali

  3. Jul 7

    Inflation, Sound Money, and Silver: David Morgan on Protecting Your Wealth From a Broken System

    Inflation, Sound Money, and Silver: David Morgan on Protecting Your Wealth From a Broken System In this episode of *Investing to Win*, host **Garret Wong** sits down with David Morgan to dive into: - Why inflation quietly erodes savings, and why holding cash in a bank guarantees a loss of purchasing power over time. - How covered calls let investors "rent" their mining stocks for income, similar to renting real estate, without the headaches of tenants and toilets. - Flipping Maslow's hierarchy of needs, redefining legacy wealth, and what David Morgan believes true success and winning actually look like. …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, Garret Wong sits down with David Morgan, publisher of The Morgan Report and one of the most recognized voices in precious metals investing, for a conversation that challenges nearly everything most people believe about money, banks, and the financial system. David opens by explaining why inflation, not market crashes, is the silent force eating away at the average person's savings, and why the government's own inflation metrics understate the true cost of living. He walks through how a sound money system historically allowed a dollar to buy more over time, and why that stands in stark contrast to today's economy. The conversation moves into food quality, government overreach, and rent control policy, with David and Garret comparing real-world outcomes between Canadian provinces to illustrate how well-intentioned regulation often backfires. David then shares his own path into finance, from a childhood dream of flying to a decades-long career analyzing gold, silver, and mining equities, and explains why he believes individualism and personal responsibility matter more than waiting on political solutions. The back half of the episode gets tactical. David breaks down his approach to covered calls, a strategy he calls "renting your stock," and explains how investors can generate consistent yield from top-tier mining companies while managing risk. Garret and David also compare real estate investing to equities, discuss the sobering statistics behind small business failure, and share real stories of using silver as a medium of exchange at farmers markets. The episode closes on a philosophical note, with David flipping Maslow's hierarchy of needs on its head and offering his personal definition of what it means to actually win. --- ## 🎯 Key Takeaways Recognize that official inflation figures understate the real cost of living, since food and energy were removed from the CPI calculation after 1980.Avoid holding excess cash in savings accounts during inflationary periods, since interest rates rarely outpace true inflation.Consider mining equities alongside physical metals for added benefits like dividends, leverage, and more favorable tax treatment on exit.Learn how covered calls work as a way to generate consistent yield from stock holdings, similar to renting out real estate.Focus on what you can control, including personal spending habits, critical thinking, and self-reliance, rather than waiting for political or economic rescue.Redefine success around legacy and service to others rather than external markers like possessions or titles. --- ## 🧠 Topics Covered Why inflation is understated by official government metricsThe difference between a sound money system and fiat currencyHow food quality and GMO crops tie into consumer purchasing powerRent control policy compared across Canadian provincesDavid Morgan's career path from aviation to precious metals investingIndividualism, political skepticism, and voting with your dollarPhysical metals versus mining stocks and royalty companiesCovered calls explained as "renting your stock"Real estate investing versus equities for building legacy wealthWhy most businesses never reach a million dollars in revenueUsing silver as a medium of exchange in everyday transactionsFlipping Maslow's hierarchy of needs --- ## 🔍 SEO Keywords David Morgan, The Morgan Report, silver investing, gold investing, precious metals investing, inflation protection, sound money, covered calls strategy, mining stocks, real estate versus stocks, legacy wealth, financial independence, Investing to Win podcast, Garret Wong, wealth preservation, personal finance education, macroeconomics, silver as money, small business statistics, Maslow's hierarchy of needs --- ## ⏱️ Timestamps 00:00:00 – Introduction: what most people don't understand about banks and inflation 00:02:09 – Why sound money means you may never need a financial plan 00:04:22 – Comparing real inflation rates between the US and Canada 00:05:16 – Food quality, GMO crops, and the case for conscious capitalism 00:07:50 – A rent control case study: Manitoba versus Alberta 00:09:38 – Who is David Morgan? Four decades in precious metals investing 00:11:20 – Physical metal versus mining stocks: dividends, leverage, and tax advantages 00:12:43 – From aspiring pilot to founder of The Morgan Report 00:14:23 – Breaking from the mainstream: politics, lobbyists, and self-reliance 00:18:24 – What can one person actually do? The power of voting with your dollar 00:20:00 – Living within your means and redefining the meaning of life 00:23:04 – Real estate versus stocks: the "tenants and toilets" debate 00:24:01 – Introducing covered calls: how to rent your stock like a landlord 00:28:57 – Protecting a losing position using covered calls 00:31:41 – Building wealth as an entrepreneur instead of relying on the system 00:32:29 – The real story behind launching The Morgan Report 00:34:13 – Why 93 percent of businesses never reach a million dollars in revenue 00:37:09 – Silver as money: real stories from farmers markets and beyond 00:40:22 – Flipping Maslow's hierarchy of needs on its head 00:44:28 – Explaining Maslow's pyramid and David's inverted approach 00:45:47 – The final question: how David Morgan defines success and winning --- ## 👤 About David Morgan David Morgan is the publisher of The Morgan Report, a financial newsletter he has produced since 1999 focused on resource investing, with a specialization in precious metals including gold, silver, platinum, and palladium. With more than four decades of experience spanning aeronautical engineering, real estate, insurance, and financial planning before founding his own newsletter, David is widely regarded as one of the world's most trusted voices on precious metals and macroeconomics. He is the author of The Silver Manifesto and Second Chance, and has been featured in financial documentaries including Four Horsemen, with an upcoming documentary titled Silver Sunrise. David's work centers on educating everyday investors about sound money, wealth preservation, and building legacy wealth through real assets. --- ## 🔗 Episode Links & Resources • Guest Website: https://www.themorganreport.com/ • LinkedIn: https://www.linkedin.com/in/thedavidmorgan/ --- ## 📘 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**

    Inflation, Sound Money, and Silver: David Morgan on Protecting Your Wealth From a Broken System

  4. Jun 30

    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**

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

  5. 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**

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

  6. 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**

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

  7. 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**

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

  8. 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**

    Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood
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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
    156
  • Rating
    Clean
  • Copyright
    © https://garretwong.com/investing-to-win/
  • Show Website
    Investing To Win