Where can I listen to this podcast?

This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

No, this podcast does not typically feature guests.

Investing To Win

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by Garret Wong

4.8(41 reviews)

154 episodes

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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/

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Recent Episodes

June 30, 2026

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 FintechIn 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 SummaryIn 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 Keywordsinvesting 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 ChuEric 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**

June 23, 2026

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 EmployeesIn 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 SummaryIn 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 KeywordsAI 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 WongGarret 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**

June 16, 2026

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 MeadowsIn 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=UULFRs3SSmwVFbR2QEjIDqU0UgThis 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 SummaryMany 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 KeywordsEntrepreneur 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 MeadowsKenyada 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**

154 total episodes available with 1 transcripts

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What is Investing To Win?: 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/
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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