Investing To Win

Hosted by Garret Wong

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Jun 2026

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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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June 16, 202644 min

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**

June 9, 202651 min

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 & AIIn 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=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 SummaryIn 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 Keywordsmultifamily 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 PouliotMichael 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**

June 2, 202651 min

Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood

Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy EllwoodIn 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=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 SummaryAndy 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 KeywordsEntrepreneurship, 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 EllwoodAndy 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**

May 26, 202653 min

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 AzarIn 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=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 SummaryIn 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 Keywordsreal 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 AzarJohn 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**

May 19, 202650 min

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

Blockchain Investing for Family Offices: Stablecoins, Tokenization, and the Next Financial InfrastructureIn 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=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 SummaryMitchell 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 MechigianMitchell 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**

May 12, 202643 min

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 PivotIn 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=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 SummaryAfter 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 Keywordsentrepreneurship, 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 WilsonChris 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**

May 5, 202638 min

Vacant Land Investing: How Brent Bowers Built $17K/Month in Passive Income Without Tenants

Vacant Land Investing: How Brent Bowers Built $17K/Month in Passive Income Without TenantsIn this episode of *Investing to Win*, host **Garret Wong** sits down with Brent Bowers to dive into:- Vacant land investing- Seller financing and land note cash flow- Real estate market adaptation and affordable housing strategies…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/EguL52oRMbs&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 SummaryIn this episode of the Investing to Win Podcast, Brent Bowers breaks down how he built a highly profitable vacant land business generating over $17,000 per month in recurring income—without tenants, toilets, or traditional rental headaches. Starting from mailing tax-delinquent landowners while serving in the military, Brent shares how he turned overlooked and unwanted parcels into cash-flowing assets through seller financing.Brent walks Garret through the mechanics of land investing, including how to identify sellable markets, structure blind offer letters, analyze land comps, and create multiple exit strategies such as assigning contracts, flipping to neighbors, and seller financing buyers over long-term payment plans. He explains why land offers a lower-emotion, lower-friction investment compared to residential real estate and how simplicity creates scale.The conversation also dives into Brent’s entrepreneurial journey—from military deployments and family sacrifice to creating financial freedom through land deals. He shares how fatherhood changed his priorities and why entrepreneurship ultimately gave him back the one asset money can’t buy: time.For investors frustrated by traditional real estate, shrinking margins, or difficult tenants, this episode offers a powerful alternative model—and a timely reminder that real estate isn’t dead, it’s simply evolving.---## 🎯 Key Takeaways• Identify land markets by tracking sold comps before making offers• Use seller financing to create long-term passive income from land• Adapt your real estate strategy as markets shift and opportunities change• Remove emotion from deals by targeting underutilized vacant land• Build multiple exit strategies before taking ownership of a property• Prioritize time freedom and family alongside financial success---## 🧠 Topics Covered• Vacant land investing strategies for beginners• Seller financing land deals for passive income• Direct mail marketing to tax-delinquent landowners• How to analyze land comps and market absorption• Contract for deed vs mortgage structures in land deals• Assigning land contracts for fast cash• Manufactured housing as an affordable housing solution• Transitioning from rentals to land investing• Real estate market pivots and innovation• Entrepreneurship, family, and financial freedom---## 🔍 SEO Keywordsvacant land investing, seller financing, passive income, real estate investing, land flipping, land deals, real estate cash flow, direct mail marketing, contract for deed, land contracts, land investing strategies, manufactured housing, real estate entrepreneurship, land flipping business, tax delinquent land, real estate investing podcast, Brent Bowers, The Land Sharks---## ⏱️ Timestamps[00:00:00] – Introduction: How Brent Built $17K Per Month from Vacant Land[00:01:25] – Seller Financing Explained: Turning Land into Monthly Cash Flow[00:03:05] – Contract for Deed vs Traditional Mortgage Structures[00:04:40] – Why Vacant Land Is Easier to Reclaim Than Rental Properties[00:06:00] – Adding Manufactured Homes to Increase Land Value[00:07:55] – Brent’s Military Journey and the Family Wake-Up Call[00:10:05] – Garret’s Family-First Real Estate Turning Point[00:12:00] – Entrepreneurship, Time Freedom, and Family Priorities[00:13:00] – Is Real Estate Dead? Why Investors Need to Pivot[00:14:10] – House Hacking, Airbnb, and Brent’s Evolution into Land[00:16:55] – How Brent Finds Land Deals Using Direct Mail[00:18:15] – Buying Land for $285 and Flipping It for $5,000[00:20:55] – The 30-Day System for Finding Your First Land Deal[00:22:20] – Using CRM Systems and Offer Automation for Scale[00:23:45] – Blind Offer Letters: Why They Work in Land Investing[00:25:05] – The Psychology Behind Landowner Motivation[00:27:45] – Understanding Land Market Clusters and Sales Patterns[00:29:10] – Selling Land to Neighbors for Massive Profits[00:31:40] – Assignment Deals vs Buying and Controlling the Asset[00:32:50] – Finding the Right Land Agent for Faster Flips[00:34:10] – How Brent Defines Success and Winning in Business[00:35:45] – Final Thoughts and Where to Connect with Brent---## 👤 About Brent BowersBrent Bowers is a land investing expert, entrepreneur, and former Army officer who specializes in acquiring, flipping, and seller-financing vacant land across the United States. As the founder of The Land Sharks, Brent teaches investors how to create passive income through land deals, direct mail systems, and strategic land development, including manufactured housing solutions.---## 🔗 Episode Links & Resources• 🎥 **Watch the YouTube version:** https://youtu.be/EguL52oRMbs&list=UULFRs3SSmwVFbR2QEjIDqU0Ug• Guest Website: https://www.thelandsharks.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**

April 28, 202643 min

AI for Insurance: How Randy Thompson Built a Private Knowledge Base to Scale Sales, Protect Client Data, and Create a 4-Day Workweek

AI for Insurance: How Randy Thompson Built a Private Knowledge Base to Scale Sales, Protect Client Data, and Create a 4-Day WorkweekIn this episode of *Investing to Win*, host **Garret Wong** sits down with Randy Thompson to dive into:- Private AI knowledge bases for insurance sales and operations- Building scalable sales systems through repetition, training, and process mastery- The 4-day workweek as a retention and productivity strategy…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/8pOQ-9u3AoQ?si=C1avDrX_biV93UwP&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 SummaryIn this episode, Garret Wong sits down with insurance industry leader Randy Thompson to unpack how artificial intelligence is changing the way businesses train teams, protect client information, and scale expertise. Randy shares how he transformed 23 years of experience, over 2,000 documents, 900 hours of training, seven books, and multiple manuals into a private AI-powered knowledge base—allowing his team to access his decision-making process 24/7 without constant interruptions.The conversation dives deep into one of the most overlooked risks of mainstream AI tools: data privacy. Randy explains why using open large language models like ChatGPT, Claude, or Gemini for sensitive client information can expose businesses to compliance risks, regulatory penalties, and competitive disadvantages. He breaks down the difference between open AI systems and closed AI systems, and why proprietary business intelligence should remain protected.Randy also shares practical business applications of AI, from screening and hiring top talent to handling customer claims and improving internal decision-making. Through real-world examples, listeners get a clear understanding of how a properly built AI knowledge base can dramatically increase efficiency while preserving company standards and culture.Beyond AI, Randy reveals the leadership systems that built one of the top insurance agencies in America: relentless repetition in sales training, his “Stairs and Buckets” life insurance sales framework, and why implementing a four-day workweek over the last 15 years has helped him retain top talent, improve productivity, and create a healthier work culture. This episode is a masterclass on systems, leadership, and scaling expertise.---## 🎯 Key Takeaways• Protect proprietary business knowledge by using closed AI systems instead of public AI platforms• Build systems that replicate your decision-making to free up leadership time• Train teams through repetition, not information overload• Use AI for operational efficiency like hiring, claims support, and customer communication• Improve retention and productivity by implementing structured four-day workweeks• Measure success by improving yourself and creating impact in other people’s lives---## 🧠 Topics Covered• Closed AI systems vs open AI systems• AI compliance and data privacy in insurance• Building proprietary AI knowledge bases• Sales training through repetition and muscle memory• Hiring top-performing employees with AI analysis• Life insurance sales strategies and client education• The Stairs and Buckets sales framework• Four-day workweek implementation in business• Employee retention and company culture• Defining success through service and leadership---## 🔍 SEO KeywordsAI for insurance, private AI systems, closed AI systems, insurance sales training, insurance agency growth, sales systems, AI compliance, data privacy AI, insurance leadership, sales coaching, four-day workweek, employee retention, business automation, AI knowledge base, life insurance sales, Randy Thompson, Garret Wong, sales repetition, business systems, leadership training---## ⏱️ Timestamps[00:00:00] – Introduction to Randy Thompson and the concept of a 24/7 AI knowledge base[00:01:28] – How Randy turned 23 years of insurance expertise into a private AI brain[00:03:07] – Why closed AI systems matter for data privacy and business compliance[00:05:14] – The risks of using ChatGPT, Claude, and open AI for sensitive client data[00:07:48] – How proprietary AI protects business secrets and competitive advantage[00:10:07] – Real-world AI applications: hiring, claims management, and customer support[00:14:02] – Why generic AI fails to understand company culture and hiring standards[00:16:48] – Randy’s journey from teacher and wrestling coach to top insurance agency owner[00:18:58] – How coaching principles built Randy’s sales and leadership philosophy[00:22:15] – The power of repetition and sales roleplay in building elite performers[00:25:07] – The Stairs and Buckets framework for explaining life insurance simply[00:27:50] – Leadership, team culture, and implementing the 4-day workweek[00:31:24] – How the 4-day workweek improved retention and doubled productivity[00:34:25] – Customer expectations, boundaries, and protecting team wellbeing[00:37:24] – Randy’s definition of success, impact, and making the world better[00:39:12] – Final thoughts and closing reflections---## 👤 About Randy ThompsonRandy Thompson is a nationally recognized insurance agency owner, sales trainer, author, and business strategist based in Wyoming. With over 23 years in the insurance industry, Randy has built one of the top-performing insurance agencies in the United States while developing innovative systems for sales training, leadership development, and AI-powered business operations. He is the creator of the “Stairs and Buckets” life insurance framework and a leading advocate for closed AI systems and four-day workweek business models.---## 🔗 Episode Links & Resources• 🎥 **Watch the YouTube version:** https://youtu.be/8pOQ-9u3AoQ?si=C1avDrX_biV93UwP&list=UULFRs3SSmwVFbR2QEjIDqU0Ug• LinkedIn: https://www.linkedin.com/in/randy-thompson/---## 📘 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**

April 21, 202648 min

Crypto Cash Out Problems: Why Banks Block Transfers & How to Avoid It with Wojciech Kaszycki

Crypto Cash Out Problems: Why Banks Block Transfers & How to Avoid It with Wojciech KaszyckiIn this episode of *Investing to Win*, host **Garret Wong** sits down with Wojciech Kaszycki to dive into:- Crypto on-ramp and off-ramp infrastructure- Why banks block crypto transactions and compliance risks- Using crypto as collateral and the future of digital asset finance…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/tNJ8jDa8uhs&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 SummaryIn this episode, Garret sits down with Wojciech Kaszycki, a fintech pioneer and founder in the crypto banking infrastructure space, to unpack one of the biggest frustrations in crypto today: why cashing out can suddenly get blocked, even when you’ve done everything right. Wojciech breaks down the hidden mechanics behind banking compliance, AML regulations, and why financial institutions are often forced, not choosing to flag or delay crypto transactions.The conversation dives into the critical difference between crypto exchanges and infrastructure providers, clarifying the roles of on-ramps and off-ramps in making digital assets usable in the real world. Wojciech explains how outdated banking systems like SWIFT struggle to keep up with modern transaction volumes and why stablecoins and blockchain-based systems are emerging as faster, more efficient alternatives.Garret and Wojciech also explore practical strategies for avoiding account freezes, including how to communicate with your bank, what documentation to prepare, and why honesty is your strongest asset when dealing with compliance checks. For listeners new to crypto, Wojciech simplifies the process of buying and selling digital assets, making it accessible even for first-time users.Finally, the episode looks ahead to the future of finance, where crypto can be used as collateral, tokenization reshapes traditional assets, and digital currencies potentially replace fiat as the foundation of wealth. Whether you’re an investor, entrepreneur, or simply curious about crypto, this episode provides a clear, grounded understanding of how to navigate the system safely and effectively.---## 🎯 Key Takeaways• Understand that most crypto transaction blocks come from compliance rules—not bank intentions• Use regulated exchanges and platforms to reduce the risk of account flags• Always respond honestly and clearly to bank inquiries about crypto transactions• Recognize the difference between exchanges (trading) and infrastructure (movement of funds)• Consider using crypto as collateral instead of selling during market growth• Prepare documentation and transaction history before cashing out large amounts---## 🧠 Topics Covered• Crypto on-ramp vs off-ramp explained• Why banks block crypto withdrawals• AML, KYC, and compliance in digital assets• Differences between exchanges and crypto infrastructure companies• Stablecoins and the future of payments• Using Bitcoin as loan collateral• Real-world asset tokenization• Banking system limitations (SWIFT, legacy rails)• How to safely cash out crypto profits• The evolution of fintech and crypto adoption---## 🔍 SEO Keywordscrypto cash out, crypto on ramp off ramp, why banks block crypto, bitcoin withdrawals, crypto compliance, AML KYC crypto, crypto banking infrastructure, stablecoins explained, crypto investing, digital assets, tokenization finance, bitcoin collateral loans, fintech podcast, crypto regulation, how to cash out crypto, crypto exchange vs infrastructure, financial freedom crypto, blockchain payments, web3 finance, crypto beginners guide---## ⏱️ Timestamps[00:00:02] – Introduction and the Problem of Blocked Crypto Cash Outs[00:00:19] – Why Compliance and Banking Regulations Cause Delays[00:02:42] – Crypto Infrastructure vs Exchanges Explained Simply[00:06:11] – The Role of On-Ramps and Off-Ramps in Crypto Transactions[00:08:23] – Wojciech’s Background in Fintech and Early E-Commerce[00:11:38] – Lessons from Building and Selling a “Polish Amazon”[00:13:07] – Simple Explanation of Buying and Selling Crypto[00:17:58] – Why People Fear Crypto and Where Confusion Comes From[00:18:28] – Why Banks Block Crypto Transfers in Reality[00:21:25] – The Disconnect Between Traditional Finance and Crypto[00:25:28] – Common Triggers That Flag Crypto Transactions[00:29:35] – What Mobilum Actually Does for Users[00:33:22] – The Future of Crypto: Tokenization and Digital Assets[00:37:32] – Step-by-Step: How Beginners Buy Crypto[00:40:34] – Where the Real Differences in Platforms Exist[00:41:22] – Using Crypto as Collateral Instead of Selling[00:43:19] – How to Avoid Getting Blocked When Cashing Out[00:46:50] – Why Honesty with Banks Is Critical[00:47:38] – Defining Success and Financial Freedom---## 👤 About Wojciech KaszyckiWojciech Kaszycki is a fintech entrepreneur and the founder of Mobilum, a crypto banking infrastructure company focused on seamless on-ramp and off-ramp solutions. With a career spanning back to the early days of e-commerce and financial technology, he has built and scaled platforms across payments, brokerage systems, and digital assets. Today, he is focused on bridging traditional finance with crypto through compliant, user-friendly financial infrastructure.---## 🔗 Episode Links & Resources• 🎥 **Watch the YouTube version:** https://youtu.be/tNJ8jDa8uhs&list=UULFRs3SSmwVFbR2QEjIDqU0Ug• Guest Website: https://www.mobilum.com/en• LinkedIn: https://www.linkedin.com/in/wojciechkaszycki/---## 📘 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**

April 14, 202653 min

Climate Tech Startups: Why Cost, Speed & Reliability Beat Sustainability in Winning Customers

Climate Tech Startups: Why Cost, Speed & Reliability Beat Sustainability in Winning CustomersIn this episode of *Investing to Win*, host **Garret Wong** sits down with Josh Dorfman to dive into:- Climate tech business strategy and commercialization- Startup scaling, fundraising, and building a vertically integrated company- Product-market fit and selling innovation in traditional industries…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/-Y-HER6jG7o&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 SummaryIn this episode, Garret sits down with Josh to break down a hard truth in climate tech: if your business relies on guilt to sell, it’s already broken. Instead, Josh explains why the most successful sustainability-driven companies win by solving real customer problems; cost, speed, and reliability, while environmental impact becomes a powerful byproduct rather than the primary pitch.Josh shares the story behind Planted, a company transforming fast-growing grass into high-performance building materials that replace traditional wood-based products like OSB. From building early prototypes in a garage using makeshift equipment to securing major partnerships with large-scale homebuilders, he walks through the journey of turning a bold idea into a commercially viable product. The conversation highlights how vertical integration, supply chain control, and relentless focus on customer needs enabled the company to compete in a highly commoditized industry.Garret and Josh also dive into the realities of startup life, raising capital, navigating investor challenges, building the right team, and making difficult leadership decisions. Josh candidly shares his experience stepping down as CEO and later returning in a different role, emphasizing the importance of relationships, humility, and long-term mission alignment.This episode offers a powerful blend of business strategy, startup lessons, and personal growth insights, showing that true success in climate innovation comes from building products people genuinely need, not just ones they feel good about.---## 🎯 Key Takeaways• Build products that solve real customer problems before selling sustainability• Focus on cost, speed, and reliability to drive adoption in traditional industries• Use vertical integration to control supply chain and improve margins• Expect constant challenges in startups—from fundraising to team building• Prioritize relationships as a core driver of long-term success• Define winning beyond business, including personal and family life---## 🧠 Topics Covered• Climate tech business models and product-market fit• Building materials innovation and OSB replacement• Startup fundraising and venture capital challenges• Vertical integration strategy in manufacturing• Supply chain optimization and scalability• Partnering with large enterprise customers• Branding and go-to-market strategy for startups• Leadership transitions and founder mindset• The role of relationships in business success---## 🔍 SEO Keywordsclimate tech startups, sustainable building materials, green construction innovation, startup fundraising, venture capital insights, product market fit, vertical integration strategy, supply chain optimization, entrepreneurship lessons, clean technology, construction industry disruption, startup scaling strategies, business development, climate change solutions, founder mindset, manufacturing innovation, B2B sales strategy, sustainability in business---## ⏱️ Timestamps[00:00:02] – Introduction and bold take on climate tech sales strategies[00:00:31] – Why sustainability alone doesn’t drive real purchasing decisions[00:01:04] – The origin of Planted and building materials from fast-growing grass[00:02:02] – Why large builders care about cost, speed, and efficiency—not just climate impact[00:04:08] – Replacing traditional OSB and disrupting construction materials[00:04:33] – Startup origin story and the “hemp in the garage” moment[00:06:25] – Partnering with a former SpaceX engineer and rethinking carbon removal[00:07:56] – Early prototyping, experimentation, and building from scratch[00:10:42] – Discovering the breakthrough grass material with the Department of Agriculture[00:14:36] – Raising the first seed round and early investor challenges[00:15:59] – First major partnership and proving the product works[00:18:22] – Vertical integration and building a competitive advantage[00:21:26] – Josh’s background and early career in China and global business[00:23:37] – Transition into sustainability and entrepreneurship[00:27:58] – The reality of startup challenges and fundraising struggles[00:31:48] – Scaling the company and building the right team and culture[00:33:52] – Learning from high-pressure environments like SpaceX[00:35:11] – Branding strategy and naming the product[00:38:57] – Go-to-market strategy and why retail comes later[00:41:45] – Choosing the right customer segment for scaling[00:44:16] – Managing risk with large enterprise partnerships[00:46:35] – The importance of relationships in business and investing[00:48:21] – Stepping down as CEO and returning in a new role[00:50:01] – Defining success and what winning looks like today---## 👤 About Josh DorfmanJosh Dorfman is a climate tech entrepreneur and Chief Marketing Officer at Planted, a company developing sustainable building materials from fast-growing grass. With a background spanning international business, startups, and sustainability-focused ventures, Josh has built and scaled multiple companies focused on greener consumption and innovation. His work sits at the intersection of climate, manufacturing, and supply chain transformation.---## 🔗 Episode Links & Resources• 🎥 **Watch the YouTube version:** https://youtu.be/-Y-HER6jG7o&list=UULFRs3SSmwVFbR2QEjIDqU0Ug• Guest Website: https://getsuper.cool/• LinkedIn: https://www.linkedin.com/in/dorfmanjosh/---## 📘 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**