Wealth Strategy Secrets of the Ultra Wealthy Podcast
Welcome to "Wealth Strategy Secrets of the Ultra Wealthy," a masterclass in wealth creation, preservation, and legacy building, hosted by renowned wealth strategist Dave Wolcott. This podcast dives deep into the lesser-known, often secretive strategies that the ultra-wealthy use to amass and protect their fortunes. Each week, join Dave, a seasoned expert in wealth management, as he unveils the complex world of high finance, investments, tax strategies, and estate planning. Dave brings his decades of experience to the table, offering listeners an insider's view on how to think about wealth, leverage opportunities, and avoid common pitfalls that can erode financial success. In "Wealth Strategy Secrets of the Ultra Wealthy," you won't just hear from Dave. The show features a dynamic lineup of financial experts, successful entrepreneurs, and influential thought leaders, all sharing their insights and personal stories of triumph and resilience. These conversations aren't just about accumulating wealth; they're about cultivating a mindset for prosperity and understanding the responsibility that comes with significant wealth. Whether you're an aspiring millionaire, a seasoned investor, or simply looking to improve your financial literacy, this podcast is your gateway to understanding the sophisticated techniques of the world's financial elite. Dave's engaging, accessible approach breaks down complex concepts into actionable advice, making the world of ultra-wealthy wealth strategies accessible to everyone. Tune in to "Wealth Strategy Secrets of the Ultra Wealthy" and embark on a journey to transform your financial future. Learn, get inspired, and start applying the secrets of the ultra-wealthy to your own wealth journey!
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Best of 2025: Tax Strategies, Financial Education, and Mindset Shifts for Lifelong Financial Freedom
01/07/2026
Best of 2025: Tax Strategies, Financial Education, and Mindset Shifts for Lifelong Financial Freedom
Today’s episode is packed with powerful insights as we welcome a distinguished panel of guests, including Stephen Hall, Sharon Lechter, Ani Manian, and Aaron Hofrichter, alongside your host, Dave Wolcott. Together, they bring a wealth of experience in tax strategy, wealth acceleration, financial education, and the mindset required for lasting prosperity. We kick things off with Stephen Hall, a second-generation tax expert from Robert Hall and Associates, who breaks down the crucial differences between tax planning and tax preparation, and shares actionable tips for structuring your investments to minimize your tax burden. Next, Sharon Lechter, renowned co-author of "Rich Dad Poor Dad", takes us on her personal journey—from her childhood lessons around the dinner table to fundamentally changing the landscape of financial education across the globe. We’re also joined by Ani Manian, who explores the deeper meaning of wealth—beyond just financial figures—and explains why cultivating abundance begins with your mindset. Wrapping up, Aaron Hofrichter combines his experience as a CPA and real estate investor to share practical strategies for maximizing returns and steering clear of common tax pitfalls. This episode is simple, educational, and focused on empowering you to take control of your financial future, whether you’re an entrepreneur, investor, or someone looking to start your journey towards wealth. In this episode, we discuss: The difference between tax planning and tax preparation Strategies for tax-efficient investing and avoiding IRS “dirty dozen” pitfalls The importance of financial education for adults and children The mindset shifts needed to achieve true wealth and abundance Learn more: Get Dave's Free Book:
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Wealth Begins With Self-Awareness with Richard Coyne & Bill Zahller
01/02/2026
Wealth Begins With Self-Awareness with Richard Coyne & Bill Zahller
In this episode, Dave Wolcott joins the Road Less Travel Show to share the personal journey that shaped his approach to wealth, leadership, and purpose. From growing up in a middle-class household in Connecticut to serving four years in the U.S. Marine Corps, Dave reflects on the lessons of leadership, integrity, and teamwork that stayed with him long after his military service. After transitioning into corporate America, he found himself frustrated by the lack of mission and purpose—until discovering Robert Kiyosaki’s Cashflow Quadrant, a moment that fundamentally changed how he viewed business, investing, and financial freedom. Dave unpacks how years of running a technology consulting business while investing “underground” in alternative assets ultimately led to the creation of Pantheon and his book, The Holistic Wealth Strategy. He offers practical advice for anyone considering a major career or life pivot, emphasizing the importance of self-awareness, doubling down on your strengths, and building a team to support the areas where you’re not naturally wired. Dave also highlights tools like the Kolbe Index to better understand your instinctive strengths, avoid burnout, and design a path aligned with who you truly are—both in business and in life. Download a free copy of Dave’s book at and join the investor community for exclusive education, opportunities, and resources. Want to go deeper? Book a call to explore the Virtual Family Office or apply for the Mastermind to start building true generational wealth.
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Living Your Legacy: Building Connection, Harmony, and Purpose Within Your Family
12/31/2025
Living Your Legacy: Building Connection, Harmony, and Purpose Within Your Family
Today’s episode features an inspiring conversation with Karishma Ismail, an expert in helping high-achieving entrepreneurs and families create meaningful connections and lasting legacies. Joining host Dave Wolcott, Karishma Ismail brings her personal journey as a first-generation immigrant and successful entrepreneur, highlighting the struggles and lessons learned along the way—from witnessing her father’s tireless work ethic to navigating her own path through burnout, success, and ultimately, clarity about what matters most. Throughout this episode, Karishma Ismail peels back the layers of what legacy really means, moving beyond dollars in the bank to focus on the importance of family unity, intentional connection, and self-awareness. She offers simple, practical strategies for fostering connection and harmony within families, especially for those managing wealth across generations. Karishma Ismail and Dave Wolcott also explore why family conversations can be challenging, particularly during the holidays, and how breaking old patterns and roles can spark new, authentic relationships. Whether you’re an entrepreneur, a family leader, or someone seeking deeper fulfillment and connection, this episode is packed with valuable lessons for building a legacy that isn’t just inherited, but truly lived every day. In this episode, we discuss: Why disconnect happens in families—especially among high achievers and across generations How to create intentional connections and safe spaces for family conversations Practical strategies to break old patterns and foster ongoing family harmony The power of living your legacy today, not just planning for the future Learn more: Get Dave's Free Book:
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How the Top 1% Actually Build Legacy Wealth
12/26/2025
How the Top 1% Actually Build Legacy Wealth
In this episode of Wealth Strategy Secrets of the Ultra-Wealthy, Dave Wolcott joins Brett Swarts on the Build With The Billions podcast to unpack the mindset and strategies behind true legacy wealth. Dave shares his personal journey—from growing up in a middle-class household and serving as a Marine Corps captain to becoming a father of triplets overnight, a moment that forced him to rethink everything he had been taught about money. When traditional advice like maxing out a 401(k) fell short, Dave embarked on a decades-long mission to study how the top 1% and 0.01% actually build and protect wealth. Together, Dave and Brett explore why alternative investments like private equity, real estate, and energy are primary strategies for the ultra-wealthy—not “alternatives.” Dave explains how this realization led to the creation of The Holistic Wealth Strategy, a framework designed to help entrepreneurs move beyond Wall Street’s limitations, scale intelligently, and build wealth with purpose. This episode challenges conventional thinking and offers a clearer blueprint for those seeking long-term freedom, impact, and generational legacy. Download a free copy of Dave’s book at and join the investor community for exclusive education, opportunities, and resources. Want to go deeper? Book a call to explore the Virtual Family Office or apply for the Mastermind to start building wealth the way the ultra-wealthy do.
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Energy Investing Strategies: Minerals, Royalties, and Non-Op Interests for Sophisticated Investors
12/24/2025
Energy Investing Strategies: Minerals, Royalties, and Non-Op Interests for Sophisticated Investors
Today we're bringing you an insightful conversation with Tim Pawul, one of the clearest voices in energy alternative investments. Tim is the founder of a merchant bank specializing in oil and gas mineral rights, royalty interests, and non-operated working interests—a sector most investors have heard of but few truly understand. Based in Houston, Texas, Tim has spent over a decade at the forefront of oil and gas investing, earning a reputation as an expert and thought leader in this space. In this episode, Tim joins Dave Wolcott to demystify how sophisticated investors can harness the powerful returns and tax advantages of mineral and royalty investments, even without direct experience in the energy sector. Tim shares his journey from Rice University graduate to becoming a central connector of institutional players, managers, and investors in oil and gas. You'll gain an exclusive look into the recent institutionalization of these asset classes, why technology has transformed the sector, and what sets it apart from conventional public energy stocks. Whether you're looking to diversify your portfolio, minimize risk, or learn about 1031 exchanges and energy-backed passive income, this episode offers a masterclass in understanding both the macro trends and the nuts-and-bolts of investing in the booming minerals and royalties market. In this episode, we discuss: Tim’s path to becoming a leading expert in oil and gas minerals, royalties, and non-operated interests Macro trends and institutional evolution shaping energy investments How minerals, royalties, and non-op interests work—and their unique risk-return profiles Strategies for tax efficiency, portfolio fit, and leveraging 1031 exchanges in energy investing Download Dave’s book for free at and get access to the investor community for exclusive education & opportunities. You can also book a call to explore the Virtual Family Office or apply for the mastermind to go deeper into building generational wealth.
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Infinite Banking: The Missing Liquidity Strategy Most Investors Ignore
12/19/2025
Infinite Banking: The Missing Liquidity Strategy Most Investors Ignore
Most investors believe wealth is built by accumulating assets and waiting until retirement to enjoy them. But the ultra-wealthy play a very different game—one focused on control, liquidity, and velocity of capital. In this Deep Dive, Dave Wolcott breaks down why traditional accumulation strategies often fail high-earning investors and how a more holistic approach to wealth changes everything. Dave explains why over-concentration in real estate can quietly create risk, how Infinite Banking works when structured correctly, and why family offices have used this strategy for decades to improve cash flow, protect capital, and fund future investments without relying on banks. This episode pulls back the curtain on one of the most misunderstood wealth strategies—and shows how investors can regain control of their capital while accelerating long-term wealth. Learn how the ultra-wealthy think about capital—and how you can apply the same principles in your own portfolio. Download Dave’s free book, The Holistic Wealth Strategy, at:
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Deferred Sales Trust Explained Strategies to Defer Taxes and Multiply Passive Income
12/17/2025
Deferred Sales Trust Explained Strategies to Defer Taxes and Multiply Passive Income
Today’s episode features a powerhouse in the world of tax strategy and wealth building—Brett Swarts, CEO of Capital Gains Tax Solutions. As one of the nation’s leading experts in advanced exit planning, Brett Swarts brings a wealth of knowledge on how entrepreneurs, business owners, and investors can dramatically reduce their tax burden during major liquidity events. If you’re tired of feeling like the IRS is your largest beneficiary when selling highly appreciated assets, this episode is a must-listen. With a background in real estate, business brokerage, and a deep understanding of the tax code, Brett Swarts specializes in unveiling strategies that most advisors aren’t even aware exist. He goes beyond traditional approaches like the 1031 exchange, introducing listeners to the Deferred Sales Trust—a game-changing tool that can preserve 20% to 50% more of your net proceeds. In this episode, Brett Swarts and the host break down exactly how the Deferred Sales Trust works, who it’s best suited for, and how its flexible team-based approach makes it the “Netflix” to the traditional 1031 “Blockbuster.” Whether you’re planning to sell a business, real estate, crypto, or even collectibles, this conversation will open your eyes to tax-saving strategies that could shape your family’s wealth for generations. In this episode, we discuss: The mechanics and benefits of the Deferred Sales Trust How to offset capital gains tax and retain more wealth at exit Key differences between DSTs, 1031 exchanges, and other strategies Building the right team and mindset for generational wealth preservation Learn more: Get Dave's Free Book:
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From Middle-Class Mindset to Ultra-Wealth Strategy
12/12/2025
From Middle-Class Mindset to Ultra-Wealth Strategy
In this episode of the Wealth Strategy Deep Dives solo series, Dave Wolcott sits down with Chris Larsen to share the personal turning point that pushed him beyond traditional financial advice and into the world of alternative investing. After serving in the Marine Corps, transitioning into tech, and suddenly becoming a father to triplets, Dave realized that “max out your 401(k)” wasn’t a true wealth-building plan. This launched a 20-year journey exploring asset classes like real estate, oil & gas, private credit, and more—ultimately shaping the Holistic Wealth Strategy, a five-phase framework modeled after how the ultra-wealthy think, invest, and protect capital. Dave and Chris break down the phases of this strategy, beginning with vision and mindset, then elevating financial IQ, building a dream team of advisors, creating infrastructure for wealth protection, and ultimately building multiple streams of passive income. They discuss the multiplier effect of financial education, relationship capital, and whole life insurance as a powerful liquidity + protection tool used by family offices for generations. If you’ve ever wondered how to transition from retail investing to structured, generational wealth building—this conversation is your roadmap. Download Dave’s book for free at and get access to the investor community for exclusive education & opportunities. You can also book a call to explore the Virtual Family Office or apply for the mastermind to go deeper into building generational wealth.
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Wealth Beyond Numbers: Holistic Strategies for Fulfillment, Presence, and Purpose
12/10/2025
Wealth Beyond Numbers: Holistic Strategies for Fulfillment, Presence, and Purpose
Today’s episode features a truly transformative conversation with Ani Manian, an entrepreneur, master coach, and the aptly named “Mind Whisperer.” Ani brings a unique and profound perspective to the Wealth Strategy Secrets of the Ultra Wealthy podcast, challenging listeners to rethink everything they know about wealth. With a background spanning from working with billionaires to overcoming a childhood marked by extreme scarcity, Ani offers insights that go far beyond dollars and passive income. Host Dave Wolcott welcomes Ani to share his journey and unpack what it really means to be wealthy—shifting the focus away from mere numbers and traditional financial goals. Ani delves into what he sees as the true architecture of wealth: a state of being that combines full ease and deep aliveness in the present moment. He reveals how childhood experiences, our nervous systems, and the stories we carry deeply shape our behaviors around money and fulfillment. Throughout the episode, Ani and Dave go deep into actionable ways listeners can begin to cultivate a sense of internal wealth, regardless of external circumstances. They emphasize that true wealth is available to everyone right now, and reframing your relationship with time, energy, and identity is the real key to sustainable prosperity. In this episode, we discuss: Ani's powerful redefinition of wealth as a state of ease and aliveness How early life experiences and trauma shape our financial behaviors The pitfalls of chasing wealth in the future versus embracing it now Actionable steps to experience true wealth by cultivating gratitude in the present moment Learn more: Get Dave's Free Book:
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From Investor to Wealth Architect: Your Next Level
12/05/2025
From Investor to Wealth Architect: Your Next Level
In this episode, Dave Wolcott breaks down the framework inside the Holistic Wealth Strategy and explains why wealth acceleration isn’t just about investing—it’s about having the right team behind you. Dave shares his early journey as an LP investor across real estate, private credit, energy, and alternative assets, and how two decades of experience led him to build a blueprint inspired by how the top 1% manage wealth. He introduces the 5 phases of the Holistic Wealth Strategy: mindset, financial IQ, building your dream team, asset repositioning, and finally, creating powerful passive income streams. Dave also highlights why most investors plateau—not because of lack of opportunity, but lack of infrastructure, strategy, and guidance. He explains why wealth needs protection, proactive tax planning, and advisors who specialize in alternative investments—not generic financial planning. You’ll learn how to assemble your own wealth “Dream Team,” avoid blind spots, simplify complexity, and navigate toward a 100-year wealth plan with clarity and confidence. Download Dave’s book for free at and get access to the investor community for exclusive education & opportunities. You can also book a call to explore the Virtual Family Office or apply for the mastermind to go deeper into building generational wealth.
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Why Legacy Wealth Fails and How to Create Lasting Impact for Your Family
12/03/2025
Why Legacy Wealth Fails and How to Create Lasting Impact for Your Family
Today, we have a truly inspiring guest joining us, Barry Garapedian. Barry is a 39-year Wall Street veteran and founder of Mag7 Consultants, and he’s made it his mission to empower the next generation of leaders. With decades of experience in family governance, coaching heirs, and guiding young minds, Barry has distilled what he calls the “16 attributes of high performance”—essential skills, habits, and values that go far beyond what’s taught in schools. Barry’s impact reaches deep into the lives of Gen Z and young professionals, helping them build character, confidence, and real-world legacy—not just financial wealth. Through Mag7, he works directly with clients aged 13 to 28, giving them unfair competitive advantages, from networking and high-performance habits to emotional intelligence and the art of connection. His approach is hands-on, with practical methods like writing gratitude notes, cultivating high-performance habits, and tackling healthy challenges that drive growth and self-esteem. In this episode, Barry opens up about why legacy wealth often disappears by the second generation, how to create true family values and governance, and the practical actions families and young minds can take to sustain and multiply impact for generations. His passion for helping others become value creators and his actionable strategies make this conversation an absolute must-listen for entrepreneurs, parents, and anyone seeking to build lasting legacy. In this episode, we discuss: Why legacy wealth often disappears by the second generation The 16 attributes of high performance Building confidence and self-esteem in young minds Practical strategies for family governance and creating lasting value Learn more: Get Dave's Free Book:
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How the 1% Really Build Wealth
11/28/2025
How the 1% Really Build Wealth
In this episode, Dave Wolcott shares the pivotal journey that pushed him beyond traditional financial advice and into the world of alternative investing. From serving in the Marine Corps to suddenly becoming a father of triplets, Dave realized that maxing out retirement accounts wasn’t enough to secure his family’s future. That moment launched a 20-year pursuit into real estate, private credit, oil and gas, and other non-correlated assets—ultimately shaping the investment thesis behind Pantheon and the Holistic Wealth Strategy. Dave breaks down why active real estate often becomes a second job and why most investors are better served focusing on their strengths while leveraging passive investments that deliver cash flow, tax efficiency, and long-term appreciation. He closes with actionable advice for 2025: invest in yourself, prioritize your health and relationships, and elevate your financial IQ through mentors and masterminds. Download Dave’s book for free at and join the investor community for exclusive education, new opportunities, and resources to accelerate your path to financial freedom.
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The Million Dollar Decision: Outsmarting Fees and Creating Financial Freedom
11/26/2025
The Million Dollar Decision: Outsmarting Fees and Creating Financial Freedom
Today we have a truly insightful guest, Robert Rolih, joining host Dave Wolcott for an episode packed with hard-earned wisdom on building and protecting wealth. Robert Rolih is the international bestselling author of "The Million Dollar Decision," a book that has empowered thousands of investors across 70+ countries to simplify their investing approach, slash risk, and win long-term. Having built his own fortune as an entrepreneur before losing much of it by trusting the wrong financial advisors, Robert Rolih shares his candid journey—from growing up in a small village in Slovenia to discovering the hidden pitfalls that quietly erode investor wealth. Through personal stories and practical advice, Robert Rolih reveals the most common mistakes investors make, especially around fees, financial industry incentives, and overcomplicating wealth strategy. This episode goes beyond surface-level tips—Dave Wolcott and Robert Rolih dig deep into how simple changes and a conservative approach to investing can set you on a path to financial freedom. If you’re tired of paying too much in fees, confused by market volatility, or want to learn how to create a purpose-driven portfolio that you can stick to, this conversation offers a roadmap for making smarter, safer decisions. In this episode, we discuss: Robert Rolih’s personal journey: From entrepreneurial highs to profound investing lessons. The hidden impact of fees, taxes, and inflation on long-term returns. Six “dark forces” that quietly drain investor wealth. Expert insights on crypto, gold, and building a simple, resilient portfolio for prosperity. Learn more: Get Dave's Free Book:
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The Playbook for Financial Freedom: Mindset, Masterminds & Real Assets
11/21/2025
The Playbook for Financial Freedom: Mindset, Masterminds & Real Assets
In this dynamic solo episode, Dave Wolcott and Justin Donald dive deep into how investors can move beyond Wall Street’s one-dimensional approach to wealth building and adopt the same frameworks used by the ultra-wealthy. Dave shares his personal journey—from being raised on the traditional “go to school, get a job” mindset to discovering the Cashflow Quadrant and building a diversified portfolio across real estate, private equity, oil and gas, and other alternative assets. Alongside Justin, author of The Lifestyle Investor, they unpack the missing blueprint between knowing you can build wealth differently… and actually doing it. Together, they explore the Holistic Wealth Strategy—a five-phase roadmap beginning with mindset and vision. Dave reveals why success starts with rewiring your financial beliefs, surrounding yourself with the right community, and creating habits that align with your goals. Justin adds critical insight into why the ultra-wealthy allocate most of their wealth into alternative investments—assets that generate tax efficiency, passive income, and appreciation simultaneously. Whether you’re just starting to build your financial independence or scaling into multi-generational wealth, this episode is a masterclass in breaking free from the Wall Street playbook and creating a life by design—not by default. Download your free copy of Dave’s book at and join the investor community for exclusive education, new opportunities, and resources to accelerate your path to true freedom and legacy wealth.
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Airbnb Investing: Data, Cash Flow, and Tax Hacks for Real Estate Success
11/19/2025
Airbnb Investing: Data, Cash Flow, and Tax Hacks for Real Estate Success
Today’s episode features an illuminating conversation with John Bianchi, recognized as an Airbnb data savant and former head of data for the largest short-term rental investment fund in the US. Joining host Dave Wolcott , John Bianchi brings his deep expertise in Airbnb investing, data analytics, and business strategy to shed light on the world of short-term rentals. Having managed millions as a financial advisor before pivoting to Airbnb, John Bianchi shares his unique perspective on the differences between traditional financial planning and hands-on real estate investing. He details his personal journey—from opening 15 Airbnbs in Chicago to surviving market downturns and establishing a data-driven consultancy that helps investors identify profitable properties across the US. This episode is packed with practical advice for new and experienced investors alike, focusing on how to leverage data for smarter investments and how to navigate the challenges of the Airbnb market. John Bianchi and Dave Wolcott break down the critical aspects of successful short-term rental investing, including management strategies, tax advantages, and risk mitigation. Whether you’re looking for tax-efficient cash flow, ways to hedge against inflation, or simply want a resilient investment strategy, this episode delivers actionable insights with clarity and honesty. In this episode, we discuss: The differences between financial advising and active real estate investment How to analyze Airbnb data to find winning properties Tax strategies for short-term rental investors, including the STR tax loophole Building a resilient Airbnb investment portfolio and managing market risks Learn more: Get Dave's Free Book:
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The Hidden Structure of Wealth: Inside the Ultra-Wealthy’s Family Office
11/14/2025
The Hidden Structure of Wealth: Inside the Ultra-Wealthy’s Family Office
In this Wealth Strategy Deep Dive episode, Dave Wolcott breaks down one of the most powerful yet misunderstood frameworks used by the ultra-wealthy — the family office. While most investors think financial planning is the full picture, true wealth management operates on multiple dimensions: strategic tax planning, estate and asset protection, risk management, investment strategy, and even philanthropy. Dave shares how the elite structure their teams of top-tier advisors to make every decision—from investments to tax planning—work together in harmony. He reveals why most entrepreneurs outgrow their advisors and how creating a “virtual family office” can help you run your wealth like a business, reduce risk, and accelerate legacy growth. You’ll discover how integrating your advisors across all key areas creates 360° alignment, ensuring that every financial move supports your long-term vision and protects your family’s future. Whether you’re managing your first million or building generational wealth, this episode gives you the blueprint to start structuring your own virtual family office today. Get your free copy of Dave’s book at and join our investor community for access to exclusive education, private investment opportunities, and expert resources to help you build true freedom and legacy wealth.
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How the Ultra Wealthy Build Resilient Portfolios and Embrace Alternative Investments
11/12/2025
How the Ultra Wealthy Build Resilient Portfolios and Embrace Alternative Investments
Today’s episode features an exceptional guest, Mike Alexander, who brings over two decades of deep expertise in family offices, institutional investing, and alternative assets. Recently joining the Pantheon team as Director of Alternative Investments Portfolio and Capital Markets, Mike Alexander offers a rare, insider’s perspective on how the ultra-wealthy strategically build and protect wealth. Host Dave Wolcott invites listeners to take a behind-the-scenes look at what truly drives effective asset allocation—and how individual investors can leverage these same principles to accelerate their own wealth journey. Throughout the episode, Mike Alexander shares his origin story in the investment world, from early days at a major insurance company to managing billions for multi-billion-dollar family office clients. He reveals the key differences that set the ultra-wealthy apart, diving into alternative investments like private equity, private credit, and real assets. Listeners will hear how a disciplined investment process and thoughtful due diligence can lead to more resilient, high-performing portfolios that weather any market cycle. If you’ve ever wondered how top-tier families and institutions invest, or how you can adopt a wealth strategy rooted in long-term thinking, simplicity, and tax efficiency, this episode offers invaluable insights. In this episode, we discuss: Mike Alexander’s personal journey and lessons learned managing billions in family office assets The ultra-wealthy’s approach to diversification, asset allocation, and risk The importance of clear investment process and rigorous due diligence Strategies for individual investors to adopt an “endowment model” and invest for long-term success Learn more: Get Dave's Free Book: Your financial freedom starts with one conversation. Schedule a 30-min call with Mike Click here:
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Designing Your Future: Creating a Vivid Vision for 2025
11/07/2025
Designing Your Future: Creating a Vivid Vision for 2025
In this transformative solo episode, Dave Wolcott explores one of the most overlooked foundations of wealth creation — vision. Joined by visionary strategist Jennifer Hudye, founder of Vision Driven and partner of Cameron Herold (author of Vivid Vision), this conversation dives deep into how top entrepreneurs clarify, articulate, and live out their three-year vision for both business and life. Jennifer shares her own powerful story — from hitting career milestones like working with Tony Robbins to realizing success without clarity feels empty. Through her journey, she discovered that true fulfillment and momentum come not from chasing goals but from designing a vivid, integrated vision that guides every decision. Listeners will learn how to identify their North Star, communicate it effectively with their team and family, and use it as a filter to separate aligned opportunities from seductive distractions. Whether you’re scaling a company or refining your next chapter, this episode will inspire you to think bigger, act with intention, and build wealth through clarity and purpose. Download your free copy of Dave’s book at and join the investor community for exclusive access to educational content, opportunities, and resources to accelerate your path to financial freedom. Learn more:
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The Truth About Cash Flow, Tax Strategies, and Risk in Alternative Investments
11/05/2025
The Truth About Cash Flow, Tax Strategies, and Risk in Alternative Investments
Today’s episode features a dynamic conversation with Spencer Hilligoss, Founder of Madison Investing, and your host, Dave Wolcott—serial entrepreneur and author of the bestselling book "The Holistic Wealth Strategy." Spencer brings a wealth of experience as both a technologist and seasoned real estate investor, having gone full cycle on over 20 private real estate deals across asset classes like multifamily, self-storage, and medical office. Together, Spencer and Dave help investors cut through the market noise and navigate the complexities of alternative investments. In this educational and insightful discussion, Spencer and Dave candidly share their personal investing journeys and the key lessons they’ve learned from recent shifts in the real estate landscape—especially in the wake of rapidly rising interest rates and tightening commercial debt markets. They emphasize that building true wealth requires strategic planning, rigorous due diligence, and thoughtful risk management, especially when promises of cash flow and “preferred returns” might not be as certain as they seem. Listeners will gain practical advice on how to evaluate deals, spot pitfalls, and leverage the collective wisdom of investment communities. Spencer also shares how to align investment choices with your unique “Investor DNA” and long-term vision, rather than chasing shiny objects or relying on projections alone. In this episode, we discuss: The truth behind cash flow projections and preferred returns How depreciation and tax strategies impact real estate investments The risks and nuances of preferred equity and rescue funds Practical portfolio construction and recession-proofing your wealth strategy Learn more: Get Dave's Free Book: Connect with Spencer: Business website: Personal bio website: LinkedIn profile: Twitter:
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Understanding the K-1: The Tax Advantage the Ultra-Wealthy Never Miss
10/31/2025
Understanding the K-1: The Tax Advantage the Ultra-Wealthy Never Miss
Welcome back to Wealth Strategy Secrets of the Ultra Wealthy! I’m your host, Dave Wolcott, and in this solo Wealth Strategy Deep Dive, we’re unpacking one of the most misunderstood yet powerful tools in alternative investing — the K-1. If you’ve ever invested in a real estate syndication, private equity deal, or energy partnership, chances are you’ve heard, “Don’t forget your K-1.” But what exactly is it, and why does it matter? In this episode, Dave breaks down how the IRS Schedule K-1 works, why it’s essential for investors in pass-through entities, and how it delivers one of the biggest wealth-building advantages, the ultra-wealthy leverage — tax efficiency. You’ll learn how income, losses, and deductions flow directly from your investment to your personal tax return, allowing you to keep more of what you earn. From depreciation in multifamily real estate to deductions in energy investments, the K-1 isn’t just a form — it’s a gateway to smarter, tax-advantaged investing. Learn more: Get Dave's Free Book:
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Hospitality Real Estate: Contracted Cash Flow, Tax Benefits & Legacy
10/29/2025
Hospitality Real Estate: Contracted Cash Flow, Tax Benefits & Legacy
Today’s episode brings you an inspiring conversation with hospitality entrepreneur and real estate visionary, Josh McCallen. As the founder of Accountable Equity, Josh has carved out a unique path at the intersection of purposeful business, real estate investing, and family legacy. Beyond building a portfolio of luxury resorts spanning over 1,000 acres, Josh stands apart for the culture he fosters in both his companies and his own home—he is a proud father of ten, and together with his wife Melanie, leads by example in instilling the timeless values of hard work, humility, and service. Josh joins the show to share his extraordinary journey: from managing resort developments for high-net-worth families to launching and scaling his own portfolio with accredited investors. Along the way, he offers a behind-the-scenes look at how deep-rooted core values can shape not only a thriving business, but also nurture generational wealth and impact entire communities. Listeners will gain practical insights into the business of hospitality real estate, the importance of aligning wealth-building with a strong sense of purpose, and how involving the next generation in business can create invaluable teaching moments. Josh’s wisdom goes beyond spreadsheets and proformas—he reveals how integrating joy, humility, and service at every level can be a true differentiator for success. In this episode, we discuss: Building family legacy and core values for future generations Innovative hospitality real estate strategies with built-in investor benefits The unique advantages of involving family members in business operations How to align wealth creation with purpose, impact, and community Learn more:
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Alternative Investments Explained: Building Wealth Outside of Wall Street
10/24/2025
Alternative Investments Explained: Building Wealth Outside of Wall Street
In today’s episode, we’re joined by Vicky for a special solo series focused on wealth strategy secrets of the ultra-wealthy. Vicky dives into the lesser-known approaches that set high-net-worth individuals and family offices apart from the typical investor. While most people tend to concentrate their portfolios in stocks and bonds, Vicky reveals that the wealthiest families allocate nearly half their portfolios to alternative investments—assets that go beyond the realm of Wall Street. Vicky breaks down complex financial concepts in a simple, actionable format, making this episode ideal for anyone looking to build or refine their legacy wealth. Drawing from years of expertise, Vicky explores how alternative investments such as private equity, venture capital, real estate, hedge funds, commodities, and even collectibles can offer unique benefits—like diversification, steady cash flow, and exposure to opportunities rarely found in traditional markets. This episode is packed with practical insights aimed at helping listeners create generational wealth. Whether you’re just starting your journey or looking for new ways to expand your portfolio, Vicky offers valuable guidance on strategies used by the ultra-wealthy to achieve financial freedom and safeguard their assets. Visit to start your journey toward a Holistic Wealth Strategy. Download your free copy of Dave’s book at
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Ditch the 4% Rule: Passive Income Over Accumulation
10/22/2025
Ditch the 4% Rule: Passive Income Over Accumulation
Today’s episode features an insightful conversation with Derek Coburn, wealth advisor, author of "Let’s Retire Retirement," and founder of the Cadre community. Derek brings decades of experience helping entrepreneurs and high achievers rethink conventional views on wealth, freedom, and the age-old concept of retirement. Derek’s journey started in traditional financial advising, where he noticed how many people fell into outdated patterns—saving for a distant finish line while sacrificing health, relationships, and personal purpose. He eventually took a different path, focusing on building deep relationships and meaningful communities instead of sticking to the typical accumulation mindset. His book and philosophy challenge listeners to move away from the 18th-century idea of retirement and instead focus on creating freedom and fulfillment right now, not just someday in the future. In this thought-provoking discussion, Derek and host Dave Wolcott dive into why the old model of working hard today for a delayed payoff tomorrow no longer fits our lives. They explore the mindset shifts needed to prioritize well-being, relationships, and purpose, while still making smart financial choices. Derek’s practical tips and real-world examples will help you reconsider what it means to live and invest wisely. In this episode, we discuss: Why the traditional retirement model is outdated and may not serve your real goals The difference between accumulation theory and passive income—building freedom today, not just for the future Mindset shifts to prioritize relationships, health, and meaning over postponing happiness Actionable strategies to align your wealth plan with your true priorities and avoid future regrets Click here to learn more:
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The Trifecta: The Ultimate Return Profile the Ultra-Wealthy Use to Build Real Wealth
10/17/2025
The Trifecta: The Ultimate Return Profile the Ultra-Wealthy Use to Build Real Wealth
Welcome back to Wealth Strategy Secrets of the Ultra Wealthy! I’m your host, Dave Wolcott, and in this Wealth Strategy Deep Dive, we’re breaking down one of the most powerful frameworks the ultra-wealthy use to build and protect their wealth — The Trifecta Return Profile. Most investors chase yield or the next hot stock, but the truly wealthy design portfolios that work smarter — optimizing for tax efficiency, passive income, and upside potential. In this episode, Dave reveals how to evaluate any real asset — from multifamily real estate to private credit — through this lens and why this strategy consistently outperforms the Wall Street casino. Learn how depreciation can eliminate taxes on cash flow, how recurring passive income buys your freedom, and how equity growth compounds your wealth over time. By the end, you’ll understand exactly how to build a “Trifecta Portfolio” that delivers returns in money, time, purpose, and relationships. Visit to start your journey toward a Holistic Wealth Strategy. Download your free copy of Dave’s book at
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Mindset + Skillset: Align Values to Build Wealth
10/15/2025
Mindset + Skillset: Align Values to Build Wealth
Today’s episode features a dynamic conversation with Keala Kanae, a true testament to the power of mindset in achieving extraordinary success. Keala’s journey is as inspiring as it is educational—he went from working as a minimum-wage barista and struggling with 12 years of failed attempts, to building and exiting an eight-figure education company. Now, he dedicates his work to helping founders, investors, and high performers reach their next level through deep mindset transformation and personal development. Dave dives in with Keala to unlock what really separates high achievers from everyone else. If you’ve ever felt “stuck” despite investing in books, courses, and skill-building, this episode is for you. Keala shares how most barriers to success aren’t about lacking skill or opportunity, but about being misaligned with our true values and purpose—a lesson rooted in the science of axiology, or the study of values. Listeners will discover how to move from short-term motivation to lasting inspiration, align goals with personal values for effortless progress, and avoid the common pitfalls of self-sabotage and procrastination. This conversation is packed with actionable wisdom and science-backed strategies to help you unlock more purpose, fulfillment, and wealth. In this episode, we discuss: Keala’s personal journey from minimum wage to entrepreneurial success The difference between skill set and mindset—and why both are essential The science of values (axiology) and how to align your goals with your true values Practical strategies to replace motivation with durable inspiration for lasting achievement
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Why Cash Is Trash in 2025 — The Smart Investor's Hedge
10/10/2025
Why Cash Is Trash in 2025 — The Smart Investor's Hedge
In this powerful episode, Dave Wolcott tackles one of the biggest threats to your financial freedom today: the silent erosion of your wealth through dollar devaluation. With the U.S. dollar losing nearly 10% of its value in 2025, this episode breaks down why inflation isn’t just a temporary headline—it’s a long-term wealth destroyer hiding in plain sight. Dave reveals why traditional stock and bond portfolios often fail to protect purchasing power and how even “conservative” savers are unknowingly losing ground. He explains the difference between chasing yield and structuring true wealth, exposing why you can’t out-earn a broken monetary system. You’ll learn how the ultra-wealthy hedge against inflation by owning real assets—income-producing real estate, energy projects, infrastructure, and farmland—that not only preserve value but thrive when fiat currencies fall. Dave connects these timeless principles to today’s investing landscape and shares actionable steps you can take now to diversify outside the dollar and secure your financial independence. If you’re ready to stop reacting to inflation and start owning assets that create lasting wealth, this episode is your roadmap. Learn more about building your own portfolio of real assets at or schedule a call with the Pantheon team to discover how the Holistic Wealth Strategy can help you keep—and grow—your wealth outside of Wall Street. Download your free copy of Dave’s book at
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Build Cash-Flowing Businesses: Systems, KPIs & Exit Readiness
10/08/2025
Build Cash-Flowing Businesses: Systems, KPIs & Exit Readiness
Today’s episode features an enlightening conversation with business coach and entrepreneur, Tanner O’Brien. As a partner in a thriving family-owned ActionCOACH franchise, Tanner has firsthand experience navigating the challenges and triumphs of entrepreneurship—from nearly running out of cash to building a business that truly operates as an asset, not a job. Tanner’s diverse background in fitness, finance, and leadership, coupled with his journey as both a business owner and coach, provides a rich foundation for today’s discussion. Throughout the episode, he unpacks practical strategies for transforming your company into a machine that can work for you, instead of relying on you. Host Dave Wolcott leads the conversation, drawing out actionable advice for audience members at all stages—whether you’re a seasoned business owner, an aspiring entrepreneur, or someone ready to transition from passive income to a business of passion. Tanner emphasizes the importance of building a strong foundation, leveraging systems, tracking key metrics, and aligning your team for scalability, freedom, and long-term success. Drawing from decades of ActionCOACH’s proven frameworks as well as his own personal lessons, Tanner gives both encouragement and tactical steps to help entrepreneurs prepare for growth and even a future exit. In this episode, we discuss: The biggest mistakes business owners make and how to avoid them How to create systems, KPIs, and team alignment to build a business that truly runs without you The fundamental steps every entrepreneur should take before hiring or scaling Exit strategies and how to prepare your business for a successful transition in the future Click here to learn more:
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The Pyramid of Private Market Sponsors Explained (Real Estate, Energy & More)
10/03/2025
The Pyramid of Private Market Sponsors Explained (Real Estate, Energy & More)
When it comes to investing in private markets, not all sponsors are created equal—and understanding the differences can dramatically impact your wealth strategy. In this solo episode of Wealth Strategy Secrets: Deep Dives, Dave Wolcott breaks down the three tiers of private market sponsors—emerging, mid-market, and institutional—and what each means for your portfolio. From entrepreneurial sponsors offering higher projected returns but higher execution risk, to mid-market players delivering strong risk-adjusted performance, to global institutions prioritizing stability over upside, Dave shares how to evaluate the trade-offs at every level. You’ll discover why mid-market sponsors often represent the “sweet spot” for sophisticated investors, how institutional alignment brings safety but compresses yields, and the hidden risks of chasing pro forma numbers that look too good to be true. Whether you’re diversifying into real estate, energy, private credit, or other alternative assets, this episode equips you with the framework to analyze where your capital is working—and how to strike the right balance between risk, return, and predictability in building legacy wealth. Download your free copy of The Holistic Wealth Strategy and access exclusive investor resources at
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From Flipping Houses to $500K Passive Income: Commercial Real Estate Strategies
10/01/2025
From Flipping Houses to $500K Passive Income: Commercial Real Estate Strategies
Today’s episode features an inspiring conversation with Matt Aitchison, a true example of resilience and growth in the world of real estate and entrepreneurship. Matt is a real estate investor, entrepreneur, and host of the Millionaire Mindcast podcast. His journey—from flipping his first “cat house” in his early twenties using 100% other people’s money to building a diversified portfolio of shopping centers, hotels, medical offices, and mobile home parks—is a masterclass in persistence, creativity, and lifelong learning. Matt’s story stands out not only for the impressive deals and assets, but for his dedication to surrounding himself with mentors and peer communities that drive accountability and continuous development. Throughout the episode, you’ll hear about how Matt shifted from hustle-driven house flips to cash-flowing commercial properties, as well as his philosophy of becoming a “whole life millionaire”—achieving true wealth across finances, relationships, health, and impact. Matt shares actionable insights on how to structure your life and investment strategy for long-term success. He offers valuable lessons learned from both his wins and setbacks and highlights the importance of likability, mindset, and creative approaches in today’s market environment. In this episode, we discuss: 1. Matt’s entrepreneurial start and breakthrough first deal 2. The transition from active income flips to passive commercial real estate investing 3. Why mentorship, community, and lifelong learning are critical to wealth building 4. Practical strategies for thriving in today’s changing real estate market Click here to learn more
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The #1 Risk That Can Destroy Your Portfolio
09/26/2025
The #1 Risk That Can Destroy Your Portfolio
Welcome back to Wealth Strategy Deep Dives, a special solo series of Wealth Strategy Secrets of the Ultra Wealthy. In this episode, Dave Wolcott unpacks a hidden danger that silently threatens most investors: over-concentration risk. History proves the stock market doesn’t move in a straight line—the dot-com crash of 2000 (-50%), the 2008 financial crisis (-57%), and the COVID crash in 2020 (-34% in weeks) all wiped out years of progress for investors who were fully concentrated in equities. The math is even harsher: a 50% loss requires a 100% gain just to break even. The ultra-wealthy know better. They build resilience by spreading their capital into cash-flowing alternatives and non-correlated assets that protect wealth no matter what the market is doing. Your takeaway is simple: don’t let over-concentration be your blind spot. Smart diversification not only safeguards your wealth but also helps you sleep better at night. 👉 Download your free copy of Dave’s book at and join the investor community for exclusive strategies and resources to accelerate your path to financial freedom.
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