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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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:
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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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Energy Investing: Oil, Gas, and Infrastructure Opportunities for Accredited Investors
09/24/2025
Energy Investing: Oil, Gas, and Infrastructure Opportunities for Accredited Investors
Today’s episode features a remarkable guest, Ben West, co-founder of Pragma Energy and an accomplished expert at the crossroads of energy and capital markets. Ben brings close to a decade of experience working globally with C-suite leaders, family offices, and institutional investors, lending him a unique 360-degree perspective on the energy sector. As demand for energy surges worldwide and innovations like artificial intelligence push U.S. power needs to unprecedented heights, Ben joins host Dave Wolcott to unpack the real risks and opportunities in this critical, often misunderstood, asset class. Ben’s journey into energy investing began in Europe and has taken him from brokering high-level industry relationships to launching Pragma, a platform providing pragmatic, holistic conversations around energy needs and capital reinvestment. In this educational episode, Ben breaks down the complexities of energy investing for both newcomers and experienced investors. He discusses how changing global dynamics—from post-pandemic supply shocks to shifts in public policy and evolving international markets—are driving capital flows, shaping infrastructure challenges, and presenting exceptional opportunities for those willing to lean into the sector. Listeners will walk away with a clear understanding of why energy remains foundational to our economy, and how passive investment in the sector can unlock consistent cash flow, powerful tax advantages, and long-term upside. In this episode, we discuss: The fundamentals and investment landscape of the energy sector How global demand and technologies like AI are transforming infrastructure needs Opportunities and challenges in the natural gas market Key risks and due diligence considerations for energy investors Click here to learn more:
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Tax Planner vs. Tax Preparer: Why 95% of People Overpay the IRS
09/19/2025
Tax Planner vs. Tax Preparer: Why 95% of People Overpay the IRS
In this episode of Wealth Strategy Deep Dives, Dave Wolcott breaks down one of the most costly misconceptions in wealth building: the difference between a tax preparer and a tax planner. While most people rely on preparers who simply record history and file returns, the ultra-wealthy take a proactive approach with planners who design structures, leverage incentives, and use the 6,000+ page tax code as a roadmap for wealth creation. Dave shares how this shift transformed his own financial journey and why it can literally save you hundreds of thousands—or even millions—over your lifetime. Using Robert Kiyosaki’s Cash Flow Quadrant, Dave illustrates how employees and the self-employed often pay the highest tax rates, while business owners and investors can legally minimize their tax burden—sometimes down to 20% or even zero. The key is playing offense, not defense, by partnering with the government through business, jobs, and investments. The lesson is simple: wealth isn’t just about how much you make, but how much you keep and multiply to create freedom of time, money, and purpose. Learn how to build your dream team and partner with the right tax planner at HolisticWealthStrategy.com
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Exit Planning Secrets: Maximize Business Value and Avoid Costly Mistakes
09/17/2025
Exit Planning Secrets: Maximize Business Value and Avoid Costly Mistakes
Today we have a remarkable guest joining us, Cameron Bishop. Cameron is a Managing Director at Raincatcher and a seasoned veteran in the world of business acquisitions and exits. Over his career, Cameron has sat on every side of the table—as a CEO, a buyer, and an advisor—shepherding deals totaling more than half a billion dollars. He has seen first-hand why nearly 80% of businesses that attempt to sell never actually do and understands the emotional and financial stakes involved in selling a company. In this episode, host Dave Wolcott dives deep with Cameron into the often misunderstood and emotional process of selling a business. Cameron draws on his decades of experience to reveal the biggest traps that business owners fall into when planning an exit, from messy accounting practices to the dangers of a business being dependent on the owner. He sheds light on how proper planning can turn a business sale from a disappointing letdown into a life-changing opportunity, and why you should start thinking about your exit plan on day one, whether you’re planning to sell in three years or thirty. One of the most valuable aspects of this conversation is Cameron's focus on the human side of business transitions and future life planning, ensuring business owners thrive both during and after an exit. In this episode, we discuss: The most common mistakes that kill business deals and how to avoid them Key steps to maximize your business’s value before selling The emotional journey and life planning required for a successful transition Current market trends and opportunities for both sellers and aspiring buyers Learn more:
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Private Credit Investing: High Yields, Diversification & Cash Flow
09/12/2025
Private Credit Investing: High Yields, Diversification & Cash Flow
In this Wealth Strategy Deep Dive, Dave Wolcott unpacks one of the fastest-growing opportunities in alternative investments—private credit. With traditional banks tightening lending standards, private credit has surged from $500 billion a decade ago to nearly $2 trillion in 2025. This asset class offers investors higher yields, downside protection through collateralized loans, and steady, non-correlated income streams that outperform traditional bonds and many real estate investments. Through real-world examples—like Florida roofing companies who turned to private credit after hurricanes to quickly fund growth—Dave illustrates why billionaires and institutions have been pouring into this space. You’ll learn how private credit funds generate double-digit returns, why short loan cycles can accelerate compounding, and how they create stability and diversification in a portfolio that’s heavy in equities or real estate. For more insights and resources on this strategy, visit . Take the next step: Head over to to download your free copy of Dave’s book, The Holistic Wealth Strategy. You’ll also gain access to our investor community, exclusive educational content, and new opportunities to accelerate your path to freedom. Ready to go deeper? Book a call with our team to explore our Virtual Family Office services or join our mastermind group to start building true generational wealth.
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Cash Flow Over 401(k)s: Build Passive Income with Real Assets
09/10/2025
Cash Flow Over 401(k)s: Build Passive Income with Real Assets
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Invest in Yourself: The #1 Wealth Strategy for High Achievers
09/05/2025
Invest in Yourself: The #1 Wealth Strategy for High Achievers
In this Wealth Strategy Deep Dives episode, Dave Wolcott unpacks one of the biggest common denominators among highly successful people: they invest in themselves first. From masterminds and personal development to daily habits like meditation, journaling, and fitness, Dave explains why focusing on your growth delivers the highest ROI—often 10x to 100x. He also reminds us that success isn’t just about net worth. It’s about advancing consciousness, designing your life intentionally, surrounding yourself with the right people, and creating lasting impact. Money follows when you focus on building yourself, your habits, and your vision for the future. Ready to take the next step? Visit to download a free copy of Dave’s book and join our investor community. You’ll also gain access to exclusive content, opportunities, and resources to accelerate your path to freedom. Book a call with our team or join our mastermind to go deeper into building true generational wealth.
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Build Wealth with Banks’ Money: Creative Financing & Credit Stacking Strategies
09/03/2025
Build Wealth with Banks’ Money: Creative Financing & Credit Stacking Strategies
Today’s episode is packed with inspiration and practical strategies as we welcome Brandon Elliott, a self-made real estate investor with a journey unlike any other. Brandon is the founder of Credit Counsel Elite, and his story takes us from a childhood of scarcity, through dangerous setbacks, and ultimately to financial freedom. After surviving a life-altering explosion, Brandon transformed his mindset and set out to master the art of leveraging banks’ money—what he calls “OBM: Other Banks’ Money”—to build an impressive $14 million real estate portfolio and generate over $50,000 per month in income. Brandon hasn’t followed a conventional path to wealth, and certainly not the Dave Ramsey approach. Instead, he’s used creative financing, strategic credit stacking, and under-the-radar banking strategies to make capital available and accelerate his investments—without relying solely on his own savings or high-interest options. His mission now is to help other business owners, real estate investors, and entrepreneurs learn the “rules of the game” that banks use, so they too can tap into life-changing funding opportunities. In this episode, Brandon shares the real-life lessons that took him from financial rock bottom to thriving success. You’ll hear actionable insights and step-by-step advice for creating capital out of seemingly thin air. In this episode, we discuss: Brandon's journey from hardship to financial independence Creative ways to leverage credit and bank relationships to generate investment capital The fundamentals of the BRRRR strategy and credit stacking Actionable tips for building strong credit profiles and accessing zero-percent bank funding Click here to learn more:
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The Blueprint for Building Wealth Beyond Wall Street
08/29/2025
The Blueprint for Building Wealth Beyond Wall Street
In this solo episode of Wealth Strategy Deep Dives, I share the foundational principles behind building true, lasting wealth outside of Wall Street. Over the past 25 years, I’ve invested in alternative assets, studied passive income theory versus accumulation theory, and built businesses that focus on both growing and protecting capital. What I’ve discovered—and what I share in today’s conversation—is that wealth isn’t just about tactics like real estate or oil and gas investments. Those are tools. The real key is clarity. Clarity around your vision, your values, and how financial capital fuels other critical forms of capital: spiritual, emotional, social, and physical. At the end of the day, money is not the end goal—it’s the energy that empowers you to live with purpose, create impact, and build legacy. This episode unpacks why the “just hit a retirement number” approach of traditional financial planning falls short, and why creating a holistic wealth blueprint allows you to align money with meaning. If you’ve ever wondered how to move beyond simply chasing returns to creating real freedom for yourself and your family, this episode is for you. If this episode sparked something, head to to download a free copy of my book. You’ll also get access to our investor community where we share exclusive educational content, new opportunities, and resources designed to help accelerate your path to freedom. And if you want to go even deeper, book a call with our team to learn about our Virtual Family Office services or join our mastermind group where we dive into building true generational wealth.
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How to Build Wealth Like a Family Office Using Alternative Assets
08/27/2025
How to Build Wealth Like a Family Office Using Alternative Assets
Today we have a fascinating episode with Daniel Brereton, Director at Equity Multiple, and a true expert in both traditional and alternative investments. Daniel’s journey is as impressive as it is educational—after serving as an Army officer, he translated his leadership and analytical skills to the world of private markets, first at UBS advising pensions and endowments, and now helping everyday investors unlock access to institutional-quality real estate deals. Host Dave Wolcott explores Daniel’s evolution from the military to the cutting edge of wealth strategy, shining a light on how family offices and leading endowments invest beyond the stock market. Daniel shares his firsthand knowledge of asset allocation and explains why alternatives like private credit and real estate can be game-changers for building a diversified, resilient portfolio. In this engaging conversation, Daniel breaks down what true financial freedom means, what he learned by working with some of the world’s most sophisticated investors, and how regular investors can benefit from private market opportunities—without needing to write million-dollar checks. Listeners will gain actionable advice on evaluating risk, choosing the right partners and sponsors, and building wealth with patience and intention. In this episode, we discuss: The fundamentals of asset allocation and diversification beyond traditional stocks and bonds Why private credit and real estate are especially attractive in today’s market cycle How to assess risk, sponsor quality, and market opportunities in private market deals Actionable tips for gaining access to institutional-quality investments and accelerating your wealth trajectory
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Why Building a Dream Team is the Secret to Lasting Wealth
08/22/2025
Why Building a Dream Team is the Secret to Lasting Wealth
In this solo episode of Wealth Strategy Deep Dives, Dave shares one of the most powerful keys to building legacy wealth—creating your dream team. Too often, investors try to grow alone, but the ultra-wealthy know that scaling wealth requires surrounding yourself with experts who can help you protect, preserve, and multiply your assets. Dave walks through the essential roles every investor should consider, from a functional medicine doctor and nutritionist who keep you performing at your peak, to proactive tax planners, asset protection attorneys, insurance strategists, and risk managers who safeguard your wealth. He explains why the right advisors should not just be at your level—but 10x above you—so you can accelerate your path to becoming your future self. This episode challenges you to ask a game-changing question: If I were to 10x my wealth today, who would I need on my team to make that happen? The answer may transform not only your portfolio, but your entire life. Ready to take the next step? Download a free copy of Dave’s bestselling book The Holistic Wealth Strategy at . You’ll also gain access to our exclusive investor community, packed with education, opportunities, and resources to accelerate your path to freedom.
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What Wall Street Won’t Tell You: True Wealth Strategies Using Self Directed IRAs
08/20/2025
What Wall Street Won’t Tell You: True Wealth Strategies Using Self Directed IRAs
Today’s episode is an absolute must-listen for anyone eager to take charge of their financial future and break free from the Wall Street roller coaster. We’re joined by Kaaren Hall, the founder and CEO of U Direct IRA Services, and a true force in the world of Self Directed IRAs. With a background rooted in real estate, mortgage servicing, and loan origination, Kaaren brings over a decade of hands-on experience empowering investors to diversify their retirement funds beyond conventional stocks and bonds. Throughout this informative conversation, Kaaren unpacks the opportunities and realities of self-direction. She shares her journey from the mortgage industry to building her own self-directed IRA firm, and reveals how investors are using these accounts to tap into real estate, private credit, precious metals, syndications, and even cryptocurrencies. Kaaren also tackles the myths and misconceptions about diversification as sold by Wall Street, emphasizing the importance of understanding your investments and taking full responsibility for your financial decisions. Practical, step-by-step advice is offered on how to open, fund, and invest through a self-directed IRA, as well as how to avoid common tax pitfalls like UBIT and UDFI. Whether you’re looking to reposition idle retirement assets or just want to raise your financial IQ, Kaaren’s expertise will help illuminate the path toward greater control and smarter diversification. In this episode, we discuss: The basics of self-directed IRAs and how they work Real-world myths and truths about investment diversification Tax considerations such as UBIT and UDFI How to select and perform due diligence on alternative assets Click here to learn more:
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Accumulation Theory Vs. Passive Income
08/15/2025
Accumulation Theory Vs. Passive Income
In this special solo episode of Wealth Strategy Secrets of the Ultra Wealthy, Dave Wolcott breaks down one of the most misunderstood concepts in wealth building—the difference between an accumulation strategy and a passive income strategy. While traditional financial planning focuses on building a nest egg for retirement, Dave explains why shifting your mindset to prioritize consistent, sustainable cash flow can give you true freedom—no matter your age. He challenges the conventional retirement narrative, showing how freedom of purpose, time, and relationships matters far more than a “magic number” in your bank account. Dave also debunks the myths around passive income, revealing why many so-called “passive” streams like Airbnb, YouTube channels, or Amazon stores are actually businesses requiring years of effort before becoming hands-off. He dives into the deeper question of why you’re seeking passive income in the first place, emphasizing that clarity of vision and intentionality often matter more than the money itself. With parallels between health and wealth, Dave shares how mindset, intellectual capital, and even longevity practices tie into building a truly holistic life—where your wealth fuels vitality, purpose, and impact. Grab your FREE copy of The Holistic Wealth Strategy and get access to our exclusive investor community here: Want to go deeper? Book a call with our team to learn about our Virtual Family Office services or join our Mastermind to accelerate your path to generational wealth:
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Sharon Lechter on the Real Wealth Mindset: Assets, Legacy & Financial Freedom
08/13/2025
Sharon Lechter on the Real Wealth Mindset: Assets, Legacy & Financial Freedom
Today’s episode features a true legend in the world of financial education—Sharon Lechter. Sharon is the co-author of the globally renowned book, Rich Dad, Poor Dad, a bestselling CPA, and a former advisor to two U.S. Presidents. Her mission: to elevate financial IQ and empower people everywhere to achieve financial freedom. Dave Wolcott sits down with Sharon for a comprehensive conversation that goes behind the scenes of the Rich Dad story—how it began, why it resonated with millions, and the powerful legacy it’s still creating today. Sharon shares her unique upbringing around the language of assets and cash flow, her early business ventures, and the pivotal moment that led her to collaborate with Robert Kiyosaki and create the groundbreaking Cashflow board game. Listeners will gain a fresh perspective on wealth-building, as Sharon breaks down complex ideas like good and bad debt, the importance of true diversification, and why “assets are sexy.” She also shares practical, actionable wisdom for navigating today's uncertain markets, and timeless advice for teaching children the mindset and skills they need to be successful with money. Whether you’re just starting your wealth journey or looking to take things to the next level, Sharon’s insights are guaranteed to change the way you think about money and legacy. In this episode, we discuss: The origin of Rich Dad, Poor Dad and Sharon’s journey to financial literacy advocacy The difference between real asset diversification vs. Wall Street’s version Understanding good debt vs. bad debt and how to leverage it wisely How to break the cycle of financial ignorance for the next generation Click here to learn more:
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