Wealth Strategy Secrets of the Ultra Wealthy Podcast

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: https://pantheoninvest.com/episode191 

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 holisticwealthstrategy.com 

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 https://pantheoninvest.com/episode190 

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 HolisticWealthStrategy.com and join the investor community for exclusive strategies and resources to accelerate your path to financial freedom.

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: https://pantheoninvest.com/episode189 

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

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: https://pantheoninvest.com/episode188 

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 PantheonCreditFund.com. Take the next step: Head over to holisticwealthstrategy.com 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.

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 holisticwealthstrategy.com 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.

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: https://pantheoninvest.com/episode186 

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 holisticwealthstrategy.com 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.

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 https://pantheoninvest.com/episode185 

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 holisticwealthstrategy.com. You’ll also gain access to our exclusive investor community, packed with education, opportunities, and resources to accelerate your path to freedom.

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: https://pantheoninvest.com/episode184 

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: holisticwealthstrategy.com   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: pantheoninvest.com

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: https://pantheoninvest.com/episode183 

In this Wealth Strategy Deep Dive, I challenge the conventional wisdom around diversification that Wall Street and traditional financial planners promote. Most investors are told to split their portfolio in a 60/40 allocation between equities and bonds, or maybe diversify further across different market caps and international equities. But in reality, that's just moving risk around within a single asset class that's still correlated to the market—and still vulnerable to volatility. Drawing from the playbooks of ultra-high-net-worth investors, family offices, and sovereign wealth funds, I break down what true diversification looks like. It goes beyond the stock market and includes non-correlated asset classes such as real estate, private equity, and businesses. But it’s not just about adding asset types—it’s about strategically managing risk across different environments. After all, going all-in on real estate carries its own interest rate risks too. True wealth strategy means building a portfolio that can weather any storm by thoughtfully spreading your investments across multiple, uncorrelated areas. If this episode sparked a new way of thinking for you, grab a free copy of my book at https://holisticwealthstrategy.com/  and join our investor community. You’ll get exclusive access to new opportunities, deep-dive educational content, and the tools you need to create multi-generational wealth. For those ready to go further, connect with our team to explore our Virtual Family Office or join our Mastermind for advanced strategies.

Today’s episode is a powerful detour from traditional wealth-building strategies as we welcome Nels Jensen to the show. Nels is the CEO of Williamsburg Learning, a thriving entrepreneur, and a dedicated yoga instructor who has mastered the art of integrating business, personal growth, and family. Unlike most stories you hear about the ultra-wealthy, Nels reveals how he became a “time billionaire”—someone who has intentionally created an abundance of free time and peace, not just financial success. In this enlightening conversation, Nels shares his journey from building a fast-growing online education company to structuring his life and business in a way that allows him to take months-long sabbaticals and truly be present with his family. He opens up about the mindset shifts required to move beyond the typical entrepreneurial trap of busyness and burnout, and instead cultivate intentionality, clarity, and harmony. Nels and host Dave Wolcott also explore the deeper aspects of living a fulfilling life—touching on consciousness, personal rituals, and how to invest your time and energy with as much precision as your money. Nels even offers actionable tools like the “Teach the Class” mindset to help listeners break free from self-imposed limitations and find more peace. In this episode, we discuss: How Nels became a “time billionaire” and structured his business for maximum freedom The importance of intentional living and mindset in breaking free from the trap of busyness Creating a personal “time and energy investment thesis” to live with more purpose and less stress Practical strategies for cultivating peace, harmony, and consciousness in everyday life Listen here: https://pantheoninvest.com/episode182 

In this new Wealth Strategy Deep Dives episode, Dave redefines what it truly means to be wealthy—not just in terms of dollars and cents, but through a holistic lens that includes emotional, intellectual, spiritual, and social capital. Drawing from his own journey and inspired by thinkers like Dan Sullivan, Dave unpacks how true wealth is rooted in freedom—the freedom of money, time, purpose, relationships, and location. If you've ever felt that being "rich" isn’t the same as being fulfilled, this episode is your wake-up call. Dave explains why chasing material success alone leads to burnout, and how aligning your wealth strategy with your values and purpose is the real secret to living a life of freedom, prosperity, and impact. This isn’t about retirement—it’s about never wanting to stop doing what you love. Download the free Holistic Wealth Strategy Framework: https://www.holisticwealthstrategy.com/  Explore exclusive alternative investments and build true wealth outside of Wall Street with Pantheon: https://pantheoninvest.com