Wealth Strategy Secrets of the Ultra Wealthy Podcast

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 HolisticWealthStrategy.com 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.

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: https://pantheoninvest.com/episode196 Get Dave's Free Book: https://holisticwealthstrategy.com/ Your financial freedom starts with one conversation. Schedule a 30-min call with Mike Click here: https://calendly.com/mike-pantheoninvest/30min

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 HolisticWealthStrategy.com and join the investor community for exclusive access to educational content, opportunities, and resources to accelerate your path to financial freedom. Learn more: https://pantheoninvest.com/pantheonmastermind

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: https://pantheoninvest.com/episode195 Get Dave's Free Book: https://holisticwealthstrategy.com/

Dive into the intricacies of the K-1 form, a crucial yet often misunderstood tool in alternative investing. Discover how it enhances tax efficiency for investors, particularly in real estate and energy sectors. Unpack the significance of depreciation and deductions that can maximize your earnings while minimizing tax liabilities. Learn the process of receiving your K-1 and its vital role in documenting income and savings opportunities. This discussion reveals why savvy investors never overlook the advantages that K-1s offer.

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: https://pantheoninvest.com/episode194

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 pantheoninvest.com to start your journey toward a Holistic Wealth Strategy. Download your free copy of Dave's book at holisticwealthstrategy.com

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: https://pantheoninvest.com/episode193

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 pantheoninvest.com to start your journey toward a Holistic Wealth Strategy. Download your free copy of Dave's book at holisticwealthstrategy.com

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