Wealth Strategy Secrets of the Ultra Wealthy Podcast

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/ Connect with Spencer: Business website: www.madisoninvesting.com Personal bio website: www.spencerhilligoss.com LinkedIn profile: www.linkedin.com/in/shilligoss/ Twitter: x.com/SpenceHilligoss

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

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 PantheonInvest.com 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 holisticwealthstrategy.com

Join Tanner O'Brien, a seasoned business coach and partner in a family-owned ActionCOACH franchise, as he shares his entrepreneurial journey from fitness to finance. He highlights the significance of measuring KPIs to identify bottlenecks and make informed decisions. Learn practical frameworks for building systems, achieving team alignment, and creating a business that thrives without relying on its owner. Tanner also discusses the importance of profitability targets for exit planning and advises on avoiding common pitfalls like premature hiring.

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