Wealth Strategy Secrets of the Ultra Wealthy Podcast

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 

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.