Wealth Strategy Secrets of the Ultra Wealthy Podcast

Today’s episode features an extraordinary entrepreneur and thought leader, Chad Jenkins. Chad is a prolific business builder, having launched over 50 companies and authored impactful books like "Just Out of Zero" and "Friction Fuel." With a passion for helping other entrepreneurs unlock exponential business growth, Chad brings a fresh perspective on leveraging what he calls “collaboration currency”—an often overlooked but incredibly powerful asset in both business and personal wealth building. Host Dave Wolcott guides the conversation as Chad shares his unique journey from humble beginnings on a small farm to building multiple thriving businesses. Chad breaks down the essential mindset shifts and frameworks that have fueled his lasting success, including his VCR model (Vision, Capability, Reach) and the transformative power of collaboration. He invites listeners to see friction not as a frustration, but as an opportunity for innovation and value creation—whether you’re an experienced business owner or someone seeking to create new income streams. This episode is packed with actionable wisdom and real-world examples, including how to identify untapped value in your skills, build meaningful strategic partnerships, and apply simple, repeatable models that deliver massive results. If you’re looking to scale your existing business or take your first entrepreneurial leap, Chad’s insights provide a clear roadmap to 10x—or even 100x—your impact. In this episode, we discuss: Why friction is your greatest opportunity for innovation and profit The VCR framework: Vision + Capability x Reach Harnessing “collaboration currency” to create new revenue streams without extra capital or risk How simple, effective collaborations can unlock exponential growth for any entrepreneur

In this solo episode of Wealth Strategy Deep Dives, Dave unpacks the top three reasons most entrepreneurs and investors lose wealth: overpaying in taxes, lack of true diversification, and low financial IQ. Dave reveals how smart tax planning—using incentives designed for business owners and investors—can create exponential returns, and why traditional methods like 401(k)s might be holding you back. He also shares why relying solely on your business or the stock market is risky, and how building your financial IQ can unlock opportunities others miss. From real estate and energy to creative deal structuring, Dave shows how education and strategic thinking can lead to powerful wealth creation—even without large amounts of capital. 👉 Download your free copy of The Holistic Wealth Strategy and join the community at https://www.holisticwealthstrategy.com 👉 Book a call to explore the Virtual Family Office or join the mastermind: https://www.holisticwealthstrategy.com/schedule

Today’s episode is packed with value for anyone thinking about the daunting challenge of college costs. Our guest, Seth Greene, is the founder of HowToFindMoneyForCollege.com and a leading authority in helping families navigate the ever-increasing expenses of higher education. Drawing from his personal journey and years of experience, Seth’s company has helped families save over $30,000 per year, per child, through smart financial aid optimization and strategic planning. Host Dave Wolcott dives deep with Seth, who shares not only his own story—starting with his family’s struggle to pay for Syracuse University—but also the surprising methods his firm uses to “game the system” and maximize college financial aid legally and intelligently. In a market where tuition is rising and the value of a degree is under constant debate, Seth’s advice offers hope and real solutions for parents, grandparents, and even future students themselves. Listeners will find this episode especially useful whether their children are toddlers or already in college. Seth’s straightforward strategies are designed to protect family wealth and open doors to significant college savings—sometimes well into six figures over four years. In this episode, we discuss: The biggest misconceptions about who qualifies for college financial aid How to legally manipulate your Expected Family Contribution (now called the Student Aid Index) Why 529 College Savings Plans might actually hurt your financial aid eligibility Creative structures like using cash value life insurance and business income planning to reduce college costs Tune in to discover actionable, little-known strategies that could transform your family’s education funding—and your overall wealth trajectory.

Today’s solo episode takes a hard look at what’s really broken in the traditional wealth planning model—and why it’s failing so many investors. Dave breaks down the flawed assumptions behind conventional strategies like the 60/40 portfolio, tax deferral, and one-dimensional public market investing. From the dangers of underestimating taxes, fees, and inflation, to the risks of outliving your money, Dave shares why relying on outdated financial advice may be sabotaging your long-term freedom. With his entrepreneurial mindset and deep experience, Dave challenges listeners to think beyond Wall Street’s narrative. He introduces smarter, more efficient ways to build wealth—through strategy stacking, alternative investments, and a focus on control and legacy. If you’re tired of riding the market rollercoaster or wondering if you’ll have enough in retirement, this episode will give you the clarity to start thinking differently about your financial future.   👉 Download your free copy of Dave’s book and learn more: https://holisticwealthstrategy.com  👉 Book a call with our team or join the mastermind: https://holisticwealthstrategy.com

Today’s episode features an insightful conversation with Robin Waite, a seasoned entrepreneur, business coach, and author of Take Your Shot. Robin has helped thousands of coaches, consultants, and service providers build thriving businesses with clarity and purpose. He’s joined by our host, Dave Wolcott, serial entrepreneur and author of The Holistic Wealth Strategy. Together, they break down one of the most accessible – yet often overlooked – ways to build wealth: launching and scaling a service-based business. Robin brings a unique perspective that combines deep business strategy with powerful lessons on pricing, psychology, and money mindset – two critical areas where most entrepreneurs struggle. Drawing from his journey of leaving a traditional job to become successfully “unemployable,” Robin shares hard-earned lessons from 21 years of building, scaling, and selling businesses. He explains why service-based businesses can offer unmatched freedom, creativity, and scalability, especially in today’s world where tools like AI and online marketplaces make starting up more accessible than ever. Robin and Dave also dig into common pitfalls, such as the dangers of vanity metrics and the “sales cycle of doom,” while giving actionable advice for anyone considering entrepreneurship or looking to take their existing business to the next level. Whether you're dreaming of leaving your W2 job or refining your pricing strategy, this episode provides practical frameworks and mindset tools to create true financial and personal freedom. In this episode, we discuss: How to transition from a job to entrepreneurship and why a gradual approach works The advantages of launching and scaling a service-based business Pricing strategies and overcoming money mindset barriers Why clarity, purpose, and values matter more than chasing vanity metrics  

Welcome back to Wealth Strategy Deep Dives—your shortcut to building real wealth outside of Wall Street. In this episode, I walk you through two real-world wealth avatars: Conventional Carla and Strategic Sam. One is stuck in the traditional financial system. The other is scaling with clarity, control, and cash flow. Carla follows the mainstream playbook—401(k)s, high taxes, and financial advisors telling her to “just ride it out.” But she's frustrated, taxed to the max, and out of control. Then there's Sam: a business owner playing a 3D wealth game with passive income, tax strategy, infinite banking, and a full dream team supporting his legacy vision. This episode will challenge you to ask—which game are you playing, and is it getting you where you want to go? 📘 Grab your free copy of the book: www.holisticwealthstrategy.com 🎥 Watch the episode with visuals: Pantheon Invest YouTube Let’s break free from conventional traps—and play offense with your wealth.  

In this engaging discussion, Matt Sumner, founder of Outbound Investment, shares insights from his 15+ years of guiding clients in international wealth strategies. He highlights the increasing demand for global mobility and dual citizenship in today's rapidly changing world. Matt also presents a four-pillar framework centered on mobility, tax strategies, asset protection, and global investments. He emphasizes the importance of diversifying risk through international opportunities and adapting to the evolving geopolitical landscape.

Welcome back to another episode of Wealth Strategy Deep Dives, where we distill powerful wealth-building strategies into short, tactical episodes. Today we’re uncovering one of the most essential frameworks behind building sustainable wealth: The Cash Flow Strategy of the Wealthy. In this solo episode, I walk you through the exact cycle the ultra-wealthy use to create capital, protect it, and compound it over time. We’ll cover how to generate value through your business or W2 income, then use tools like infinite banking to amplify your wealth before investing into tangible assets like real estate and private equity. I also explain how tax-free wealth, passive income strategies, and alternative investing work together in this flywheel—giving you the roadmap to achieve financial independence and build lasting legacy wealth. It all starts with getting in the game, and then it becomes rinse and repeat. 📘 Grab your free copy of the book: www.holisticwealthstrategy.com 🎥 Watch the episode with visuals: Pantheon Invest YouTube  

Gary McDermid, a former Navy officer turned entrepreneur and cash flow engineer, shares his remarkable journey toward financial freedom through real estate investment and strategic planning. He reveals how military advice sparked his wealth-building path and discusses overcoming self-limiting beliefs. Gary delves into the integration of real estate with tax planning to enhance cash flow and wealth generation. Plus, he highlights key insights from his book, ‘Set Your Own Goals or Someone Else Will,’ focusing on mindset shifts essential for achieving personal goals.

Welcome back to Wealth Strategy Deep Dives—your shortcut to building real, lasting wealth. In this episode, I break down the cash flow strategy used by the ultra-wealthy to scale capital, protect their assets, and generate tax-efficient passive income. We start with the most powerful source of capital—you. Whether you’re a business owner or a W2 earner, your income is the launchpad. But instead of spending it, the wealthy channel it into tangible assets like real estate and energy, stack strategies like infinite banking, and create a rinse-and-repeat wealth engine that multiplies over time. I walk you through the step-by-step cycle that turns earned income into legacy wealth—and how to start doing it yourself. 📘 Grab your free copy of the book: www.holisticwealthstrategy.com 🎥 Watch the episode with visuals: Pantheon Invest YouTube Let’s move from active earning to passive scaling—and unlock the true strategy behind financial freedom.