In this Wealth Strategy Deep Dive, I’m unpacking a powerful question: what does true financial freedom really mean for you? We hear the term all the time, but few people break it down beyond the money. Inspired by my mentor Dan Sullivan, I explore the four freedoms — freedom of money, purpose, time, and relationships — and add a fifth: freedom of location. These elements combined create a life of intention, energy, and fulfillment that money alone can’t buy.

Take a moment to reflect: are you living with these freedoms today, or is your wealth just funding someone else’s plan? If this episode gets you thinking, dive deeper with us — grab your free book at holisticwealthstrategy.com, discover curated investment opportunities at pantheoninvest.com, join our investor community, or book a call to explore our virtual family office and mastermind for building generational wealth. Stay tuned for the next Deep Dive!

Today, we have an insightful guest joining us, Omar Khan, founder of Boardwalk Wealth and a seasoned expert in private equity and multifamily real estate. With over $800 million in transactions under his belt, Omar stands out for his unique combination of institutional finance experience and multi-generational entrepreneurial background. His deep knowledge and strategic approach have helped him and his investors navigate the complexities of acquisitions, developments, and restructurings in ever-changing markets.

In this episode, Omar sits down with host Dave Wolcott to pull back the curtain on what’s really happening in today’s commercial real estate landscape. Omar shares his entrepreneurial journey, starting from his upbringing in a financially sophisticated family, and how that foundation led him into private equity and large-scale real estate deals.

Throughout the conversation, Omar candidly discusses the challenges facing syndicators and investors in the current market, and why disciplined underwriting and choosing the right partners are more critical than ever. He also demystifies common misconceptions about the housing shortage, emphasizes the importance of liquidity alongside returns, and shares how his team’s innovative development strategies are helping them deliver cash flow faster while minimizing risk, especially in the Midwest.

Whether you’re an experienced investor or just getting started, Omar’s insights into smart portfolio allocation, due diligence, and navigating market cycles offer practical wisdom for building lasting wealth.

In this episode, we discuss:

1. Why liquidity is just as important as generating returns in your portfolio

2. The truth about the so-called housing shortage and where demand really lies

3. Key lessons in due diligence and underwriting deals during down cycles

4. How innovative development strategies can outperform in today’s market

Click here to learn more: 

https://pantheoninvest.com/episode176 

In this special solo episode of Wealth Strategy Deep Dives, Dave breaks down one of the most misunderstood — and often taboo — strategies in traditional retirement planning: the idea of exiting your 401(k). Dave walks you through the math, mindset, and practical considerations behind taking control of your retirement capital and putting it to work in more tax-efficient, high-yielding private investments. Using the brand-new 401(k) Exit Calculator, Dave demonstrates how to objectively analyze your own situation and see whether staying locked into Wall Street truly aligns with your wealth goals.

If you’ve ever wondered whether your 401(k) is really “free money” or whether your capital could be compounding far faster elsewhere, this episode will open your eyes and empower you to run the numbers for yourself.

Get your FREE 401(k) Exit Calculator : https://exityour401k.com/

Download Dave’s free book and explore more hidden wealth strategies: holisticwealthstrategy.com 

Explore vetted investment opportunities: pantheoninvest.com

Join our investor community & mastermind or book a call to discover how our Virtual Family Office can help you create generational wealth.

Today we have a truly inspiring episode featuring Jennifer Hudye, founder of Vision Driven Global, and one of the leading experts on helping entrepreneurs and high achievers get radically clear on their personal and business visions. Jennifer’s passion for vision work comes from her unique entrepreneurial upbringing in a small Canadian town, where she learned early on the power of crafting a compelling vision for life and business. After bootstrapping her first business and discovering the incredible impact that a vivid, emotionally driven vision had on her success, Jennifer dedicated her career to guiding others in transforming vague dreams into actionable, strategic blueprints.

In this episode, Jennifer breaks down why having a vision isn’t just about dreaming big—it’s about creating a clear, detailed roadmap that shapes your identity, influences daily decisions, and rewires your belief system for lasting transformation. Host Dave Wolcott and Jennifer dive deep into the psychology behind vision, addressing why so many people unknowingly live from their past rather than their true potential, and how to overcome those barriers with simple, practical steps.

Jennifer shares her proven process for crafting a vivid three-year vision, explains how our subconscious mind responds to clear imagery and emotions, and offers actionable advice for getting started—even if you’ve never been taught how to dream beyond your current circumstances.

In this episode, we discuss:

• The real difference between a goal and a true vision

• Why most people struggle to get clear on what they really want

• Tangible steps to design a vivid, emotionally charged three-year vision

• Practical ways to align your actions and beliefs with your future self

Tune in to unlock the secrets of vision and start living a more intentional, purpose-driven life!

Click here to learn more: https://pantheoninvest.com/episode175 

In this Wealth Strategy Deep Dive, Dave Wolcott introduces the Pantheon Wealth Pyramid, a smarter, more strategic way to visualize and structure your wealth. Rather than relying on Wall Street's pie charts, Dave breaks down how this pyramid framework helps investors minimize risk and maximize returns—starting with a solid foundation through infinite banking and then layering in cash-flowing, tax-efficient assets like real estate, energy, and private credit.

Dave also explains how to think about higher-risk assets like crypto and public equities in your portfolio and why traditional advice often misses the mark. If you're ready to step away from the Wall Street model and create a portfolio that serves your long-term goals, this episode will reshape how you approach your wealth strategy.

Explore the investment blueprint behind the Wealth Pyramid:

Learn more at Pantheoninvest.com

Download your free copy of Dave’s book and get exclusive access to the investor community:

https://www.holisticwealthstrategy.com/

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:

1. The biggest misconceptions about who qualifies for college financial aid

2. How to legally manipulate your Expected Family Contribution (now called the Student Aid Index)

3. Why 529 College Savings Plans might actually hurt your financial aid eligibility

4. 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