Mindset + Skillset: Align Values to Build Wealth
Wealth Strategy Secrets of the Ultra Wealthy Podcast
Release Date: 10/15/2025
The Playbook for Financial Freedom: Mindset, Masterminds & Real Assets
Wealth Strategy Secrets of the Ultra Wealthy Podcast
In this dynamic solo episode, Dave Wolcott and Justin Donald dive deep into how investors can move beyond Wall Street’s one-dimensional approach to wealth building and adopt the same frameworks used by the ultra-wealthy. Dave shares his personal journey—from being raised on the traditional “go to school, get a job” mindset to discovering the Cashflow Quadrant and building a diversified portfolio across real estate, private equity, oil and gas, and other alternative assets. Alongside Justin, author of The Lifestyle Investor, they unpack the missing blueprint between knowing you can...
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Airbnb Investing: Data, Cash Flow, and Tax Hacks for Real Estate Success
Wealth Strategy Secrets of the Ultra Wealthy Podcast
Today’s episode features an illuminating conversation with John Bianchi, recognized as an Airbnb data savant and former head of data for the largest short-term rental investment fund in the US. Joining host Dave Wolcott , John Bianchi brings his deep expertise in Airbnb investing, data analytics, and business strategy to shed light on the world of short-term rentals. Having managed millions as a financial advisor before pivoting to Airbnb, John Bianchi shares his unique perspective on the differences between traditional financial planning and hands-on real estate investing. He details his...
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The Hidden Structure of Wealth: Inside the Ultra-Wealthy’s Family Office
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...
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How the Ultra Wealthy Build Resilient Portfolios and Embrace Alternative Investments
Wealth Strategy Secrets of the Ultra Wealthy Podcast
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...
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Designing Your Future: Creating a Vivid Vision for 2025
Wealth Strategy Secrets of the Ultra Wealthy Podcast
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...
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The Truth About Cash Flow, Tax Strategies, and Risk in Alternative Investments
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...
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Understanding the K-1: The Tax Advantage the Ultra-Wealthy Never Miss
Wealth Strategy Secrets of the Ultra Wealthy Podcast
Welcome back to Wealth Strategy Secrets of the Ultra Wealthy! I’m your host, Dave Wolcott, and in this solo Wealth Strategy Deep Dive, we’re unpacking one of the most misunderstood yet powerful tools in alternative investing — the K-1. If you’ve ever invested in a real estate syndication, private equity deal, or energy partnership, chances are you’ve heard, “Don’t forget your K-1.” But what exactly is it, and why does it matter? In this episode, Dave breaks down how the IRS Schedule K-1 works, why it’s essential for investors in pass-through entities, and how it delivers one...
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Hospitality Real Estate: Contracted Cash Flow, Tax Benefits & Legacy
Wealth Strategy Secrets of the Ultra Wealthy Podcast
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....
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Alternative Investments Explained: Building Wealth Outside of Wall Street
Wealth Strategy Secrets of the Ultra Wealthy Podcast
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...
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Ditch the 4% Rule: Passive Income Over Accumulation
Wealth Strategy Secrets of the Ultra Wealthy Podcast
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...
info_outlineToday’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