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PODCAST

Wealth Strategy Secrets of the Ultra Wealthy Podcast

Welcome to "Wealth Strategy Secrets of the Ultra Wealthy," a masterclass in wealth creation, preservation, and legacy building, hosted by renowned wealth strategist Dave Wolcott. This podcast dives deep into the lesser-known, often secretive strategies that the ultra-wealthy use to amass and protect their fortunes. Each week, join Dave, a seasoned expert in wealth management, as he unveils the complex world of high finance, investments, tax strategies, and estate planning. Dave brings his decades

business investing

All Episodes

03:41

Understanding the K-1: The Tax Advantage the...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/31

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

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36:38

Hospitality Real Estate: Contracted Cash Flow, Tax...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/29

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,

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03:43

Alternative Investments Explained: Building Wealth...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/24

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

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45:36

Ditch the 4% Rule: Passive Income Over Accumulation

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/22

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,

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05:01

The Trifecta: The Ultimate Return Profile the...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/17

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

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50:43

Mindset + Skillset: Align Values to Build Wealth

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/15

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

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Why Cash Is Trash in 2025 — The Smart Investor's Hedge

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/10

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

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36:52

Build Cash-Flowing Businesses: Systems, KPIs & Exit...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/08

Today’s episode features an enlightening conversation with business coach and entrepreneur, Tanner O’Brien. As a partner in a thriving family-owned ActionCOACH franchise, Tanner has firsthand experience navigating the challenges and triumphs of entrepreneurship—from nearly running out of cash to building a business that truly operates as an asset, not a job. Tanner’s diverse background in fitness, finance, and leadership, coupled with his journey as both a business owner and coach, provides a rich

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08:55

The Pyramid of Private Market Sponsors Explained...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/03

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

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46:39

From Flipping Houses to $500K Passive Income:...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/10/01

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,

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04:43

The #1 Risk That Can Destroy Your Portfolio

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/26

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

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45:00

Energy Investing: Oil, Gas, and Infrastructure...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/24

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

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06:11

Tax Planner vs. Tax Preparer: Why 95% of People...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/19

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

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43:45

Exit Planning Secrets: Maximize Business Value and...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/17

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

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09:07

Private Credit Investing: High Yields,...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/12

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

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46:15

Cash Flow Over 401(k)s: Build Passive Income with...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/10

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07:49

Invest in Yourself: The #1 Wealth Strategy for High...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/05

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

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41:53

Build Wealth with Banks’ Money: Creative Financing &...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/09/03

Today’s episode is packed with inspiration and practical strategies as we welcome Brandon Elliott, a self-made real estate investor with a journey unlike any other. Brandon is the founder of Credit Counsel Elite, and his story takes us from a childhood of scarcity, through dangerous setbacks, and ultimately to financial freedom. After surviving a life-altering explosion, Brandon transformed his mindset and set out to master the art of leveraging banks’ money—what he calls “OBM: Other Banks’

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05:57

The Blueprint for Building Wealth Beyond Wall Street

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/08/29

In this solo episode of Wealth Strategy Deep Dives, I share the foundational principles behind building true, lasting wealth outside of Wall Street. Over the past 25 years, I’ve invested in alternative assets, studied passive income theory versus accumulation theory, and built businesses that focus on both growing and protecting capital. What I’ve discovered—and what I share in today’s conversation—is that wealth isn’t just about tactics like real estate or oil and gas investments. Those are tools

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44:19

How to Build Wealth Like a Family Office Using...

Wealth Strategy Secrets of the Ultra Wealthy Podcast ·

2025/08/27

Today we have a fascinating episode with Daniel Brereton, Director at Equity Multiple, and a true expert in both traditional and alternative investments. Daniel’s journey is as impressive as it is educational—after serving as an Army officer, he translated his leadership and analytical skills to the world of private markets, first at UBS advising pensions and endowments, and now helping everyday investors unlock access to institutional-quality real estate deals. Host Dave Wolcott explores Daniel’s

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221 results

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