261: Building Family Offices To Invest and Protect Your Assets with Richard Wilson
Zen and the Art of Real Estate Investing
Release Date: 07/21/2025
Zen and the Art of Real Estate Investing
In today’s episode of Zen and the Art of Real Estate Investing, Jonathan sits down with experienced investor and author Joel Miller, who has spent nearly five decades building wealth through rental properties. Joel walks through his early days as a mobile DJ, his accidental path into real estate, and how he grew a portfolio of rentals, flipped over 100 houses, and became a trusted hard money lender in his community. Joel shares his unique perspective on incorporating real estate into an existing career without sacrificing a passion or day job. He emphasizes that real estate doesn’t have to...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan speaks with Nick Disney, founder of Sell My San Antonio House. Nick built a thriving home-buying business by focusing on what matters most—helping sellers solve real problems, not just pitching offers. He guides listeners through the transformation from a small-scale side hustler to one of the most trusted local investors in Texas, prioritizing trust, consistency, and problem-solving over quick profits. Nick shares how he launched his business with a few flips and grew it through consistent marketing and...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Neal Bawa, founder and CEO of Grocapitus and a nationally recognized leader in data-driven real estate investing. Known as the “Mad Scientist of Multifamily,” Neal brings a tech-forward approach to real estate, combining sharp market analysis with a clear-eyed view of risk, strategy, and opportunity. Neal shares how he went from running a tech company in Silicon Valley to building a $660 million real estate portfolio. He breaks down the importance of data modeling, boots-on-the-ground research, and why...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Richard Wilson, founder and CEO of the Family Office Club, to break down how the ultra-wealthy build, protect, and grow their assets. With more than 100,000 members and 18 years at the helm, Richard has helped thousands of family offices form investment strategies that create generational wealth. The episode opens with a look at what sets billionaires apart from the rest of us, from their appetite for risk to how they move quickly and avoid herd thinking. Richard explains that the most successful investors make...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan speaks with architect and multifamily syndicator Mark Shuler of SGRE Investments about how government regulation continues to hamper housing development across the country. With over 40 years of experience in architecture, urban infill, and multifamily project management, Mark brings a unique dual perspective that blends design expertise with investment strategy. Mark outlines the real-world consequences of permitting delays, inconsistent local regulations, and overreaching planning departments. From Seattle’s...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Brad Johnson, co-founder and Chief Investment Officer of Vintage Capital. With over $3.3 billion in commercial real estate transactions under his belt, Brad brings a deep well of experience in structuring long-term, risk-adjusted investments, especially in the mobile home park space. Brad’s journey into real estate began in his twenties, when he and his friends started buying single-family rentals with profits from a startup. Over time, he transitioned from remote investing to institutional asset...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan interviews Andrew Cushman, founder of Vantage Point Acquisitions, to explore the evolution of his investing career and how he helps others build wealth through multifamily real estate. After leaving a stable career in chemical engineering in 2007, Andrew made a bold leap into house flipping and eventually multifamily investing, where he has now syndicated or repositioned over 3,000 units. Andrew explains why flipping quickly became unsustainable for him and his wife, and how they transitioned into multifamily with the...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Austin Masket, founder and Chief Investment Officer of Riverly Capital. With a background as a commercial broker and portfolio manager for a family office, Austin brings a seasoned and data-driven approach to multifamily investing and distressed debt acquisition. His firm focuses on creating risk-adjusted, tax-advantaged returns in key U.S. markets like Denver, Atlanta, and Phoenix. Austin’s early exposure to real estate came from his family, but his professional foundation was shaped at Marcus &...
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In this episode of Zen and the Art of Real Estate Investing, Jonathan speaks with Owen Barrett, founder and CEO of Shine, a solar company built by apartment owners for apartment owners. With a background in finance and clean energy, Owen brings a pragmatic and results-driven mindset to a traditionally misunderstood corner of multifamily investing—onsite solar energy. Owen shares how his first exposure to real estate came after achieving financial independence through his solar ventures. Instead of starting small, he jumped into a 64-unit building, testing how large-scale solar could be...
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In today’s episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Peter Neill, co-founder and partner at GSP REI, for a conversation that blends capital raising, real estate development, and a commitment to rebuilding underserved communities. Peter shares how he moved from a sales and marketing role at a distressed mortgage firm to managing funds focused on affordable and workforce housing throughout the Mid-Atlantic. Along the way, he discovered that long-term success in real estate hinges on experience, consistency, and assembling the right team. Peter reflects on early...
info_outlineIn today’s episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Richard Wilson, founder and CEO of the Family Office Club, to break down how the ultra-wealthy build, protect, and grow their assets. With more than 100,000 members and 18 years at the helm, Richard has helped thousands of family offices form investment strategies that create generational wealth.
The episode opens with a look at what sets billionaires apart from the rest of us, from their appetite for risk to how they move quickly and avoid herd thinking. Richard explains that the most successful investors make bold, independent decisions, act fast, and play a long game within a narrow set of skills or markets.
Richard also shares the three-bucket model he teaches for wealth management: public market investments, real estate, and direct investments in the business niche that created the wealth. He walks through how families allocate risk across these buckets and why having asymmetric returns and trust in your operators is crucial.
The conversation turns to why the most successful investors don’t chase pitches. They chase relationships. Family offices look for high-quality people, not just high-potential deals. Richard emphasizes that value-added connections, thoughtful deal structuring, and strong mental models are what win attention in a noisy space.
He and Jonathan also discuss the importance of fast decision-making, the rise of AI tools to enhance due diligence, and how Richard’s journey from a basement apartment to launching billionaires.com reflects the same lessons he teaches investors: add value first, go deep in your niche, and build something no one else can replicate.
In this episode, you will hear:
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Traits that distinguish billionaire investors from the average high-net-worth individual
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Ways family offices allocate capital across asset classes
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The role of trust and consistency in attracting investor interest
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How asymmetric returns and thoughtful deal structures build long-term wealth
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Richard’s approach to applying AI tools to improve decision-making
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Factors that make niche expertise more valuable than broad exposure
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How fast, focused action drives better outcomes in competitive markets
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Supporting Resources:
Family Office Club website - familyoffices.com
Centimillionaire Strategies on YouTube - www.youtube.com/user/familyofficesgroup
Family Office Club on Facebook - www.facebook.com/familyofficeclub
Family Office Club’s Instagram - www.instagram.com/familyofficeclub
Connect with Family Office Club on LinkedIn - www.linkedin.com/company/familyoffices
Richard Wilson on X - x.com/RichardCWilson
Connect with Richard on LinkedIn - www.linkedin.com/in/singlefamilyoffice
Family Office Club’s TikTok - www.tiktok.com/@familyofficeclub
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
TikTok - www.tiktok.com/@trustgreene
Zillow - www.zillow.com/profile/StreamlinedReal
Bigger Pockets - www.biggerpockets.com/users/TrustGreene
Facebook - www.facebook.com/streamlinedproperties
Email - [email protected]
Episode Credits
If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.