Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights

Richard C. Wilson, CEO of Family Office Club
  • 4.2 (71)
  • Investing
  • Weekly

The Family Office Podcast features interviews with billionaires, centimillionaires, family offices, industry titans and private investors, plus the strategies founders and capital raisers use to build relationships with them. New episodes every Monday, Wednesday, and Friday.Hosted by Richard C. Wilson, founder and CEO of Family Office Club and owner of Billionaires.com. Richard has helped create, formalize, and run 250+ family offices, structured over 200+ deals with clients and 44 deals off his own balance sheet, and closed 19 transactions for a publicly traded client his team sources opportunities for. Today he helps run two single family offices.Richard has also spent 3,000+ hours building hundreds of AI agents and implementation projects for centimillionaires, publicly traded clients, Family Office Club members and his own company. The 50 AI tools he built for members have been used more than 50,000 times.Our investors look at every type of deal. Episodes also feature family businesses and companies doing $10 million to $500 million in revenue, along with the owners and successors behind them.Topics include family office investing, single and multi-family office structures, private equity, venture capital, real estate, private credit, deal structuring, capital raising, family business succession, and AI for investors.Family Office Club at a glance: Operating since 2007340+ live events hosted, often with billionaires and centimillionaires on stage$1 billion+ in transactions closed between members17 million members across our social media communitiesSee upcoming events and membership at FamilyOffices.com or text (305) 333-1155. 

  1. 19h ago

    Investors Are Walking Away From $100 Million in Personal Guarantees

    Send us Fan Mail One investor walked away from a $22 million personal guarantee, and he's not alone. This panel breaks down why owners are handing back seven-figure and eight-figure real estate assets rather than refinance at today's rates. Backed by insight from operators inside Family Office Club's 16 million-member investor community and 19 years of tracking real estate cycles, this episode covers why banks are quietly delaying foreclosures on distressed multifamily and office assets in markets like New York City.  https://familyoffices.com/

  2. 2d ago

    The Syndication Bubble Popped: Why $1 Trillion in Debt Is Coming Due

    Send us Fan Mail A trillion dollars in real estate debt resets in 2026 alone, and this panel explains why the easy-money era of 2012 to 2021 is officially over. Drawing on insight from operators inside Family Office Club's 16 million-member investor community and 19 years of tracking capital markets, this episode breaks down why capital now follows trust, not a polished projection. Meet these operators in person at the Capital Raising Bootcamp, August 17-20, 2026. Are you still underwriting like it's 2021? https://familyoffices.com/

  3. 4d ago

    AI Doesn't Write the Check — Humans Do.

    Send us Fan Mail Family offices are already using AI to run their operations, but this panel doesn't agree on how far it should go. One principal breaks down using AI safely with confidential client data. Another pushes back hard on the idea that technology should reshape how humans treat each other. It's a rare, unscripted disagreement on stage about where AI belongs in family office investing, and where it doesn't. https://familyoffices.com/

  4. Oct 23

    How to Actually Get in Front of a Family Office

    Send us Fan Mail Every capital raiser wants to know the answer to this question... how do you actually get a family office or angel investor to take your call? This panel gives the real playbook: find the internal champion, lead with shared values over contracts, and know the difference between a hard "no" and a "not yet." One panelist doesn't even list a phone number on his website... here's why that's the point. https://familyoffices.com/

  5. Oct 21

    The Most Powerful Insight for Investors: Asymmetric Risk

    Send us Fan Mail What separates good investors from great ones? A billionaire's answer to "how did you get here" reveals the asymmetric risk-return principle that changed how one family office thinks about every deal. Plus... why treating other people's money like it's your own and betting on the entrepreneur (not the technology) is the real edge in venture and private equity investing. https://familyoffices.com/

  6. Oct 19

    The Harshest Reality in Fundraising

    Send us Fan Mail Family office and angel investors get brutally honest about what founders and capital raisers get wrong. From "most of your portfolio companies will fail" to "know when to say no to yourself," this panel breaks down why relationships, self-awareness, and knowing your audience matter more than a polished pitch deck. If you're raising capital, this is the reality check nobody else will give you straight. https://familyoffices.com/

  7. Oct 17

    Silicon Valley Summit: Key Trends, Unique Strategies & Powerful Insights From Our Investors

    Send us Fan Mail What can entrepreneurs and investors learn from how family offices build wealth, evaluate opportunities, structure deals, and develop relationships? After 19 years of working alongside family offices, centimillionaires, billionaires, investors, and entrepreneurs, Richard C. Wilson shares 10 lessons on building wealth and getting more deals done. These lessons cover creative deal structuring, raising capital, building trust, positioning yourself to attract better opportunities, turning competitors into partners, using AI to move faster, and developing the long-term mindset that sophisticated investors expect. One of the biggest lessons: **it’s not how big your network is—it’s how many people think of you first.** In this presentation, Richard shares why family offices often take a different approach to wealth and deals, including how to: • Structure deals around what the other side actually wants   • Turn competitors into partners through co-GP and JV opportunities   • Build trust before asking for capital   • Use creative collateral and seller financing to reduce risk   • Position yourself to see more—and better—deal flow   • Become top-of-mind within your niche   • Build relationships that compound over years   • Use AI and specialized intelligence to move faster   • Recognize opportunities others overlook   • Think long-term about wealth, health, relationships, and business Family Office Club gives members three core advantages: proximity to family offices and ultra-wealthy investors, superintelligence through applied investor knowledge and AI tools, and scale through better deal structures, capital, relationships, and strategic chokepoints. Subscribe for more family office, capital raising, deal structuring, investing, AI, and wealth-building strategies. https://familyoffices.com/

  8. Oct 16

    Meet the Panel: Family Offices, Angels & a $2.4B Real Estate Playbook

    Send us Fan Mail Meet a panel of family office principals and angel investors as they introduce themselves and their strategies. From a Puerto Rico-based impact family office targeting 10x-40x returns, to a $2.4 billion real estate and private equity operation behind the Nashville Yards deal, to an angel investing veteran with 150+ New York angels backing him... this is who's actually writing the checks. Learn how a global multi-family office platform, a shared-infrastructure single family office, and an angel group with an 800x miss on their record think about deal flow. https://familyoffices.com/

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About

The Family Office Podcast features interviews with billionaires, centimillionaires, family offices, industry titans and private investors, plus the strategies founders and capital raisers use to build relationships with them. New episodes every Monday, Wednesday, and Friday.Hosted by Richard C. Wilson, founder and CEO of Family Office Club and owner of Billionaires.com. Richard has helped create, formalize, and run 250+ family offices, structured over 200+ deals with clients and 44 deals off his own balance sheet, and closed 19 transactions for a publicly traded client his team sources opportunities for. Today he helps run two single family offices.Richard has also spent 3,000+ hours building hundreds of AI agents and implementation projects for centimillionaires, publicly traded clients, Family Office Club members and his own company. The 50 AI tools he built for members have been used more than 50,000 times.Our investors look at every type of deal. Episodes also feature family businesses and companies doing $10 million to $500 million in revenue, along with the owners and successors behind them.Topics include family office investing, single and multi-family office structures, private equity, venture capital, real estate, private credit, deal structuring, capital raising, family business succession, and AI for investors.Family Office Club at a glance: Operating since 2007340+ live events hosted, often with billionaires and centimillionaires on stage$1 billion+ in transactions closed between members17 million members across our social media communitiesSee upcoming events and membership at FamilyOffices.com or text (305) 333-1155. 

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