Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
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...
Why Banks Would Rather Sell Your Debt Than Cut You a Deal
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A bank would rather sell your $100 million loan to a brand-new buyer at a discount than knock $10 million off what you personally owe. This panel explains why.
Closing out this Family Office Club real estate panel, built on 19 years and $1 billion-plus in community transactions, the operators break down the real logic behind distressed debt sales, debt forgiveness, and why the original sponsor rarely gets a second chance. Would you take the haircut, or walk away?
https://familyoffices.com/
What Next-Gen Investors Want Differently From Real Estate
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A first-gen wealth creator will take an 18% return and call it a win. The next generation wants 11% and a mission. This panel breaks down what's really shifting as capital passes to the next generation.
Part of Family Office Club's ongoing work with a 16 million-member investor community across 19 years, this episode covers how GP/LP structures are evolving as veteran operators without succession plans open the door to new capital. Is your next-gen investor strategy ready?
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The 18.6-Year Real Estate Cycle That's About to Repeat Itself
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Real estate runs in 18.6-year cycles, a pattern that holds up across 200 years of U.S., U.K., and Australian data, and this panel says we're heading into the next inflection point right now.
Drawing on 19 years of tracking market cycles across Family Office Club's 300+ events and 16 million-member community, this episode covers the exact questions to ask any operator about how they handled the last recession before you invest. Do you know how your operator performed the last time the market turned?
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How to Rebuild Confidence in Real Estate After Getting Burned
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If you got burned in the last real estate cycle, this panel has one piece of advice before you deploy another dollar: find the operator who lives in the income and expense numbers, not the projections.
This conversation comes from a Family Office Club real estate panel, drawing on lessons from over $1 billion in community transactions and 19 years of watching investors succeed and fail through full market cycles. What's the first question you ask before writing a check again?
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Investors Are Walking Away From $100 Million in Personal Guarantees
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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/
The Syndication Bubble Popped: Why $1 Trillion in Debt Is Coming Due
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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?
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AI Doesn't Write the Check — Humans Do.
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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.
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How to Actually Get in Front of a Family Office
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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.
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The Most Powerful Insight for Investors: Asymmetric Risk
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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.
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The Harshest Reality in Fundraising
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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/
Silicon Valley Summit: Key Trends, Unique Strategies & Powerful Insights From Our Investors
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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 bi...
Meet the Panel: Family Offices, Angels & a $2.4B Real Estate Playbook
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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/
How to Use AI to Raise Capital, Structure Deals and Outperform 99% of Founders in 2026
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This is our 341st live event - a Family Office Club webinar hosted by Richard C. Wilson covering the latest AI tools, trends, and strategies for founders, investors, and capital raisers.
00:16:24 Welcome and What’s New Today
00:17:52 Free Resource: Deca Millionaire Trail Guide
00:20:02 3 Types of AI Tools and Which Level You Should Be At
00:22:15 Claude Design: Pitch Decks, Websites and One-Pagers in Minutes
00:25:07 How to Build Custom AI Skills
00:26:53 The SEO and AEO Optimization Skill
00:28:43 AI Whitewashing: Sound Human, Not Like AI
00:30:34 Dewey, Clara, De...
10 Proven Strategies to Scale to $100M From 1,500 Talks at Our 300 Events Over 19 Years
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What does it actually take to scale a business, investment platform, or balance sheet toward $100M?
After 19 years of running Family Office Club, hosting 300+ live events, and learning from more than 1,500 investor talks, Richard C. Wilson breaks down 10 of the most important strategies for scaling faster and building long-term wealth.
These are not theories pulled from a textbook. They are patterns observed from family offices, centimillionaires, billionaires, founders, capital raisers, and investors operating at a high level.
In this presentation, Richard covers how to:
• Position yo...
The Ex-Intel Exec Who Told His CEO: "You're Losing to Nvidia
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A former AI engineer and Intel engineering executive, who worked on early large language models years before ChatGPT existed, shares the moment he told his CEO that Intel was losing the AI race to Nvidia... and got laughed off. He lays out a bold thesis: most enterprises will run on 80% AI and 20% human labor within five years, and why he believes this won't shrink the economy but multiply it several times over. The panel closes with a live, half-serious debate on whether AI itself should be taxed. Filmed at a Family Office Club...
The #1 Reason 90% of Capital Raise Pitches Get Ignored
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A real estate platform investor operating on both the equity and debt side explains how his firm has spent 14 months acquiring non-performing multifamily loans below replacement cost... and why execution, not acquisition price, is what actually creates returns. He breaks down why his team is rolling up debt platforms and mortgage brokerages, and delivers a candid take on why most capital-raise pitches fail: founders don't invest the time to understand what the investor is actually looking for. Part of Family Office Club's single family office mandate series, drawing on insights from over $1B...
This Investor's Warning: There Won't Be a Middle Class Left
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A second-generation real estate investor who has structured over $2.3 billion in equity capital shares hard-won lessons from deals like Nashville Yards ($4B) and an Austin property later acquired by Elon Musk. He makes the case for hard assets over financial engineering as markets transition, discusses restructuring distressed multifamily debt, and delivers a stark warning about capital concentration in the years ahead. Captured live at a Family Office Club single family office summit, one of 300+ events FOC has hosted for its 16 million-member global investor community. Want to hear more conversations like this in person...
The One-Minute Rule This Investor Uses to Nail Every Pitch
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A New York City-based single family office investor focused on growth-stage venture reveals the one filter that matters more than the technology itself: the founder. She explains why her firm defers technical diligence to outside experts on deep tech, why timeline-to-exit matters more than "the most incredible technology in the world," and shares a real story about walking away from a game-changing climate tech deal over one issue: leadership readiness. Featured as part of Family Office Club's ongoing single family office mandate series, drawn from over 1,250 investor talks across 19 years of FOC events...
Why This Family Office CEO Won't Invest If You're "Indifferent" on ESG
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A Dubai-based single family office CEO, now leading his family's third-generation investment operation, breaks down why sustainability can't be an "indifferent" answer in any GP conversation... and why that's non-negotiable at the first meeting. This episode covers commercial real estate acquired below replacement cost, renewable energy investments spanning solar to hydrogen electrolyzers, and an inside look at industrial waste recycling as an overlooked asset class. Filmed live at a Family Office Club single family office summit, part of the 300+ events FOC has hosted over 19 years for its 16 million registered members. Want direct access...
From Homeless 2x to Multi-Billionaire: 10 Strategies, Stories & the Mindset to Create Wealth
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Join Richard C. Wilson of the Family Office Club as he interviews legendary entrepreneur and philanthropist John Paul DeJoria — the force behind iconic brands like Paul Mitchell and Patron Tequila. In this inspiring conversation, JP shares the gritty details of his journey from homelessness and door-to-door sales to building billion-dollar brands.
You'll hear about:
- His humble beginnings and early hustle as a kid
- The mindset and lessons learned selling encyclopedias
- How he bootstrapped Paul Mitchell with just $700
- Creating ultra-premium tequila and launching Pa...
A 9-Year NFL Veteran's Advice on Money, Mentors, and Purpose
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Closing out this athlete panel, a nine-year NFL veteran reflects on the credit card mistake that shaped his approach to money, a chance mentorship encounter with an NBA legend that stuck with him for decades, and his current work bringing an education and augmented reality project to underserved communities in Jacksonville.
Family Office Club has run 300+ events over 19 years, building the world's largest family office investor community. Come see what 16 million members are building together.
Who's the mentor that changed the direction of your career?
About the sp...
From the NFL to Buying European Football Clubs: Parker Graham's Story
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A former NFL offensive lineman who once weighed 325 pounds now runs a tech company involved in buying and selling European football clubs worldwide. He breaks down the risk-taking and network-building that fueled his transition from the league into business, why mentorship is the ultimate cheat code, and how growing up with a single mother shaped his definition of purpose.
Family Office Club has run 300+ events over 19 years, building the world's largest family office investor community.
What's one risk you took that changed the trajectory of your career?
Ab...
Exclusive Interview: From $100K to a $1B Balance Sheet & 700 Employees
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Saeed Amidi is a seasoned investor and executive with more than 30 years of experience building businesses across real estate, bottled water, packaging, and technology investing. In this exclusive interview, Richard C. Wilson sits down with Saeed to explore his journey from entrepreneur and family business executive to one of the leading figures in global startup investing.
Saeed shares the story behind Plug and Play and the Palo Alto building that became known as the "Lucky Building," where early-stage startups included companies and founders such as Google, PayPal, Logitech, and Danger. The...
He Went From MLB Pitcher to Insurance Exec at a Top-3 Global Broker
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A 12-year MLB veteran turned insurance executive at the world's third-largest broker shares what family means to him, the mental game behind elite performance, and what he wishes he'd known about financial literacy before going pro. Backed by 19 years and 300+ events,
Family Office Club connects investors and operators across every industry. Join our 16-million-member network.
What's one piece of advice you'd give parents raising the next generation of athletes?
About the speaker:
Mike O’Connor is a former Major League Baseball pitcher who played for the Wash...
Booking Golf Trips Just Got Easier: Inside a Travel Tech Startup
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Coming from a family of Olympic and professional athletes, this founder pivoted from a wellness travel startup that couldn't scale into a golf-focused booking platform, now partnered with major names in the golf industry, solving the fragmented process of booking hotels, tee times, and events in one checkout.
Family Office Club has spent 19 years building the world's largest family office investor community, 16 million members strong. See how founders like this one connect with capital.
What similarities do you see between elite athletes and elite founders?
About the sp...
The $1M Mistake That Changed How This Ex-Pro Baller Invests
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A former professional basketball player who competed overseas in Germany opens up about the discipline that built his career, the financial mistake that cost him early on, and his next chapter: launching an NIL academy and performance facility in Los Angeles alongside a former Laker, plus a docuseries following young athletes through the realities of Name, Image, and Likeness deals.
Family Office Club has hosted 300+ events over 19 years connecting builders like this with capital. Explore our community of 16 million members. What's the biggest financial lesson you learned the hard way?
Fees, Staying In Your Lane, and Why The Next Generation Matters Most
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A family relations director explains how staying disciplined in one investment lane can also mean missing generational opportunities like early AI bets, and why bringing the next generation in as genuine innovation partners (not just heirs) is what keeps multi-generational wealth resilient. The panel closes with the fee-structuring reality of when to pay $2,000-an-hour specialists versus mid-range project managers, and the one rule every operator on this panel was taught on day one: don't lose money. Family Office Club has connected 16M+ members and facilitated $1B+ in transactions over 19 years and 300+ events, built...
The Legal Mistakes Quietly Destroying Family Office Wealth
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A trust and estates attorney explains why so many wealth holders set up asset protection or estate tax planning trusts and then quietly break the rules that make them work, plus the governance failures (no family council, no investment policy statement) that wreck multi-generational wealth long before any lawsuit does. You'll also hear the real net worth thresholds (roughly $250M to start a single family office, $750M-$1B before hiring an internal CIO) that determine when a family actually needs this structure. Family Office Club has spent 19 years building the operating playbook for...
Why 99% Of Deal Pitches Sound Identical (And How To Fix It)
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A family office investor explains why a 1970s multifamily deal in Dallas looks identical to one in Houston or San Antonio, and why having an actual investment thesis (not just chasing AI or the herd) is what separates sponsors who get funded from sponsors who get ignored. Real examples include an industrial outdoor storage thesis built around inflation uncertainty. Family Office Club's community has closed over $1B in transactions across our 16M+ member network because operators here learn to think like allocators, not just pitch like fundraisers. If you had 60 seconds with a...
How Family Offices Filter Deal Flow (And The Red Flag That Kills A Deal Instantly)
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A family office investor breaks down why humility beats overconfidence every time a sponsor walks in the door, including the real story of a first-time textile mill conversion that nearly got rejected on the spot. You'll hear exactly how trusted-source referrals and co-investment due diligence sharing speed up decisions across multiple family offices at once. Family Office Club has hosted 300+ events over 19 years connecting 16M+ registered members with the operators and capital allocators who move real deals. This is the kind of conversation that happens at every one of our events. What would...
What 4 Family Offices Wish They Knew Before Managing Serious Wealth
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Coming into serious wealth changes everything. But almost nobody tells you the right things at the right time.
In the closing segment of this Single Family Office Summit panel, four principals share what they actually wish someone had told them - and the answers are not what you'd expect. One panelist explains why vulnerability is the fastest path to real trust, and why he acts first before asking investors for anything. Another issues a challenge to rethink pain: wealth creates comfort, comfort creates complacency, and complacency quietly erodes what built the fortune...
Capital Raising Hot Seats: Pitch Decks, Structures & Investor Relations with Richard C. Wilson
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Richard C. Wilson runs a live Capital Raising Hot Seats webinar, giving real-time feedback to Family Office Club members on investor relations, pitch decks, deal structures, and capital raising strategy.
Family Office Club by the numbers: 4 Family Office Super Summits per year, 12 Family Office Masterminds, 50 in-house AI tools built for members, and $1B+ in member deals closed.
In this session, Richard covers:
The Trust Formula Family Offices Actually Use
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Everybody wants to do business with family offices. Almost nobody understands what actually builds trust with them.
This panel goes deeper than the usual advice. One of the moderators opens with a story from Milken - a capital raiser so focused on the opportunity, he forgot to wash his hands. He lost the room before he opened his mouth. From there, four family office principals break down what trust actually looks like from their side of the table. A 45-year veteran of the national family office space explains why relationships and co-investment...
How 4 Family Offices Are Deploying Capital Right Now
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4 family offices. 4 completely different strategies. One honest conversation about where serious capital is going right now.
In this panel from the Single Family Office Summit, a family office principal who built his wealth through Silicon Valley tech exits breaks down why he calls his approach "boring" - and why that's the point. Private credit, real estate, and a floor of steady income that funds high-conviction angel bets in defense tech. Another panelist explains how his family invests based on stories - backing art and crypto not as speculation but as instruments of...
Private Credit Is Not Created Equal - Family Offices Debate the Risk
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Private credit is one of the most talked-about asset classes in the family office world right now - but is the hype justified?
In this panel discussion from the Single Family Office Summit, three family office principals share exactly where they stand on private credit in today's market - and the answers are more divided than you'd expect. One says it's nearly impossible to underwrite properly at current lending rates. Another is avoiding it entirely for cross-border capital. And a third has 60% of their portfolio allocated there - with a very specific...
How to Pitch Investors, Work With International Capital, and Allocate Your Attention Strategically
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The final segment of this Single Family Office Summit panel delivers some of the most practical insights of the day. A brand strategist and communications founder opens with a direct challenge to anyone raising capital: stop leading with everything you do. Investors have roughly eight seconds of attention available. Lead with what matters to them, earn the next minute, and work from there.
A cross-border family office advisor follows with a framework for working with Asian capital: lead with relationships not transactions, recognize that every family defines risk and value differently, and...
Exit Lessons From Experienced Investors: Trust, Skin in the Game, and Building a Business You'd Own Forever
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What do you actually learn after scaling and selling a major platform? In this episode, two investors who have done it give their most honest answers. The first says the single rule that has never failed him is this: if a co-investor won't put their own money in, he walks. Trust and aligned incentives aren't nice-to-haves. They're the entire filter.
The second shares the structural lesson his institutional capital partner taught him during a major platform build: think about what you're building as if you'll own it for 100 years. Companies built for...
Bitcoin for Family Offices: Why No Position Is Now a Position | Richard C. Wilson x Eric Runge
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No Bitcoin position is not a neutral position anymore. Richard Wilson sits down with Eric Runge, a Bitcoin-focused RIA founder and active Family Office Club member, in a conversation that started the same week a $1.5 billion trust company reached out to Family Office Club asking who in the community specializes in institutional Bitcoin strategy.
Family Office Club has run 300+ investor events over 19 years for a 16 million member community, and this episode breaks down how family offices are actually approaching Bitcoin today: on-chain versus ETF exposure, sizing frameworks, custody decisions, the payment-rail...
The Case for Alternative Residential Real Estate: Student Housing, Senior Housing, and the Demographic Opportunity
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This CIO co-founded a housing-focused investment firm after scaling one of the largest single-family rental platforms in the country alongside a major institutional capital partner. The playbook hasn't changed: find fragmented, alternative residential asset classes where institutional-quality operations haven't yet arrived, and build the platform that gets them there.
In this episode, he breaks down why student housing and senior housing are the firm's most active deployment targets right now - and why the national narrative on student housing misses what's actually happening at the market and school level. He also explains...
Family Office Club Hot Seat Webinar: Live Capital Raising Q&A With Richard C. Wilson
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This is the Family Office Club Monthly Hot Seat Webinar from August 2026. Every month I get on live with verified members, Charter members, and community participants to answer questions in real time - no slides, no script, just direct Q&A on whatever challenge is in front of you right now.
Topics covered in this session include how to raise capital for a protein business with 2 million pounds a month of beef processing - including finding the right investors in agricultural Midwest markets like Omaha, structuring a custom deal for a...
