

Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights
Richard C. Wilson, CEO of Family Office Club
The Family Office Podcast released 3-7 episodes a week of interview mandate interviews, private investor strategies, innovative investment structures, and wealth management related insights. We use this podcast to interview billionaires, centimillionaires, investors, and family offices and help founders, entrepreneurs and investors scale their platforms and invest more effectively.If you are looking to grow your business, get sharper at investing and scale you are in the right place.Our program provides investors with insights on setting up their own single family office, virtual family office, or selection of a multi-family office to help them manage their wealth. We cover private equity, real estate, income investments, commercial real estate, hard money lending, private loans, and innovative structures such as performance-fee only and Co-GP investment opportunities. The Family Office Club has over 7,500 registered investors and our online investor community has over 700 recorded investor mandates, with a normal 15 live events hosted a year with 6,500 participants at those live events. To learn more please visit http://FamilyOffices.com or text (305) 333-1155
Episodes
Mentioned books

Aug 21, 2025 • 4min
How Investors Spot the Real Deal – Family Office Club Panel | Due Diligence, Proof & Red Flags
Send us a textIn this Family Office Club investor panel, seasoned investors share exactly how they separate real opportunities from overhyped pitches. From customer validation to live product demos, this discussion covers the due diligence mindset used for deals ranging from $500K to $15M+.Key insights from this panel:📊 “The customer never lies” — why customer feedback and behavioral data are the most reliable indicators🧮 Simple, non-sophisticated adjustments that reveal the truth about a business’s revenue and renewals📝 Early-stage investing reality — “anything’s possible on a PowerPoint” and how to see past the fluff🚤 Example: Electric hydrofoil boats by Navier — tech innovation that extends range, reduces noise, and decarbonizes ocean transport🛠️ Proof through experience — why seeing and testing the product is critical for hardware investments🌍 Focus on sustainable innovation that reduces pollution and has a real, scalable market📍 Established company investing — why due diligence can be simpler when buying proven, local businesses💹 Crypto & public markets approach — only investing in SEC-regulated products and top market-cap leadersWhy watch?If you’re a founder, capital raiser, or investor looking to understand what convinces investors to move forward—and what makes them walk away—this panel reveals practical, experience-driven screening methods.📌 Recorded live at a Family Office Club investor event.🔗 Learn more: https://FamilyOffices.comhttps://familyoffices.com/

Aug 21, 2025 • 7min
AI & Investing – How Artificial Intelligence is Transforming Capital Deployment | Family Office Club Panel
Discover how artificial intelligence is reshaping the investment landscape, from monitoring ocean data to enhancing sales strategies. Learn about AI's role in tracking illegal fishing and flood risks using satellite technology. Delve into the challenges of securing high-quality data and the efficiency boost AI brings to customer service. Explore why blue-collar businesses and baby boomer entrepreneurs must embrace AI to thrive. With insights into AI's unparalleled wealth-building potential, this discussion uncovers both opportunities and risks in the evolving tech-driven marketplace.

Aug 20, 2025 • 5min
Global Investor Insights Panel – Family Office Club | Deal Flow, Sectors, & Investment Strategies
Send us a textJoin us for an exclusive Family Office Club investor panel discussion where seasoned investors share their current focus areas, deal flow needs, and strategies for deploying capital in today’s market. This in-person session covers diverse sectors—from Hawaii’s hospitality and infrastructure to global ocean sustainability, early-stage venture, and digital assets.You’ll hear from investors on:• Target sectors including hospitality, construction, infrastructure, and sustainability• Global investments in green shipping, maritime decarbonization, and ocean data products• Flood risk monitoring and B2G recurring revenue models• Early-stage co-investing and customer-centric venture models• Digital asset investment strategies and market timing• Deal flow needs and opportunities for founders & service providers• Check sizes, accelerator programs, and partnership opportunitiesWhy watch?If you’re a founder, dealmaker, or investor seeking to understand where active investors are deploying capital and what they’re looking for right now, this panel is packed with actionable insights.📌 Recorded live at a Family Office Club investor event.🔗 Learn more: https://FamilyOffices.comhttps://familyoffices.com/

Aug 20, 2025 • 2min
The “Buy-Cheap and Buy-Even-Cheaper” Strategy in Venture Capital
Send us a textAn expert on Venture Capital shares why traditional VC math doesn’t add up and how his team flips the model. Instead of paying inflated valuations and hoping for one breakout, they buy in early at favorable terms, use growth-hacking to add measurable value, and structure warrants for a second bite at a lower price.Key Takeaways:• Challenge the VC Norm – Paying 10× in hopes of 100× rarely works.• Early Entry Advantage – Secure low entry valuations before hype inflates prices.• Value Creation via Growth Hacking – Actively improve portfolio performance post-investment.• Use Warrants Strategically – Lock in the right to invest again at your target price.• Portfolio Mindset – Don’t rely on just one “winner” to carry the fund.📌 About Family Office ClubWe host 30+ investor events annually, connecting family offices, private investors, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 19, 2025 • 11min
Best Investing Advice from Family Office Leaders
Send us a textIn this lively exchange, top family office investors share the principles and mental models that guide their decisions — from gut checks to focus discipline.Key Takeaways:• The Mom Test – If you can’t explain the deal in one minute so a smart outsider understands, it’s too complex.• Happiness First – Success without personal fulfillment isn’t worth it; assess downside risk and personal payoff.• The Twitch Factor – Listen to your instincts when markets feel “off”; holding cash is sometimes the best move.• Focus on Your Niche – Stick to industries where you have expertise, relationships, and proven track records.• More Than Money – Family offices increasingly look for opportunities where they can add strategic value, not just capital.📌 About Family Office ClubWe host 30+ investor events annually, connecting family offices, private investors, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 19, 2025 • 8min
Family Office Leaders on Navigating Uncertainty & Spotting Opportunities
Send us a textIn this panel segment, seasoned family office investors reveal how they approach turbulent markets, rising interest rates, and global instability — and why chaos can be a prime time to invest.Key Takeaways:• Uncertainty can create the best deals — savvy investors profit while others hesitate.• Real estate and ancillary businesses remain hot targets during market volatility.• In tech, initial seed investments are “toe in the water” opportunities — follow-ons are where big gains happen.• Strategic involvement (board roles, connections, guidance) is as valuable as capital for early-stage companies.• Liquidity is power: cash reserves allow nimble moves when valuations correct.• Diversification across real estate, operating businesses, and liquid portfolios ensures long-term stability.📌 About Family Office ClubWe host 30+ investor events annually, connecting family offices, private investors, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 18, 2025 • 2min
What Makes a Deal Stand Out to a $2B Family Office
Send us a textThis expert Family Office shares exactly what makes them lean forward when reviewing investment opportunities — from real estate to early-stage tech.Key Takeaways:• In real estate: Proven sponsors, strong track records, and completed entitlements are non-negotiable.• In technology: It’s all about a qualified, cohesive team and defensible intellectual property.• Seed-stage valuations are tough, but patents and strong leadership make a deal compelling.📌 About Family Office ClubWe host 30+ investor events annually, connecting family offices, private investors, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 18, 2025 • 12min
Investor Mandates & Creative Deal Structures: Family Office Panel
Send us a textIn this high-level Family Office Club panel, leaders managing billions in assets share their current investment mandates, how they’re navigating market uncertainty, and the creative deal structures driving results right now.Hear from experts in real estate, venture capital, alternative investments, and private equity as they discuss diversification strategies, opportunistic investing during times of distress, and the importance of listening for unexpected opportunities.What You’ll Learn:• Why chaos in the markets can create once-in-a-decade investment opportunities• How to structure revenue-sharing, co-GP, and joint venture deals for win-win outcomes• The overlooked role of diversification for long-term portfolio resilience• Sectors top family offices are targeting right now — from AI to energy storage to hospitality• How relationship-driven investing uncovers deals others never see• Why alternative investments are becoming the dominant allocation for UHNW investors📌 About Family Office ClubWe host 30+ investor events annually, connecting family offices, private investors, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 16, 2025 • 9min
The #1 way to secure warm introductions to the right investors | Family Office Club Investor Panel
Send us a textFrom capital raising realities to the non-negotiable role of trust, this Family Office Club panel brings together seasoned investors and family office leaders to share hard-earned lessons from decades of deal-making.Whether you’re an investor looking to sharpen your vetting process or a founder trying to break into the world of direct and co-investments, this discussion delivers unfiltered insights you won’t find in a textbook.What You’ll Learn:- How “fake it till you make it” destroys investor trust (and what to do instead)- The #1 way to secure warm introductions to the right investors- The deal-killing red flags every investor spots instantly- How to position your startup to appeal to industry leaders and strategic partners- Why relationships still drive investment decisions in today’s digital era📌 About Family Office ClubThe Family Office Club hosts 30+ investor events a year, connecting capital raisers, founders, and dealmakers with investors worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/

Aug 16, 2025 • 3min
The #1 Question Top Investors Ask Before Funding a Deal | Family Office Club Panel
Send us a textIn this candid Family Office Club investor panel, leading family offices and venture investors reveal the first question they ask when vetting a CEO or deal — and why it can make or break an investment.From uncovering hidden debt to testing a founder’s execution plan, these seasoned investors share the sharp, direct questions that quickly separate great opportunities from time-wasters.What You’ll Learn:- Why undisclosed debt can instantly kill a deal- How to spot red flags in founder relationships (including co-founders who are secretly married)- Why “real revenue” beats letters of intent or purchase orders every time- The critical importance of use-of-funds and 5-year execution plans- How to pressure-test competitive strategy in markets dominated by giants (e.g., Elon Musk)- The fastest way to save time in due diligence and avoid dead-end meetings📌 About Family Office ClubThe Family Office Club hosts 30+ live events annually, connecting investors, founders, and dealmakers worldwide. Learn more: https://familyoffices.com/https://familyoffices.com/