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

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/

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/

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/

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/

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/

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/

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/

Send us a textAt this Family Office Club investor panel, top investors, venture accelerators, and wealth managers share how they source, evaluate, and negotiate direct and co-investment opportunities.Learn real-world strategies for finding exceptional deals and securing favorable terms.What You’ll Learn:- How family offices and angels source exclusive, off-market deals- Why relationships and trust are critical to deal flow- Strategies to negotiate special terms, control provisions, and board seats- The role of accelerators and networks in securing top opportunities- Examples of asymmetric, high-value investments (music IP, niche real estate, tourism tech)How strategic co-investors can unlock more capital faster📌 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/

Send us a textRecorded live at the Hawaii Family Office Retreat, this powerhouse panel explores how leading investors are leveraging their entrepreneurial roots, NextGen family members, and innovative business models to allocate capital and scale effectively.Key Topics Covered:- How to source and acquire undervalued businesses from retiring founders- The “silver wave” opportunity and wealth transfer trends- Leveraging systems like EOS for scalable growth- Identifying niche asset classes like RV parks for cash flow & appreciation- Using AI to optimize hiring and due diligence- Structuring deals for both short-term returns and long-term legacy building- NextGen engagement, intergenerational wealth transfer, and family valuesWhether you’re an investor, family office executive, or entrepreneur, this session is packed with actionable insights on scaling smart, building legacy, and creating resilient portfolios.📌 Hosted by: Richard C. Wilson, Family Office Club📍 Event: Hawaii Family Office Retreat👉------------------------------------------------------------I founded the Family Office Club 18 years ago—now with 20 team members, over 1,000 active investors, and 25 events annually. We’ve built over 40 AI tools using data from 300 events.  Event calendar: https://familyoffices.com/ Ways to join: https://familyoffices.com/join/Our most popular YouTube series covers capital raising, investor strategies, and billionaire interviews on Billionaires.com.Want free resources or one of my books on investing, family offices, or raising capital? Just ask. Richard@FamilyOffices.com | Text/WhatsApp: (808) 600-9260https://familyoffices.com/

Send us a textIn this inspiring segment, hear from this CEO on how purpose-driven investing can create real impact. She shares how her firm champions women founders, women leaders, and innovators who drive change worldwide. Learn her approach to building wealth with intention, giving back, mentoring future leaders, and balancing success with meaningful contributions.Discover insights on:- Investing with purpose and long-term vision- Empowering women entrepreneurs and leaders- Building intergenerational wealth responsibly- Mentorship and guiding the next generation-Combining profit with positive impactRecorded live at the Family Office Club investor event in Hawaii.📌 About Family Office ClubWe connect investors, founders, and dealmakers through 30+ live events annually. Learn more at https://familyoffices.com/ https://familyoffices.com/