Family Office Podcast: Real Estate Investments, Co-investing, Capital Raising, And Private Equity Business Strategies

Send us a textWhat happens when one of the most feared UFC heavyweights of all time transforms from warrior to healer?In this powerful episode, Cain Velasquez, 2x UFC Heavyweight Champion, opens up about his journey from fighting legends in the octagon… to leading transformational work with veterans, athletes, and corporations today.We dive into:- What it’s like to spar with the world's toughest fighters- How he developed relentless discipline, strategy, and mental toughness- His shift into healing work through breathwork, ancient practices & psychedelics- What he's doing now on his 300-acre ranch to help others find their inner powerLessons on trauma, visualization, identity, and becoming your own medicine

Send us a textBoda Borg is revolutionizing experiential entertainment with “questing” — real-life gaming adventures that blend technology, teamwork, and immersive challenges. With 11 global locations, 5M+ guests, $20M+ in annual revenue, and 30 years of innovation, Boda Borg is not just another escape room — it’s a whole new category.In this interview, David Spigner, CEO of Boda Borg, shares how he’s scaling reality gaming, insights on expansion into California and beyond, and why major companies like Google use Boda Borg for team-building and corporate events.Diversify your investments with the leader in Questing, a proven experiential live-action gaming platform with 11 locations, serving nearly 5 million Guests, and generating annual revenue of $20+ million.

Send us a textDiscover how to identify the single best use of your energy, attract higher-quality deal flow, and position yourself as the go-to authority in your niche. In this session from the Family Office Club event, Richard Wilson shares proven frameworks and insights from billionaires, top investors, and business leaders on how to:Zero in on your most valuable niche and dominate itAlign passion, skill, and profitability for long-term successAvoid the herd mentality and stand out in competitive marketsSpot industries with the most inevitable future demandBuild an “unfair advantage” over your past selfUse clarity to multiply action and reduce stressPosition yourself for exponential growth over the next decadeWhether you’re running a family office, private investment firm, or growth-stage company, this talk will give you the tools to focus, differentiate, and scale strategically.

Send us a textJoin Richard C. Wilson, founder of the Family Office Club, as he shares 18 years of insights from running the world’s largest ultra-wealthy investor community. In this powerful mastermind session, Richard covers:How the Family Office Club connects 7,500+ investors, including 1,500+ deca-, centi-, and billionairesCutting-edge AI tools for sourcing deals, performing due diligence, and scaling investor outreachProven capital raising strategies from billionaires, Shark Tank investors, and top dealmakersWhy trust, relationships, and in-person meetings matter more than ever in the AI eraThe three levels of AI sophistication and how to implement them in your businessCase studies on using AI for real estate, investor relations, and business growth

Send us a textIn this Family Office Club panel discussion, top investors share the next big trends they believe will shape the future of investing. From AI with baby boomer businesses to sustainable ocean ventures, Web3, and the data revolution, you’ll hear where seasoned dealmakers are placing their bets before the rest of the market catches on.Key insights from this panel:AI combined with 15–20 year cash-flowing baby boomer businessesData as a major investment category, with opportunities in cleaning, managing, and leveraging it as AI adoption acceleratesGrowth in compute space and data centers to support AI, autonomous vehicles, and other high-demand technologiesInvestment opportunities in immersive, transformative experiences as demand for novelty growsWeb 3.0 and decentralized platforms for protecting freedom of speech, creator ownership, and personal brand/IP rightsSustainable ocean and climate investments, including reducing pollution, alternatives to plastics, and circular economy solutionsThe “milkma

Send us a textJoin Richard C. Wilson, founder of the Family Office Club, for an in-depth workshop on AI tools, thought leadership, and capital raising strategies used by top investors and dealmakers. In this presentation, Richard shares:Why thought leadership is the “holy grail” of raising capitalHow to clarify your one-liner to attract more deal flowAI-powered tools for sourcing, due diligence, and investor outreachHigh-impact sales and marketing strategies including text marketing, live chat, and asynchronous communicationInsights from billionaires and top entrepreneurs on scaling businesses and building lasting wealth

Send us a textIn this Family Office Club panel discussion, seasoned investors share the single most important factor they consider when deciding whether to invest in a company. From passion and grit to systems, community, and track record, you’ll hear what truly tips the scale in the decision-making process.Key insights from this panel:Passion as a driver — dedication to solving a problem beyond making moneyTenacity & resilience — surviving tough markets and pushing through challengesSystems over hustle — moving from “Viking stage” (pure grit) to “Gladiator stage” (scalable systems) to build lasting companiesCommunity power — how a strong, fanatical following can drive market cap, even without revenueCulture fit — using tools like Culture Index for personality testing and role alignment in service-based businessesConsistent track record — seeking founders with a long history of success across multiple life stages and industriesEmotional intelligence — why EQ combined with grit predicts success in any envi

Send us a textIn this Family Office Club investor panel, speakers reveal the markets and sectors they’re eager to deploy capital into—but have been waiting for the right CEO, operator, or “jockey” to lead the charge. From decarbonizing global shipping to betting big on India’s deep tech future, this session highlights where investors see the next massive waves of opportunity.Key insights from this panel:

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:

Send us a textIn this Family Office Club investor panel, global investors share how artificial intelligence is impacting their industries, portfolios, and deal flow strategies. From ocean data satellites to compute power, sales automation, and blue-collar business integration, this conversation dives deep into the real opportunities and risks AI presents today.Key insights from this panel:

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 wha

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.

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.

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.

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.

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

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

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

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

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.