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

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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?

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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...

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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...

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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...

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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...

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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...

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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:

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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...

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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...

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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...

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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...

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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...

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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...

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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...

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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...

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This investor didn't start in energy. He started as a real estate borrower, learned the mechanics of private lending from the inside, and then made a deliberate decision to become the lender. Today, his firm deploys capital into residential real estate loans and has quietly built a portfolio of strategic energy investments - including a hydrogen technology company that has earned recognition from the National Science Foundation, the Department of Energy, and produced a Fulbright Scholars Award-winning researcher.
In this episode, he explains the principle that guides every pivot: only enter an...

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This investor's edge isn't capital - it's communication. As a brand strategist and communications founder, she has helped take companies to multi-billion dollar IPOs and record-breaking public market debuts. She backs founders she believes in and uses brand strategy to amplify their growth from the inside. Her investment thesis is simple: if a company can't connect on a human level, the product doesn't matter.
In this episode, she introduces the B2H framework - Business to Human - and explains why the most common mistake she sees from founders is leading with...

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We just had a billionaire keynote at our Capital Raising Bootcamp here in Dallas at the RSM offices. He has a couple of publicly traded companies and spent 40 years building his portfolio. Here are the notes I wanted to share from what he said on stage.
Build a super diverse skill set. You have to be a decathlete to be successful raising capital, building a platform, and scaling something.
Underwrite conservatively. If a deal does not make sense and you do not even know why - back away. Say no. Be...

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After 11 years working across two single family offices in industries spanning oil and gas, media, sports, and healthcare, this advisor launched her own boutique family office advisory firm. In under a year, she onboarded three Asian family clients and is now actively helping them allocate into U.S. markets - including a live mandate from a Hong Kong family office for positions in major private technology companies.
In this episode, she shares how cross-border family office advising actually works - the role of trust, the challenge of translating not just language but...

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This investor has spent decades doing one thing: buying right. From a 10,000-unit apartment portfolio sold to a major real estate buyer, to a pharmaceutical company purchased for $18M and exited at $358M, to two insurance companies flipped for significant returns - the track record is built on cash flow, not speculation. In this episode, he shares his full investment history and explains why today's market has made it nearly impossible to find the kinds of companies he used to target.With interest rates reshaping private equity valuations and private credit crowding out...

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Most athletes talk about what they've done. These four are talking about what they're building next. Dan wants capital partners to scale multifamily across Dallas over the next decade. Alvin is looking for partners with intelligence, initiative, and integrity for syndications and M&A. Otis has a vision for a micro wellness resort - saunas, cold plunge, health tech, community, built into land outside Austin. And Bronson wants to keep connecting people to the tax and family office strategies that change how athletes think about money.

This is the closing segment...

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Fear paralyzed him on Bitcoin. A decade in prestigious law firms surrounded by smart, unhappy people showed him what success without purpose looks like. And a stranger in Home Depot delivered a message that changed the direction of his business. Otis Grigsby played 6 years in the NFL, practiced law at large firms for 6 years, and is now part-legal, part-growth, part-strategy at his wife's health tech marketing agency - and watching ChatGPT recommend their services to strangers without any programming on their end.
In this episode, Otis delivers one of the most honest 10...

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8% of pro athletes are broke within 3 years of retirement. Dan Breezy watched it happen to his friends and decided to do something different. After multiple X Games gold medals in urban snowboarding, he took the same "inch wide, mile deep" focus that made him one of the best in the world at one discipline - and applied it to becoming one of the best value-add multifamily operators in Dallas-Fort Worth, working alongside mentors like Ken McElroy and Bobby Castro.

In this episode, Dan breaks down the visualization principle that let him...

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Most people think diversification means spreading your attention. Alvin calls it focused diversity - mastering one thing per day so that by Sunday, you have a full tool belt. That framework took him from the NFL and CFL to aerospace engineering to running operations on the M&A side, taking $10 million companies to $100 million valuations, while building a ground-up 4-unit multifamily development in Los Angeles.
In this episode, Alvin Scioneaux, Jr. unpacks the three I's that have driven every career move: intelligence (sharpening your mindset), initiative (moving before you're ready), and integrity...

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Your NFL contract is an exit. The ultra-high-net-worth understand that - and they plan for it. Bronson spent 7 years in the NFL as a W-2 employee, got crushed on taxes his first year sitting in muni bonds at 3%, and decided to spend the rest of his career learning exactly how family offices and top operators structure their wealth. Now he's the one opening those doors for other athletes.

In this episode, Bronson breaks down the exact mindset rituals he used to stay present during competition - writing 2-3 actionable words before...

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The closing segment of the last panel of the day — and one of the most honest. A family office investor argues that most people are walking past million-dollar opportunities every day: the car wash owner with no succession plan, the small hotel operator whose kids just want the cash. These businesses can be acquired without large amounts of capital if you bring the right non-cash currencies — experience, network, operational expertise. A second-gen family office investor closes with a reminder that AI is accelerating the pace of everything, human connection is becoming the scarcest reso...

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The most tactically dense episode of the panel. A former Air Force pilot who built the US military's AFWERX innovation program explains exactly how he structures deals around government contracts — using the Electra hybrid electric aircraft as a live example: $65M pre-money valuation, with a $30M Air Force contract not factored into the price. His fund put its check in escrow, the government signed, and the investment dropped in at an automatic discount because government revenue adds no dilution. Then: warrants, options, and capped valuations as tools to manufacture 80-95% discounts. Closes with th...

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Four insights in one episode, each from a different voice. A second-gen family office investor says ego is the single biggest destroyer of wealth — it makes you miss small details, over-rely on past success, and walk into deals you should have walked away from. An audience member introduces private placement life insurance — a custom IRS-compliant policy structure that lets your family office hold alternative assets in a tax-deferred environment. A software investor explains why poor board governance is the number one reason deals go sideways, and why preferred shareholders need a board seat to p...

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 Hi, Richard Wilson here, founder of Family Office Club. I just wrapped our Monthly Live Forum on AI, and I wanted to make sure this one actually gets used, not just watched.

Here's what I walked through in this session: why context engineering matters two to three times more than prompt engineering right now, and how to actually build it into your own workflow instead of just chatting with ChatGPT or Claude like it's a search engine. I showed you the three levels of AI maturity most founders get stuck at l...

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Three rapid-fire insights that the room had not heard before. First: gross revenue royalty deals — a family office founder who has done 17 of them explains why investors love them, almost nobody uses them, and how a dental practice scaled to $30M in revenue returned the full initial investment through monthly cash flow royalties before the exit even happened. Second: deal terms are where most investors get quietly destroyed — preference shares and waterfall structures can leave LPs with nothing even when a deal performs. Third: Grizz Ali reveals that almost no family office is depr...

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Five family office investors and operators introduce themselves — a former Air Force pilot who built the US military's innovation arm, a second-gen family office focused on drone and security tech, a distressed real estate fund manager, a first-gen family office founder who invented a sleep supplement, and a 25-year PE managing partner. The intros lead directly into a live deal breakdown on distressed office space: a 200,000 sq ft Chicago building that traded at $25M bought for $2.5M, and a 390,000 sq ft downtown Chicago building that was a $160M deal acquired for $18.5M. The th...

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The most candid segment of the panel. A private investment banker says the most expensive mistake he made was not paying for expert legal counsel — and explains why a cheap lawyer costs more on the back end than a good one does upfront. A family office CFO cites his first private investment loss to make a principle: founders must have skin in the game and LP capital must come back first, always — the Richest Man in Babylon principle applied to modern private investing. A serial entrepreneur says his most painful lesson was firing hims...

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Three things every investor needs to hear. First: a banker flags the growing SPV-on-SPV problem in today's VC market — 24-hour close emails, unverifiable shares, unvested stock — and explains why reading the actual paperwork has never mattered more. Second: on the PE side, capital scarcity means investors are winning more board seats, tighter terms, and preferential return structures. Third — and most shareable — a serial entrepreneur delivers a direct warning: AI is a tsunami, the window to get ahead of it is five years or less, and the operators who integrate it first will eat everyone...

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Post-2022, valuations have come back to earth — but how do you actually price an early stage or pre-revenue deal right now? This segment breaks it down: a family office CFO explains when EBITDA multiples work and when a convertible note is the smarter tool, giving investors the flexibility to clip a coupon if the deal underperforms or convert to equity if it overperforms. Then a serial entrepreneur explains how he acquired 14 franchise locations at $5,000 each — against a $250,000 market rate — by building a relationship with the franchisor instead of the franchisee. A deep tech founde...

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Four panelists — a private investment banker focused on growth equity and tech, the CFO underwriting deals for a $2 billion family office, a serial entrepreneur deploying AI into distressed franchise businesses, and a deep tech founder building programmable structural materials — each introduce themselves and immediately state what they are actively looking for. BTR co-GP deals, seed-stage medical devices, distressed wellness franchises, and long-horizon deep tech infrastructure. A fast, high-signal opening for anyone trying to understand where sophisticated capital is actually flowing today.

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The most shareable segment of the panel. Each investor shares the most memorable pitch they ever received — a collapsible cup prototype that wowed on every fact but failed basic physics, a 12-year-old's DJ business PowerPoint that hit credibility, clarity, and whimsy better than most professionals, and a founder who went from childhood paralysis to top-10 Halo gamer to tech CEO. Then the full panel answers the question every new capital raiser needs: how do you attract serious investors when you have no track record? Six investors, six answers — and a close that every foun...

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Most investors see 100+ deals a week and give each one-pager 10 seconds. The panel critiques real one-pagers live — a tech-driven safe deposit box company that nailed the name but buried the product, a luxury real estate fund missing its hold time and minimum investment, a healthcare firm with a billion-dollar track record that still couldn't answer what it actually does, and one that finally scores well. The rule that runs through every critique: graphs not paragraphs.

About Family Office Club

The world's largest investor club in the family office space. 19 ye...

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A one-liner has one job — earn the next 30 minutes, not close a deal. Investors rate multiple real one-liners submitted by members: a real estate credit platform promising 15% preferred returns, an AI venture fund called out for buzzword bingo with no differentiation, and a last-mile logistics company tripped up by its own jargon. You see in real time which ones make investors lean in and which get skipped. Plus: the FOC AI tool that generates 7 one-liners from your pitch deck in minutes.

About Family Office Club

The world's largest investor cl...

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Six investors introduce themselves — an angel, a VC general partner, a physician investor, an attorney-turned-real estate investor, and two accredited investor group members. Then, without a break, they immediately grade two real pitch videos on the spot. One company scores high. One gets torn apart. The episode ends with the investor who reveals the 3-part framework behind every score: Credibility, Clarity, and Whimsy — and exactly what each one means.

About Family Office Club

The world's largest investor club in the family office space. 19 years. 300+ events. 16 million members. $1B+ in comm...

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What is the most valuable advice centimillionaires would share after decades of building wealth? In this closing segment, successful investors discuss the lessons that matter most: health, family, long-term thinking, legacy, and preparing the next generation.

Hear why many wealthy families prioritize education early, stewardship over consumption, and creating structures that preserve both values and capital across generations.

This episode is ideal for entrepreneurs, investors, and anyone focused on building lasting wealth with purpose.

Recorded live at the Family Office Club Investor Summit featuring family office executives...