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

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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 minutes on this stage: fear is an absolute killer, it paralyzes your training, it makes you forget everything you've built - and it shows up daily whether you have a two-year-old at home or a nine-figure deal on the table. He talks about missing the Bitcoin run, what Christmas in big law looks like when IBM needs a deal closed, and the four-month delay before he finally followed the advice that unlocked his business. Family Office Club has hosted 300+ events over 19 years and $1 billion+ in community transactions - Otis is the kind of operator you only meet in rooms like this.
What is the one thing in your business you keep holding onto that you know you need to let go of? 

About Family Office Club

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

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Otis Grigsby spends most of his time helping his wife raise two exceptional young children. When he's not making wildly helpful and entertaining parenting content for Parent Like an Athlete, Otis serves as the Director of Growth at Distill Health, a Healthtech marketing agency. Otis is a licensed attorney who spent five years at Taft Law and Pillsbury Law before working at two venture-backed Sports Healthtech companies, Players Health and Oculogica. Before attending law school at the University of Kentucky, Otis hit people for money in the National Football League for over six years, playing defensive end for the Miami Dolphins, Carolina Panthers, and Minnesota Vikings.

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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 land tricks he had never attempted before - seeing it perfectly in his mind's eye before he ever hit the jump. He connects that directly to real estate underwriting: if you can't see the answer clearly, stay back. He shares the painful lesson of running too optimistically without accounting for market cycles, how to structure debt based on where you are in the cycle, and why getting crushed in taxes as an athlete was the catalyst for everything. Family Office Club has hosted 300+ investor events and connected investors across every asset class - Dan is a case study in what specialization looks like at the highest level.

Are you spread across 5 asset classes or going a mile deep on one? 

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
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📩 Membership: FamilyOffices.com/join

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Dan Brisse is the Co-Founder and Managing Partner of Granite Towers Equity Group, where he provides strategic leadership across operations, acquisitions, and investor relations. His background is rooted in real estate investment, with a focus on optimizing asset performance in multifamily properties, and successful capital raising and capital markets execution.

Before real estate, Dan was a professional snowboarder for over 13 years, earning multiple X Games gold medals and recognition as one of the world’s top urban snowboarders. He brings the same discipline and execution mindset to investing. Dan co-hosts the Keeping It Real-Estate podcast, co-authored 4 Steps to Successful Passive Investing, and lives in Southern Washington with his wife and three children.

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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 (your environment - you are the average of the five people around you). He shares his biggest financial lesson - partnering with people who don't carry all three - and breaks down what he's currently building in real estate syndications and M&A. Family Office Club has facilitated over $1 billion in community transactions at 300+ events, and Alvin is exactly the kind of multi-discipline operator our network was built to surface.
You don't have to choose one lane. But you do have to master the framework first. Watch this episode and ask yourself - do the five people closest to you have intelligence, initiative, and integrity?

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join 

https://familyoffices.com/

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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 every practice, staying out of fear (which lives in the future) and regret (which lives in the past). He shares the story of his father coming from Tonga at 8 years old with cardboard in the bottom of his shoes, and how remembering that story keeps him grounded, hungry, and humble. Family Office Club has connected capital raisers and family offices at 300+ events over 19 years - athletes like Bronson are exactly who this community was built for.

What is the most costly financial mistake athletes make after signing their second contract? Bronson has the answer, and it will change how you think about your own exit. 

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

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Bronson attended Brigham Young University where he played both football and basketball. He graduated in Statistics with an emphasis in Analytics. He was then drafted to the Baltimore Ravens and played in the NFL for 7 years, as well with the New York Jets and Green Bay Packers.

While playing in the NFL, he invested in real estate and learned tax strategies to help himself and his teammates out. He currently helps athletes, entrepreneurs, & family offices navigate their private investments and tax alt strategies as a trusted advisor.

Bronson founded Young Athlete Society where athletes, parents, and coaches can get help for their kids mental strength training and all things needed to get to the next level, with an emphasis on athlete mental health.

He also founded Utah’s first NFL Charity flag football event called Charity of Champions, where NFL players play with people from the community to help local charities in giving back.

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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 resource, and staying close to people building in your industry is the real edge. The final word: show up every day present, energized, and grateful — and pursue the people who deserve it.

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

https://familyoffices.com/

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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 the $100K question — four panelists answer where they would put their first $100K today: distressed assets and land, India pre-IPOs doubling every year, leveraged acquisitions of aging boomer businesses, and an AI-plus-electricians play that Richard says nobody is doing yet.

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

https://familyoffices.com/

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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 protect themselves. And a former IBM M&A executive warns on cap tables: a company he backed went from a $1.4M valuation to $350M — and investors were still only 4x up because of how the cap table was structured from day one.

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

https://familyoffices.com/

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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 level one on, and how we built what I call "Intelligence Centers," one Claude project per role on my team, each with four to seven tools built specifically for that person's job. No more guessing which tool to use for what.

I also introduced you to Clara, our AI pitch architect who will critique your one-liner, your pitch deck, and your due diligence questionnaire against 1,500 investor talks recorded on our stages. And Dewey and Vetti, our due diligence and real estate stress-testing tools that can rank ten pitch decks against each other in minutes. I explained why a one-line pitch, a 60 to 90 second founder video, and a 30-question due diligence FAQ will put you ahead of 99% of the people currently raising capital, because almost nobody has all three in place.

We also got into real questions from the room: how to structure a deal when you don't have a track record or a full team yet, how family offices actually vet trust before they'll wire you a dollar, and why the relationship matters roughly twice as much as the merit of the deal itself.

A little about us, so you know why I'm confident saying any of this: I started Family Office Club 19 years ago in 2007. We've hosted 300+ investor events, we host 30+ events a year across the US, we've got 16 million registered members across our LinkedIn groups, 18.5 million followers across social, and our community has closed over $1 billion in deals together. We built 50+ AI tools specifically for founders and investors, based on 1,500 investor talks from our own stages, not random internet data.

If you want the full deployment kit for what I showed here, meaning the exact Claude project instructions, prompts, and skills my team uses daily, or you want to see our next event schedule, here's how:

Apply for membership and unlock the AI tools + member portal: https://FamilyOffices.com/Join
See our next in-person investor event: https://FamilyOffices.com

Drop your biggest AI or capital-raising question in the comments below and I will personally reply. I read every comment on these training videos.

Richard C. Wilson
CEO & Founder, Family Office Club
Call/Text: (305) 333-1155
[email protected]

What's the one thing slowing down your capital raise right now? 

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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 depreciating its intellectual property — a legal, massively underused strategy that simultaneously reduces tax liability and increases balance sheet value when seeking a line of credit.

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

https://familyoffices.com/

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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 thesis: you don't need it to rebound 100%. Buying at these prices, 50% is more than enough.

About Family Office Club

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

🔔 Subscribe for weekly content from our summits, panels, and investor interviews.
🌐 FamilyOffices.com
📩 Membership: FamilyOffices.com/join

https://familyoffices.com/