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

Send us Fan Mail

What does real due diligence actually look like in private investing?

In this fireside chat, Richard C. Wilson sits down with Marc Halpern, co-founder of the Deep Due Diligence Investors Club, to break down the tools, strategies, and real-world case studies behind smarter investing.

Marc shares how experienced private investors evaluate opportunities by looking at the jockey, the horse, and the track — meaning the sponsor, the deal itself, and the macro environment. He explains why most investors don’t go deep enough, how AI can help screen deal flow faster, and why due diligence can reduce risk — but never eliminate it.

This conversation also covers:

How to evaluate sponsors vs. deals

Why deep due diligence works best in teams

How to use AI tools for investment screening

The difference between minimizing risk and managing risk

Why diversification matters across sponsors and asset classes

How investors stress test operators during changing market conditions

Common mistakes sponsors make when raising capital

If you invest in private placements, real estate, private equity, or alternative assets, this session will give you a more disciplined framework for evaluating deals and avoiding costly mistakes.

Marc and the Deep Due Diligence Investors Club have helped put roughly $10 million of equity checks to work across deals, and this session gives you a look into how serious investors think before wiring capital.

Watch this if you want a sharper lens on:
due diligence, deal screening, sponsor evaluation, private investing, and portfolio strategy.

https://familyoffices.com/

Send us Fan Mail

YouTube recording here https://youtu.be/caEuNpa5t40

This is the Family Office Club Monthly Live Forum, a live, interactive session focused on real-time strategy, capital-raising feedback, and applied AI tools used by serious investors and founders.

This is not a presentation-only webinar; each session is designed around:

1️⃣ Live hot seats and real-time strategic feedback

2️⃣ Applied AI demonstrations used for investor research, pitch refinement, and deal structuring

3️⃣ Live pitch and platform-building feedback drawn from how family offices and sophisticated investors actually evaluate opportunities

The Family Office Club hosts over 30 investor events per year across major U.S. cities, works with 10,000+ investors, and operates a growing suite of 40+ AI tools built specifically for dealmakers. This live forum reflects how those tools, frameworks, and capital conversations are used in practice, not theory.

📌 How to prepare (strongly recommended)

Attendees who get the most value typically:

• Join live and stay for the full session
• Bring a current question related to capital raising, investor positioning, or scaling
• Review their pitch, platform, or deal assumptions in advance

Hot seat participation and deeper feedback are reserved for active members, but public attendees consistently gain clarity simply by observing how live decisions and feedback are handled.

🚀 What members receive beyond the live session

Members have access to:

• Priority hot seats and live feedback
• Session recordings and archives
• 40+ AI tools for investor targeting, pitch architecture, due diligence, and deal structuring
• 30 nationwide in-person investor events and summits

If you want to continue attending our webinars register in this link:
👉 https://familyoffices.com/webinars/

You will receive reminder emails from Zoom as the session approaches.
Please join from a stable connection and plan to be present live.

We look forward to having you join us, text me at the number below with any questions you may have and we look forward to seeing you on the webinar.

For details on our next in-person investor club event, please see our schedule here:
👉 https://FamilyOffices.com

And how to apply for membership here to instantly unlock the AI tools + member portal:
👉 https://FamilyOffices.com/Join

Richard C. Wilson
CEO & Founder
📞 Call/Text: (305) 333-1155
📧 [email protected]

Family Office Club
👉 https://FamilyOffices.com/Join

https://familyoffices.com/

Send us Fan Mail

Raising capital has never been harder.

And most fund managers are playing the wrong game.

In this episode, I sit down with Chip and Sam Perkins of Perkins Fund Marketing — a firm that has raised over $8 billion in alternative assets over nearly three decades — to unpack what actually works in today’s capital raising environment.

They’ve spent 30+ years, tens of thousands of hours, and navigated multiple bull and bear markets to refine what separates successful managers from those who never break through.

Inside this episode, we cover:

Why raising capital today is harder than 2008

The biggest mistakes managers make when working with placement agents

The communication failure that cost one manager $360M in AUM

Why “AI blasting” investors is killing trust (and what to do instead)

How to structure fees in today’s 1.25 & 20 environment

What institutional investors actually look for before writing a check

The 3-30-30 rule for getting meetings with serious investors

Where capital is flowing right now (and why niche beats generic)

The shift from 2 & 20 to founder’s pricing and alignment-first models

How trust, credibility, and consistency outperform flashy returns

We also dive into:

Private credit trends

Structured credit strategies targeting equity-like returns

Opportunity Zone real estate development

India-focused growth equity

Enhanced cash management strategies (T+3 structures)

If you manage a fund, syndicate deals, or raise capital from family offices, this episode will sharpen your positioning immediately.

Because capital raising is not about blasting emails.

It’s about trust, alignment, credibility — and surviving uncertainty.

If you’re serious about raising $10M, $100M, or $1B+ — this is required listening.

Subscribe for more advanced capital raising strategies from the $100M+ Rainmaker Series.

https://familyoffices.com/

Send us Fan Mail

What if raising capital isn’t about pitching… but about trust?

In this episode, Brian Mac Mahon, Founder of Expert Dojo — the VC arm of a $1B+ single family office — shares the 5 unique strategies behind their capital raising success across 300+ startup investments.

He breaks down:

The only 3 variables that matter in every investment decision

Why old-school networking is dead

How to build a “media company” around your brand

The power of intentional, ranked relationships

Why the next 12 months could be the biggest wealth window in 20 years

If you're raising capital, building a fund, or scaling a company — this is the new playbook.

https://familyoffices.com/

Send us Fan Mail

In this powerful and practical talk, Dr. Marc Halpern, founder of Deep Due Diligence Investors, shares the 7 most valuable lessons he’s learned from decades of investing in private placements. From the pain of losing 100% on a deal tied to macro events, to using AI tools and team-based diligence to evaluate hundreds of offerings annually, Marc walks through real-world stories and data-backed principles that every passive investor needs to hear.

📌 You’ll learn:

Why you can’t eliminate risk—but how to manage and minimize it
The difference between “lazy diligence” and deep due diligence that actually works
How to evaluate the sponsor (“jockey”), the deal (“horse”), and the market (“track”)
Why diverse perspectives in investment teams lead to better outcomes
How Marc uses AI tools like portfolio matchers, deal screeners, and due diligence assistants
The power of true diversification across 15 asset classes
Why high deal flow is critical to finding quality
And the one bonus rule: Face-to-face still matters most

🎥 Filmed live at the Family Office Club Super Summit, this session is a must-watch for LPs, private investors, and anyone looking to build a risk-managed, performance-driven private placement portfolio.
🔗 Learn more or submit your deal to Deep Due Diligence Investors at: https://FamilyOffices.com
📞 Contact Richard Wilson’s team: (305) 503‑9077

#PrivatePlacement #FamilyOfficeClub #MarcHalpern #CapitalRaising #InvestmentDueDiligence #PassiveIncome #DeepDueDiligence #AIinInvesting #InvestorEducation #LPstrategy #AlternativeInvesting

https://familyoffices.com/

Send us Fan Mail

What does a $1B+ family office actually look for before writing a $10M–$50M check?

In this episode, Martin of Prime Pulse — a $1B+ entrepreneur-backed family office — shares the real criteria they use when evaluating investments in profitable companies between $10M and $150M in revenue.

Unlike traditional PE or venture firms, Prime Pulse invests its own capital and partners directly with founders. They don’t just bet on companies — they build with entrepreneurs.

Inside this session, you’ll learn:

• Why $1B+ allocators invest in people, not companies
• The 7 leadership traits that override cap table and tech flaws
• How elite investors evaluate founding teams
• Why A-players hire A-players (and how to prove it)
• The importance of intellectual humility in an AI-driven world
• What “operational resilience” really means at scale
• Why fast decision-making beats perfect decision-making
• How AI impacts diligence, valuation, and long-term positioning

If you’re raising $10M–$50M or positioning your company for family office capital, this conversation gives you a rare look at how billion-dollar allocators actually think.

This isn’t theory.
It’s capital allocation psychology from the inside.

Subscribe for more insights from centimillionaire and billionaire capital allocators.

https://familyoffices.com/

Send us Fan Mail

How do you scale companies, raise hundreds of millions, and exit multiple times — starting as a poor kid from Brooklyn?

In this Centimillionaire Strategy Talk, Jody Chapnick shares the real capital raising and deal-closing strategies behind multiple platform roll-ups, IPOs, and nine-figure exits.

From building and selling a $500M public REIT…
To scaling a pharmaceutical company from $18M to a $250M private equity exit…
To buying insurance companies after calling 800 CEOs…

This is a masterclass in work ethic, differentiation, and finding deals before anyone else sees them.

Inside this episode, Jody reveals:

• Why raising money is easier than finding great deals
• The importance of putting your own capital in first
• How to build trust with high-net-worth investors
• How he used SEC Form D filings to find real players
• Why alignment and back-end profits beat upfront fees
• How to leverage other people’s track records early in your career
• Why accountants and lawyers are hidden deal-flow goldmines
• The real meaning of “skin in the game”

If you're serious about raising capital, structuring exits, or building long-term wealth — this conversation is required listening.

Hard work. Differentiation. Relentless follow-up.

No shortcuts.

Subscribe for more Centimillionaire Strategy Talks featuring founders, capital allocators, and multi-exit operators.

https://familyoffices.com/

Send us Fan Mail

David Bergeron went from Stanford to the NFL — and then transitioned into building a real estate investment firm.
Drafted by the Philadelphia Eagles and spending time with the Titans and Panthers, David later shifted his competitive drive into business and co-founded Reseed Partners, a real estate platform inspired by Y Combinator-style talent sourcing and hyper-local operator investing.
In this interview, David shares:
• The 1% daily improvement mindset
• Why curiosity compounds over time
• The financial mistake of leaving a Stanford social media program before Facebook exploded
• Why real estate remains hyper-local despite AI
• The importance of teammates in both sports and business
From NFL Europe to capital formation, this conversation breaks down discipline, capital strategy, and long-term thinking.

--- We’d like to extend a heartfelt thank you to Daniel Puder for joining us at the Family Office Club and contributing his time, wisdom, and energy to our athlete investor panels.  Daniel is a former undefeated MMA fighter, WWE’s $1M Tough Enough Champion, Deputy Sheriff, and Founder of MLMP. He currently serves as Co-Founder and President of MLMPI Prep Academy, Founder of My Life My Power, and Co-Founder of My Life My Brand. Beyond his impressive career, Daniel is an author, professional speaker, and passionate advocate for public education.  His purpose-driven mission to inspire youth, empower communities, and equip law enforcement and educators with mentorship tools is deeply impactful. We are grateful to have had his leadership, insights, and authentic voice on stage at our summit.  Thank you, Daniel, for helping make this event so meaningful.

----------- Inside the Minds of Business Champions: Pro Athletes Unveil the Secrets of Top .1% Performers.  Welcome to the Pro Athlete Interview Series, where we delve into the minds and stories of sports legends from around the globe! This series will provide you with rare insights into their journeys, triumphs, and the secrets behind their success.   Whether you're a die-hard fan, an aspiring athlete, or simply curious about the inner workings of greatness, this series promises to deliver compelling interviews that will ignite your passion and fuel your drive.  Start watching now and connect with the stars of the game like never before. Subscribe now and dive into the Pro Athlete Interview Series for an unforgettable journey through the hearts and minds of sporting legends!  We hope you love watching my videos. Subscribe to this channel for the latest video. Have a nice day!

https://familyoffices.com/

Send us Fan Mail

How do you actually get meetings with the most valuable investor types — and then move from “interesting conversation” to real deals getting completed?

In this Centimillionaire Investor Interview, Richard sits down with Sahil Nandwani of Calafia Group to break down the real-world mechanics of investor outreach, follow-up, and relationship-building inside the insular family office ecosystem.

Sahil shares what works (and what quietly kills deals), including how to communicate like a professional, how to anticipate investor questions before they’re asked, and why most people lose momentum simply because they don’t follow up correctly.

You’ll learn:

How single family offices filter opportunities fast (and what they look for first)

Why most capital raisers fail on follow-up, listening, and responsiveness

How to use texting, call summaries, and short Loom-style videos to close gaps faster

When in-person meetings matter most (and why “chemistry” still wins)

How to stand out through specialization and authenticity in a crowded market

What family offices are watching with AI, and why “customization” becomes a moat

How to build trust without being needy, pushy, or “fund closes Friday” desperate

If you’re raising capital, sourcing deals, building a family office network, or trying to get in front of more serious investors — this episode is a playbook for getting meetings, building trust, and completing transactions.

https://familyoffices.com/

Send us Fan Mail

What separates a $10M investor from a $100M+ centimillionaire?

And why do so many high-income entrepreneurs lose momentum after liquidity — while others quietly compound into multi-generational wealth?

In this powerful fireside chat, I sit down with Paul Karger, Partner at Twin Focus Capital, a $12B multi-family office serving clients with an average net worth of $150M–$200M+.

In the last year alone, Paul and his team brought in over $2B in new AUM — without chasing trends, running crowded trades, or playing the commoditized wealth management game.

Instead, they focus on something different.

In this episode, we break down:

🚨 The Top 7 Mistakes Investors Make

• Overpaying for commoditized wealth management
• Getting stuck in crowded trades and “long lines”
• Confusing money with wealth
• Hiring advisors who can’t solve real-life complexity
• Failing to diversify risk beyond one asset class
• Choosing strategy over people
• Waiting too long to professionalize their family office structure

💡 The 5 Things Only the Ultra-Wealthy Do

• Make decisions quickly — and don’t look back
• Protect their time and operate at highest and best use
• Build deep, durable relationships
• Play defense first: “Stay rich” > “Get rich”
• Focus on risk management as a daily discipline

Paul also shares:

Why wealth management is becoming commoditized — and how real family offices create value

How to “pay for yourself immediately” by renegotiating legacy fee structures

The mindset shift from $50M to $500M

Why authenticity builds faster trust than corporate polish

How to build relationships with billion-dollar multi-family offices

Why the next bubble may already be forming in AI

Why diversification of risk matters more than diversification of assets

If you are a founder, investor, or family office executive operating at scale — this conversation is about playing the long game.

Because once you’ve built wealth…

The only real objective left is keeping it.

No hype. No trend chasing. Just real-world insights from someone managing $12B for centimillionaires and billionaires.

https://familyoffices.com/