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

How to Build a $1B Real Estate Platform | John Lettera & Richard C. Wilson

Richard C. Wilson, CEO of Family Office Club & John Lattera (Fairbridge Asset Management)

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In this exclusive Family Office Club Fireside Chat, Richard C. Wilson sits down with John Lettera, co-founder of Fairbridge Asset Management, to explore how he built a $1 billion+ real estate platform from scratch—without an Ivy League pedigree, and with a military-honed mindset of discipline, transparency, and boots-on-the-ground diligence.

John shares:
How he scaled from $100K to $1B+ in real estate assets
Why institutional capital found him
The power of walking every property himself
Why real estate is “99% B.S.” and how to cut through it
The investor mindset shift that separates $50M players from $1B platforms

His take on sweat equity, downside risk, AI in real estate, and why he never chases capital

🎙️ This is real, raw insight you won’t hear at most conferences.

📌 Hosted by: Richard C. Wilson, Founder of Family Office Club
🌎 https://FamilyOffices.com
📧 Contact: Richard@FamilyOffices.com

#RealEstateInvesting #BillionDollarRealEstate #FamilyOffice #CapitalRaising #InstitutionalCapital #RealEstateInsights #FiresideChat

Have a nice day!

CHARLIE: So, Richard, if you want to make your way to the stage, and also if we have John Lattera, please join us up here as well. This is going to be a special session on "How to Build a One Billion Dollar Asset Platform." Let’s give them a round of applause as they take the stage.

RICHARD: Great, thank you, Charlie. One of the things I enjoy most about running the Family Office Club is getting the chance to interview people I genuinely want to learn from—right in front of all of you.

John’s firm is backed by multiple institutional investors, including Oak Tree Capital, which is backed by billionaire Howard Marks. He brings over 20 years of legal experience and 25 years in real estate debt originations. He also served four tours in Iraq with the U.S. Marine Corps. Let’s give him a round of applause for that service.

(Applause)

Do we have any other veterans in the room? Please stand so we can thank you as well.

Also, I’d like to recognize Ed, founder of Gold’s Gym, who spoke at our last event in Beverly Hills. Great to see you again, Ed.

John, thanks again for being here. Did I miss anything in your bio?

JOHN: I think you covered it all.

RICHARD: Excellent. Over the past 30 years, you've built a platform managing over a billion dollars. Most people get stuck at $30M, $50M, maybe $100M. What do you think allowed you to break through?

JOHN: Great question. First, I want to say that I speak purely from a real estate perspective—it's what I know and all I do. I’ve always tried to be authentic, transparent, and consistent with my investors.

I didn’t go to an Ivy League school. I’m a New Yorker, and I use that to my advantage. In real estate, 99% is B.S.—people exaggerate constantly. I can sniff that out fast. If I have any edge, it’s that I obsess over the downside. Only the paranoid survive. Manage the downside, and the upside takes care of itself.

RICHARD: That’s in line with what Larry Namer told me—he said in LA, assume everyone is lying until proven otherwise. Sounds like you're saying something similar.

JOHN: Absolutely.

RICHARD: Even if you say you don't have an edge, managing $1B says otherwise. What would you say is a personal superpower that’s helped you get there?

JOHN: Knowing what I know—and staying disciplined. I follow Warren Buffett's idea that diversification is a hedge against ignorance. I stick to real estate. That’s what I know. My fund, my family office—we’re all in on real estate.

The key is falling in love with the deal, not the asset. I walk away from anything that doesn’t hit our criteria: LTV, LTC, ratios, sponsor credibility—if it's off, I'm out.

RICHARD: And you're serious about in-person diligence, right?

JOHN: Every time. I walk the property with the sponsor. AI can’t replace that. Real estate is a full-contact sport. I want to be on the roof, in the utility room. No shortcuts.

RICHARD: Is your success more about hustle or strategy?

JOHN: I wouldn’t say I outwork everyone, but I focus deeply. I don’t multitask. I don’t check email while walking a site. I give full attention to whatever I’m doing.

RICHARD: How did you land your first institutional investor?

JOHN: I started in the Bronx doing bridge loans. $100K deals. I stuck to what I knew. Then expanded to the tri-state area, and eventually went national. I didn’t chase institutions—they found us. But I had to build a real platform: audits, legal structure, fund administration. Without that, institutions won’t take you seriously.

RICHARD: So even before you hit $300M AUM, you were investing in becoming institutional-ready?

JOHN: 100%. There’s no AUM threshold—it’s about building the platform. Spend the money. Get the audit. Hire the legal team. If not, you’ll never raise a dime of institutional capital.

RICHARD: We talk often about being ultra-healthy, not just ultra-wealthy. Does health factor into your business performance?

JOHN: Absolutely. Military background aside, I need to start each day with a workout for clarity and focus. That’s non-negotiable.

RICHARD: Was there a defining moment that shifted momentum?

JOHN: When we became truly institutional—monthly NAVs, audits, administration—the capital came pouring in. That was the turning point.

RICHARD: What’s one million-dollar insight you rarely hear at investment events?

JOHN: Some of my best deals started as problems. Real estate is full of them. Problems are often disguised opportunities. A problem is only a problem if it can’t be fixed.

RICHARD: Let’s talk team building. How do you find the right people?

JOHN: Almost everyone I’ve hired was someone I did business with first. I saw how they negotiated, underwrote, and handled deals. That’s the best recruiting strategy.

RICHARD: And for investors in the room, what’s your biggest red flag in a deal?

JOHN: Two things. First, "sweat equity." If someone says their 20% equity is just appreciation from holding the property—nope. I want to see real skin in the game.

Second, offering me back-end equity instead of paying a higher rate upfront. That’s a red flag. Debt is always cheaper than equity. If they’re offering equity so easily, it tells me something’s off.

RICHARD: And legally, you avoid equity positions altogether?

JOHN: We do. Too much legal risk. You could end up in lawsuits, or worse, compromise your senior position in the capital stack. I want to sleep at night, knowing I can wipe out everyone else in the stack if needed.

RICHARD: That’s power. One last question: advice for someone trying to break through to busy investors?

JOHN: Have a great deal. If it’s really good, they’ll chase you. If you're not getting a response, the issue may not be them—it may be the deal.

RICHARD: That’s gold. Everyone says they have deals but lack capital. But capital chases great deals.

JOHN: 100%.

RICHARD: That’s a perfect place to end. Let’s give John a big round of applause.

(Applause)