School of Hard Knocks Podcast

Episode: Greg Perlman | The Real Estate Billionaire Who Built a $2.5B Empire and Chose to Give 75% Of It Away

Release Date: October 9, 2025
Host(s): James, Jack & Josh
Guest: Greg Perlman

Episode Overview

This engaging episode features Greg Perlman, a Los Angeles-based real estate investor who built a $2.5 billion portfolio, primarily in affordable Section 8 housing, before deciding to give away at least 75% of his wealth over his lifetime. The conversation is a wide-ranging, candid exploration of entrepreneurship, real estate, risk, patience, personal fulfillment, philanthropy, and the pitfalls and privileges of great wealth. Greg offers invaluable advice for young entrepreneurs, shares lessons from staggering successes and painful failures, and breaks down his philosophy on money, legacy, and giving back.

Key Discussion Points & Insights

Greg Perlman's Real Estate Journey

• Building the Empire:

  • Owns or has owned over 25,000 units; at one point, more than 250 apartment complexes, valued at $2.5 billion.

    “Over 25,000.” (00:01)

  • First foray into real estate was a family-gifted retail property in LA, which sparked his love for cash flow and monthly checks.

    “I love the idea of getting these monthly checks. That was what we got to live on in college.” (02:36)

• Early Career Moves:

  • Developed a building in Hollywood; worked with mentors and leveraged relationships, eventually crossing the critical threshold where his monthly cash flow covered all his expenses (“the crossover point”).

    “The crossover point is when you have enough cash flow coming in every month that it covers your monthly nut.” (05:05)

• Portfolio Breakdown & Strategy:

  • Long specialized in affordable housing (90% of his units up to 2019). Chose the sector for its regulatory complexity (“esoteric area”) and long-term stability, especially in markets with finite supply.

    “I liked the affordable housing. It was a very esoteric area...it allowed me to use my brain to kind of figure out the nooks and crannies.” (06:30)

  • Sold a major portion of his holdings (~$1.2 billion) in 2022, anticipating market changes.

Mindset Around Money & Wealth

• Motivations & Evolution:

  • Initially driven by material goals: “the trappings” (cars, watches, homes, status)—later replaced by family stability and, ultimately, fulfillment through impact.

    "I was wanting to build wealth originally as a young person because I wanted those trappings. Now I got two kids, a wife...At the same time...now what?" (08:33)

  • Emphasizes that real estate is “slow moving” and genuine wealth is built over decades.

• On Risk:

  • Advocated for never betting the “crossover” money—security comes first. Willing to take big bets, but not reckless ones.

    “I liked… I was never going to risk the crossover money for everything.” (22:46)

• Patience & Niche Strategy:

  • Urges patience and confidence in chosen “inefficient” niches (e.g., Venice Beach, Section 8), acknowledging that information parity has made deals harder to find.

    “You got to find a niche. You got to find an area you believe in...be patient because it doesn't happen overnight.” (11:41)

Lessons from Failure

• Ego & Overreach:
  • Shared a story about a failed desert golf course and development project that cost him $25 million.

    “My ego got ahead of me, and it almost took me down...but it cost me $25 million out of my net worth at the time.” (25:06, 28:08)

  • Learned the importance of humility, graciousness (even with adversarial bankers), and operating within one's circle of competence.

Keys to Relationship-Building

• Banks & Capital:

  • Advises spreading banking relationships—don't rely on big banks, find those where you matter.

    “Smaller banks… they're dying for my business. So you kind of have to spread it around… figure out where you are in the ecosystem.” (29:14)

  • “Banks are your friend when everything's good, but when everything's bad, they're gone.” (29:14)

• Dealmaking Reputation:

  • Created a reputation of never “re-trading” (renegotiating at the last minute), making him a preferred buyer for brokers and sellers.

    “I built a great reputation of not retrading...that really allowed me to buy some of the best returning deals of my life because of that reputation.” (31:32)

• Knowing Tenants & Customers:

  • Believed in knowing his residents, especially seniors in Section 8, and providing standout amenities and support.

    “I'd hang out with my tenants...I knew I could step up and make sure that my buildings were gonna be operated great.” (15:17)

Philosophy on Philanthropy & Legacy

• Giving 75% Away:

  • Ultimate commitment is to give away 75% or more of his wealth in his lifetime—“because it's so fun for us.”

    “Our goal is to give it away and to do it in our lifetime so we can enjoy it because it's so fun for us." (02:13)

  • Started the Always Up Foundation (600+ scholarships for first-gen college students) and The Change Reaction (direct aid to Angelenos in crisis).

• Fulfillment vs. Accumulation:

  • Never felt the kind of misery described by other ultra-wealthy; attributes contentment to gradual accumulation and the fulfillment found through “heart-based giving.”

    “Everything happened slowly, you know, my wealth built slowly...So along the way, I never got over my skis.” (39:44)

  • “My best friends and partner, my best friends don't even know my business partners who are also best friends. I brought in some younger business partners...one of the reasons I did the deal in 2022 is because I was having so much fulfillment and fun giving the money away that I needed to explode my liquidity to give it away.” (38:31)

• Impact Stories & Emotional Fulfillment:

  • Measures impact by stories and thank you notes, not by recognition or naming rights.

    “I get to lift up my neighbors...I get to do this with my money.” (45:46)
    “If it cracks open, there's no stopping my wallet...my heart broke open.” (42:52)

• On Obligations of Wealth:

  • Believes the wealthy are lucky, not just skilled or hard-working—thus, there's a moral responsibility to turn that fortune outward.

    “I am rich and wealthy because I'm lucky. Let's just face it...you get lucky. First off, I was lucky. How? I was born. I was born to a really good family...Born healthy, born in this country...I was born on second or third base, you know?” (49:11)

  • “If we get that way with the wealthy doing it, you know, at some point people are going to come for the wealthy...But you naming some museum isn't going to help the guy who needs childcare.” (52:39)

Notable Quotes & Memorable Moments

On Cash Flow:

"You fell in love with the cash flow?"
"I mean. Yeah, that's just the most beautiful thing. I mean, to get a check like that every single month."
— James & Greg Perlman, (03:05)

On the ‘Crossover Point’:

“…That is a really good way to kind of keep yourself grounded. And then as I started getting more trappings in life, I started realizing that, well, wait a second, now I have everything. So now the question is, now what?”
— Greg Perlman, (08:33)

On Patience:

“Patience. You know, it's going to be, you know, unfortunately, guys, and it goes for all businesses...My wealth was created huge over 20, 25 years.”
— Greg Perlman, (11:41)

On 'Heart-Based' Giving:

“It's all heart based. That's the beauty when you have money. Because I don't need anything else…My heart can crack open on a lot of different things. And if it cracks open, there's no stopping my wallet, no stopping it.”
— Greg Perlman, (42:52, 43:31)

On Luck and Philanthropy:

“I am rich and wealthy because I'm lucky. Let's just face it…When you start to really think like that…you start to say, not that I don't deserve this, but it's like it's incumbent on me to do something more important…”
— Greg Perlman, (49:11)

On Success and Balance:

“As I said, I could count the amount of times on two hands I was in the office past six o'clock…To kill yourself, to just grind yourself to the ground to your death, just to acquire things…for what? Wasn't that important to me.”
— Greg Perlman, (55:51)

On Legacy:

“I'd like to be remembered as somebody who cared and somebody who showed up for people…when you're generous with time, you're generous with your energy, generous with mentoring, generous financially…I'd like to be…remembered for showing up for people.”
— Greg Perlman, (59:59)

Important Timestamps

• 00:01–01:34: Introduction of Greg, scale of his portfolio
• 02:36–03:30: Early inspiration and the importance of cash flow
• 05:05–06:16: The “crossover point” and pivoting from selling to holding real estate
• 06:30–07:57: Affordable housing niche and portfolio breakdown
• 08:33–11:23: Wealth, material gains, and gradual shift to bigger purposes
• 11:41–14:49: Patience, changing markets, real estate cycles, and Section 8 housing deep-dive
• 19:54–21:05: 'Big boy' partners, adversity, and lessons from the 2008 financial crisis
• 22:46–23:56: Approach to risk and not betting essential security
• 25:06–28:08: A story of ego-driven failure and $25M loss, lessons learned
• 29:14–31:32: Banking relationships and negotiation strategy
• 34:11–35:30: Critical relationships with brokers and dealmakers
• 35:34–38:51: Decision, evolution, and mechanics of philanthropic giving
• 39:44–43:31: Fulfillment from giving, “heart-based” philanthropy, and emotional stories from recipients
• 45:46–48:32: Why not all billionaires give, and the power and joy of direct impact
• 49:11–52:39: On luck, moral obligations of wealth, and societal perceptions
• 55:51–58:14: Emphasis on health, life balance, and not grinding for the sake of acquisition
• 58:33–60:54: Final guiding principles for the next generation and hopes for legacy

Guiding Principles & Closing Thoughts

• Find Balance:

  “Please keep balance. I just don't think—I'm not—I don't love the overwork. I love the balance in life that people can get…Create the balance. Figure out what's important.” (58:33)

• Live for Impact, Not Ego:

  “Don't do it for ego. That's my number one thing. I feel like that's what I did, and that's why I walk around happy and smiling and fulfilled in life pretty much 99% of the day.” (58:33)

• Give Back, From the Heart:

  “I'd like to be remembered as somebody who cared and somebody who showed up for people...generous with all those aspects, not just my money…” (59:59)

This episode is a masterclass in the slow, steady grind of real estate, the gradual shaping of self and legacy, and the deep joy and fulfillment that comes not from wealth itself but from sharing it freely and authentically. Greg Perlman’s practical, heartfelt wisdom is a rare and needed reminder that success is not only about what you build, but about who you become—and how you reach back to help others reach forward.

For more:
Check links in the episode description for resources, Greg’s organizations, and more content from The School of Hard Knocks.