April 29, 2026 · 1 hr 13 min
With Randall Kaplan — Co-founder, Akamai Technologies
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Randall Kaplan, Co-Founder of Akamai Technologies, shares his extraordinary journey from failed lawyer to building a $35 billion unicorn company in this powerful No Vacancy Podcast interview with…
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Randall Kaplan, Co-Founder of Akamai Technologies, shares his extraordinary journey from failed lawyer to building a $35 billion unicorn company in this powerful No Vacancy Podcast interview with commercial real estate broker Taylor Avakian. From writing 300 personalized cold letters to land a dream job with Eli Broad at SunAmerica, to co-founding Akamai during the dot-com era, navigating massive success and setbacks, mentoring with Sam Zell, and lessons on extreme preparation, relationship building, and giving back — this is a masterclass in grit, opportunity, and long-term thinking. Chapters: 00:00 Intro & Welcome 01:15 The 300 Letters Campaign That Changed Everything 04:46 Landing the Job with Eli Broad at SunAmerica 11:45 Lessons from Working with Eli Broad & the AIG Sale 16:31 The Akamai Story: From MIT to $35 Billion Valuation 24:22 Meeting & Friendship with Sam Zell 31:18 Starting "In Search of Excellence" Podcast & Giving Back 33:18 Building Authentic Relationships (Not Transactional) 44:49 Real Estate Investing: LP to GP Lessons & Challenges 51:47 Advice for Young People & Where Opportunity Lies Today 1:01:52 How to Dominate as a Real Estate Broker 1:07:18 Key Takeaways from Interviewing Legends 1:10:26 Proudest Achievement: Giving Back & Changing Lives Randall Kaplan Akamai, Taylor Avakian No Vacancy Podcast, entrepreneurship, cold outreach, Sam Zell, real estate investing, career advice, extreme preparation, dot com bubble, success mindset. Sponsor - Loan Titan Upscale your experience with https://loantitan.com/ Sponsor - AI for CRE Collective AI for CRE Community: https://www.skool.com/ai-for-cre-collective/about?ref=3b3ff2c0ccce44ba8039fafd54bf291a Subscribe and Stay Ahead! Stay informed and empowered in the multifamily real estate market. Subscribe to the channel for exclusive insights, rental updates, and expert analyses on the Los Angeles market. 🔔 Don’t miss out on the latest trends and tips to maximize your property's potential: https://www.youtube.com/c/TaylorAvakian 📈 Connect with me: Website: https://www.thegroupcre.com/ Email: taylor@thegroupcre.com X: https://x.com/TAYVAY_ LinkedIn: https://www.linkedin.com/in/tayloravakian/#podcast #business #realestate
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What's going on, Randy? And I said, I think I can bring in business. And we have this staring contest. And it was one of those moments where you can't break the stare. Do not look down. Do not blink. Do not do anything. And she said, "Okay." She closed the door and she walked out of the office.
So, I was like, "Oh, shit." Randall Kaplan is a serial entrepreneur, venture capitalist, and co-founder of Akamai Technologies, a $14 billion company that serves nearly 30% of the world's web
traffic. One of the things when people come to me for funding, I'll ask how much of your own money are going to put in. And if the answer is zero, why would I eat your cookie if you're not going to eat it, too? Where I grew up, it was polite not to talk about your success. It's better to be rich and no one know about it than be rich and people know about it. We don't like California. We don't like the rent control coming in. We don't like the lawsuits. So, we started going to Nashville. AI is all the rage right now. Yep. There's going to be more millionaires created, I think, in the next 5 years than ever before in history. Everybody who's listening or thinking about someone who's very successful, they don't realize everybody is a human like everybody else. They have problems like everybody else.
What makes their stories unique
is This episode is sponsored by Loan Titan, a leading residential financing loan company specializing in both conforming and non-conforming mortgage solutions. Loan Titan offers Fannie Mae, Freddie Mac, non-QM, and private money hard money loan programs, helping borrowers who need flexibility beyond traditional lending guidelines or speed-driven financing solutions. Whether you're purchasing, refinancing, or investing, Loan Titan is known for smart structuring, clear communication, and reliable execution. Visit loantitan.com and mention Taylor Veachian to get started. Thanks for Loan Titan for supporting the channel. Welcome to Podcast. My name is Taylor Veachian, and I am here with my esteemed guest, Randy Kaplan.
Randy, thank you for being here. Thanks for being here. I'm honored.
This is awesome.
Right now, you're on the other side of it. I am on the other side of it. And then [Laughter] talk. It feels a little different, right? I know.
I've been a guest on a couple shows and it's different because I feel like I tell the same story sometimes, right? And it's a little bit more fun when I'm hosting because I get to have a new conversation each time, whereas people ask me some of the same questions every time. And I want to like liven it up. I know someone's going to ask me a question and I'll write down a story to like make it a little more interesting. Yeah. Because what I found is the people that I enjoy being a part of and listening to are just such great storytellers, like incredible. Your Rolodex is absolutely insane. And that was one of the first things when I came across you, which was randomly where we had friends in common, but I'm like, how [sighs] the hell is this guy interviewing some of the greatest people in the world,
like genuinely? And it it it blew my mind. So, I I went down deep dive, and one of the first people and the stories that kind of blew me away was this 300 letters and Eli Broad. And Eli Broad is a legend in the real estate space. So, would you mind telling the story of the 300 letters and and how you ended up working with Eli?
So, we have to back up a little bit. Okay. So, I started my career as a lawyer, very unsuccessful lawyer. I moved out to LA with $3,000 in the bank. Started a job, and 5 and 1/2 weeks later I got fired. And I waited tables in college and law school. I was thinking, "Oh jeez, what am I going to do?" The legal market was in the tank. So, I really was a couple weeks away, and then I got a job in Orange County in Costa Mesa. I'd never heard of Orange County or Costa Mesa. So, we'd drive at 5:30 in the morning. When the bagel store opened, Suge Knight and I would be at the bagel store at three mornings a week. He'd be rolling in his Bronco, open windows. I had a huge bodyguard. Yeah, we had a we had a nodding relationship.
I did that for 6 months.
Like, "Hey, sesame seed bagel." And after 6 months I went to the main office in downtown LA, and I said to the managing partner, "I want to move to Los Angeles." He said, "No, you got to leave. Move or leave." And I said, "Well, I'm not going to live in Orange County." So, I was looking for my third legal job in 8 months. So, I thought, you know, this is not working. I didn't like law school and I always wanted to go into business. I sold t-shirts in college and I thought about yeah, and I thought about okay, am I going to go back to business school? I already went to a good school at Northwestern for law school and I figured Stanford or Harvard were going to be the only ones that was you possibly help me and I wasn't going to get in because I tested poorly.
And so, I thought all right, what am I going to do? I'm going to start a letter writing campaign. I'm going to make a list of 300 CEOs of the largest companies in Los Angeles. I'm going to write them cold letters asking for informational interviews, not job interviews. Job interviews goes in the trash, informational successful people sometimes will stop and read the letters. They want to give back. The key to those letters was the quality and the content and the time I spent on every letter. So, people ask me all the time, you know, how do you get these meetings, etc., etc. If you just send a cold standard letter, it's not going to happen. But, if you spend 5 hours each on a letter, which I did and made it unique, which was it came with a cellophane cover, a quote the CEO
had given at some point in their career, it was tabbed, it had a three-page single-space letter, which listed every job they'd ever had. CEO of Marriott's first job was scooping ice cream at Disneyland when he was 16 years old for $1.37 per hour. Now, who knows that? Very few people know that. One newspaper feature from 21 years before had mentioned that one little piece. And so, everyone when I started writing this letter writing campaign, everyone said, "Stupid, complete waste of time. Don't do it." I said, "You know what? At the end of the day, you got to trust your gut." So, I did it. I got 80 meetings out of 300. Eli Broad, I was working as a lawyer across the street. His assistant called me and said Mr. Broad would like to meet with you and I said, "All right, let's go."
So, I meet with him for 90 minutes and it was the longest time I'd ever sat with him and he asked me all these questions and I nailed everyone and then I prepared a list of questions to ask him questions that I knew no one had before including questions from the footnotes of a company's financial statements regarding GAAP accounting principles I had no idea what they meant. And when you start asking questions that are detailed that show you do the work good things happen. At the end of the meeting he said I want you to take a business class but I'm not making any promises whatsoever. So I left the office I drove to UCLA double parked ran around like a crazy person to get extension catalog went back and I got back to my car I had a $97 ticket on the windshield went back to my
apartment on veteran and I typed the thank you letter had it back in his office in 57 minutes. Oh my God. And people will say oh jeez you know you got to write a thank you note send it the next day. No there's a difference between giving it in an hour there's a difference in 4 hours 5 hours. Don't email a thank you letter that's just the laziest thing in the world. Yeah. So his assistant called me 3 weeks later said Mr. Brode would like you to take one of two classes and I said tell him I'll take them both. So a few months later uh actually a few weeks later a guy named Jay Wintro who was a former assistant to the chairman called me at 7:00 in the morning I'm in my office at 7:00 in the morning I pick up another job interview and then on
my 27th birthday I got the offer letter in the mail to be the assistant to the chairman of Sun America a dream job and it was crazy cuz I'd been 10 miles beneath the earth. Yep. It was embarrassing even go out you know what do you do I moved LA I didn't know anybody here and everyone would mumble and I was a single guy oh what do you do and you mumble you know nothing I'd be embarrassing. And then there I was
And you're like I'm not even in the movies I'm not even trying to make it in the movies. [Laughter]
I'm trying to do business. Less than 3 years later I I was 10 miles above the earth and it was also there's so many lessons in that Taylor it was don't listen to people trust your gut and be nice to everyone all the way around because the world is a very round place at the end of the day. I was so far under and then I had this amazing job and all the law firms that had turned me down were now clients of Sun America where I wasn't controlling the work, but I was a senior person dictating some of the work. So it just you got to be nice to everyone no matter where you are in your career cuz crazy things happen. We've all been up and down and You never know.
You never know. What um did you learn this kind of like what Did you Did you hear something about someone writing letters? Did you hear something about getting back to someone really quickly? Like how did you come up with that?
I honestly don't know. I just woke up one day and said to how am I going to do this? You have an end goal. The end goal was to get a professional MBA without going back to school. The opportunity cost was huge. Back then a lawyer at a big firm was making 70,000 a year. Today the starting salary at a big firm, if you go to a good law school, 265,000. But 70,000 a year I was rich. Totally. I mean I could do whatever. I mean it's Yeah. It's relative. But then to go back to business school would have cost probably $200,000 and the opportunity cost. I said, "Okay, how am I going to do this without going back to school?" And I had a goal and I said, "All right, how am I going to get from A to Z without doing all these other things in between?"
So writing letters Okay, who's going to answer the letter? They're not going to answer a regular letter, but they're going to answer a unique letter. So the thought was do more work than anybody else and earn your way into the door. And so that was the impetus for it. And then it's all right, I'm going to go through and what what's interesting there was no Google back then. Now it's easy to do all the research much easier. So our firm has something called LexisNexis. It's a subscription and you can go back in time, but it's very expensive to use. And so law firms will buy an all you can eat monthly subscription to it. And as a lawyer you got to go in you got to type in what it's for. So tailor real estate company and they're going to charge
you the the firm's going to generate a bill based on the searches that I do, and it's going to go on your bill. But, I charge things to client development. And so, I had my list of 300. I'm typing all this, and I'm printing all of this out. And one day, Sue Mengers, the manager of the office, comes in, she closes the door, and she said, "I have an $80,000 client development bill this month. What's going on, Randy?" And I
looked at her, and I said, "I think I can bring in business." And she looks at me, and we have a staring contest. And she said, "Really?" I said, "Yeah." And it was one of those moments where you can't break the stare. Uh-huh. Do not look down. Do not blink. Do not do anything. Yep. And she said, "Okay." She closed the door, and she walked all the office. I was like, "Oh, [bleep] [gasps] I got through that one." But, I got through that one. Yeah. And then, another part of the story that I think is very interesting is these letters had a cellophane cover. It had tabs in them. It was one of those black thin binders. Yeah. But, if I had gone to Kinko's, it would have cost thousands of dollars. I wrote 300 letters. But, I was buds with everyone in the mail room.
And there's a lesson here for everybody, which is a lot of people do not know the names of the people in the mail room. So, I knew their names. I brought them lunch. They told me I was the only person in the firm, the lawyers, who knew their names and treated them well. So, my boys in the mail room would be churning out these letters at 6:00, 7:00, 8:00. Sometimes they'd be there till 10:00 with these guys, just, you know, using the huge copy machines, putting these things together for me. That's incredible. And you know, when I landed my job, they were I mean, it was a team effort. It's like, if you're winning the Super Bowl, and you thank all of your linemen, or you thank all of your teammates, these guys were my teammates, and I would not have been able to do it financially without uh their
generosity. Yeah, it just shows you what what actually caring about people. And again, like you said, any long rung on the ladder, Like, you never know who can be your support system to both make whatever you're trying to accomplish your goal happen.
Yeah, I mean, I was in Las Vegas a year or two ago and I'm staying at the Vidara Hotel. You know, you got to show your key card to get up to your room and there are guys there and I was going back and forth for a few days and I finally stop and said to the guy, "Hey, what's going on? How's your day?" I actually stopped walking. And he looked at me like I I was kind of funny and I had a conversation, "Oh, what do you do?" He's a retired Navy veteran. And then when we're done, he said, "I want to give you this $250 gift card." And I'm looking, "What? Why?" He said, "Cuz you're the only one all week who actually stopped to talk to me." Wow. And I thought, "God, that's just What What does that say about our society?
What does that say about people?
I mean, these guys have a tough job." And it's sort of like the guys in the bathroom at a nice restaurant at night. Think about these people. I mean, everybody has a dream. Everybody has a dream. And you wonder, "What What's their dream?" Um and their dream is probably to make a living. They're there in a smelly bathroom with no windows all day long. People drunk, not treating them well. No one asked for their name. So, every time I'm in a bathroom with someone in the bathroom giving out the Lifesavers or the towels or whatever it is, I give them $20 and I ask them their name and I say, "Thank you." Wow. I think it's just so important to to treat everybody well and you think about people that have these really We would consider you and I jobs that we would never want to have.
But everyone starts somewhere.
100%.
And it's just the little things. It's the little things. It's just the little things. Was there anything when you were working with Eli that shifted your perspective or the way that you approach certain situations? Like, because not a lot of people get to see a high-level, very successful, very wealthy individual who can move mountains, right? Just with their influence. Was there anything that you picked up when you were working with them, deals? I know you were involved in the AIG sale. It's like, what was the lessons from that period in your life?
Yeah, I mean, first of all, I was not involved in the sale. Okay, but you were there during the period when they were doing that? I was there right before they they and and that's a crazy story, too. And I'll we'll we can go there now and then we can backtrack a little bit. So, my time there, I was 27 years old. I they asked me what titles I wanted. This is to the chairman and managing director. And I said, "You pick." And J. Wintrob said, "That's a bad I thought it was being politically appropriate. He said, "That's a bad answer. The assistant to the chairman, people outside the firm, are going to think you're getting coffee for us. But you're dealing technically I was in the corp dev department, so I'm dealing with major investment banks, very senior people.
So, I had a managing director title at 27 years old. Wow. And so, it was a very interesting job in that sense. And man, I met with senior people at all the investment banks and I'm participating in these meetings and it's Eli J. Wintrob, the vice chairman, the senior vice president corp dev, and one other person and actuary. And I'm just seeing how it all works and I'm I I was a research guy essentially on this very senior team. So, we were looking at companies to buy in the financial services sector. Sun America stock had appreciated 6,000% over 5 years. It was the number one performing stock on the New York Stock Exchange for 1, 3, 5, and 7 year period of time. So, the assistant to the chairman job historically had been 1 year in and out. You'd get promoted to one of six corporate VP level jobs.
The issue with that is there's going to be no movement because with the stock appreciating so much, all the VPs were worth between 10 and 30 million dollars of stock. So, you're there heads down, focus to learn. And after a year, I was a little bit not bored, but I wanted more to do. I'm the kind of person who measures their wins on paper. And so, I went to him and they said, "Randy, you're my first round draft pick. You'll get more playing time this year." And then that second year, a little bit more playing time, but I still wasn't fulfilled. Yeah. And so you think about do I want to leave? I have the best job of all my friends. I'm learning a ton. Eli's worth five billion dollars at the time. He's worth 400.
There was nobody who wouldn't take my call and I was meeting all these neat people in that job, but at the end of the day I wasn't fulfilled. So you have all these conversations with yourself. Should I leave? Should I not leave? And this is the key. He had been so good to me and I said, "I'm not going to go behind his back to look for a job." I was going to go to him and I'm going to say, "Hey, I want" I mean, he knew I was a very motivated person at the end of the day. And so I went to him thinking, "God, I'm either going to get fired or I'm not going to get fired." And he said to me, "I appreciate you coming to me and I think you're making a mistake. So" But you can stay here as long as you want.
So at that time, I looked around at a lot of different things. I thought about buying laundromats and going into unsexy businesses. I talked to uh Bill Gross, who was another uh person in Los Angeles who was starting all these companies. I had an opportunity to be CEO of a uh startup and I I just I thought about writing books. I love fiction and I want to try my hand at writing a fiction novel. Then I met these guys from Boston and we uh started a tech company. But when I left Sun America, three months after I left, Eli sold the company to AIG for 18 billion dollars. When I left, I left two million dollars. I thought of in the money stock options on the table and with the takeover premium it was around two and a half million dollars. Was paying for our own wedding.
Uh we're getting married. I was getting married to my first wife, Lauren, and I think, "Oh my god, what have I What have I done? This This thing This thing This thing must must You know, I hope it really works out." But one of the keys as well is you have to be a good corporate citizen when you're in a high profile job. So here my boss is Force 400. He's probably the most powerful person in Los Angeles. He started a MOCA. He built Disney Hall, essentially. I mean, he took these leadership positions. Everyone wanted to know what kind of person he was. And everyone wanted to basically have me say something negative about him. And number one, I had nothing negative to say. And even if I did, I wouldn't say it. Mhm. Right? You're in that job, and it's the party line.
But, he was an incredibly fair boss. If I did great work, he'd call me up. And if I did [bleep] work, I remember being in the doghouse once for I didn't hear from him for 10 days. And I'm like, "Oh my god." And you go home thinking, you know, when when am I going to get out? Yeah, right. But, you know, be good to your boss. Don't go behind his or her back. And always be a good corporate citizen, cuz it's a small world at the end of the day. And everyone knows what everyone else has to
say.
100%.
And that bet ended up working out pretty well for you, right? So, you want to tell me the story of Akamai?
Yeah. So, Akamai came along as I was looking at all kinds of opportunities. And I actually had an opportunity to be the assistant to the chairman of a company called Global Crossing, which at the time was laying fiber optic cable on floors of the ocean. This is like '98? This was '98, '99. So, yeah, 1998. internet bubble, everything is going. There was no way to get the traffic from the US around the world. So, you're laying all these fiber optic cables a mile deep on the floor of the
ocean. People don't know that the internet is still connected in the ocean with these
cables. I mean, it is a lot of it now comes from satellites. But, but, but back back then, I mean, this was the only way to do it. And Gary had raised a little bit of money, $450 million. I would have been the sixth employee there. And Global Crossing eventually got to a $40 billion valuation before our company had gone public. And I said, "Oh my god, that would have been a nine-figure payday." As well. So, I had the Sun America Yeah, almost $3 million then I had a $100 million payday at Global Crossing. I'm like, holy [bleep] This outcome I think better work. Uh and thankfully it it worked. But the the way that came about is my girlfriend's brother was best friends with one of my partners. So he made the introduction.
Originally I was just going to be a board member, put a little money in not that I had a lot of money. And then I had relationships in Los Angeles with content providers. So that was very very helpful. I had a law degree even though I was no longer a licensed lawyer. And I helped write this business plan. So I was working at Sun America at 10:00 at night helping write the business plan it from 10:00 to 2:00, 3:00 in the morning. Again, this is people want to know, what's it like to make sacrifices? You got to make a lot of sacrifices. I was getting very very
little sleep at the time, but I thought, okay, this is great. I want to learn something about technology. I know nothing about. My partners were absolutely brilliant. And so I helped negotiate the licensing deal out of um MIT, which is where they they were based. A professor student and first-year Sloan Business School student were my partners. And managed to get beta contracts. We had 10 beta customers. Seven came through me. MGM, MTV, Playboy. And it was it was great. And then there was $8.25 million and two of that came from angels. $2.25 came from angels and a lot of that came through someone that I had been mentored by. And we rounded up some of his friends and I invested $100,000 of my own money. At the point where I saved $400,000, it went from zero to $400,000. I invested $100,000 of my own money.
And again, that's something that I still haven't seen today ever. And one of the things when people come to me for funding, I'll ask how much of your own money are going to put in. And if the answer is zero, why would I eat your cookie if you're not going to eat it
too?
Yeah.
Very interesting. I mean, it's it's such a crazy story because I think especially nowadays, right, with where people are the the youth cuz everything is so visual and everything is so accessible and social media has really been able to you see these people doing drop shipping and making a ton of money or trading crypto and it's so visible to see these young people making a [bleep] ton of money that there's almost becomes this like, oh, I need to do that or I need to you have the dreams of having an exit having an AI company be bought by Facebook or Google or something like that. And it's crazy that you actually did it.
Especially back then. Yeah, I mean, to have a unicorn back in the day, no one called it that. I mean, to have a billion-dollar valuation, I mean, that was very, very rare. Today, you can start a AI company and if you have the right resume, you're up to a billion dollars 3 months down the road or if you have the resume, which is crazy. You're doing a seed round at a billion dollars. But it was just a different time and we filed to go public basically a year after we started the company, legally started the company and we went public I think 464 days after starting the company on GAAP revenue of $3.2 billion and our peak valuation that year, 1999 December 31st, 1999 was $35 billion on $3.2 million of GAAP revenue. Oh my gosh. insane. Holy crap. insane.
I mean, you're you're you're you're you're you're you're you're you're you're living something that you can't even believe is happening to you and I remember at that time I I had become very close to a woman named Robin Newstead who was a chief of staff at Goldman Sachs. She was a senior partner there. I remember being on my apartment in Vetera next to the Jack in the Box. It was 10:00 at night. I don't know what she was doing at 1:00 in the morning, but we were talking and said, you know, how how's it feel? And I said, you know, Robin, it doesn't feel real. And she said to me, oh, Randy, it's real. But at that point I couldn't sell anything and you know, I was just waiting for the lockup to expire.
When your company goes public, you have to wait certain amount of time to sell your stock. Yeah. So, I just, you know, please don't let me get hit by a car, you know, it's like just counting the days, driving driving under the speed limit. You know, let me have, you know, let me let me sell some stock.
Yeah, right. And when when that moment came, when when there was a liquidity event, did you know, cuz then you ended up starting um the family office effectively, right, Pat?
Yes. Yeah, it started as a a VC firm. I started investing in tech deals. One of One of the And And just to go back to our company going public, there's a lot of luck involved. While we were raising money, one of the biggest hedge funds in the world, Long-Term Capital Management, blew up. So, we had all these VC firms hot to trot. We were turning down money, and then we were negotiating all these term sheets, and suddenly nothing. No one would return our call, the market was coming to an end, Wall Street was coming to an end. Like, okay, this is crazy, and then it finally picked up again. And so, just, you know, up and down.
There was a blip.
Yeah. Uh but at the end of the day, I mean, obviously we got lucky. Yeah.
Yeah, I mean, that's Mark Cuban, right? He sold like before to Yahoo for 4 billion or something like that, and I would say that probably I I think they ended up shuttering it down, right?
But Yeah, so Mark sold for 4.7 billion dollars to Yahoo, and he what he did is he collared his stock. So, he put on a trade where even if the stock decreased to a certain price, he would then the trigger would be to sell the stock, and Yahoo stock ultimately collapsed. And so, but he made his trade will go down as one of the most brilliant trades ever on Wall Street. But Mark was on my show, In Search of Excellence, so for everyone who hasn't watched, I hope you guys check it
out. guests are incredible, so
But um Mark said, you know, um it's impossible to become a billionaire without being lucky. And I 100% agree with that. From talking and meeting a bunch of billionaires, it feels like there's there's a a level of luck that just has to occur. It's not just billionaires. I mean, I'll take Mark's comment and I'll tone it down a bit. I think any successful person has some degree of luck that contributes to their success. Now, we've all heard the saying that uh luck favors those who are most prepared. You got to be ready for it. And I think that's true and take advantage of it. But at the end of the day, there are some things beyond your control. The markets are beyond your control. Sometimes you go public at a window, sometimes you don't. But we were at a certain point in time where we were very lucky.
I don't think there should be another company ever that goes public 467 days after they start the company, uh especially on $3.2 million
revenue.
For 35 billion, that's absurd.
Yeah, never going to happen again. We have a mutual mentor. You you're a little bit closer to him or work closer to him. But when I heard this story when we were we were chatting, I was like, that's incredible. And someone whose book I'm a huge fan of and just being a real estate I love studying real estate history. So, this this man's history is just freaking awesome. Sam Zell, can you tell me about your relationship with Sam and what's that What is that story?
I grew up in Detroit, Michigan in a in a humble home. And where I grew up, it was polite not to talk about your success. And it's better to be rich and no one know about it than be rich and people know about it cuz all kinds of things come when when people know. So, our company goes public. The head business writer for the Detroit Free Press, which is the main newspaper, John Levin, calls me out of the blue. I'm John Levin and I'm going to write a feature about you. I come out going public. And I said, there's nothing interesting here. He said, "Oh, there is. You know, this Detroit kid making it big in technology." I said, "Well, I prefer you not write the story." And he said, "Why?" And I said, "Just because I I don't need the publicity."
He said, "Well, I'm going to write it with or without you." I said, let me call you back. Eli is from Detroit. I call him and said, "Hey, do you know Jerome Levin?" He said, "I do. What do you think about him?" He said, "I think he's fair." I said, "Okay, great." And I said, "I I don't want to write the story." Eli loved the press. I didn't want any press. And so, he said, "You should do it. It'll be your coming out party." I didn't want a coming out party. So, he said, "Then there's one reason to do it." And I said, "What is that, Eli?" He said, "Cuz you can influence the outcome of the story." So, the bell rang. I called Jerome back. I said, "I'll do the story." So, he comes out to LA and we're driving around in my Acura
Integra and we're going to this house that I'm building that's a wood frame and we spent time together and I really liked him. Uh-huh. I mean, we sat for hours. And then the piece comes out and my mom could not have written a better piece if she tried. It was like It was like Yeah. It was incredible. Yeah. And he called me and said, "What do you think of the piece?" I said, "You know, Jerome, I mean, this is amazing. Thank you so much. It came out great. I'm glad I trusted you to do the story." And he said, "By the way, do you know Sam Zell?" I had gone to Michigan. Sam Zell had gone to Michigan for those who don't know. Sam was an original Forbes 400 member. He started a ton of companies in the real estate business.
He's largely known as the father of the modern REIT, real estate investment trust. And he's a god in the real estate business. Was a god in the real estate business. And his name is adorned on every building at Michigan. He had given hundreds of millions of dollars to the university. So, Jerome says to me, "Do you want to meet Sam?" And I said, "Yeah, but I'm thinking, what reporter actually knows Sam? I mean, one of to make the introduction." He says, "All right. Call you back." Like, "You're going to call me back?" He said, "Yeah, I'm going to call you right back." 10 minutes later, Jerome calls me back. He said, "Here's Sam's number. He He wants you to call him." I'm thinking, "What? Sam Zell wants to wants to call me." So, Sam and I got together, I think maybe later that week or the following weekend.
He had a home on Broad Beach in Malibu. So, I just bought my dream car. I bought a Porsche. Used to go to the Porsche dealership when I was a kid, sit in the car, you know, a couple times a year and say, "One day I'm going to get a Porsche." So, I'm driving down PCH. I got the top down. It was a 996, which is the 911 essentially. It's just, you know, a different model number. And I'm driving down PCH. I got the top down. The music's blaring. I'm going to meet Sam Zell. I'm living my dream. Yeah. Uh and and that was my dream. Yeah. And And Sam and I sat for 3 hours that day, just shooting the [bleep] talking about everything, growing up, starting companies, being a human being, philanthropy, what it's like to be wealthy and to deal with wealth, extreme wealth. Mhm.
And he just became a very close mentor and a very close friend.
He's just an amazing human being. Gosh, man. It's just And it's cool and and we talked about it, too, but I've heard is he was like the pioneer of being authentic. Like he would go into these boardrooms with jeans on when that was frowned
upon, jeans. And he'd be smoking pot, by the way. Yeah. He'd just have a joint.
He'd have a joint with him at all times. the in the studio, right? Like And that's that is so um so
cool because I think a lot of times, too, especially what I'm seeing as well, being around uh these people who are at the top, sometimes you can tell those who are comfortable in their skin and some who still feel like there's a little bit of impostor syndrome. Yeah. And it's just admirable because sometimes, personally, I feel like, you know, you have that impostor syndrome sometimes in the room. But I love I love to be around people who are so unapologetically themselves that
it's just refreshing sometimes. Yeah, I mean, Sam wrote He's famous uh for riding a motorcycle to work in Chicago, no security. Funny story about Sam. So, Sam invites my wife and I to dinner at his house with Ken Moelis is there from Moelis & Company. Yeah. And we're sitting there at dinner, and my wife Laura is pregnant with twin girls. And Sam lights up. And Helen, his wife, said, "Sam, what the [bleep] are you doing? She's pregnant. You got to go in the kitchen and go smoke." So, Sam goes in the kitchen, he goes smoke he goes to smoke, and I had just left a party with Laura, a kids pool party, because people were smoking. I'm not going to be around this pool party. I said, "Laura, we're leaving." She said, "You're leaving? You're you're you know, prudent, so what?" I'm like, "We're getting in the car, we're leaving."
So, I know what's coming, cuz I didn't leave Sam's place. So, we get in the car, and I know I'm going to get screamed at, which I did. She said, "The only [bleep] reason that we didn't leave this party when Sam smoking is cuz he's Sam Zell." And I said, "You want to know what? You're [bleep] right that's the reason why we're not
leaving."
100% man.
You do not leave Sam Zell in that situation.
That's so true. And and and I had lunch with Sam two months before he died. No one knew he was sick. And the the great part about that is that I never told him the story, and that's that was the last thing I said.
Wow. I can tell he meant a lot to you.
Yep, he did. Anyway. We'll move on.
Yeah, of course. Now, I appreciate you sharing that. It's for me when I get to meet these people through the stories of the people who they've impacted, the books, the interviews. For me, it's one of the reasons that I enjoy doing this thing is because and why I push some of these owners, cuz I interview a lot of these apartment investor owners who are like, like I don't want to be the spotlight that they're a little bit similar to what you were saying is like the spotlight is negative and bad for me. And I one of the things that has resonated with me is is like, sure, right? but you have so much experience, so many stories, so many unique things to be able to share with someone that one person who's listening to this and watching this changes the trajectory of their life by something you say? Yep.
Like that is worth more than a in my opinion bad press or someone coming like it just I get it. I understand it, but at the same time I'm like think about that person the impact of personally for me I think and I'm not at the level where you are, but money is becomes no more of a problem for someone it's like what do you want to do? It's I think it's impact, right?
It's the impact that you can share and give back to people. Million million percent. I mean I started a podcast called In Search of Excellence years ago 5 years are coming up now and I did it primarily to give back. Yeah. I'd done well in my career. I had a lot of lessons. I knew a lot of people and when I was in college there were not was not just there was no such thing as a podcast. Yeah. Um there was no YouTube. There was no nothing. So to learn and get motivated by people you'd have to see something posted on a uh telephone pole or bulletin board so-and-so was coming to campus. And so I thought all right. Well, now I know some people. I'm going to start a podcast to motivate people and you start with a blank canvas.
So I think you we talked a few weeks ago at a friend's party. Shout out to Sandy Man by the way. An amazing amazing guy. He he's the man. And it's like how you want to build a great company. You have a blank canvas and you want to start with a poll customer or podcast guest. And my first podcast guest was Sam, but we were friends and I never really asked Sam for something. He was just a mentor and Yeah. Uh it it was just that kind of relationship. I was very nervous to call him and you know ask for something. So I called Sam and I said Sam, I'm starting a podcast. Would love for you to be my first guest and I was barely able to finish the words before he said I'd love to. Wow. And and so I had a great first guest
as just giving me some credibility and then I turned stone as my second guest. Cliff Kingsbury the football coach as my third guest and then just built from
there. We have a sponsor for today's episode and that is AI for Siri Collective. 25 listings at the moment. We're closing four or five deals a month. It's been incredible. So, if you want to learn, if you're in commercial real estate, how to use AI in your business, whether you're a property manager, a broker, an investor, really anyone, we have a huge group of over 400 people in this community and the website, if you want to go check it out, is AI for siricollective.com. So, appreciate you guys. Now, back to the episode. I got to ask you because this is something that I'm one, I know you're really good at it, clearly, but how do you go about thinking of relationships? And not in the transactional standpoint, but but like you are so I mean you just said four incredible names right there, which anyone in in their dreams of
they have a podcast would hope to get those people on, right? So, like is this something that you have tailored over time? How do you think about building relationships with people?
Yeah, I mean let's take Sharon and Cliff first. This is our crazy story. So, I'm a hockey fan and I grew up in Detroit and Jimmy Carson was all the rage back then. We're the same age. You grew up in Grosse Pointe. I grew up in Birmingham and as a hockey fan I I, you know, worshipped him. He was number one pick in the draft when he came out. Our company gone public and then my friend Gil Stahlsmith called me and said, "Do you know who Jimmy Carson is? He loves him." I mean of course I know Jimmy Carson. I said, "Jimmy come to LA." We meet, we we hung out. He introduced me to little bow tie who's an amazing guy. He was a podcast guest as well. And then they said, "Do you you should really meet Bruce McNall." Bruce owned the Kings.
He was serving time in prison. He was in a halfway house. And so Bruce and I became friends. Bruce is an amazing guy. Um he owned the Los Angeles Kings. He brought Wayne Gretzky to Los Angeles for Jimmy. Um that was the trade. Wow.
Can you imagine being the guy traded for Wayne Gretzky?
Brian Mulroney, the Prime Minister of Canada, tried to stop that trade. That's crazy. It was insane. So, Bruce and I became friends and then I remember being at dinner with Bruce and we were at a restaurant I don't recall Toscana and I said Bruce,
what are you up to right now?
He said I'm producing a movie with Sharon Stone and Justin Timberlake and he said so I said why aren't I in that movie? I never acted. I took a class in college one thinking okay, it's going to be fun easy you know, get some public speaking out of it. So I go to the bathroom I come back and Bruce says you have a casting call 1:00 on Monday. I'm like and what? So the long story short there is Nick Cassavetes had just come off The Notebook. I went in for this casting call but it was I mean all these kids that there have CAA and they have their scripts and they're nervous and I'm thinking God you know, they're running late half an hour late. I'm like I don't know if I should [bleep] this cuz I had to get back to the office or if I'm
going to sit in. So Nick walks in to the room he said you want to be in the movie? I said yeah, I want to be in the movie. He said all right, you're in the movie. Just like that just like that. So fast forward the movie was about Jesse James Hollywood a middle class someone who grew up middle class whose younger brother was kidnapped and murdered over a drug debt. So I played a police officer who questioned the mother of my two little movies. So I I got so Nick said come to the set and come find me. Okay, so I go and I change in a little bathroom into a police uniform with a rubber gun and they said do not take the gun out of the holster. I'm like okay. So I go in there and he said come find me.
I come find him you know, we're in a neighborhood in Tarzana and there's all these people around him and I'm like hey Nick. I'm like yeah. Randy Quaid.
What?
You know, oh yeah yeah yeah. So he just yells to know on pen and paper just to go to the air. So someone gives a clipboard or whatever there's a police officer guarding the set
what would you say? So okay, well what would you say?
So name date of birth social all these questions what was he wearing etc., etc. So, I'm jotting all this stuff down. And then, two, we get to the room. I'm waiting there for maybe 2 hours. I'm the only one who's actually going to be in the shot. There's all these stand-ins that are there. Sharon Stone sits down in front of me and doesn't even look at me. Just straight stare. I'm thinking, I got to say something to Sharon Stone. In front of me. And I'm thinking, got my boys back in Detroit. They would would never Yeah, I mean, my boys back in Detroit would never guess where I am right now. So, I said, "You know what? I'm not going to be intimidated." I said, "Sharon, Randy." She said, "Nice to meet you." And boom. So, Nick calls action. Now, I haven't read the script. I've never acted.
There's 20 cameras, boom mics, 40 people in the room. And here I am. I have to read name, date of birth, social. Cut, cut, cut.
What?
Wait for her to answer. So, like, okay. So, we did again. Cut, cut, cut. Wait for her to answer. Now, I'm thinking I'm going to get kicked off. So, next time I waited and Sharon's getting all this emotion, all this emotion. She finally SCREAMS, "FIND MY SON!" I'M LIKE, "HOLY FUCK!" LIKE, I I felt like someone had just hit me with a torpedo off my jet. Like, holy [bleep] The scene went fine. I actually enjoyed it. Years later, my friend Price Arana, shout out to Price, tells me she's best friends with Sharon. And so, Price corrected connected me with Sharon. I met Price on a plane by the way. You know, always be friendly with people you talk to. You never know who you're going to meet on an airplane. I met met Price on a plane. And then, somehow she told me
she's best friends with Sharon. I said I'd love to have Sharon on the on the show. Uh Price and I had a great relationship. We always talked business and and she became a close personal friend of of mine. And so, that relationship with Price got me Sharon. Cliff Kingsbury, we're at a wedding in the Bahamas where Tom Brady was the best man. And I knew all these peaches people were there and we went to this place called Baker's Bay and they have pigs nearby. So you take a boat with pigs, you know, to go see the pigs and my wife and her friends, you know, two good looking friends on the boat and said, "Can I bring this cute guy in the boat?" I'm like, "Yeah, cuz I don't want to just sit there while you the three of you are yapping together." So this guy comes on the boat.
What do you do?
I'm a football coach. You know, high school? No, college coach. And like, "Okay, you know, D3?" No, I'm a division one coach and like, you know, offense, defense? No, I'm I'm the head coach. Just so mellow about the whole thing. So where do you coach? Texas Tech. I was like, "Oh, that's cool." And so we went snorkeling that day and there was a captain on the boat named Willis. Willis is about 5'4", very cut. And the boat had It's a regular boat and then there's one of those towers on the boat. And so the girls went snorkeling and this way Cliff and I went this way. Meanwhile, we're probably like two or 300 yards from the boat and we're sucking water. I mean, Cliff's in good shape, I'm in good shape and we just are struggling. We're looking at each other like, "Are we okay?"
And then we're swallowing some water. We can't get back to the boat. And Cliff and I are I mean, when you get nervous, even with the snorkeling and you're fighting against the current. Yeah, it's it's I mean, we're going to get swept away, but I don't know how we're going to get back to the boat. There's coral everywhere also. So Cliff and I are like, "Willis, Willis." We're screaming, "Willis." Here comes this 5-ft four guy with two of those you know, buoys and Willis basically helped tow us in. Cliff and I and we're so when we get back to the boat, we're hyperventilating. We can hardly breathe. You know, we swallowed so much water. Our mouth tastes like salt and we're looking at each other. This is the most emasculating event we've both ever had. The girls come back to the boat. "God, that was so great. Wasn't that great?"
We look at each other. "Oh, yeah. Yeah, that was That was great." So we felt so That's how Cliff and I became very good friends. He's an amazing guy. We almost drowned together. So, so you never know how you're going to bond with something. So, I pretty you know, Sam, Sharon, and Cliff, those are my first three
guests. That's incredible. I mean, it is so funny and and you know, the plane, right? It was the plane conversation, the relationship there. It's like you never know. And again, this comes back to this this what we talked about earlier is like treat everyone like they're they're special because they are they are unique and and everyone has something to share and give and that's just so cool that that you've been able to to do all those cool things and meet those cool people and build relationships with them, which
is You know, I mean, again, you you never know. Um and it's really important. You said something very important. Don't build relationships on a transactional basis. Have real relationships. Do something meaningful to people. I mean, I get now a lot of incoming LinkedIn requests. Could you meet with me for 15 minutes, etc., etc. And the answer is no, I can't. I've no interest in meeting you.
Why?
Because you put no effort into meeting me. You haven't looked at my LinkedIn. You haven't listened to my podcast. I'll meet with everyone who spends 5 hours on writing me a letter just like I did. 100% of the time. But if you're just sending me something and and people say, "Well, how how how can you mentor somebody?" I say, "Well, you have to earn the mentorship, too. You can't just say, 'Will you be my mentor?' No, add some value to someone. Ask a question. Show them you've done the research." And so, these relationships that are transactional, they don't work. Build relationships over time. Stay in touch with people. Put Google alerts with names into the phone cuz I did I started doing that years ago. And whenever someone's name would pop up, "Hey, you know, congratulations, you know, like you know, congratulations," something like that.
Yeah, easy. Nothing.
And I super easy.
I actually just gave a talk about networking cuz I would say I'm I'm that is one thing that I've put a lot of energy into and I call it the barbell strategy. So, it's you spend the quick touch points, the Google alerts, hey, congrats, thinking about you, or this is awesome. Hey, saw this, thought of you. These quick just little touch points that you're staying on top of mind and you're thinking about that person. And then the other side of the barbell is deep relationships, snorkeling, spending hours on, you know, at a dinner, at events. It's like these these deep time together, hours and hours and hours, because that's how you really get to know someone. But I think it's the it's the coffee meetings, it's the the in between where you don't get the full ex perience of getting to know someone.
It's just kind of like a you know, there's not as much substance I think that you can get in 30 minutes as you can with someone when you spend half of a day with them or when you're continuously just staying in touch. So I think having kind of a strategy to be able to continue to to feed these relationships and and not in the expectation of selling it, but like if any anything in life, everything is has value to be give, right? Even your parents when you were a kid, there's value that was given through that transaction. So understanding that and being able to give, I think without the expectation of receiving, has been monumental for me in terms of just a mindset shift of like, who knows what's going to come out of this, but hopefully that makes that person's day, or hopefully that helps them in some
way. Million percent. I mean, one thing that I ask too is I like to give more than I get. Yeah. So I will call somebody on the phone I want to learn, I want a relationship, I want something of of value, but I'll always make sure that I've done my research to offer something of value back. And here's something that I do that I don't see people doing that I think is really important for people to do. It's a it's a it's something that will add value and lead to a higher probability of success. At the end of every phone call say, "What are you working on that I can help you with?" And everyone's shocked by that question. And it's just It's just one simple thing. And sometimes and I say I I mean it. Yeah.
And what I'll do is sometimes people say, "Oh, I'm I'm good to now." I'll actually jot down a note and I'll put it in my calendar. Call Taylor back a month from now. Again, I'm not only asking the question, I'm following up on the question. Not because I'm trying to do something phony cuz I really do want to
help.
Totally.
I mean, and think about how much where you're even if it was me, right? You call me and I'll be like, I don't need any like you've done enough. I come on the show. But it's like the fact that someone and this is more of a psychological thing, but someone quote-unquote who's thought of as having more influence or power, right? Reaching out to you in a follow-up like that means the world. Like even if you do it once, it just shows how much you care and I think people just want to know that you care.
Yeah. Right?
Okay, I want to talk about real estate really quick because we talked about this too. You started a GP side of the business, but first you were a limited partner. So I want to talk about what the transition was from a limited partner in these real estate investment deals and then what was the moment or what prompted you to then go do the GP stuff and I want to get real and like what your experience has been thus far.
Yeah. Okay. So you make a bunch of money. Asset allocation is critical. So you've got on the safety side cash which you could lose money in inflationary, right? Environment. You got bonds. You got stocks. Then you go into the risk spectrum and it could be real estate. Again, as you know, real estate there's 20 different kinds. Yep. Income producing property is less risky than development. So you want a higher rate of return if you're building something and even in the building sector you've got all kinds of loans that layered in there. So there's different risk levels on that spectrum and then you talk about venture capital being one of the most risky and starting 10 years ago crypto being maybe the most risky or one of the most risky. So in real estate I started investing in deals as a limited partner and you go to people who have experience.
A lot of those deals have not gone well. Some of the deals I've been in have been in for 21 years or so and if I invested in the index in the real estate VNQ index Vanguard, I would have done a lot better tax-wise, and I could sell it and it's liquid. So, one of the things that I realized and all the people out there who are going to put money in these deals,
it's illiquid.
So, if you don't if you need your money in the next 5 to 7 to 10 years, forget it cuz you have no say whatsoever. Yeah. So, I invested in apartments, shopping centers, development, real estate loans, did it all. Mhm. And I like to learn about it, too. I read everything I get and real estate funds. Mhm. And I read everything, so I learn everything. And then uh my trainer John Gallagher uh started buying small buildings with his mom in Long Beach. And he was doing well, making $100,000 to $200,000 there. And I said, "You know what? I want to be a general partner. I can be a limited partner cuz you can make money on the fees." Mhm. Right? You get 20% of the up, sometimes 30% depending on the return. You got a management fee, so we started buying apartment buildings in Long Beach. We bought four.
And then we ended up selling one for a little bit of a profit. Uh very small deals. A four-unit, we have a seven-unit building we still own. We raised money for the last two, 11 and 10. We sold an 11-unit building. Um and these were small deals, and the goal was these were multi-family kind of B- minus to C- minus buildings. The name of the game is to redo the buildings, you know, mark up the rents. So, we got 40% rent increases. Massively increased the value of the building. One of the buildings, of course, was in a historical district, which we didn't know. So, we made the building beautiful, as nice as the building in the neighborhood. And then the city basically made us take off the paint. So, to take off white paint on a big building is a lot more expensive than painting the building itself.
They made us take down safety lights. They made us take down all kinds of stuff. And in that unit in particular, you know this and a lot of people on the podcast, someone gets inside the unit, they have no rights at all, but they They in the front door, they have full rights as a tenant. Yep. And so we had this squatter, for lack of a better word, and we couldn't kick her out. And so this is also during COVID.
We have mortgage payments. There's no forbearance on the payments, and obviously the return to investor, you have one out of 11 units, it's not good. Yeah. And so we started thinking, okay, this is a pain. We don't like California. We don't like the rent control coming in. We don't like the lawsuits. All right, where are we going to look? So we started going in Nashville. Nashville was booming. It was the short-term rental capital maybe of It was It was a bachelorette capital of the United States. So we ended up buying 17 short-term rental properties within 18 months in Nashville. Wow. And we had a master tenant on all of these. Where basically it functioned like a regular lease. And we got a certain amount of fixed rent every month. And then the our tenant was a short-term rental management company, and he
was responsible for taking the risk of renting these out. Got it. So we had 17. We had a personal guarantee. You do all your due diligence. And of course he defaulted on the lease within four months. So that invites a lawsuit, which we've been in for years. Gosh. Um and who knows if he's going to be able to pay. I mean, he's threatened bankruptcy, but I I don't think that's going to help him. We got, you know, 10 years to you know, collect on that. But the other thing that happened is the city of Nashville stopped giving out permits at the end of, I think, 2022 or 2023. Okay. So everyone rushed to get the permits in, and they had a 40% increase in supply that year which nobody saw coming. And so obviously the daily rents came down, the vacancies went up, um
and it really had a a drag on the market. But um our units today are doing well. We sold a few. We're going to sell more, and hopefully uh before all the mortgage resets happen at the end of next year, where we're we're going to we're going to clear out that portfolio. So would you invest in real estate again? I I would. I mean, I invest in a real estate fund, JRK. Jim Litman is probably the most successful multi-family investor in the country. I think in 55 years he's never lost money on a single deal. That's crazy. Jim is the goat. Yeah. And so I've been investing with Jim for 25 years now. And it's been one of my most successful investments. He's He's incredible. His team is incredible. Bobby, his family now is invested. You know, runs runs the firm. It's He's the goat.
He should come on the podcast. I'll Yeah, I mean, I'm happy to ask him for you. I'm happy to ask him for you.
I'm I'm not sure I can get that done. No, I get it. I get it. The reason I ask you that too is because um I see a lot of investors, sometimes first-time investors, cuz we have a spectrum of the building values that we sell. So, I've sold buildings as as low as 300,000, which was a 10-unit mobile home park in Carson, um to, you know, 25, 26, 30 million dollars. And it's a different investor type in each. Right. But sometimes I see these doctors and these attorneys and people who make high income cuz they want to get the depreciation for taxes and and they buy these shitty deals. And I'm like okay, I like I hope this works out
for you.
And I I get it, you're getting the appreciation and stuff, but it feels like there's not a level of preparedness that I think is needed when if you're playing in a space that someone's full-time job is to try to understand how to make money in this. And you're expecting to do the same. Right? It's like you're playing a different game. It's It's It's It's They're playing the pros and you're coming in here expecting to be able to compete with the pros. Like there's a reason, right? Um you take such a level of preparedness that I feel like anything you jump into, you're going like 17 levels deep trying to get a PhD in this thing before you make moves. Have you felt like with the real estate it's only become more of a strength? Like do you know, have you felt or figured out where your angles are or
is this still a percentage of allocation of investments where I know you have other companies that you're running too. Like how do you think about the risk reward time investment money investment when you're thinking about the the the broad spectrum of your portfolio?
Well, I think about how much time I have available in a day and I think about passion Yep. income producing wealth creation and you look at all those things and you lay them down on on a piece I do a lot of professional coaching. So a lot of people are are also wondering you know, they come to me and say God I don't know what they I want to do. I have three different companies or things that I want to start and I I focus on those. Real estate I thought was going to be a large wealth creation event. It turns out that it hasn't been except for Jim Litman's fund. That's been a huge wealth creation. His funds have just killed it. But I don't have a passion for it at the end of the day. And I'm much more comfortable now giving money to
someone else like Jim who's been an investor for a long time and I'm not giving money to people who have a first time Totally. fund or it's a first deal or something like that. Especially it could be a one-off like a family friend or a former Sure. intern or a mentee something like that just to help them out. But real estate has been a very important part of my investment portfolio. Mhm. I have experience now as a limited partner. I've probably done 40 deals investing in deals and now I have owned 21 units separate properties. It's very time consuming as you know. The reports are are time consuming. You review all the K-1s. You review the legal documents. There's mortgage stuff coming in every single month. I'm getting, you know, 20 electric bills and it's just a lot of work. Totally. And for me I'm more passionate about building companies.
I'm more passionate about my podcast in search of excellence. I'm building a brand called extreme preparation. I'm writing a book called extreme preparation. I'm most passionate about my coaching and changing lives. So, when I think about real estate today, it's going to remain an important part of my portfolio. I'm basically giving it all to Jim and say run with it. Past performance is not an indication of future success, but Jim Jim's done an amazing job. And that's that's how I think about where real estate is today and I advise everyone pursue your passions, especially when you have the money to do what you want and I'm grateful and lucky that I do. You know, it didn't work out the way that I wanted it to, but at the end of the day I am glad I did it and I I've learned a lot and I'm still doing it.
You know, we have a lot of properties to manage, so we'll see what happens. Yeah, I love that. I love that.
I think I agree with you wholeheartedly and I tell I have a younger brother and younger sister too and they're like college my brother graduated a couple years ago, my sister just graduated and they're asking me like, "Hey, you know, what should I do? Can you make an introductions? I'm thinking about going in this and this and I'm like, let me tell you exactly how I feel about this. Do whatever you are absolutely obsessed with and do go to a place where you can learn the most. It is not about the money in the beginning, it is about who is the best person for you to learn from and where are you absolutely assess obsessed that you're going to do more than anyone else cuz you just love it. It looks like work to other people, but it feels like play to you.
And that to me is a sign that you're in the right place and where you should be. For me I found that in in brokers in real estate and it I just got lucky with that. And I think that there's a part of someone when you're competitive and wanting to compete and like this innate ability an entrepreneur as you like entrepreneurship felt like you were almost bred to do that. There was a part of you who who was called to do that. But it's super interesting when you're coaching and when you're talking to these people and seeing this stuff. Like if you were 21 years old again today or 25 or in your 20s, right? So, let's take passion out of it for a second. Where would you try to I guess put a lot of focus and energy and where do you see the opportunity in today?
All right, let's I just want to back up and I'm going to lean forward into that question. I think today anybody in college from 20 years old or 19 years old till even their 30s has tremendous anxiety. They don't know what they want to do in their career. It comes up all the time in my coaching, my mentorship, anything. Yeah. I think today there is a misplaced hope that you are just going to be successful right out of the gate instead of doing the actual nitty-gritty, what I call [bleep] work. Mhm. If you can survive with a difficult boss doing things you don't like and be successful in working hard and doing the [bleep] work, I don't think you're going to be successful end of the day black and white, that's the way it is. I have a friend who just moved here. She's in the private jet business.
It's a very difficult business. She's in training, she's cold calling 100 calls a day and she doesn't love it. And I'm I'm I'm coaching her. We become very close friends and she wants to be an entrepreneur and start her own business. We talk about this all the time. I wish I could do it right now. I said, "No, just suffer through this, get some clients, have success, you're going to meet people Totally. especially in that business. Rich people, successful people that can afford to spend 100 grand on a one-way flight going to New York on a G6. Yeah. And it's it's a common misplaced hope to get rich quick. Mhm. So, if you don't have the mentality to actually do the work and do all the things that have made people successful in the past, you got to rethink your priorities and think about how you're going to get there.
So, now to move into if I was 21 or 25 years old, what would I get into? AI is all the rage right now. Yep. Right? There's going to be more millionaires created I think in the next 5 years than ever before in history. AI is changing the world. Just like the dot com craze, however, most of these companies are going to be complete failures. Yeah. There are companies right out of the gate that are raising $100 million at $500 million valuations. I just heard of one on my drive over here that my son knew about and I said, "What's the resume of these people?" I'm like, "Oh gosh, you know, it's interesting. It's like in the crypto craze, billions of dollars were raised on a white paper without any utility in these tokens just based on 25-year-olds or 27-year-olds who had an interesting idea in the crypto space. Mhm.
Could you
name one crypto coin that people actually use to do anything legitimate? I mean, there's there's very few use cases. No one's buying Bitcoin, you know, to go buy a car. I mean, you used to be able to buy Bitcoin to buy a Tesla. I don't think they take the payment anymore. But, I think AI is the way to go and I think people, even if you work at an unsuccessful company, it doesn't matter you have experience in the AI space. Like any business or any job you have, the person you work for is more important than the company you work for. Obviously, the company has a brand name, but if you have a shitty boss who doesn't want to mentor you, doesn't like you, not going to people, not going to back you, not going to promote you, that's a situation that you don't want to be in.
So, you want to find someone and, you know, you don't know until you get there. But, another common misperception is everyone wants a job and today you read, I mean, AI is killing these jobs. I read in the Wall Street Journal today that there are recent graduates paying people to help them get jobs with recruiters. Man, has this changed. Crazy. It's really changed, but if you're interviewing, it's a two-way interview. Mhm. And that's what a lot of people don't understand. When I come in and someone wants a job, I'll ask, "What questions do you have of me?" And if someone says, "I don't have any," Yeah. done. You're done. Yeah, done done. Yeah. So, I think you can do your own due diligence to find out if this is the right fit for you. Obviously, the company has resume value, but way more than that.
You have the boss who's going to promote you, teach you.
Are you going to learn?
Just like you said. And so, I look at AI. I think if you have a financial acuity, I think working in a hedge fund is amazing. Me, too. The the model there is absolutely insanity. Yeah. Uh people are making gobs and gobs of money doing that. And I think if you go into investment banking, that's also a great career choice. But like you said, um if you do great in any job, the money should come at the end of the day. And it's you you you got I mean, you asked the question, "What would you do?" And I think my answer would depend, and this is what I talk a lot about in my coaching, what are the five most important things in your job? Mhm. Now, at 21 years old, it's going to be money first, probably, because you may not be lucky enough to find a job
to pursue your passion. But as you get older, there's all kinds of things that matter: money, job, company, location. Mhm. Lot lots of different things. So, it really does depend on kind of where you are in your
No, but I agree with you. And I that's what I was expecting, too. And I'm Funny you mentioned uh hedge funds and and private equity and stuff like that, cuz I look back and I'm like, "Damn, dude. If I'm working 100 hours a week on this, like, where's the equity build up? How do you think" I I think about equity a lot, cuz for me, brokerage is a industry it's you don't really get to sell a book of business. It's not like an insurance brokerage or business. So, we have to make money investments in other ways, which is either buying real estate or I know people who've had a because of the network, you've been able to invest in companies or VC or funds of funds and whatnot. But I have to take the earned income, which is that the higher cash flow part of the
brokerage business, the quick money, and go and invest it in long-term investments.
So, I think about that a lot. You guys also have a massive conflict of uh interest situation. You find a great building. Yeah.
Do I buy for myself, or do I give it to a client?
Yeah. And if If give it to the client, he finds out or she finds out that you bought it for yourself. You'll to "Hey, Taylor, what's up?" Uh-huh. And so that that's an interesting one. I know a lot of brokers who created significant wealth by buying their own buildings. But when you bought that building, you clearly had a choice. Yourself or client. Yep.
100% It's super weird and that it is it is a great dilemma. Um but yes, 100%. Um I'm going to be selfish really quick because I want to leverage your knowledge and experience. Um if you were a broker or you had to start your own brokerage firm, all right? How would you try to build a company to be the number one brokerage firm in an area? How would you grow to try to dominate a market share in terms of brokerage? Think about like the business model of brokerage.
Right.
How would you do that?
Okay, the first thing I would do is you got to make sure you're the best broker as a leader of the team, okay? Okay, and people ask me all the time, how do I get a new client?
How do I get a meeting?
So I take my friend Luke Rivera. Yep. Luke played minor league hockey. He got out of 25 years old. He got out during COVID. So I got him leasing industrial real estate. He was working for a guy at the end of his career. And he drove around for a year, nothing. 100 cold calls a day, nothing. So he got on a walk during COVID, a a safe walk. Uh-huh. And I said to him, "This is a sure way to get a new client, okay? The first thing I said is how much are you willing to pay for a meeting?" Looked at me like I was nuts. "I'm not going to pay for a meeting." I said, "Why won't you pay for a meeting? I mean, you're going to close some of these, right?"
So I said, "You got to think of yourself as Luke having a marketing budget like a company, Luke Inc." Mhm. So I said, "How much are you willing to spend now?" He made, I think, $300 a week playing hockey, staying at somebody's house, had really not saved any money, but I said, "Okay." So we came up with $1,000. I said, "You're going to go to Starbucks. You're going to buy some mugs. You're going to buy a coffee. You're going to send over a basket and you're going to write a note, 'Dear Taylor, would love to drink coffee with a a person, Luke.'" And I said, "You're going to get a bunch of meetings. During a non-COVID situation, you'd probably go 10 for 10. Yeah. Right? And you're going to get 10 calls back. So, you're going to have a 100% success rate doing that.
This is during COVID, as you know, uh people that are in those buildings are generally older in their 70s. No one wants to come in and die to meet with Luke. But Luke did get two meetings out out of that and they liked them. Yeah. So, Luke sold himself. He's a great guy. He'd done the research to meet these people and he got them to like them enough that the following year these two gentlemen referred him to people who became his first two clients. I think Luke the next year made 215,000, 512,000 the next year, and 1.5 million the third year, just using the same technique. So, he's one of my coaching clients. He's going to be on the randallkaplan.com website as a case study. Anyone can do that. By the way, it works in your personal life.
And and and the way Here's another story and I'll I'll just tell you where this came from. Um back in the day when I was single um I had 7 and 1/2 years between my first marriage and my second marriage. Um I would go on Facebook um Instagram now and you can see pictures and you friend people that you think are attractive or you may want to meet. And there's a reporter at Channel 2 that I wanted to meet. So, I sent her a message on Facebook Messenger, nothing. Like, you know what? I'm going to just send her some coffee. Deliver it at the studio and just, you know, leave it at the gate and with that same note. You know, "Dear Brittany, I'd love to drink this with you in person. Randy." So, I don't know how many minutes after she she got
it she called and we went out. And not only works in your personal life, but it works in your business life. I love that. That's incredible. That's so good. So, start by being the best broker you're going to be as a leader the team. The second thing I would do as I'd go find people who you want to recruit who are the best of the best. Okay, so the typical split if you're in the highest category you're you're 90/10 and the brokerage firm is lucky to have you but that's rare. Right? So you want to go to a lot of these firms are older, they're political so you want to create something new. You want to talk to people in advance.
What's wrong with your firm? What don't you like?
Talk to some subset of people. A sample size of two is probably not what you want to do but take notes on everything. Then find out all right, I'm going to build a firm based on these four principles of things that other firms aren't doing. Okay, then I would say what's your split there? I'm going to increase the split and what can I do in addition to that recruiting you? I would take less margin to have superstars coming here.
Why?
Because you recruit two or three superstars even if you're getting 3% who cares? People are going to want to work with them. That's how you start building this incredible roster. The volume will take care of itself at the end of the day and I'll just keep going one by one by
one and just knocking them all down. Yeah, it's the who not how. It's like that that is so powerful the more and more I'm growing a business, right? You realize that it's the who. It's in in A players make up for themselves in spades. Like it is it is almost they you they hear of like 10x developers when it comes to coding and whatnot who knows but AI but it's there's 10x employees, there's 10x sales people, there's 10x people that HR people like there are 10x people in the world that if you can get them on your team everything else becomes better. Everything else grows off the back of building a solid A
team. It's like Tom Brady coming back to Tampa being the quarterback. I mean he got Gronk to come out of retirement just to play with him. Everyone wants to play with a Tom Brady. It's just that simple. If you're great, people want to be part of your team.
Before we wrap up, I just want to talk about the podcast a little bit and your experience with that. Like, what are some things maybe that you were surprised with or some takeaways that you've had from interviewing, I mean, the greatest some of the greatest athletes and talent and entrepreneurs in in the world. Like, what are some things that you've walked away with and said, "Wow, that was that was
special." I think number one Tony Robbins? Everyone puts these Well, Tony Robbins when I started the show was my number one guest that I wanted. And I went and and I would tell people that. And they'd say, "Oh, I'll introduce you to Tony, but come to my mastermind for $25,000 and I'll introduce you to Tony." So, I'm going to pay 25K to shake Tony's hand? Uh no, I'm not going to do that. I'm not going to pay to go to mastermind. I'm not going to pay to get a podcast guest, either. So, one day I'm sitting at lunch
with my friend uh Doug Evans, who I just met at a conference in Las Vegas. I knew who he was, he knew who I was. Somehow Tony's name came up and he said, uh "Would you ever want Tony on your show?" And I said, "I'd love Tony on my show." He said, "Well, let me call him." I said, "You really know him?" I said, "Yeah, I've spoken at some of his things." I said, "Okay, great." So, that night Tony Robbins leaves me a message voicemail on my phone. I mean, I got chills thinking about it. Then he invited me down to his house in Palm Beach to shoot the show. And it was it was incredible. Um so, I I And he's the goat. So cool.
I listened It was one of my favorite episodes that you've done. It was He's just like so everything he said he says out of his mouth, it's like it resonates again even more. It's like, "Gosh, this is it it it like hits your soul."
He knows how to speak to your soul. Um I don't listen to my own podcast once they're finished, but I've listened to that one a few times after after done. But you asked me a good question, you know, what are some of the things that I've learned by talking and having amazing conversations with some of the most successful people in the world. Everybody who's listening or thinking about someone who's very successful holds this up on a pedestal. Right? They don't realize everybody is a human like everybody else. They wake up like everybody else. They breakfast, they go to the bathroom like everybody else. They have problems like everybody else. They've had challenges at the end of the day. And what makes their stories unique is they've all had some negative event in their life that significantly impacted their future and they've overcome it on their path to success.
So, one of the great things is sharing stories. Now, I think I'm 190 episodes in, something like that. It's sharing different levers and different experiences with people, how they pulled themselves up and made them successful. I mean, one story is better than the next. And it's been one of the great surprises of my show. When I started the show, I never really thought about it. I know everyone has a different story, but you realize just how deep and different the stories of everybody
are. Thank you for sharing that and being able to get those people to come on because I just enjoy when I get a chance to listen because like you said, this wasn't available, you know, 10, 15, 20 years ago. You didn't have access to these kind of people. So, thank you for for sharing their stories and and providing person like myself who loves to learn Yeah. a chance to actually learn from them. Thank Um okay, there was a there's a question that you like to ask at the end of your podcast. I'm going to leave you with this last question. Is what is one question that you wished I had asked you?
What's the proudest thing in your career that you've done over all these years? And the answer to that is giving back. Because number one, that's number one is you don't have to have money to give back. I was giving back long before I made any significant amount of money. Um giving back your time is more important than giving money even when you're older cuz now I have the ability to put things together and put teams together and there's nothing more valuable than your time. Having said that, if you're more productive as a fundraiser, then you should be a fundraiser, but I've established scholarships at Michigan, a Foster Care scholarship in my grandmother's name, merit-based scholarships I've created two events, the Imagine Ball for the homeless, the Justice Ball for a nonprofit legal law firm. I've raised close to $15 million. Wow. And it's amazing to be able to
give back, change lives especially if you're changing the life of someone today who would otherwise be on the street, on drugs, go to jail not go to college and you change the lineage of those people for the rest of their lives and generations to come. There's nothing more rewarding in life than
that. Randy, thank you very much.
Appreciate you being here. it. Thanks for having me. Congrats on all your success as well. Thank you very much. Appreciate you.