In Search Of Excellence - Mike Meldman: From Blackjack Dealer to Real Estate Mogul | E164

Episode Date: June 6, 2025

Mike Meldman is the mastermind who turned luxury and lifestyle into a business empire. As the founder of Discovery Land Company and co-founder of Casamigos Tequila alongside George Clooney and Rande Gerber, Meldman built a world where wealthy clients don’t just buy homes — they buy Incredible family-oriented experiences. This is the inspiring story of how he redefined real estate, community, and luxury - and went on to create a billion-dollar spirits company and become part owner of the Las Vegas Raiders.Randall KaplanEXTREME PREPARATIONListen to this episode on the go!🍎 Apple Podcasts: https://podcasts.apple.com/us/podcast/in-search-of-excellence/id1579184310 🟢 Spotify: https://open.spotify.com/show/23q0XICUDIchVrkXBR0i6LFor more information about this episode, visit https://www.randallkaplan.com/Follow Randall!Instagram: https://www.instagram.com/randallkaplanTikTok: https://www.tiktok.com/@randall_kaplanTwitter / X: https://x.com/RandallKaplanLinkedIn: https://www.linkedin.com/in/randallkaplan/Website: https://www.randallkaplan.com/1-on-1 Coaching: https://intro.co/randallkaplanGet More Excellence! In Search of Excellence Clips: https://www.youtube.com/@iseclipsCoaching and Staying Connected:1-on-1 Coaching | Instagram | YouTube | TikTok | LinkedIn

Welcome to In Search of Excellence. My guest today is Mike Meldman. Mike is a real estate guru, the founder of Discovery Land Company, which operates 36 high-end luxury resort properties around the world. He's a co-founder of Casamigos Tequila, which sold a few years ago for a billion dollars.

He's an amazing investor, many companies including Vioris, and he's the new owner of the Las Vegas Raiders. Mike, welcome to In Search of Excellence. Thanks for being here. I always start with family because it shapes our futures and who we grow into. Your mom Maggie was a travel writer. Margie. Margie was a travel writer. Your dad Bert went to law school, didn't practice, sold insurance. And I want to talk about, they went on a trip to Thailand in 1998 and your mom wrote this blog about he was whined and dined his whole life because he was so successful in terms of he hit his quota

and he went all on these trips around the world. So what was it like watching your dad sell insurance? That's not a product that we wake up one day and say, I need life insurance today. Someone calls you up and say, hey, you wanna buy some life insurance? Yeah, so my dad was a true salesman, right? And he was successful.

But we lived and I grew up, I would say, a very nice life, very middle class, didn't really want for anything. But anything I wanted, I had to go earn by working. So if I wanted a bike, I went out and got a job and bought a bike. So it was a happy life. My parents were great.

My dad was always there when I went to school. He was always there when I got home from school. He coached me, all my sports, you know, little league, football. So he's a great, great family life living in Milwaukee. Did your dad tell you what he did at a young age and he explained to you, hey, this is how I go out and sell something? No, I did a, I remember, I can't remember what grade I was in, but I did a, like a report

on selling life insurance. The only thing I really remember from it was the word breadwinner, because everything in the insurance business seemed to be about the breadwinner. So that was kind of the thesis of my report when I was in third or fourth grade. I remember always going to the office with him, like on a weekend when no one was there and going to the general agent's office and sitting in the big chair and you know my dad said someday this could be you know could be yours. Parents watching them what they do very influential in my life and in your life too. When your dad was your coach in Little League he would often prop up the

kids who weren't doing so well or who weren't good. What was that like watching your dad do that to people who, you know, as a kid, I wasn't a great baseball player and I didn't have a coach who said, hey man, come on, come on, you just didn't play if you weren't good. Yeah, well my dad was the opposite.

My dad was a great coach and he made everyone play. And I remember this as, I still remember it. It's a big impact, made a big impact on my life. We were probably in third or fourth grade and we were in the softball championship game. The rule was everyone had to play. You play softball, not fastball? This was softball because we were probably too young, too young for hardball at the time. Or it might have been hardball.

I can't remember. But we didn't have tee ball or anything like that. So it was a baseball game. We were down by one run. We had two outs. And my dad realized that Randy Burns didn't play. The rule was everyone had to play. So my dad put Randy Burns didn't play. The rule was everyone had to play. So my dad put Randy Burns in, two outs, we're down by one.

I don't know if bases were loaded. I don't know if it was quite that dramatic, but Randy went up and he struck out and we lost the game. And everybody went up to Randy and kind of consoled him and hugged him. And my dad's speech to us was You know the other team who was like the other neighborhood team who we knew all the players They go they didn't play everyone so they didn't play fair

you know we played fair so you know, we can be proud of ourselves and hold their heads high and You know, we even though we'd lost, that took the sting away. And even though Randy struck out, no one was mad or angry or a bad sport about it because we realized we did the right thing and played by the rules. You were also close with your grandfather, and I wanna know his influence in your life, and I also want you to talk about Thomas Jefferson as well.

Okay, well, yeah, my grandfather and my dad were probably the two most influential people in my life because they always did the right thing. My grandfather set a great example. We called them the Gump Grandpa. The Gump? The G grandpa. The gum grandpa. Because every time he came over, he would have, um, you know, the round gumballs. So we would all run over for gum.

And let's say we're playing football in the front yard. All my friends would run over and they go, the gum grandpa is here. And we'd all get a piece of gum. So that was kind of his his trademark and Every Sunday When we'd go to his house for dinner, he'd bring us all to Baskin-Robbins for ice cream. He was a lawyer a great guy. Everyone loved them All us cousins loved them and he you know, just him and my dad Like I said, they just always did the right right thing obviously that was a great lesson for me and

inspiration for me. You're known to have a great personality I think people that have great personalities generally do better than people who don't tell us about a high school tell everyone what the key club is and then tell everybody about you ran for governor against your best friend and there's a total slaughter at that point. Yeah, that was boy state. There's a key club was a service organization that was sponsored by Qantas.

Like all the football players were in it, like all the cool guys were in it. So I got, when I was a sophomore, I became a member just because the juniors and seniors on our football team were in it, so I thought it was cool. And then they had these conventions, and we were in a three-state key club division.

It was Arizona, New Mexico, and West Texas. And so by the time I was a junior and running for governor, I won. And so I was a governor for those three states, or two and a for governor. I won, and so I was a governor for those three states, or two and a half states. The reason I wanted to be governor is because I was at the Key Club Convention the year before, and the governor got to pick the Key Club sweethearts.

And so he got pictures and resumes from hundreds of different girls from the different high schools. So I go That sounds cool. And so that was literally the reason why I ran for I ran for governor What do you do by the way as governor? I basically Visited different high schools across, you know Arizona, New Mexico West, Texas met with the different key clubs Talked about what key club is, what we were doing, things like that.

So I was kind of just a figurehead. But Key Club was a service organization. And what I remember mostly from what I did at Key Club, I coached Special Olympics. And the person I coached, two years in a row. So that was something I was proud of. But you did stuff like that, right? You had car washes and raised money for certain causes. It just taught you to give back.

And so it was a good lesson and something I, part of the core of who I am is giving back. And so it was a good lesson and something I, you know, part of the core of who I am is giving back. From Key Club, then I went to Boys State. And Boys State is sponsored by the American Legion. The idea behind Boys State is you take the best all-around students and they go to Boys State. So my high school happened to be a big high school. I had probably 3,000 kids in my high school. We got five people who got to go to Boys State. I was one of the five. My best friend, two of my best friends, Eric Hedlund and Robbie Robinson, were also selected to go to Boys State. So we go. My roommate was Eric Hedlund, my best friend. You have like,

it's a mock government basically. So I lived in a city called Orth. So you started with the city government, then a county government, and then the state government. And everyone was nationalists or federalists, whatever, there was two parties. So it was basically to teach you about government. For governor, I ran against my roommate,

which is weird, who's my best friend, and we both went to the same high school. So all this is was kind of strange. Usually the person wins by three or four votes because you'll get your friends from your high school to vote for you and cross party lines. And so I ended up winning by 60 votes, which was like historic because everyone knew me as key club governor. So I had a huge, huge advantage actually. On the student front, you get straight A's,

you go to Stanford, history major, fraternity guy, you promoted concerts, you were a Deadhead fan. Tell us about this bar called, I think it was called the Penn, and then blasting rock and roll music over the ocean. And then we can flip into the rock and roll at the golf clubs a little bit later in the show. Okay. The Nepenthe was the bar.

The Nepenthe. The Nepenthe is a place in Big Sur that kind of overlooks the ocean and the forests of Big Sur and it's kind of a hamburger joint. And so I used to go down there if I was in Carmel or even drive from Stanford, you know, if I had a date that I wanted, you know, to impress and we'd go there and like I said, it was a hamburger joint. You'd sit over looking the forest and trees and they just blasted rock and roll. And so I always liked that. I kind of grew up in the rock and roll era. I've always had an affinity for classic rock. When I started Discovery, I would on the golf course at the driving range, I'd blast classic rock that came from

all those burgers and beers I had at the Pentea. But I also did it to make golf fun. And the irony of all this is I never golfed when I started Discovery and I was never a member of a country club in my life. So I didn't, you know, grow up like a golf snob and a lot of people who develop golf courses are very traditional to the rules of golf but I wasn't. So blasting rock and roll just made it more fun for me. I'd go to the driving range and try to learn how to golf and at least I sucked.

So at least I had rock and roll to listen to. I grew up in Detroit, classic rock guy. Rush is my favorite band of all time. Detroit's got a lot of rockers. A lot of rockers. How did you become a promoter at Stanford? Because was this just something, hey, I'm a popular guy. I want to get people together.

I want to get everyone in a room and make money. No, it was more that my friends were in charge of whatever it was called, the Associated Students of Stanford. And they basically did these concerts. And so I was living there in the summer, so they got me and my best friend, Bill Maloney, involved. And so what we would do, we were like in charge of hospitality,

which is kind of ironic now. And so we'd go, as Joan Baez, we'd go to, it was probably before Costco, but we'd go somewhere and buy granola bars and things that the Joan Baez crowd would eat. I remember doing Huey Lewis's first concert. I think it was Huey Lewis, Pogo, and Dave Mason. And Huey Lewis was in the back of the stage

and just sticking food in his pocket. And Huey Lewis was like in the back of the stage and just like sticking food in his pocket. You're stealing food? Yeah, I mean, he just, you know, he's a young kid who, you know, it was his first show. And I remember we had to go to him and go, look, don't steal the food, you're welcome to it. And kind of teach him how to behave because he's probably stoned out of his mind or something. But it was kind of teach him how to behave because he's probably still in that

of his mind or something but it's kind of funny because he's obviously turned into a big, you know, big star. College today is a big topic about parents. Should we go? Should we not go? 57% of kids who go to college take on debt. The average debt's $30,000. Takes 20 years to pay off. These are 10-year loans, even though it takes 20 years to pay off. And we'll go through your jobs one by one. But should kids go to college today? Do they need to go to college?

Well, I think so. I mean, I think besides the education, the socialization, and the people you meet is important for life. Like, my friends from college are still my best friends. So I think yeah it's very important. But also you know my best friends from high school I'm so close with and my best friends from Milwaukee you know from when I was really young are still very close to me. So yeah I think it's important for education and socialization. 50 companies, I've invested nearly 100, including Google lift and Seagate. And I also co-founded a company

that today is worth more than $15 billion. I've been incredibly blessed in my journey. And at this stage in my life, I wanna give back. I wanna share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others.

I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions, and if you're a good fit, my team will reach out

so we can build a game plan together. All right, now let's get back to the video. So the plan was also, you grew up with a family of lawyers. Everyone went to Marquette Law from Milwaukee. So you were going to go there until you weren't going to go there. So let's not jump ahead in terms of where you went next. But I'm curious, you said it was the best thing that happened to you in your life. I mean, I'm sure your kids. Yeah, I was destined to go to law school.

My parents spent a lot of money on my Stanford education. $6,000 at the time was a lot of money. It was $6,000 a quarter. A quarter. So it was $18,000 a year. Whatever it was, it was a lot. I worked a lot and made a lot of money when I was in college. The whole idea of sending me to Stanford was that I would then go to law school and be a lawyer.

And so I took the LSATs and I probably hung over, didn't realize what the LSATs were and how important they were. And I had good grades at Stanford, so the grades weren't really an issue. I just bombed the LSATs. I don't even remember what I got, but it was a low enough score that I was too embarrassed to apply to law school. Maybe I got my name right. Other than that, I don't know really what happened.

I went to Lake Tahoe with three of my three buddies from college played or learned how to deal blackjack. And so I went to two weeks of blackjack school, graduated and I think graduating blackjack school is more exciting than graduating Stanford. And I dealt blackjack at here for the the summer and I met a guy and he basically said to me do you want to make as much money as you want and work as little as you want I go yeah sounds like a great idea so I started as a commercial real estate broker in San Jose. Let's back up a few steps if we can so you didn't have a plan B when you didn't go to law school, right?

So should people have a Plan B? Because right now I think people say, you gotta go for it, you gotta go for it. And if you have a Plan B, you're not gonna be as successful as if you're focused on one plan. Well, I guess you should have a Plan B. I didn't, I didn't.

It's kind of funny, because I was the only one who went into real estate for my college class, or even all four classes when I was at Stanford. who went into real estate from my college class or even all four classes when I was at Stanford. Everyone went into technology. I was kind of the outlier, but it worked out because all those guys ended up buying in my projects

once I got to the place where I had projects. I always thought I was a history major, so I didn't have any real technical skills or training or expertise. Like my friends who were electrical engineers or mechanical engineers. Stanford is a liberal arts school. Like when I was going through the interviewing process with different companies, my line was it's not what you learned, it's that you're capable of learning. And that was kind of my philosophy at Stanford,

because it's a history major. You either go to law school or you teach history. And I actually would have been fine teaching history, because I like doing that. I also went to law school, but I went to Michigan before I went to Northwestern Law School. Don't test well. I didn't test well getting into Michigan,

but I did well at a private school. I graduated magna cum laudeude in very difficult private school. Then I went to Michigan and I graduated top 1% of my class there. Not because I'm the smartest person in the room. I think if you are, you're in the wrong room. But I worked very, very hard. I was at the library till 10 o'clock at night when nobody was there. Wanted to go to law school. Well, I actually want to go to business school, but knew I wasn't gonna test well. They made you work for two years.

I needed to get out and make money. So I also took the test and got a 36 of 48. I think it was something like the 58th or 60th percentile. My friends who did as well went to best schools, Harvard, Stanford. Of course, I got rejected and I don't know how it happened, but my backup school was Northwestern and I went there. It was a good thing I went there.

But I hated law school, so maybe you didn't miss that much. We all have menial jobs that we do. I waited tables in law school, I waited tables in college, I bagged groceries in high school for extra money to go on dates. I had a long distance phone bill I had to pay. You worked at Lucky's twice, high school at Stanford in the summer. You were in a slaughterhouse, for lack of a better word, hanging cattle on Arizona beef. It was a slaughterhouse.

A slaughterhouse. And then you worked on a rig as a roustabout. Tell everyone what a roustabout is and then tell everyone how it was the first lesson in liability and insurance liability for people getting injured on that rig. Yeah. So I was a roustabout, which is the little man on the totem pole on the oil rig. Laborer, essentially. Yeah. I mean, I was like, when there's nothing to do, I'd be like chipping paint and repainting, you know, things on the boat.

But I was really the, you know, helping the crane operator. So when pipes came in or supplies came in, the crane would take it off the ship, you know, the little tugboat that brought it out, and then it would bring it to the boat. And then I had to like guide the, you know, the pipes or the supplies on the pallets onto the boat and then I had to like guide the you know, the pipes or the supplies and on the pallets onto the boat and then unload everything. Pretty hard, you know, hard labor. It was 12 hours on, 12 hours off for two weeks.

So you were, I was literally offshore for two weeks. You would take a boat to this huge rig, the kind of rigs you see in the ocean? Yeah, you see, we would leave Port Wynemi and go out, you know, the Santa Barbara coast on one of the rigs. The first day out there, the guy who was teaching us, I went with a friend of mine, John Wolachka, the two of us did it together. And we had a guy, an experienced guy who was showing us the ropes, who actually got caught in between pipes and a pallet of stuff had to be airlifted off the first day.

So it was just the two of us. You know, we knew nothing about what we were doing, so we just had to kind of, wasn't that hard, we were just, had to try to stay safe. And before we took the job, they sent me a letter that basically, I had to have my parents sign, and it basically gave an amount of money for each limb if I lost one.

What was the most expensive limb? I can't remember, but I'm sure it was a leg. The summer before my freshman year in college, I worked construction. I worked in this dirt pit that was going to be built the World Weight Watchers Headquarters. And I was this skinny kid and I'm looking around and I was thinking to myself, this is definitely not what I want to do. But I think the hard labor is a very good experience to look around and this is how most of the world works. When you were on that rig and were hanging beef in a

slaughterhouse, were you saying to yourself, I'm doing this for the money? And did it motivate you to say, all right, I'm definitely going to go out and I'm not going to do this for the rest of my life? Well, I definitely did for the money because they were hard jobs and they paid well. I think that two weeks on, two weeks off, I was making $2,000 or $3,000 every two weeks. I worked three two-week stints. I went into my senior year with $6,000 in the bank, so that was meaningful and I probably should save some of it, but I had a fun senior year. And I just, the hard work, like I said, I did for the money, but it's also good.

I'm a pretty disciplined person. And so I didn't mind the physical labor because I was always trying to stay in shape or be in shape and like lugging cattle. I literally had to take the cattle, you know, half the cattle's there. I'd go like this, they'd cut it off and learned how to balance it on my shoulder like without even holding it. And then I'd have to throw it onto a meat hook on the truck and then we'd drive to Safeway or Lucky's and then I'd have to take the half of cattle off or quarter of it off

the truck into the butcher shop in the store. And I worked from like 10 or 2 a.m. to 11 a.m. So kind of screwed up my days. But it's hard work and I liked it because it was physical. You touch upon this already. You meet this guy who says you want to make as much money as possible. So much of our success is taking a risk. It was a startup. And then a lot of our risk too is just being at the right place at the right time. So tell us about Fremont and this location of Silicon Valley and then the cold calling

experiences that you learned calling on a bunch of farmers. Basically the office was in San Jose in like an industrial park, so it wasn't glamorous. It wasn't, I had no mentor or anyone showing me the ropes. So my whole training was go to Fremont, and it was farmland, look up, go to the microfiche, because at the time, you know, you would find the APN number and pull in this like Microfish and figure out who owned it.

And then I'd go call on him and try to get a sign up. So my whole real estate career started by just putting signs up. And the guys that put signs up, they're going to call you and then you sell them something. And so I did that and I got signs up all over Fremont. People started calling and I started doing deals. And I had a really good knack for making deals. I think I made 50 or 60 deals my first year. A lot of the deals, the minimum commission was 250 and you have to split with, I had

to split with my broker and some had another broker. So I had a lot of checks for $62.50, but added up and I ended up doing pretty well my first year. And I remember leasing property, like a commercially zoned house to a termite company. And they had asked me questions on the lease and I had no idea what the answer was. So I'd call my manager and I said, hey, what's a stoppile? And so he explained it to me. Then I'd go to the termite guy, explain to him what a stoppile was. He'd sign the lease. I would leave. And I still didn't know what a stoppile

was. But I was able to kind of just talk my way through things Were you cold calling on the farmers? I mean, I know you put up signs but oh, we ever just see a driving up this dirt road with cornfields or fruit trees Up and and just saying hey is yeah, I'm not farmer Bob here. Yeah knock on the door I knew their names right because of the microfiche and I'd knock on the doors and they were older. And so, you know, it seemed like everyone always liked talking about real estate. So they'd invite me in and sometimes, you know, they didn't have friends or something and would just talk to me, you know, about real estate.

And so, you know, that's how I got going. And as I was putting these signs up, it's kind of funny. There's a Cushman Wakefield broker who kind of controlled Fremont. And he would call me, you know, and say, you know, take your sign down. And I'd say, no, I got permission, you know, from Farmer Lopez. And he goes, well, I have an exclusive with them. And I go, well, no, I've got permission. I'm not taking it down.

And we would fight. And the guy's name was Steve Beret. And so that summer, I was up in Seattle for seafair. And we had a big group. It's all my college buddies. And Steve Beret happened to be part of the group. And so we became friends instead of enemies. And so at the end of Seafarer,

which was like early August, he said, why don't you just come work with me so we're not fighting and work together. And he was at Cushman and Wakefield. And so Cushman and Wakefield was the big company. After a couple couple months, I went to work for him at Cushman and Wakefield. And the following year, we sold all of Freemont. I mean, it was the developers had a run on it. Between him and I, we kind of, we didn't control the owners, but we knew them pretty well.

So we were able to assemble basically all the land. At the end of the year, I think I was the fourth highest paid broker in Cushman Wayfield in the country and he was third. So what were you making? How much money back then? I think of the thing, I think it was probably 700,000. And you're how old at the time? 24, 25?

24, 23. It was a lot of money. Still is, but really a lot of money back then. Yeah, I was going, well, that was easy. I go, the guy at the blackjack table is right. And then you started doing bigger deals. You want to go off on your own. So tell us about your first deal,

300 acres in Portela Valley, and how you raised $5 million for that deal, including from a Saudi prince. Yeah, well, I bought it from a Saudi prince. So the one thing I didn't like about being a broker, you didn't have real control over anything. And so, like I said, these guys would let me in and talk to me, and sometimes, you know, for hours.

And, you know, I realized they don't care about selling their land, they just want someone to talk to. And a guy in my guy at Bishop Hawk, which was the first company I was at, told me the one thing, the most important thing about being a broker is you need to realize when a deal will happen

or can't happen. Because a lot of people spin their wheels on deals that just won't happen and have no business ever becoming a deal. And I remember I drove down to Alameda and met with this dentist who owned this big piece of property in downtown Fremont next to Macy's. And it was zoned for like a high rise condo

and I get the listing and I'm like, oh, this is the greatest thing that's ever happened to me. I'm going to be rich. This is going to be the greatest project. And after like three months of trying to sell it, I realized, well, there's absolutely no high rise condo market in Fremont and probably never will. Something that got me so excited and so jazzed and something that I thought was gonna change my life Literally was a waste of time zero, you know zero impact Except for it kind of woke me up to have a little better control

Over my well-being basically and so that's when I moved out of brokerage Got into development and the first thing I did, I bought this ranch in Portola Valley. And Portola Valley is right outside of Stanford and Palo Alto. And so it was 300 acres. And I bought it from a Saudi prince. And he had this Lebanese guy who kind of this Lebanese guy who kind of handled the negotiations. I tied it up for $5 million, had the deal, thought it was great, and then he goes, now what are you gonna pay me for the development right? I mean, what are you talking about?

We just cut a deal. No, for the property, I had the development rights. So I think we had to pay him like a half a million dollars, which at the time was a lot. And so we got it done, bought it. It was zoned for 28 lots. We had 300 acres. It took over 10 years to get improved because every environmental constraint was on the

property. You had this big hill that was covered in landslides. You had the San Andreas Fault run through it. You had wildlife corridors, biological corridors, and the people who were fighting me were all like Stanford professors, right? So like I have a consultant on the San Andreas Fault to show how we could stabilize everything

Well the town's geologic committee just happened to be like the guys who started USGS And you know the biology people fighting us were biology professors at Stanford I really had to learn how to develop properly and through the environment, right? Because everyone wanted to save the environment. And so it gave me a PhD in development well over 10 years. And I remember going to like my Stanford friends, hey, can you show up at the public hearing

in front of the planning commission? They go, no, no, no. I'm like, why? And they go, oh, my wife hates you. And they were friends. I don't think she really hated me. And I'm like, why? And they go, oh, my wife hates you. And they were friends. I don't think she really hated me. And I'm like, why? Because you're ruining the environment.

I go, we're not. And have to explain how we're doing and what we're doing. And so, like I said, after 10 years, it finally got approved. And the good news is it was kind of the peak in the market. So we went through a few dips on the way. It ended up being a great learning lesson. It ended up being profitable and I have friends who actually live there.

I hope you're enjoying this video so far. But before we jump back in, I want to know if you've ever thought about what you need to do to reach a nice level of success in your life. Over the last 25 years, I wanna know if you've ever thought about what you need to do to reach another level of success in your life. Over the last 25 years, I've been an advisor to more than 50 companies. I've invested nearly 100, including Google lift and Seagate. And I also co-founded a company that today

is worth more than $15 billion. I've been incredibly blessed in my journey. And at this stage in my life, I wanna give back. I wanna share the lessons I've learned so you can reach incredible success way faster than I did. In my own journey, I've learned that having the right mentor is a massive advantage to achieving our goals. I'm hugely passionate about mentoring others.

I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So that's you, I've got an opportunity. In the description of this video, there's a link where you can apply to work with me. All you need to do is answer a few simple questions. And if you're a good fit, my team will reach out so we can build a game plan together.

All right, now let's get back to the video. Explain to people how a long development cycle could kill a return on your investment because people may say, all right, you sold it. Let's say you bought the whole thing for $10 million. And you sold it for $30 million to someone who might not get the math behind that, that may be a terrible return and actually is a terrible return. And when you think about $20 million gain 10 years later, I mean, it's not on a risk reward basis, it's not what you should be getting on real estate development deals.

What people do, you normally judge investments by internal rates return. Internal rate return is basically how much money you make every year compiling. And so if you invested 10 and made 20 over 10 years, that's a bad internal rate of return. Probably around 4% of the compound or something like that. Which you don't, which would be bad. But it's a decent multiple. So we're always internal rate of return driven, or most people are. But in our business, we're not really

internal rate of return driven today. I mean, we always were early on because our investors were. But today, we're more multiple driven, which means that the brand today is so strong that we could start a deal and have things pre-sold. So a lot of times we allocate, let's say, $100 million for a project that we think is what the capital needs are. And we end up only spending $3 million because the brand's so big, we're able to pre-sell.

And so we could supplement the buyer's money with our money. Obviously, the IRR is huge when you don't spend any money. Right. You don't spend any money, but we really want multiples. And so what we're driven for is just creating as much value as we can. You know, we look at like if we put in 100 million,

we wanna make a billion dollars, okay? We don't, you know, if we put in 100, we don't wanna make 20 million. You started Discovery in 1994, and you bought 640 acres out essentially at that point in the middle of nowhere as a cattle ranch. So tell us about Mark Solenberger and Paul Fay and what happened after Mark gave you a call.

It was around 1994. And we were, the early 90s for real estate for a lot of people were tough. It was ending the RTC days, which is the, when all the SNLs basically blew up. Our motto was stay alive to 95. Since I went to high school in Arizona, I called a few friends and said, hey, I'm looking for some land because I wanted to get out of California because California was really, from a real estate perspective, done and gone at the time.

And so I wanted to do like a big master plan community, like a Sun City, but not age-restricted, but golf courses, big density, a big project. So that was the idea I had in my head. And so a friend of mine told this to Mark Sullenberger. And Mark called me and said, hey, I have this great piece of land. They should come look at it. And it's at Pinnacle Peak.

And I go, where at Pinnacle Peak? And he goes, Pinnacle Peak. And I'm like, and Pinnacle Peak is a landmark in North Scottsdale. I kept asking him where, and then he finally explained to me, it's actually, you would own Pinnacle Peak. so to me that sounds cool. I went out there they were trying to do a like 3,000 room hotel and they were gonna have a golf

course that was attached to True North and True North was kind of the hot high end resort course or you know public course and so they explained the deal. I go 3,000 rooms sounds like a lot. It's gonna take a lot of money to build it. The Phoenician, which is one of the great hotels you'll ever see, is in bankruptcy. The owner just went to jail. Doesn sound like the right the right thing to do and so there was a transfer from the resident or the resort density into 800 units and so Pinnacle Peak was a mountain that was had the most lush Landscaping and swarrows everywhere

I mean it was just a beautiful piece of property. Scottsdale's flat, and this is one of the mountains in the middle of it. We were able to do 800 units. We tied it up. I got Tom Fazio out there. You knew Tom already? No. I did research.

What were the best? Again, you gotta remember, I didn't golf. Knew nothing about golf. But the best, again, you gotta remember I didn't golf, knew nothing about golf, but the best clubs on the West Coast at the time were the Vintage Club, Maroon Creek and the Quarry. And Tom Fazio did all three of those. So I co-called Tom Fazio. He said he wouldn't do it because he just did a course called Greyhawk. A friend of mine owned Greyhawk, so I asked him if it was okay if we could hire Tom. We were gonna do a private club.

His was a resort course, so people paid to play it. So he said, he gave Tom permission. We went out there. Tom basically designed, which I still think is one of the best golf courses anywhere. We reduced the density from 800 units to 243 units. We did that because the landform was so impressive

that everything I learned from the years in Portola Valley, I actually put to practice. The roads were all along the contours. We left everything in its natural state. We de-veggied all the vegetation, boxed it up, and then replanted it. So by the time the course was done, the roads were in,

it looked like nothing happened to the site. It was a beautiful property. We had probably the first sales in Arizona for over a million dollars for a lot. We were selling, like a lot at True North was 60,000, like our cheapest lot was 250,000. So that's when I realized by investing in the amenity package, the privacy and exclusivity, you're going to get way more money than your neighbor.

The lower density is a little counterintuitive because the more density, the more money you think you make. And to get more density, you'd have to do a lot of mass grading, which not only ruins the environment, but also costs a lot of money to grade. So this whole environmental, you know, lesson I got in Porto Valley made real sense because it's really the most cost effective way to develop. And so if you go to a stonics today, even with the homes,

you can't really tell us the development because the homes even blend into the mountain and the backdrop. It was my first project, I think I was like 34 when I started it. Like I said, I knew nothing about golf and it's today's probably still the best golf course in Arizona. There's all kinds of ways to get sales. And when we don't have a track record, we need to resort to all kinds of things. Let's talk about Whitefish, Montana. And is your advice to people to get your first

customers flying for people out on a private jet to come have a look? That's an expensive marketing trip. That's kind of how it works. So at Astancia, it was a golf Mecca, right? Scottsdale is known for golf. We were surrounded by some of the great golf in the country. Now, we had Tom Fazio, everyone else had Moritz Weisskopf or Jack Nicholas. So we separated ourselves just by the definition

of what we were, which was less members, in my opinion, better golf. And so the golfers kind of migrated. So I didn't have to fly people there. But I had to figure everything out on my own because people were telling me how to do things and what to do, agree with it, or I had to really think to figure it out.

I fortunately made a lot of the right decisions. And basically the decisions were based on spending money appropriately and properly. My attitude was, okay, we're going to build this clubhouse. It's going to be the best clubhouse in the state. The course is going to be the best in the state. The food's got to be the best. You know, everything has to be the best.

Everyone tried to convince me to save money here and there I You know didn't right? So my attitude was if you spend the extra 10% instead of cutting the extra 10% That's a 20% difference and your quality is so much better and everyone then told me Okay, go get kiosks at the airport go do ads in the Wall Street Journal You know they were trying to convince me to do all this stuff and I go. It just didn't make sense. It seemed like too much of a shotgun approach. When we opened the course, you know, I was going around meeting everyone since I

wasn't golfing and I knew who all the guests were, right? Because they were like big time people, known people, and the members we had at the time, you know, were fairly substantial people for Phoenix. So I said, okay, this is what we're gonna do. We're gonna put all our marketing dollars into the course, into the place, because if they're here golfing, that means they come to Arizona and they golf. So that's your target audience. The whole place started by doing that and I

would give out hats and t-shirts and you know these rich people like free stuff. So you know little things like that made a big difference. The comfort stations made a big difference. So it was really making the person feel like a member where most clubs make the member feel like a member and the guests feel like a non-member and not very welcome. And I always use this line from the movie with Janet Gretzky was in. The movie was called The Heartbreak Kid. They were playing gin rummy and they were at this fancy beach club in New York and the loudspeaker said, the fireworks show are for members only. All non-members, please look away.

So that's how private clubs were. And so I said, let the members look at the fireworks, or the guests, let's take care of the guests. And that was our marketing, okay. And then my next course was Court of All, and it was a local market. We turned it and made it into a Socom Valley CEO club, which it still is. A gentleman from Estancia helped me with it.

His name was Don Valentine, who was kind of one of the founders of Silicon Valley. Sequoia. Sequoia Capital. Which for those people who don't know, they funded every big Apple, every big company back in the day. Cisco, Apple.

And he was one of the Fairchild five. They came out of Fairchild Semiconductors and he went into venture, won one of the PR. I mean, there was a kind of a, he it was a big deal and he was very helpful there. So I had these two projects and then we started Iron Horse. Whitefish, Montana was kind of an outlier place, but it was beautiful. It had lakes and Glacier National Park

and Whitewater Rafting and had all this amazing stuff. And so when I went and visited, I go, boy, if there were the Four Seasons here, it'd be the most popular Four Seasons in the world. We bought it, but I had to get people there. I would charter like a Lir 35, and I'd bring my friends up there. And they'd go, okay, we'll come, but we're not going to buy. And I would take them fly fishing and we just do You know the Montana

experience And after three or four days that they'd be going Okay, show me some real shake. We show me some real shit I go I didn't think you wanted to buy and they all ended up buying by starting with the Stan saying court of all membership and they all ended up buying. By starting with the Stance and Cordovaal membership, especially Cordovaal, because it's all big Silicon Valley executives, that helped get Iron Horse going, and then it all kind of spiraled upward from there. I want to talk about Casa Migos, but there's a lot there,

so I want to take it step by step. And I want to talk about Jerry Weintraub. And you were in a movie, and then you met some interesting people. And then we'll stop the story right there, and then we'll continue it at that point. Okay, so Jerry was a very, was like, a son of my father, my grandfather.

Probably the third, like, big influence and mentor in my life. He was a big personality. And when I moved to LA, he embraced me. And just his embrace gave me a lot of credibility in LA because he's kind of known for recognizing talent. And he took Elvis Presley on tour, Frank Sinatra. And at this time, he was doing the Ocean's 13 movies. I was moved LA, he kind of moved me into his house and the reason why I think he liked me so much, we did a project in the early 2000s called The Hideaway.

It started as Country Club of the Desert, and the developers basically stole money. And so the financial partners shut it down. We ended up joint venturing it with them. Is this nationwide? Nationwide. There's a big insurance company for people who don't know. Right, nationwide is on your side. Jerry wanted to do the deal.

And Jerry lived at Bighorn, who's a member of the Quarry, knew everyone at the vintage, which are three of the great clubs in the desert. And everyone said, no, it's not going to work. All those clubs are kind of in coves in the mountains. And so they were telling, this is not in the mountains. It's got view of the mountains, it's in the flat, and it will never work.

We bought it, we repositioned it, and probably sold 600 lots in 18 months, and it was a huge success. And so Jerry's like, who is this kid? And so he kind of sought me out and embraced me, was just very helpful to me going forward. I had cameos in some of the Ocean movies and I was, let's say on Ocean 13, I was like the 14th person, right?

I would go with them to all the premieres, would hang out, I was probably there every day at Warner Brothers when they were shooting. I became very close, obviously, with George and the cast. And then you met two guys who were in the movie. Well, one guy who was in the movie, and he was best friends with another guy. Yeah, so George obviously was in the ocean movies. And George has this group of friends, right?

And he's there basically his friends from acting school only, you know, when he struggled and first came to LA and they're all still his best friends. So Jerry George is a very, you know, good friend and loyal person and Randy was one of those friends. He didn't go that acting school with them, but they just became good friends because I think Cindy and George shared at one time the same agent.

Just to make it clear to people who don't drink tequila, we're talking about George Clooney, Randy Gerber, and Cindy Crawford. And Cindy Crawford, yeah. That was the high madam of his group. George is pretty good too at calling the herd in his group because if someone does something they don't like, I mean, he's pretty good to it, calling the herd in his group because if someone does something he doesn't like, I mean he's pretty good about, I have too many friends,

you're not my friend anymore. And he's really good at being loyal, but you know if you break that loyalty he's pretty good at abandoning you as well. And so I was fortunate that you know he had his friend group already established. He wasn't looking for more friends, but because of Jerry, we became really close friends. And Randy and George ended up being one of the first buyers at El Dorado. They built these two beautiful Leguereda houses,

who's a very famous Mexican architect. And they called the house Casamigos. Which means House of Friends. House of Friends, it's a made up word, but it means House of Friends, is where he'd bring his boys, right, for vacations and golf and play basketball and things like that.

And I became part of that group. I was lucky enough to, you know, do that because they're all great guys. We were drinking different tequilas. We didn't really love anything. And so we decided to make our own, but just for ourselves, right? I figured I could put it in all my clubs. Randy could put them in his bars,

and George could just drink a lot. So between the three of us, I thought we would have a business. And so we went to this distillery, and we said we like Clausse Azul, but it's a little sweet, and we like 42, but it's a little bitter. And so we came up with this formula

that if you actually do a blind taste test, we won every time. Because 42 on its own isn't that bitter, but when you taste it next to us, it's very bitter. And Clausiasil is so sweet when you taste it next to us. So we kind of came up with what we thought was the perfect recipe. We did all these taste tests, we won it all, then we went to Southern Wine and Spirits

and we said, hey, what do you think? And they tasted it and said, we love it, we think you've got a winner, we'll take it. Can we stop it there for just one second? Because I think this is critical to the story. Tell people what Southern Wine and Spirits is, and it's very hard to get on that truck because someone else comes off that truck, right? It's just hard to get that deal. So what was that? What is the process and how did you get onto that truck and that distribution system?

Okay. So Southern Wine and Spirits is the distributor for maybe 80% of all the liquor in the United States. We started with this gentleman, Larry Ruvo, who sold him and Steve Wynn had the distributorship for Nevada. Southern bought it. Larry ran it. So we came in and Larry liked it. And he said, you guys need a Blanco to go with it and we'll take it.

And I said, well, we don't drink the Blanco, we drink the Repo so we don't want a Blanco. And he goes, well, 85% of the market's Blanco. And I said, okay, we'll do a Blanco. So we created a Blanco to go with it. They said, if you do 20,000 cases your first year, it'll be a huge success. We went out and we made 20,000 cases.

It cost us a million eight, so we each road checked for $600,000. We sold the 20,000 cases the first two days. We did a little road show to the different distributors, because they're the ones who really buy it from us and then they sell it to the stores or the restaurants. And we sold out literally the first day. So we made another 20 from that first check we wrote, about 600 each.

We never had to put any more money in because it just kept selling, selling, selling faster, faster, and faster. I think it's very interesting. Explain what a road show is. And then I remember my good friend, John Terzian, who's in my wedding party with Madison, who you also know, my wife.

You went into a nice guy one night, and you said, John, I want you to carry my Casamigos there. And of course, it's hard for him to carry new spirits because again, he has relationships with people and just like you, he's got a lot of Venues, but I remember thinking that's really interesting, you know, Mike meldman who's very successful guy Who's a cent a millionaire going into a restaurant to ask a guy that owns a restaurant I mean, it's a one-off and obviously is high-profile places to carry your tequila. I love that story.

Yeah, well we worked it. I mean, all three of us worked it pretty hard. It's hard to say no to you. Yeah, well, one of the good things is like, people at Discovery is a great platform for good products. What I did is we made Casamigo bars at every project. And so you get it to the right people. And when I say influencers, I don't mean like influencers, like people are used to, I mean

like guys who own Kroger's, guys who own Albertsons. And like at Baker's Bay, the money behind Albertsons Safeway, both were members at Baker's Bay. The chairman was a member at Madison. You know, I went to them, hey, can you do me a favor? You know, we just started this tequila, could you put it in, you know, Safeway and Albertsons? And they go, absolutely, we'll make it like our house tequila. Any Safeway, Albertsons you go into or any of your people go into and we don't have it, we'll put it there the next day.

So I'm kind of the guy who is the favor giver. I don't like to ask for things and I don't normally ask for things, but this was kind of an easy ask, right? Because they're selling tequila anyway. We didn't have to pay for anything. It's a pay for play, even though it's illegal to do that, not supposed to be. But it's amazing the shakedown you would get. Obviously, we didn't play that way. And even like my friends would try to shake me down, I go, look, if you don't do this, you're never going to El Dorado again for the rest of your life. Or any other club.

Yeah, he goes, OK, OK. We were able to really get it in places quickly and easily. We had the distribution because Southern was really, really behind us. And there's the CEO of Southern, this guy named Brad Vassar, who became one of my best friends. And he grew up in Sonora, California, which is kind of up by Angels Camp. It's kind of the best friends. And he grew up in Sonora, California, which is kind of up by Angels Camp.

It's kind of the go country. And it's pretty, you know, a lot of meth labs. I mean, it's pretty rough, but it's literally the go country. And one of my first projects that I ever did, and this was like five years before Stansia, was a golf community called Saddle Creek and it was right outside of Sonora when I found out he was from Sonora and then I did Saddle Creek there was a Immediate bond about that. Yeah, he was a huge help because whatever he said anyone at Southern had to do and he's a Scary guy could be a scary guy part of having consumer successes You've got one shot at it, right? You get someone goes out, they taste something, it could be a product, it could be a software

product. I mean, as a VC and being a board member for now, 50 plus companies, it's we tell the founders, don't launch something before it's ready because you get one shot and then they're not coming back. You went through 400 different variations of Costa Migos before you actually said, all right, we got it now? Yeah. Well, that was Randy.

I mean, I was happy with the first one, but Randy's very particular. His palate's very good. And so he really worked it hard. And we're doing a non-alcoholic beer. Right now, we had the tasting yesterday. There's like four of them. I go, this is it. Everyone agreed. And Randy is still, hmm, we could still make it better, which is good because that's what Randy adds value that way. We got it right and then we knew it was going to work because everyone liked it right and the juice was good and if it wasn't no matter who was behind it it wouldn't work and you've seen a lot of people

since our success try to imitate it and it's just not a lot of it's our success try to imitate it. And it's just not, a lot of it's just not that good. So it doesn't work. If we didn't have good juice, no matter who was behind it, it wouldn't have worked. And the reason it worked, besides the three of us all had different strengths and attributes and contributions, it was good.

Four years later, after starting, Casa Amigos, you sold it for a billion dollars, 700 upfront, 300 over 10-year earn-out period. What are you thinking that day? That we sold too cheap. I was the only one who really didn't want to sell. But you don't want to be the schmuck who turned down a billion dollars and then agave dries up or something like that. So I think we got the balance of the billion in a year and a half that they thought would take 10 years. And then they just

kept re-upping the contract. So we ended up doing much better than that. I mean, it was a great success, just a great success. And it's also fun to have success in a different business for all three of us. And it gave the three of us, you know, just reasons to hang out more and be together and go do different, you know, different things for the tequila. There are apparently 28 benefits

to drinking Casamigos tequila. You've assigned it a comfort drinking Casamigos tequila. You've assigned it a comfort station at your Dominican Republic Resort. And I just got to read three of these. It fixes broken hearts. It relaxes your socks. And it makes your hair soft and full.

Was this FDA tested? How did that come about? Yeah. I think my favorite one was I've been on a tequila diet. I lost three days. Let's move on to the clubs themselves. Because I think one of the things is you have a lot of celebrities at these clubs.

And I know privacy is mentioned, but I'm going to mention some names because this is all public information. I'm not disclosing. But you guys like Michael Jordan and Tom Brady and Bill Gates and the Google founders. I mean, it's everybody. You have the Kardashians. Again, this is public. I'm not sure anything Justin Bieber, but you're selling cool in some regard, aren't you? I mean, it's luxury. it's cool, it's family, but people want to be cool.

Yeah, and it probably goes back to my college days and the beginning because, like I said, I was the history major, the non-nerd. You know, probably the, I always say I was probably the dumbest guy at Stanford because I was the only one who went in the real estate because everyone else went into technology. But I always had the big parties, the fun parties, and was always turning my nerdy friends

into fun friends. So that was who I was and how I started. And I think Discovery now, you know, because the brand's gotten so well known and big that it's become, you know, aspirational for a lot of people, whether you're, you know, a businessman, an athlete, a movie star, whatever, whoever you are on a truck company, you know, whatever you do, I think it's become a very aspirational, not only investment, but part of people's life. Let's talk about the financing of one of these clubs. At the beginning, you took on debt.

Now you don't have to take on debt, right? There's 15,000 members or so. We never took on debt, and that's probably the reason we survived 08. I was always a believer in equity and land because land can become very illiquid, right? And the land cycles go up and down. And even though, you know, we create things pretty quick and sell pretty quick, so we kind of get in and out, or at least have enough success

that when a downturn comes that we're okay, even though like 08, even with no debt, it was hard because our markets slow down, they become very inelastic, which means no one's buying at any price. And so you just have to wait it out. And 08 was probably an eight months, 18 months cycle, which in height, you know, doesn't sound that bad,

but when you're going through the 18 months, it was pretty bad and difficult. But since we had no debt, we were okay. And we survived it. we ended up buying Yellowstone because of it and McKenna and some great projects. So we try to stay away from debt. We probably should use debt more to build quicker, to get more houses built faster on our account.

built faster on our account. But I've always been not wanting to put that on just because when you do have a downturn there's no way out.