We Study Billionaires - The Investor’s Podcast Network - TIP151: Billionaire Jesse Itzler - Business, Branding, Everest & More (Investing Podcast)

Starting point is 00:00:00 You're listening to TIP. About a year ago, we had the owner of the Atlanta Hawks basketball team on our show, Mr. Jesse Itzler. After airing the episode, we received so much mail from our audience about this episode that we had to try to bring him back on the show. The thing about Jesse is he's not only brilliant from a business standpoint, but he's also a hardcore endurance athlete that has accomplished incredible feats like running 100 miles within 24 hours. The last time we had Jesse on the show, he was talking about his experiment to live with a Navy seal for 31 days so that he could learn more about discipline, physical and mental stress, and becoming a better version of himself. But today we're going to explore some other areas of Jesse's life, and that's his business, decisions, and his way of thinking. One of Jesse's biggest creations was a company called Marquis Jet. Later, Jesse sold Markey Jet to Berkshire Hathaway's Net Jets.

Starting point is 00:00:53 during our discussion, we asked him about that entire experience. How did he raise the money? How did he get the idea? What was it like to sell the business and much, much more? As an additional note, Jesse talks to us about his next big physical challenge. And during the discussion, Jesse presents a bit of a surprise to me personally, which I was definitely not ready for. I really can't wait to share this episode with you guys. Jesse talks about how he started a jet company without knowing anything about the industry.

Starting point is 00:01:23 A really fascinating discussion. In this episode, you'll learn why Jesse used to send out 3,000 handwritten letters per year and how they change his life. But I think the most important takeaway you can get from this episode is the advice to his 20-year-old self. All right, so let's do this. You are listening to The Investors Podcast, where we study the financial markets

Starting point is 00:01:50 and read the books that influence self-made billionaires the most. We keep you informed and prepared for the, unexpected. All right, so how's everyone doing today? As we said in the intro, we have Jesse Itzler with us, one of our favorite guests that we bring on the show. And Jesse, such a pleasure to have you here with us. Thanks so much for taking time out of your busy day to talk to us and our audience.

Starting point is 00:02:20 It's great to be back. I missed you guys rapping, so I figured the only way to do that was on the show. Oh, my God. Probably one of our most embarrassing moments on the Investors podcast. If you haven't heard our rap song, I guess we'll put a link in our show notes so we can embarrass ourselves even more. So let's kick this off. So last time we talked, you were here and we were talking about this incredible book that

Starting point is 00:02:45 you wrote called Living with a Seal, where you hired a Navy Seal to come live with you for a month. I can honestly say that was probably one of the most entertaining reads we've ever done on the show, probably one of the funniest reads we've ever done on the show. But love the book. But this time, we're bringing you back because we want to talk business. we really want to get into some of the nitty-gritty things that you've accomplished in your life, which is just beyond profound. And we think that it's going to be really inspirational for a lot of people on the podcast

Starting point is 00:03:12 to kind of hear some of these stories and to hear what it was like for a person to build such a huge business from the ground up. And kind of those initial stories. I don't know if you've read the book by Phil Knight, Shoe Dog, but he does a great job in that book talking about the early days of Nike. So many people that have really accomplished these big things want to talk about everything that happened at the end. But Phil did a great job talking about what happened on those very first days founding the business. And that's kind of what we want to hear from you on Marquis when you founded Marquis Jet. So how did you come up with the idea and talk to us about the early days of founding the company?

Starting point is 00:03:50 Sure. Well, first of all, I just got a chance to hear Phil Knight live at a conference speak for one hour. And I didn't read the book. I'm familiar with it. I'm going to read it. But what was interesting about his story is how many times he almost went out of business in the start of Nike and how they were able to get through it and the belief and just the trust. And he had a couple of partners, just the trust in each other. And they just gutted it out, you know?

Starting point is 00:04:17 Yeah. And I could relate to his story in some regard. And I think a lot of your listeners will is that, you know, he had no prior experience in the shoe business. so it's not like he went sneaker school or, you know, there weren't even running sneakers really on the market at that time. Maybe they were just basics. And for a lot of people, not having prior experience can be a big deterrent. You know, so that's a dream crusher. So, okay, I want to open a restaurant business, but I've never done that before.

Starting point is 00:04:44 I want to have an apparel company. I don't know anything about manufacturing or the apparel world. And people either shy away from that. It's too scary. But for him and for me, and for me. all my adventures, it was a great blessing because it guaranteed that we would do things differently and get different results. So a lot of times, there are hidden blessings. And for me, and for Phil, not comparing myself to him at all, that was a hidden blessing. Now, as far as Marquis Jett goes,

Starting point is 00:05:12 which was a great success for my partners and I and for our team, perfect example. I had no background on an aviation. I was a guest on a private plane in the late 1990s. And when I walked on the plane, it was like the scene in the Wizard of Oz when everything goes from black and white the color. I could believe that people actually fly this way and how convenient it was. And I didn't have to take off my shoes and there were no lines. And I could create call and say, hey, guys, we're running 15 minutes late. And by the time my partner and I were on the flight landed, we're like, we need to figure out how we could fly privately more often. And we had this great idea. We're like, well, imagine if we could just have access to our own plane with none of the

Starting point is 00:05:58 responsibilities. So it could be ready on eight hour notice anywhere in the country. And it would work like a debit card. There was like a Starbucks card for private aviation. The problem was we had no airplanes. Hard to start a private jet company with no airplanes. But the idea really came from, I think like a lot of entrepreneurs with similar stories of how they started, we were frustrated consumers, you know, we found the need. We realized when we investigated the world of private aviation that it was super expensive, so we wanted to make it more affordable. The options out there weren't great. It required a lot of capital, usually a long-term commitment. There were issues around consistency of the airplanes if you chartered.

Starting point is 00:06:39 So we wanted to just get rid of all that, make it really. really simple, make it way more affordable, not lock people into this long-term commitment. And we really just thought about what would be the perfect program for us and thousands and tens of thousands of people out there if we could create it from scratch. So we thought backwards from there and designed this program that ultimately became in the marquee jet card that ultimately did, you know, billions of dollars in sales. That's incredible. I just love how you described it. It changed to color. You know, you become more aware.

Starting point is 00:07:15 You look at your own life and say like what's missing or what product could be improved or what problem can be solved. And when it hits you, it is like that, that clarity. It's totally gray and cloudy. And then when it hits you, the idea, you don't even have to ask people just for validation. You know, in your heart of hearts. You know, a lot of people ask, make a mistake, I think, quite honestly, early on in their journey. and they ask people in their inner circle for advice or their opinion.

Starting point is 00:07:44 And a couple of things. One is you can get talked out of it. You know, when my wife started Spanx, if she would have asked her parents or close friends about, you know, footless pantilers, they would be like, if it's such a good idea, Sarah, why have the big guys done it yet? And that might have scared her off. Or they might have said, Sarah, you've never even taken a business class.

Starting point is 00:08:02 What are you doing? And that might have scared her off. And really just to seek validation, you know, you know, when the idea hits you, if it's good. Well, I think what you're getting at, Jesse, is being naive. So one of the advantages of being, you know, somebody who doesn't have that background, doesn't have that experience is they're very naive as to all the challenges and difficulties of actually pulling it off.

Starting point is 00:08:25 Being naive like that is sometimes a really good thing because if you knew how hard it was, you might not ever take that first step. Yeah, it's very true. So that goes back to, you know, not knowing what you're not. don't know is a gift. That's a very interesting realization, especially for entrepreneurs, I guess. Okay, Jesse, so I'm curious about this. When you were just starting my kid jet, how did you go about raising money? Was it something you needed outside investors for? And what's your thought process about giving up equity of your business? Well, it's a great question, Stig, especially if you're

Starting point is 00:09:01 starting something that's capital intense, like, you know, a private jet company. I would just say that, you know, taking in money, it comes with great responsibility. So you really have to think through who you're taking the money from. What are you going to use the money for? Why do you need the money? When is the right time to raise the money and recognize that that's going to put a great amount of stress on you because you lose yourself a dollar. It's one thing. But if I lost, you know, you pressed it and you stig money. So there's a great responsibility with that. And that responsibility comes with communication, updating your investors. I mean, this might sound obvious, but it's a reality.

Starting point is 00:09:40 You don't just take money in. It comes with communication. It comes with questions that are going to have responding to. If you have 50 investors, that could be 50 calls a month. What's going on? Why aren't we advertising here? You have to just really think through that, because that could dictate where the money comes from, right?

Starting point is 00:09:59 So I never even knew that people really raised money. We started Markey Jet when I was 28 to 29 years old. So this was a completely new process to me. And I went about it like because no one told my partner and I really had to raise money, we went about it like, you know, Kermit the Frog would go about it. But again, it was a good thing. We had already secured a partnership with Netsjet, who provided us with the airplanes. And that was sort of contingent on us putting in our own money and raising additional capital.

Starting point is 00:10:31 So we didn't go at PowerPoint stage. We went when we already had a partnership in place that would make it a little bit easier for people to bet on two people that had no experience in aviation. Right. Let's say I went to my financial advisor. I'm an investor and say, I want to put money in something. Let me tell you about it. There are two CEOs that have never done this before in their life.

Starting point is 00:10:53 They have zero experience. It's in a super capital intense business. Airplanes, private aviation. We're going to sell time on. private jets with two guys that have never done it. They don't have an office. They're going to go figure that out. Oh, they have no employees. They have no experts on their side. They really don't even have much of a business plan. You'd be like, are you nuts? You know, but that's really what we were. So we had to build something around that. So the first thing we did is we secured rights.

Starting point is 00:11:20 We had a partnership with net jets. The second thing is we brought in two people to help us. We hired our weaknesses immediately. The first thing we did. And we put in our own capital. Not a lot because I didn't have much money at the time, but my partner and I both put money in. So we had skin in the game and we were also not just risking reputation, but capital. So that was kind of the process. So we had minimized a little bit of the risk in the sense that we had this partnership. And then the next thing is we talked about valuation stig. We wanted to make it fair. So for us, it wasn't like, let's keep as much equity as we can. and let's try to get this crazy high valuation.

Starting point is 00:12:01 We were like, let's make it really fair for us and really fair with a ton of upside for anybody that bets on us. And we weren't sicklers about that. I mean, we put a flag in the ground and everybody got the same deal. You know, everybody, oh, was this the best deal? Can we get free hours? No, everybody got the same thing. It was most favorite nations.

Starting point is 00:12:20 And we went out and we went to friends and family first because we felt like that would be the easiest way to take in money. That would be the least amount of responsibility emotionally. And then we could say that, okay, we have X amount raised to date before we went out to the street and tried to raise additional capital. And then we tried to bring in a big name. We tried to bring in someone that was credible to help others follow suit. And that doesn't have to be a seasoned investor. It could just be someone, I mean, it could be a neighbor that's a lawyer and say, look, we have so and so in. He's done several investments in his life. This is fully vetted. He's fully vetted this already, that kind of thing to create a story that could attract additional capital.

Starting point is 00:13:08 And that was sort of our process. And we were fortunate to bring in some credible people on Wall Street, some credible entrepreneurs. And that helped. We raised $5 million. Part of that was from our own money. But in total, we raised only $5 million. That's not a lot of money at all. It doesn't give you a lot of breathing room or runway. But we didn't want to take in, you know, at this point, we were like, let's see if we can make it work with just this amount of money. We never did another raise beyond it and just bootstrap our way from there. Let's take a quick break and hear from today's sponsors. All right.

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Starting point is 00:17:42 That's Shopify.com slash WSB. All right, back to the show. That's absolutely incredible. So it kind of gets a question I wanted to hit on next, which was your customer acquisition approach. So you were saying that you had some people from Wall Street and that you got some like celebrity type people to endorse it to give this authority. Are you just like cold calling these people or like how are you going about that? Because that sounds like a lot of hard work. I'm just curious how you guys got through this.

Starting point is 00:18:13 Right. So after Marquis-Jet, I was involved in a company called Zico Coconut. out water. And we had a sample. The way we acquired customers was predominantly by trial. So we had to demo our product all over the place, get people to taste it, hope it converted. We had the best product on the planet to demo. Just if I could fill a plane that held 15 passengers and call NBA players and say, you want to lift to the All Star game or flying privately. And they got on, if I could get people on the airplane, 50 to 60 percent, of them, maybe 100% of them, would be addicted the second they walked on the plane. It was a drug.

Starting point is 00:18:53 So for us, a lot of the acquisition came from guests of people that already had purchased time on Marquis jet. So that was a big strategy for us was demo the plane, show the plane, get people on the plane, have people bring guests, do our own trips and always fill the plane. If we had an FD.C., Preston, come with us, man. I know you live in D.C. You want to come to Chicago for dinner. Literally, that was a big strategy. The other thing is, I'm a big believer in PR because it's so inexpensive relative to advertising. So we had a great PR machine. In fact, we were, I believe we were on episode two of The Apprentice, the second episode ever of The Apprentice, which was risky because we didn't know if it would be a success or a failure. And that was a

Starting point is 00:19:39 big driver for us. And then word of mouth, you know, we cared more than anybody else. We cared more than anybody we showed up at every flight initially. We carried bags. We followed up with phone calls. If you were flying, Stig from your home to Mexico on a vacation, we would send you a book about where to go. I mean, we out cared everybody. And that created word of mouth. That created, you should see what these guys are doing.

Starting point is 00:20:05 They have an unbelievable product, but they're building this amazing business. I really trust them, that kind of stuff. And then there was no decision. If you were looking to get into this space and you wanted to fly privately, how could you not at least give us a call? And then once we got the phone call, service to hell out of them. So it was a lot of hustle, though, right, Jesse? I mean, you were calling. You were trying to find people that knew other people.

Starting point is 00:20:31 I mean, this was a lot of hard work, a lot of networking taking place. This stuff just doesn't happen. I mean, you were aggressively just hustling all the time. We were. And quite honestly, the work started before we launched. Marquis Jett. The work started when I was 21 years old earlier. The work started when I was in high school when I started friendships and kept those relationships for my whole life, kept my college relationships, you know, was out networking when I was 21 through 28 years old every night,

Starting point is 00:21:03 every day. I was sending 10 letters a day every day to people that I was grateful for. I mean, that's 3,000 people I would hit in one year that probably never got to be. I was going to I got a personal handwritten letter in the mail. Hold on, hold on. I was speaking my network. Explain this letter stuff even more because we've talked to a guy named Guy Spear and he swears by, he's this big value investor. He's like, if I could put my emphasis on doing value investing or sending letters to people, thanking them for what they've done to me in my life, I would put my interest in the letter sending every day of the week.

Starting point is 00:21:38 So I want to hear your story on this because this is fascinating. Well, I just, you know, I just realized that there's a lot of clutter. At a young age, I was fortunate to recognize that I never got mail. And I got so excited when I get a letter. You know, now with email or something, there's no mail. But I remember as a kid at Sleepaway Camp, when I got a letter, I'd be ecstatic. Well, my mom would hand me a letter and say, Captain Kangaroo fan club sent you a letter. I'd be like, what?

Starting point is 00:22:07 And it was memorable. So I just decided, like, I had no money out of college. I was like, I'm going to get to as many people as I can in the least expensive way, 32 cents, 32 cents to change someone's life and become part of their life forever. So I started writing 10 letters a day to people that impacted me, they could be strangers. It could be like, can I have your business card, Mr. Dorman, that you were so nice, or Mr. Waiter or the manager of a restaurant. Hey, you guys took great care of me.

Starting point is 00:22:39 Next time I walked into the restaurant, I was king of the restaurant for 32 cents. But everybody, you know, if you took a meeting with me, I did your podcast, if I had your business card and you impacted me, you were going to get a letter. And I kept the list. And I built this network through not just that, but that was a great tactic. And it made me feel good. Yeah. I felt great writing them.

Starting point is 00:23:02 And even last year, I wrote 50 letters on New Year's Day to 50 people that last year really, I wanted to thank for just being good friends and helping me and going out of their way. And it felt great to write. Apparently, it felt great to receive. But that simple, inexpensive exercise, I didn't even know it was the start of Markey Jet because those were people that I stayed in touch with that I could tap into when I had to sell the first 20, 30 card, Markey Jet cards that I could say, hey, give me a shot. You know, when you started Markey Jet, and I just wanted everyone out there to know it, it starts today, no matter what you're doing. Like, you know, whether you're trying to acquire customers, you know, email lists, whether you're

Starting point is 00:23:48 trying to, you just never know. You know, look, 50 Cent, before he was 50 Cent, was my intern. He was a boxer. He was 18 years old. I had a music and marketing company in New York and the DJ, Jam Master Jay from Run DMC was working with this young artist out of Queens named Curtis. He said he needs a place for the summer. He came in. He worked, you know, and I had no idea later he would become 50 cent. Fast forward 10 years. We start Markey Jet.

Starting point is 00:24:18 You know, we're a couple years into the business. And I get a every day the flight manifest of everybody that's flying with us. And I see that 50's on a plane going somewhere for one of his shows. So I wrote him a note. I said, 50, you never, ever, ever going to believe this. It's Jesse Itzler. Congratulations on your success. You're on one of my airplanes.

Starting point is 00:24:38 We had a small little office. And, you know, from that moment, he basically committed to fly with us. So my point is, you never know who's going to be the next 50 cent. You never know who's going to be what. When I started writing team songs for NBA teams, Adam Silver was his first year at working at the NBA. Now he's the commissioner. I'm part owner of the Atlanta Hawks. He's the commissioner.

Starting point is 00:25:00 You never know. It starts early. It starts today. It starts by building your network, being nice to everybody. That costs nothing. You don't have to be the smartest. You don't have to be the best looking, but anyone can be the nicest. You got to be thankful. Yeah. You got to be thankful. When I look at the letters, it's a win-win. But at the end of the day, you have to be a person of gratitude and to be thankful to even take that step what you're talking about. So I think it talks a ton about your character. And I think that anybody else out there that's doing something similar, it speaks a lot. lot of their character, that they're a thankful person. They've got a lot of gratitude for the people in their lives. Amazing. I love that. Okay, so we started in 2001, where you co-founded Marquis JET. And then eight years later, it was very successful, and you decided to sell the company. Now, what was you major motivation for this? And why did you decide to sell it to Net Jets? We had been working super hard for eight or nine years at the time. The marketplace was changing. So all of a sudden, there were new jet card programs.

Starting point is 00:26:05 Delta got in the game and others got in the game. So there was competition. The market changed. We changed. We got older. We were growing. We wanted to expand into other areas outside the United States. We wanted to buy more airplanes, which required more money.

Starting point is 00:26:23 And there were great efficiencies with partnering or selling to, ultimately for us, was net checks, Berkshire Hathaway, Warren Buffett company. And also just to monetize it. We have been monetizing it. It was cash flowing and it was an amazing business. But it just felt like after eight years, it was time. So we had a great partner in Netsets. They were the natural exit for us.

Starting point is 00:26:50 And because they supplied us with the airplanes and the infrastructure and they were the back office and they wanted to do it. So they've been great to us. We've been good to them. And it was just one of those fits. We weren't out shopping this to other companies. We built it up. We proved ourselves.

Starting point is 00:27:05 We had loyal customers. The market changed. We needed more money. They felt it was the right time. And that was that. Interesting. Now, how long did that process take whenever the initial conversation started to happen? Was it quick?

Starting point is 00:27:20 Did it take a year or two? Talk us through a little bit of that. It was quick because they knew our business so well. So they knew everything under the hood. There were no skeletons. we've been partners for eight years. The way our model worked is we piggybacked off of their fleet of 700 airplanes. Convinced sounds like manipulated, but we discussed and agreed that in our initial meeting

Starting point is 00:27:44 that we would use their airplanes. So like we didn't have a lot of capital expenses because we didn't have to go long airplanes. When if you were to buy 25 hours from us, we would then go buy it from that jets. It's not like we'd have buy all this time or inventory. So they already knew our customers. They knew our model. They knew everything. So it was a fairly easy and quick transaction and a good one for everybody.

Starting point is 00:28:10 Jesse, so I would consider you an expert at branding. Whenever I look at what you're able to do and kind of networking, all that, I read an article where you said that unless you start with $100 million marketing budget, any brand you start from a PowerPoint is just about inducing trial, changing customer habits and getting repeat business. And can you elaborate on this idea more for our audience and talk to us about branding and how you think through this? Because you had mentioned that you brought celebrities into your Markey Jet early on. I see that as just a very smart and branding, marketing kind of position and play that you guys put on.

Starting point is 00:28:44 Talk us through this. Talk us through how you think through branding. Well, before branding, I think it starts with product. That will induce trial and get people to do something or buy something one time. but if the product isn't great, it'll never work. So before branding, I think the first investment is getting the product 100% right, not cutting corners, not rushing to put it out, but making sure that the whole experience as it relates to your product is amazing. Packaging, customer service, if it requires customer service, follow up, everything,

Starting point is 00:29:19 soup to nuts is the best it can be. Then it's time to talk about brand. And for me, it's always been about trying to create that real strong emotional connection, talking about the why and not the what of the product. Why am I doing this and what problem is it solving and generating that emotional connection? You want to be memorable. You want to be loud. You want to be different.

Starting point is 00:29:44 You want to stand out. But you really want to talk to people and let them know why you're doing this and what's in it for me quickly in a short amount of time and in a very digestible way. And I think people often make that mistake. They talk at the customer. Or let me tell you what this does. Let me tell you what this does. And not like why I started it or why this can help you.

Starting point is 00:30:06 And that's a big common mistake. Look, we live in a world where if you don't stand out in a couple of seconds, you know, or less, really fast, it's going to be really hard to make it and survive and to thrive. So for me, that's sort of the foundation of where how I look at branding comes from. In your quote, which I love, and I might have to edit that a little bit now that I rehear it, Preston. But one thing I would change about that quote, having heard it now, is getting people to change their habit is super duper hard. I might tweak that quote a little bit around the part about getting people to break a habit because that's a really, really hard thing to do. So I agree with you, Jesse, but I have to come forward with a story here.

Starting point is 00:30:53 So you have actually changed one of my worst habits in my life, and you don't even know it. So before we did our interview with you last time, I had a bad habit of drinking energy drinks. Horrible habit. And so you came on the show, and at the very end of the show, I don't know if you remember you giving us a book recommendation. And you said, you know, if you could recommend one book, the name of the book was fit for life. and so we were, Stig and I after the show was over, we kind of looked at each other, we were like, that was kind of a strange book recommendation. Well, Stig goes out and Stig reads the book.

Starting point is 00:31:25 Okay, I'm sitting on my hands, still drinking my energy drinks. Stig goes out, he reads the book and he then reports back to me and he says, Preston, you've got to read this book. This book is like absolutely incredible and it's changed the way I eat. And I said, all right, now I've got two people that I really respect saying this. So I go ahead and I read this book. and this book is life altering. Like, I'm telling you it has changed my health in such a dramatic way.

Starting point is 00:31:51 I used to get colds all the time. And like, so I read this book. I stopped drinking the energy drinks completely, haven't had one since I read the book. And I can't tell you how much. So you actually have in a way had me stop drinking coffee. You had me stop drinking energy drinks. And you completely changed my habits. And I have to thank you personally right now because I've been doing this for a while now,

Starting point is 00:32:14 Jesse and I can tell you, I mean, fruit until lunch every single day. I do it and I love it. It's absolutely incredible what you've done for me and Stig. We both do this now. Well, that's amazing. You bring up a really good point. A lot of people when they start, either when you get older as they start businesses, go out of balance, right? You're spending so much time and you lose, you know, you're not working out, and you're eating habits, maybe change, you gain some weight. But health is such an important part and how you feel. If I said to you right now, Preston, you know what? You're worth $10 billion.

Starting point is 00:32:48 You're on a deserted island with 50 Victoria's Secret models feeding you grapes. Okay, you're on top of the world. You have all the money in the world. You have these beautiful models. You're on island. They're feeding you grapes. But guess what? You got a sore throat.

Starting point is 00:33:02 You don't care about your 50 billion or the 50 models or the island. All you care about is every time you swallow that your throat doesn't hurt. that's how important health is to you. And if like if you have a sore throat on this journey, it's not going to be good. I spend a lot of time working on how I feel. You know, I mean, if you have all the money in the world, then you're not happy. It means nothing. I'd rather be literally, basically broke and super happy than be a gazillionaire and unhappy.

Starting point is 00:33:34 And, you know, there's a great quote. If you have health, you have hope, if you have hope, you have everything. So I'm glad that, you know, you're doing it. that and I hope you reap the benefits and feel energized and don't get any more colds because when you have a cold, you don't care about how much money is in your bank account. You just want to get better. This might not even sound believable, but since I've been on this diet, I can honestly say I have not had one cold since I've been on this diet. And that's just, it was crazy. It sounds believable to me. I've been doing it for 27 years. I've missed maybe three days of work.

Starting point is 00:34:05 Yeah. So we knock on wood, but I have crazy energy. I've run over 50 marathon distances. ultra-marathons, you know, four kids, running a business. I mean, like my day, I feel like I got 30 hours in a day. Just because of the energy level. And I think, you know, not to get sidetracked here, but I think that what you eat plays a big role in how you feel, how you feel translates into how you operate in business. So listening to your story is not just about business,

Starting point is 00:34:34 but also about how you adopted a practice of handwritten letters, how you're taking care of your health. If you have the ability to go back in time and speak to your 20-year-old self, what would be your advice? A really good question. I would have to say, I mean, there's a lot of things. You know, as you get older, you learn all these things. You say, I wish I knew that when I was in my 20s.

Starting point is 00:34:58 Being vulnerable, my relationship with being vulnerable would be something that I would have a conversation with myself about. Vulnerability is so important to success. Most of the things that I look back on my life now came with being. totally exposed. So understanding that that's a good thing, I've recently become friendly with Tim Grover, who is Michael Jordan and Kobe Bryant's coach, trainer, mind coach, whatever you want to call it. And he basically had mentioned that pressure is a privilege. And it is. You know, if you get a raise or new job, you know, you get higher up at your office or whatever, that might

Starting point is 00:35:37 come with more pressure, but it's a privilege. Someone's trusting you, putting out a, book, living with the seal, it's going to get reviewed, people are going to critique it, they might hate it. It's just you're totally vulnerable, but those things have been the things in my life that have given me the best pleasure and best reward, running 100 miles. Either you finish or you don't. You're totally exposed. And those, I would have told myself at 21, that's a good thing. Don't shy away from that vulnerability. When that happens, that means you're probably onto something. So I really like you advised, Jesse, about being vulnerable.

Starting point is 00:36:15 But I guess if you expose yourself and your myth with adversity, I guess we all are from time to time, how do you handle that? Do you find that to be so much harder because of the vulnerability? Or how do you handle it? A lot of self-talk to myself saying, you know, just go ahead, go. Like, go now. Don't talk myself out of it. don't overthink it. Don't shy away from it.

Starting point is 00:36:40 It's become part of my life. Stick now. I mean, it's like every day I'm trying to do something that is outside of my comfort zone or makes me uncomfortable or puts pressure on me. I'm trying to take on more. So it's literally part of my lifestyle because I find it so rewarding. It's scary. Believe me, this is podcast.

Starting point is 00:37:01 You know, like what if people hate it? What if the reviews are all thumbs down? What if you guys, people say, oh, Jesse's a jerk. and I'm unsubscribing. I mean, everything. You just don't know. But you just go ahead and you do it because, to me, that leads to the most rewarding gifts. Let's take a quick break and hear from today's sponsors.

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Starting point is 00:40:46 And in the article, he says that Warren Buffett taught me how to think in a positive direction. And he says that Warren Buffett's one of the most positive thinkers. And later in the article, he says, you know, a lot of people would look at that and say, well, of course he's a positive thinker because he's got. the most money in the entire world. You know, like, that's what Bill Gates says, I don't think that that's why he's happy. I think because he was a positive thinker is the reason that he was able to become so wealthy and accomplish so many things.

Starting point is 00:41:12 And so getting kind of at the root of what Stig was saying, and I look at what you've done, Jesse, in order to keep trugging along and doing a hundred mile race, you have to be a positive thinker. You have to say, you know what, I can do that. You have to start off with that positive direction saying, I can do these insanely difficult things. Well, I just want to say one thing to that, Preston. It starts with thinking. I think we live in a world now where we're bombarded with emails and voicemail and boxer and all these things that we actually have forgotten how to think. We don't take time to think. So clearing your calendar to spend a little time to actually think and visualize and plan is so important. And I think so few of us do it today. You know, we're just always on the go. The second we get up, up, okay, I'm going to go. I'm going to work out. I'm going to go to work.

Starting point is 00:42:01 I'm going to this. And take the subway. I'm going to do this. Call this guy. This is like, when are we taking time? I'm sure Bill Gates, when he was younger, all the way till now, takes time to think. Yeah. So, Jesse, you're all about doing these epic things. And in fact, you named one of your businesses after this extreme race that you did where you literally ran 100 miles in 24 hours. Most of our audience knows that you hired a Navy SEAL to live with for a month. So I guess my question is this, what in the world's next? Like, what are you going to do next? What's the next big epic thing that you have planned? Well, I have this amazing event coming up in October. I'm glad you even brought this up because I

Starting point is 00:42:45 can share it with your listeners. And I think it's going to be a once in a lifetime. And honestly, something that people can just use to invest in themselves and really grow from. So here's the deal. I rented, this is unbelievable. You guys are going to love this. rented Stratton Mountain in Vermont, the entire mountain, in October for the weekend. And we're bringing in, everyone gets their own teepee tent. It's like with a bed and a heater. I mean, it's creating our own village of tents, bringing in bands and food trucks and speakers.

Starting point is 00:43:15 So it's really festival-like, but here's the challenge. You can jog or walk, crawl, hike, whatever, up to the top of Straton Mountain. You take the gondola down, the high-speed gondola down. Go back up, gondel down, up, down until you climb Everest, 29,000, 29 feet. I love this. Okay. You call it Everesting.

Starting point is 00:43:40 And I say it's an investment in yourself because it's a weekend with entrepreneurs and like-minded people where you are going to really be pushed and challenged mentally because it requires patience and determination. Meet all these amazing people. leaving like I can conquer the world. That's the goal. Anyone that's interested, if you don't mind, a quick plug, you can just go to the website, www.2.290, so 29, Z-E-R-O-2-9.com and get more information. But I love to have you guys. Stig, I want to see you on the mountain. That's who I want to see on the mountain, too. You know, Jesse, I'm there. I'm serious. I will absolutely positively come to

Starting point is 00:44:26 this if that's the invite because I would love to do this. This sounds like something that's right up my alley. Now, Stig on the other hand. Well, I'm pretty psyched about having the chance to do a third interview with you, Jesse. So are you promising me an exclusive interview at the top of the mountain if I go? I'll definitely walk some of the, it's 17 times up. You have two and a half days to do it. And after you do one, you can sit and listen to music. And when you feel like going up, you go up again. I will definitely walk a few of the hills with Preston and make sure you have fruit for your breakfast. And you'll be all set up. Stig, I'll get you whatever you need for your breakfast.

Starting point is 00:45:04 But no, I'm really looking forward to it. These are the kind of challenges. What I love about this is it's totally doable. You know, you just have to stay with it. It's a walk. It's a hike. But it's just, these are the kinds of things that make me feel super alive. But I feel like also translate into all the different areas of my life.

Starting point is 00:45:22 I feel like if I stay with something like this and I do it and I complete it, when something hard happens at work or an obstacle comes my way, I'm like, I can handle this. I do stuff like this. I've done something like this that's hard. And instead of shying away from the challenge, you know, it teaches me to attack it. So I believe this is a great weekend investment in yourself with amazing people and Preston, man. That would be unbelievable. No, I'm being serious. Like, If you're serious that I can come to this thing, I'm there. I will be there. See, what's the date?

Starting point is 00:45:55 I probably need to know the date first. It's the weekend of October 13th through 15th. And, you know, I would look at it as one part like Aspen Music Festival and one part like Spartan. It's like it's going to be super festive and fun and social, but it's also going to be don't high from the challenge. I'm looking at my calendar. Is that a weekend? It is. It's a weekend.

Starting point is 00:46:16 Okay. Awesome. I'm there, man. I got to go get clearance from my wife, you know, but I'm sure she'll, after a little convincing, I might be able to convince her. We'd love to have you. Dude, how do you think of this stuff? This is unbelievable. How do you think of this?

Starting point is 00:46:32 Oh, man, it's just, I just, it goes back to what we just talked about earlier, frustrated with the options. You know, it's like, how many marathons or races or 5Ks can you do? How many obstacle courses can you do? How many times can get zapped by, you know, at some of these races, by electric currents? like, let's do something super cool and thematic, different. I mean, I want to walk into my office and like, what are you training for? I'm training to climb the vertical Everest. I'm doing it in Vermont, 300 entrepreneurs.

Starting point is 00:47:03 So, Jesse, even though that you started out as an entrepreneur, one of the things that you're most famous for today is that you are the co-owner of the Atlanta Hawks. Now, from a business standpoint, what is the most surprising aspect of owning a sports scene. Hmm. Well, first of all, you know, I'm part of the ownership group. The ownership group consists of 14 or 15 of us and we all get along. So that's kind of rare.

Starting point is 00:47:30 I knew most of the guys beforehand, they're friends of mine, pretty much all, but one or two. Doing something with friends is amazingly fun and that's been a great part of it. I didn't realize just all the nuances. It's the sports team. So there's the product that goes on the court, but there's so much that goes into the operation, especially in this fast-evolving world of sports. Look at the sponsors in the NBA, from companies that put on Daily Fantasy to, you know,

Starting point is 00:47:59 all these new categories have emerged that weren't here 10 years ago. So there's constant evolution. The community is so passionate about the team. You know, the fans are so passionate about the team. That comes with a lot of pressure. So walking into Whole Foods or going into drop my kids off at, you know, school or going to the swim meets here, people only want to talk about the hawks, which is great. I do too. But I think the biggest thing for me is so far has been, you know, I've gotten to

Starting point is 00:48:30 be pretty close with a lot of the players. And this is a business where there are trades, there's free agency. There's, you know, if you go back three or four years ago, when I first got involved with the team as a consultant from a roster of 14 or 15 guys, there's really only two or three guys remaining. So I've gotten to be really close with the players, but it's just the nature of the sport. Players come and they go. And that's been really challenging for me because, again, you have a close friend that all of a sudden moves to the West Coast, whether there's a basketball player or a friend or a coworker or a family member, that's tough. That's been a hard thing for me, quite honestly. It's like, why can't we just keep this team intact forever? You know, that never really

Starting point is 00:49:16 crossed my mind coming into this, that that would be the case. And we're still a friend. I'm still have those relationships, but you have to constantly build new relationships and nurture them and get trust. And that's a big investment in time and a big emotional investment. And every year, that changes. So that takes a lot of energy. All right, Jesse. So that's all we have as far as our questions. We just really appreciate your precious time to come on the show and talk with us. If some of the people from our audience want to interact with you and kind of shoot you a message or whatever on Twitter, can you tell them your Twitter handle and also the address again for your Mount Everest trip? Because I think there's going to be some people that want to check out the page. Appreciate it.

Starting point is 00:49:57 On social media, Instagram or Twitter, I'm at the number 100 mile man. So the 100 mile man. And anyone that's interested in joining us on the Hill in Stratton, I'd love to have you. You can register or get more information at the website, which is www.29, the number 29, zero spelled out, Z-E-R-O-29-29.com. I really appreciate you having me on. And it's been a pleasure to say, this is round two. Round two, I felt like it might have been as good as round one for me in the ring. We'll have Jesse's Twitter handle in our show notes. We'll also have his 29029 event in our show notes for the link. So if you guys want to find it there as well, you can find it there.

Starting point is 00:50:41 So Jesse, thank you so much. What a pleasure. Thank you, guys, so much. Appreciate it. All right, guys. That was all that Preston and I had for this week's episode of the Ammasters podcast. We see each other again next week. Thanks for listening to TIP.

Starting point is 00:50:56 To access the show notes, courses, or forums, go to theinvestorspodcast.com. To get your questions played on the show, go to AsktheInvesters.com and win a free subscription to any of our courses on. on TIP Academy. This show is for entertainment purposes only. Before making investment decisions, consult a professional. This show is copyrighted by the TIP network. Written permission must be granted before syndication or rebroadcasting.

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We Study Billionaires - The Investor’s Podcast Network - TIP151: Billionaire Jesse Itzler - Business, Branding, Everest & More (Investing Podcast)

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