For a lot of people not having prior experience can be a big deterrent. That’s a dream crusher like, “Okay, I want to open a restaurant business, but I’ve never done that before. I want to have an apparel company. I don’t know anything about manufacturing or the apparel world.” Then, people either shy away from that. It’s too scary. 

However, for Phil Knight and for me, in 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. For me and for Phil, not comparing myself to him at all, that was a hidden blessing. 

Now, as far as Marquis Jet goes, which was a great success for our team. Perfect example, I had no background in 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 to color, like believe that people actually fly this way and how convenient it was. Then, I take off my shoes and there were no lines. I could create calls and say, “Hey, guys! We’re running 15 minutes late.” 

By the time my partner and I were on the flight and it landed we said, “We need to figure out how we could fly privately more often.” Then, we had this great idea: well, imagine if we could just have access to our own plane, with none of the responsibilities it could be ready on our notice anywhere in the country, and it would work like a debit card. There’s like a Starbucks card for private aviation. The problem was, we had no airplanes. It is hard to start a private jet company with no airplanes. 

However, the idea really came from, I think, a lot of entrepreneurs with similar stories of how they started. We were frustrated consumers and we found a 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 the consistency of the airplanes if you chartered. So we wanted to just get rid of all that and make it really simple, make it way more affordable, not lock people into this long term commitment. 

Then, we really just thought about what would be the perfect program for us 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 the Marquis Jet card that ultimately did billions of dollars in sales.

Preston Pysh  7:08  

That’s incredible. I just love how you described that it changed to color.

Jesse Itzler  7:13  

You become more aware. You look at your own life and say, “What’s missing or what product could be improved, or what problem can be solved?” Then when it hits you, it is like 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.

A lot of people ask, make a mistake, I think quite honestly, early on in their journey, and they asked people in their inner circle for advice or their opinion. One is you can get talked out of it. 

My wife started Spanx. If she would have asked her parents or close friends about footless pantyhose, they would be like, “If it’s such a good idea, Sarah. Why haven’t the big guys done it yet?” That might have scared her off or they might have said, “Sarah, you’ve never taken a business class, what are you doing?” And that might have scared her off. Really just to seek validation…when the idea hits you, if it’s good. 

Preston Pysh  8:11  

What you’re getting at Jesse is being naive. So, one of the advantages of being somebody who doesn’t have that background, doesn’t have those experiences, they’re very naive as to all the challenges and difficulties of actually pulling it off. 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.

Jesse Itzler  8:32  

Yeah, very true. So, that goes back to not knowing what you don’t know is a gift.

Stig Brodersen  8:40  

That’s a very interesting realization, especially for entrepreneurs. I guess. 

Okay, Jesse. So I’m curious about this. When you were just starting Marquis Jet, how did you go about raising money? Was it something you needed outside investors for? What’s your thought process about giving up equity of your business?

Jesse Itzler  8:59  

That’s a great question, especially if you’re starting something that’s capital intense, like a private jet company. I would just say that 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? 

Then, recognize that that’s going to put a great amount of stress on you because you lose yourself. A dollar is one thing, but if I lost your money, Preston and Stig, there’s a great responsibility with that. 

That responsibility comes with communication, updating your investors. I mean, this might sound obvious, but it’s a reality you don’t just take money in. It comes with communication that comes with questions that are going to [require] responding to. If you have 50 investors, that could be 50 calls a month of 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.

So, I never even knew that people really raised money. We started Marquis Jet when I was 28 to 29 years old. This was a completely new process to me. I went about it like [this] because no one told my partner and I that we really had to raise money. We went about it like how Kermit the Frog would go about it. Then again, it was a good thing. 

We had already secured a partnership with NetJet who provided us with the airplanes. That was sort of contingent on us putting in our own money and raising additional capital. So, we didn’t go at PowerPoint stage. We went when we already had a partnership in place that will make it a little bit easier for people to bet on two people that had no experience in aviation.

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. They have zero experience. It’s in a super capital intensive airplane private aviation. 

We get 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. 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?” But that’s really what we were. So, we had to build something around that. The first thing we did is we secured rights. We had a partnership with NetJets. 

The second thing is we brought in two people to help us. We hired our weaknesses immediately. First thing we did. Then, we put in our own capital. Not a lot because I didn’t have much money at the time. Though 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. 

We had minimized a little bit of the risk in the sense that we had this partnership. Then the next thing is we talked about valuation, Stig. We wanted to make it fair. So for us it wasn’t let’s keep as much equity as we can and let’s try to get this crazy high valuation. 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.” 

We weren’t sticklers about that. I mean, we put a flag in the ground and everybody got the same deal. Everybody was, “Oh, is this the best deal? Can we get free hours?” Everybody got the same thing. It was most favored nations.

Then, 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. Then, we could say that we have X amount raised to date, before we went out to the street and tried to raise additional capital. 

Afterwards, we tried to bring in a big name. We tried to bring in someone that was credible and help others follow suit. That doesn’t have to be a seasoned investor. It could just be someone. It could be a neighbor that’s a lawyer and say, “Look, we have so and so and 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. That was sort of our process. 

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. At this point, we said, “Let’s see if we can make it work with just this amount of money.” We never did another raise beyond it. We just bootstrapped our way there.

Preston Pysh  13:39  

That’s absolutely incredible. It kind of gets to what a question I want to hit on next, which was your customer acquisition approach. So you were saying that you had some people from Wall Street that you got some like celebrity type people to endorse it to give this authority. Are you just like cold calling these people or how were you going about that because that sounds like a lot of hard work? I’m just curious how you guys got through this.

Jesse Itzler  14:03  

After Marquis Jet, I was involved in a company called Zico Coconut Water, and we had a sample. The way we acquired customers was predominantly by trial. We had to demo our product all over the place; get people to taste it; hope it [would] convert them. We had the best product on the planet to demo. Just if I could fill a plane. 

It held 15 passengers and [I’d] call NBA players and say, “You want to lift to the All-Star game? We’re flying privately, and they got on… Like get people on the airplane, 50% to 60% of them or maybe 100% of them will be addicted… The second they walked on the plane, it was a drug. 

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: demo the plane, show the plane, get people on the plane, have people bring guests do our own trips, and always fill the plane. We didn’t have an empty seat like, “Preston come with us, man. I know you live in DC, 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, I believe we were on episode two of The Apprentice, the second episode ever of The Apprentice. It was risky because we didn’t know if it would be a success or failure. That was a big driver for us. 

Then word of mouth. We cared more than anybody else. 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 outcared everybody and that created word of mouth that created, “You should see what these guys are doing. They have an unbelievable product, and they’re building this amazing business. I really, really trust them.” That kind of stuff. 

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? Then, once we got the phone call, service the hell out of them.

Preston Pysh  16:15  

It was a lot of hustle, though, right, Jesse? I mean, you were calling and were trying to find people that knew other people. I mean, this was a lot of hard work, a lot of networking taking place. This stuff just doesn’t happen. You were aggressively just hustling all the time.

Jesse Itzler  16:30  

We were and quite honestly, the work started before we launched Marquis Jet. 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. [I] kept my college relationships. I was out networking when I was 21 through 28 years old every night, every day. I was sending 10 letters a day, every day to people that I was grateful for. I mean, that’s 3000 people I would hit in one year that probably never got a personal handwritten letter in the mail. 

Preston Pysh  17:05  

Hold on, hold on. Explain this letter stuff even more, because we’ve talked to a guy named Guy Spier and he swears by…and 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.” So, I want to hear your story on this because this is fascinating.

Jesse Itzler  17:32  

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 got a letter. 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. When my mom would hand me a letter and say Captain Kangaroo Fan Club sent you a letter, I’d be like, “What?” It was memorable. 

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– $0.32 that changed 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, “I have your business card,” “Mr. Doorman, you were so nice,” or “Mr. Waiter or the manager of a restaurant. Hey, you guys took great care of me.” Next time, I walked into the restaurant, I was king of the restaurant because of that 32 cents. 

For everybody, if you took a meeting with me. I did your podcast. I had your business card, and you impacted me, you were going to get a letter. I kept the list, and I built this network through not just that, but that was a great tactic. It made me feel good. I felt great writing them. 

Even last year, I wrote 50 letters and on New Year’s Day, 250 people that last year, really, I wanted to thank for just being good friends and helping me and going out of their way. It felt great. Apparently, it felt great to receive. But that simple, inexpensive exercise, I didn’t even know it was the start of Marquis 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 cards of Marquis Jet that I could say, “Hey, give me a shot.”

When I started Marquis jet, I just wanted everyone out there to know it. It starts today. No matter what you’re doing, whether you’re trying to acquire customers, email lists; whether you’re trying to… you just never know. 

Look, 50 Cent. Before he was 50 Cent, [he] was my intern. He was a boxer. He was 18 years old at a music and marketing company in New York, and the DJ Jam Master Jay from Run DMC was working with this young artist at a Queen’s named Curtis. He said he needs a place for the summer. He came in, worked, and I had no idea later he would become 50 Cent. 

Fast forward 10 years later, we start Marquis Jet, we’re a couple years into the business, and I get the everyday flight manifest of everybody that’s flying with us, and I see that 50 Cent is on a plane going somewhere or one of his shows. So, I wrote him a note. I said, “50 Cent, you never ever, ever are going to believe this is Jesse Itzler. Congratulations on your success. You’re on one of my airplanes.”

Like we had a small little office. 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 in his first year working at the NBA. 

Now, he’s the commissioner. I’m part owner of the Atlanta Hawks. He’s the commissioner. You never know. It starts today. It starts by building your network and 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.

Preston Pysh  21:03  

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 be thankful to even take that step of what you’re talking about. So, I think it talks a ton about your character. I think that anybody else out there that’s doing something similar, it speaks a lot of their character if they’re a thankful person. They’ve got a lot of gratitude for the people in their lives. Amazing. I love that.

Stig Brodersen  21:27  

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 your major motivation for this? And why did you decide to sell it to NetJets?

Jesse Itzler  21:44  

We had been working super hard for eight or nine years at the time, the marketplace was changing. All of a sudden, there were new jet card programs. Delta has gotten the line game and others as well. 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. 

There were great efficiencies with partnering or selling to. Ultimately for us, it was NetJets, Berkshire Hathaway, [a] Warren Buffett company. Also just to monetize it. We had been monetizing it. It was cash flowing, and it was an amazing business. 

However, it just felt like after eight years, it was time. So, we had a great partner in NetJets. They were the natural exit for us 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 bits. 

We weren’t out shopping this to other companies. We built it out. We proved ourselves. We [had] loyal customers. The market changed. We needed more money. They felt that was the right time and that was that.

Preston Pysh  23:03  

Interesting. Now, how long did that process take when the initial conversation started to happen? Was it quick? Did it take a year? Talk us through a little bit of that.

Jesse Itzler  23:12  

It was quick because they knew our business so well. So, they knew everything under the hood. There are no skeletons. We’ve been partners for eight years. The way our model worked is we piggyback off of their fleet of 700 airplanes. “Convinced” sounds like “manipulated,” but we discussed and agreed that in our initial meeting that we would use their airplanes, so we didn’t have a lot of capital expenses, because we didn’t have to go long [with] airplanes. 

If you were to buy 25 hours from us, we would then go buy it from NetJet. So, it’s not like we buy all this time or inventory. 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.

Preston Pysh  23:59  

Jesse, 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 a 100-million dollar marketing budget, any brand you start from a PowerPoint is just about inducing trial, changing customer habits and getting repeat business. 

Can you elaborate on this idea more for our audience and talk to us about branding and how you think through this because you’d mentioned that you brought celebrities into your Marquis Jet early on? I see that as just a very smart and branding marketing kind of position and play that you guys put on. Talk us through how you think through branding.

Jesse Itzler  24:37  

Well, before branding, I think it starts with a product that will induce trial, and get people to do something or buy something one time. However, 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. It requires customer service. Follow up everything. Soup to nuts is the best that can be. Then, it’s time to talk about brand[ing]. 

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? What problem is it solving? 

Then, generating that emotional connection. You want to be memorable. You want to be loud. You want to be different. 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. 

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.” That’s a big common mistake. Look, we live in a world where if you don’t stand out in a couple of seconds 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, I might have to edit that a little bit now that I rehear it, 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.

Preston Pysh  26:38  

So, I agree with you, Jesse, but I have to come forward with a story here. You have actually changed one of my worst habits in my life, and you don’t even know it. Before we did our interview with you last time, I had a bad habit of drinking energy drinks. Horrible habit. 

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. You said if you could recommend one book, the name of the book was “Fit for Life.”

Stig and I, after the show was over, we kind of looked at each other. We’re like, “That was kind of a strange book recommendation.” Stig goes out and Stig reads the book. 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 says, “Preston, you’ve got to read this book. This book is absolutely incredible. And it’s changed the way I eat.” And I said, “Alright! 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. 

I’m telling you it has changed my health in such a dramatic way. I used to get colds all the time. So I read this book, I stopped drinking the energy drinks completely. I haven’t had one since I read the book. I can’t tell you how much, so you actually have in a way, had me stopped drinking coffee. You had me stopped 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, Jesse. 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.

Jesse Itzler  28:14  

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’re not working out and your eating habits maybe change, and 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. 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 an island. They’re feeding you grapes, but guess what? You got a sore throat.”

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. 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. 

I mean, if you have all the money in the world and you’re not happy, it means nothing. I’d rather be literally basically broke and super happy than be a bazillionaire and unhappy.

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 that. 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’s in your bank account. You just want to get better.

Preston Pysh  29:40  

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. It was just crazy.

Jesse Itzler  29:50  

Sounds believable. I’ve been doing it for 27 years. I’ve missed maybe three days of work. Yeah, so we knock on wood, but I have crazy energy. I’ve run over 50 marathons, distances, ultra marathons, four kids, running a business. 

I mean, like my dad, I got 30 hours in a day. Yeah, just because of the energy level. Not to get sidetracked here, but I think that what you eat plays a big role in how you feel and how you feel translates into how you operate a business.

Stig Brodersen  30:21  

So listening to your story is not just about business, but also about how you adopted a practice of handwritten letters; how you’re taking care of your health. If you had the ability to go back in time and speak to your 20-year old self, what would be your advice? 

Jesse Itzler  30:38  

Really good question. I would have to say… There’s a lot of things that as you get older, you learn all these things…I wish I knew when I was in my 20s: 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 with being totally exposed. So, understanding that that’s a good thing. 

I’ve recently become friendly with Tim Grover, who was Michael Jordan and Kobe Bryant’s coach, trainer, mind coach, whatever you want to call it. He basically had mentioned that pressure is a privilege. If you get a raise or new job, you get higher up at your office or whatever. That might come up with more pressure, but it’s a privilege. Someone’s trusting you. 

Putting out a book, “Living With a 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. 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.”

Stig Brodersen  31:59  

I really like your advice, Jesse, about being vulnerable. However, I guess if you expose yourself and you’re met 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? How do we handle it?

Jesse Itzler  32:21  

A lot of self talk and myself saying, “Just go ahead.” Don’t talk myself out of it. Don’t overthink it. Don’t shy away from it. It’s become part of my life 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 the “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 podcast. You know, 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.  

Preston Pysh  33:02  

I read an article where Bill Gates was talking about the most important thing that he learned from Warren Buffett. In the article, he says that Warren Buffett taught me how to think in a positive direction. He says that Warren Buffett’s one of the most positive thinkers, and later in the article, he says 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.” 

However, 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.” 

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 trucking along and do a 100-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.”

Jesse Itzler  33:56  

Though I just want to say one thing to that, Preston. It starts with thinking. I think we live in a world now where we are bombarded with emails and voicemail. 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. I think so few of us do it today. 

We’re just always on the go. The second we get up, “Okay, I’m going to work out. I’m going to go to work now and take the subway.” 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. 

Preston Pysh  34:40  

So Jesse, you’re all about doing these epic things. 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 is next? What are you going to do next? What’s the next big epic thing that you have planned?

Jesse Itzler  35:06  

Well, I have this amazing event coming up in October. So, I’m glad you brought this up because I can share it with your listeners. I think it’s going to be a once in a lifetime [event], 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. I rented Stratton Mountain in Vermont, the entire mountain in October for the weekend. We’re bringing in, everyone gets their own teepee tent with a bed and a heater. 

I mean, it’s creating our own village of tents bringing in bands and food trucks and speakers. So it’s really festival-like, but here’s the challenge: you can jog or walk for all hype, whatever, up to the top of Stratton Mountain. You take the gondola down, the high speed gondola down. Go back up. Gondola down, up, down until you climb Everest: 29,029 feet. 

Okay, we call it Everesting. 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. 

You [will be with] all these amazing people, and then 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.29029.com, so you can get more information. I would love to have you guys. I want to see you on the mountain.

Preston Pysh  36:47  

That’s who I want to see on the mountain, too. Jesse, I’m there. I’m serious. I will absolutely positively come to this. If that’s the invite because I would love to do this. This sounds like something that’s right up my alley. Stig on the other hand…

Stig Brodersen  37:01  

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 on top of the mountain, if I go?

Jesse Itzler  37:09  

I’ll happily walk… It’s 17 times up. You have two and a half days to do it. After you do one, you can sit and listen to music. 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. You’ll be able to set up, Stig. I’ll get you whatever you need for your breakfast. But no, I’m really looking forward to it. These are the kinds of challenges [I love]. 

What I love about this is it’s totally doable. You just have to stay with it. It’s a walk. It’s a hike. These are the kinds of things that make me feel super alive. I feel like it also translates into all the different areas of my life. I feel like if I stay with something like this, and I do it, and I complete it… When something hard happens at work, when an obstacle comes my way, I can say, “I can handle this. I do stuff like this. I’ve done something like this that is hard.” 

Instead of shying away from the challenge, it teaches me to attack it. So, I believe this is a great weekend investment in yourself with amazing people. Preston, that would be unbelievable.

Preston Pysh  38:15  

I’m being serious. If you’re serious that I can come to this thing, I’m there. I will be there. See, what’s the date? I probably need to know the date first.

Jesse Itzler  38:23  

It’s the weekend of October 13 through 15th. I would look at it as one part like Aspen Music Festival and one part like Spartan. It’s going to be super festive, fun, and social. It’s also going to be “Don’t hide from the challenge.”

Preston Pysh  38:40  

I’m looking at my calendar. Is that a weekend? It’s a weekend. Okay, awesome. I’m there, man. I got to go get clearance from my wife, but I’m sure she’ll… after a little convincing, I might be able to convince her.

Jesse Itzler  38:52  

We’d love to have you.

Preston Pysh  38:54  

How do you think of this stuff? This is unbelievable. How do you think of this? 

Jesse Itzler  38:58  

Oh, man. It’s just, it goes back to what we just talked about earlier. I’m frustrated with the options. It’s like, how many marathon races or 5K’s can you do? How many obstacle courses can you do? How many times can get zapped by at some of these races by electric currents? It’s like, let’s do something super cool and thematic; different. I mean, I want to walk into my office and [be] like: “What are you training for? I’m training to climb the vertical Everest. Doing it in Vermont with 300 entrepreneurs.”

Stig Brodersen  39:29  

So Jesse, even though 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 team?

Jesse Itzler  39:47  

First of all, 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. 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 a 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 all these new categories [that] have emerged that weren’t here 10 years ago. It is constant evolution. 

The community is so passionate about the team. 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 nursery 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 [the fact that] I’ve gotten to be pretty close with a lot of the players and this is a business where there are trades. 

There’s free agency. You go back 3 or 4 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 2 or 3 guys remaining, so I’ve gotten to be really close with the players, but it’s just the nature of the sport. Players come in and they go. 

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 it’s a basketball player or a friend or a co-worker 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? That never really crossed my mind coming into this that that would be the case. We’re still friends. I still had those relationships, but you have to constantly build new relationships and nurture them and get trust. That’s a big investment in time and a big emotional investment. Every year that changes and that takes a lot of energy.

Preston Pysh  42:02  

Alright, 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?

Jesse Itzler  42:23  

I appreciate it. On social media, I’m on Instagram or Twitter on @the100mileman. 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: www.29029.com. I really appreciate you having me on. It’s been a pleasure. This is round two. I felt like it might have been as good as round one for me.

Preston Pysh  42:58  

We will have Jesse’s Twitter handle in our show notes. We will 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. So, Jesse, thank you so much. What a pleasure.

Jesse Itzler  43:11  

Thank you guys so much. Appreciate it.

Stig Brodersen  43:14  

All right, guys. That was all that Preston and I have for this week’s episode of The Investor’s Podcast. We will see each other again next week. 

Outro  43:21  

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