Randall Kaplan (3:16)

I was asking you what the.

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When did they first teach you the.

Randall Kaplan (3:21)

Value of hard work?

Jesse Itzler (3:24)

Well, they never taught it to me. I just was around it. I mean my dad was my dad, not my coach. So I just watched what he did and he worked six and a half days a week but still managed to show up for everything. So yeah, I mean I was just, I was watching real hard work unfold in front of me. My life is, my life as a kid was very different than my kids lives. We didn't have people coming into our house to clean up and people, you know, like everything that happened happened because my parents did it or asked my brother and my two sisters or myself to do it. So I was just always around it and you know, osmosis.

Randall Kaplan (4:12)

You were born with what everyone says is this outgoing, gregarious personality. You were funny when you were growing up. You were popular, you had a lot of you, you're doing a lot of things. Energy. How much is your personality a part of your success?

Jesse Itzler (4:33)

A big part. I think I over indexed in that side and under indexed on the SATs and the schoolwork side. I overcompensated for things. I have like, I have really good bandwidth for certain things but terrible retention. So like I can't remember what I read. I'm reading a book now, I don't know who the author is. I mean I can't remember anything. But I overcompensate. So I had to overcompensate for stuff in meetings by being a good storyteller. So I think, yeah, I think the personality, storytelling all played a part of a big part of. Look, my entire business journey was, was built early on in my 20s and 30s through partnerships and getting people to buy into me like I was the business plan. So my personality getting people to want to do business with me was more important than the business I was in. I could have had a widget company, but if I, if, if someone wanted a manufacturer of a widgets or whatever they had, it was, it was, you know, I got people to want to be around me or work with me. Fortunately that were able to help me. So I would say it played a huge role. I definitely didn't outsmart anybody.

Randall Kaplan (5:58)

You were born with an entrepreneurial gene. I was born with it. Most people, I would say, are not born with it. Some people can learn it a little bit later in life. I want to talk about the origins of yours, which started around 100 years ago. Can you tell us about your grandfather, his paint shop and being one of 12 children in his household?

Jesse Itzler (6:19)

Well, he wasn't, he was one of, he had 12 brothers and six sisters, but six died before the age of two. So my grandfather was born into like crazy poverty in Russia, immigrated here and lost six of his brothers and sisters before they turned two because they had no medical care. Etc, etc, which actually makes it even more insane to think that I'm one or two generations removed from that and live in the house that I live in. I can't even believe that that is possible. But yeah, I mean, look like not different than so many people here. I'm, I am the grandchild of immigrants and, or the great grandchild, I guess, of immigrants and that came here with nothing, you know. And so I think my father saw his father saw his father work hard. Like the goal wasn't to like buy a Lamborghini. The goal was to like, everyone's going to like get shoes, you know. Now by the time I arrived on earth, my father, my grandfather had a paint shop, my father had a plumbing supply store and we had a house and I grew up middle class. But you know, the stories and the traditions and the expectation was already set.

Randall Kaplan (7:42)

You mentioned you weren't the best student. I think I read somewhere you graduated with a 3.0 from American University. So many people today. And I tell my own kids this, I have five kids, that education is the best investment we can make in ourselves. On the flip side, a lot of people say why do we need to go to college? What's your advice to those who are entrepreneurs or parents who have kids that are, should they go to college? Is it all that's cracked up to be and is it worth it?

Jesse Itzler (8:13)

Well, I needed college. I needed college. Not for this, for the classes that I took. Although quite honestly some of the classes that I took really impacted me like public speaking. I Took in college and really had an impact on me. But I needed college for. I wasn't ready to go to go to the pros. I needed to get my habits, routines. I needed more independence. I needed to figure things out on my by myself. I needed to experience disappointment. Like I needed four years of all that. And college, that's what college gave me. It gave me freedom, independence, decision making, friendship, survival and all skills that I brought into the world as an entre, courage, all that stuff. Like I didn't have that at 18, like I had when I graduated at 22. So for me, college was the triple A's to get me into the majors and I needed that. But everybody's different, you know, some people depends on the industry you want to go into. The other thing that college did for me was it let me try. I went to every class, I took everything. I went to every time there was a speaker, guest speaker, any topic. I went. I went to every event, every sporting event, every intramural event, every real estate program that they had. Even though I wasn't into, I just. It exposed me to so much. It exposed me to so many people. It exposed me to lectures, it exposed me to the people that were communicating. I became a better communicator. All those things happen during college. So for me, I needed that. If I was trading stocks and a day trader and I had those skills at 18, maybe I wouldn't need college. If I was an actor, maybe I wouldn't need college. But for me, I needed it.

Randall Kaplan (9:59)

So let's focus on college. And I want to focus on the mindset for a little bit. We'll start talking about your incredible career in a minute. But when we talk about being in college, we think about our futures and what we're going to do with our lives. I spent a lot of time mentoring and coaching. I have 36 interns every summer and it's a formal teaching program. And I think back to my own college days as well, where I slept on couches when we would start a company after college. During college at George Washington, I lived in the dorms. We used to get four meals on a 99 cent box of Kraft Macaroni and cheese. And when I think about my summer intern program, I think about things that mentally I was going through at the time. 95% of my students have tremendous anxiety about what they're going to do when they graduate in the future. And it's also true a lot of the young professionals I coach as well, they don't love what they do. And they always wonder, are they going to find passion and love at what they're doing in their careers? What's your advice to those people? And equally as important, what's your advice to their parents who often rely on them for advice? And can you tell us about the advice that your mom gave you on this front and how it influenced your future?

Jesse Itzler (11:17)

Well, again, I think everyone is. I don't think there's a silver bullet for it. I can only speak from my own experience. I think, you know, my parents, my mom, I remember going to college and my mom telling me like to try everything. Like she really encouraged me to take advantage of that opportunity, you know. So I was also super aware of like their college is only four years. So I was aware that like I had a very limited amount of time. And by the way, like you're gone what may through September or whatever, like it's only six months. However long it is times four, it's not that long. And I was aware of that. So like I was aware that I really try and I still live my life like that aware of like time and urgency. So I was really, I went into school. Not like, oh, I'm going to school man, I'm going to be in a fraternity and all that. Just really like within with open eyes and my mom and Kurt. So my mom had a big, played a big part of that for sure. My dad too in just. And then, and then also not directly answering your question. But my, my parents, again, like if I wanted to, they let me do whatever I wanted to do. There was no like, is that's not a good idea, that, that's not a good idea to come out of my parents mouth. It was like, yeah, go see if you like that. You know, they really encourage curiosity.

Randall Kaplan (12:53)

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 the next 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 of my life, I want to give back. I want to 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, and I'm looking for a few hungry entrepreneurs who are excited to take action on their journey to incredible future success. So if 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.

Randall Kaplan (13:50)

So let's move on to the start of your incredible career. It actually started in college. Can you tell us about Dana Dane and Mike Ross? 30 footer. In your face. Shake it like a girl. Snoop and Warren G. And in search of excellence. How important is it to find a way to get our foot in the door? And what's your advice for anybody out there who say. Say to themselves that getting a meeting with the CEO of a huge company or even a venture capital firm like Sequoia is almost impossible. So why should we even try?

Jesse Itzler (14:26)

I. I mean, that's like, that's. That. Those are good questions. Those are nine questions in one. So I'll. I'll try to break them, break them down. Going back to my journey in music. Yeah, I mean, I was. When I was in college, I was. I wanted to have a record deal. I didn't know anybody in the business. So if I would have listened to that, why do you. Why would you try to get your foot in the door Philosophy? We would not be on this podcast right now. My approach was completely different that than that. My approach was, I'm going to get in every door until someone says yes. And that's exactly what I did. I went to 14 or 15 record labels with a demo, and they all said no. Sometimes those meetings happen just by waiting in the lobby or going to restaurants where I knew that executives went, etc. Or going to someone that knew someone that knew someone that knew someone that did me a favor, that got me a meeting with someone that might know that, someone that can make a decision. But then I did get a yes. I went to a record label called Delicious Vinyl in California with my demo. And I knew that the owner of the company liked this rapper named Dana Dane. And when I called to get. Try to get an appointment, I said I was friends with Dana, which I was sort of. And they thought I was Dana. And they set up a meeting thinking that Dana was going to meet this guy Mike Ross, who owned the record company, and Mike was going to meet his favorite rapper. Except he got me. But by the end of that 30 meeting he also got I got a deal. So I was able to play my demo and got a deal. Getting your foot in the door if you can't get your foot in the door, that's basically a non starter. I'm. I'm a big believer also of getting your foot in the door and then figuring the rest out later. So like I, I just remember saying like when so many times in my life when I had a, a product or a service like I'll use this is not true, but I'll use it as an example. Like if I could get my foot in the door of Coca Cola and as an intern, if I could get there selling them this pen, then there's going to be an opportunity for me to sell Coca Cola something a lot bigger down the road. Like I just got to get in there, let me meet people, let me get in the system. I just, I'm. I need to be in the system human and if I'm in the system, I think I can create luck and I can create opportunity. I'm really good at taking advantage of that window when I get it. So terrible at grades. Not terrible, but not. I'm average at everything. Above average of getting my foot in the door. Exceptional of taking advantage of the opportunity.

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Randall Kaplan (17:47)

Sometimes we have a passion for things and we have goals for what we want to do with our lives. But despite our incredible efforts, herculean efforts, over the course of many years, things just don't work out. I teach something called extreme preparation, which we're going to talk about in a few minutes, and one of the steps is called Preparing to Persist. As part of preparing to persist, I also teach people that when we have a temporary roadblock and something doesn't work out exactly like we wanted to, it could be a career choice. Or on a much smaller level, it could be not getting an important deal or a Lucrative sale. I coach people that when they have a setback or disappointment, they should think of this as a temporary roadblock and not the end of the road. And instead, they should think of it as the beginning of a new road. And although we can't see it at that exact moment when it's happening, our greatest disappointments sometimes turn into our biggest opportunities. Can you tell us about how you slept on couches? Turbo Bubblegum, A company called in the Pain Clothing. The song Go, New York, Go, how you got into the jingles business. And Melissa and Luke cats.

Jesse Itzler (18:53)

That. That sums up my 20s. Yeah. I think the. I started out in the music business doing jingles and theme songs for sports teams. My first challenge, my business model, was just do it. Write a jingle, a commercial on spec for a company, let's say the New York Yankees, cold. Call them to try to get a meeting, which was really hard to do. And then if I got a meeting, play the song and hope that they would pay me for the song that I wrote for them more than it cost me to be in the studio. And that was what I was doing for a big part of my 20s. And I ran out of money to go in the studio and write these demos for sports teams. And I was living on a couch at the time. I lived on about 18 different couches. I wasn't homeless, but I had no revenue, no money. I didn't want to go to my parents, although I probably could on some level. I just went. I made a pact to myself. When I graduated college, I was on my own, and I wanted to honor that. So I was sleeping on my friend's couches, and one of them was this girl, Melissa Katz. And someone had offered me $10,000 for 10% of my future earnings because I needed $10,000 to build a catalog of demos that I could hopefully sell to sports teams. And I was going to do it. I was going to sell 10% of my life forever. I was like, 22 for 10 grand. And Melissa Cat said, you know, before you do that, go talk to my dad, who was a big entrepreneur, and. And he wisely talked me out of it. He asked me a very simple question. He said, you know, can you make this business work without the ten grand? He said, will you make this business work without the ten grand? And I said, I know I can. And he literally, like, became infuriated. And he said, I didn't ask you. You know, can you? I said, will you? And he explained to me the difference between saying I can versus I will. You know, I can start a podcast, I can run a marathon, I could be a millionaire. But will you, or you know, will you do it? And once he told me, like, once he convinced me to believe in myself, that, yeah, I will make this work. He was like, well then save the 10 grand, that's ridiculous anyway, and go take the things, steps necessary to make it happen. And I did. I ended up selling that company for, you know, for millions of dollars.

Randall Kaplan (21:32)

We're going to get to the sale in a minute of that company. But I'm sure you coach a lot of people and you mentor a lot of people too. Young people. And when they're in college or they're starting the first company, they don't know not to give away a percentage of their business. I tell people the same thing, if you don't need to do it, don't do it, because it's going to come back to haunt you. Especially sometimes. That 10%, it depends on the company, could be worth a billion dollars, hundreds of millions of dollars, millions of dollars. For the younger people listening or the young professionals, or even mid career professionals who are thinking about starting their own company, is there some general advice you would give them along the lines of, hey, don't take the money until you talk to somebody else who knows a little bit about this business? Or should they just trust their lawyers who often tell them that they actually should take the equity and save, save the cash?

Jesse Itzler (22:29)

I think it depends on the circumstance. I mean, some businesses require money. We couldn't have started Marquee Jet, one of my companies, without capital. Some, some businesses, you know, you don't have a choice. I, I think you have to realize that taking money in requires, comes with a lot of responsibility and pressure and you have other people's money. I have a business right now that's not doing great, but it's all my money. So like, it sucks. But all that pressure of like outside investors is off the table. No one knows the number. You know, like, it's just private. And it's like my own issue, not, I'm not bringing other families and other money into it. So that's an important thing to think about is the responsibility, the communication that comes with the money. You have to ask yourself, what am I going to do with the money? Why do I need the money, et cetera. And then, you know, I've also been in situations where I've doled out equity to employees, to friends, to family. And that also comes back to bite you a lot. Not just because, you know, you want to do that, you want them to make money, you want to be a hero. There's other ways to get people money. Profit sharing distributions, phantom equity, etc. You could get a good lawyer that can walk you through other ways to compensate your team than giving away equity. But equity, you know, then there's, it could come with rights, certain rights that you might not want to give away. Open you up for law, litigation, as, as a shareholder. You know, there's just a lot, a laundry list of things, communication that has to happen, distributions that you have to give, tax implications for those people. K1 I mean this is a, you know, this is a lot of different, a lot of different things. The other thing is, you know, sometimes you're like, oh yeah, well just help me out. Like you're starting out, you don't know, you're excited, you're a new entrepreneur. I'm going to give you 3 or 4%, you know, and, and if it doesn't work, that also could lead to like broken expectations for the other person and broken dreams. It's just, it comes with baggage that people don't really care calculate and I'm not great at that. But under promising is such a better strategy. And keeping things simple is always such a better strategy. My wife started spanx. She owned 100% of it till the, till the sale, till she exited it. So everybody and when I had Zico coconut water, I, I, I think I put 150 friends in the deal as get and I gave them equity. I gave it to them as a gift because I wanted to go to the finish line with them. I wanted them to celebrate with me. I already had a big hit and that was great when it worked. I've also done that and it hasn't worked and that stinks because people are thinking this is going to pay for my kids spring break. So it depends on the circumstances. But I'm glad you brought it up because I think what all I'm trying to do is don't make quick decisions on stuff like that because you can't take it back. You want to really, even when you're young and you're excited and everything's going to go amazing, you have to really get advice for someone from someone that's been there and think through the pros and the cons and think through the worst case scenarios, not the best case, the worst case scenarios.

Randall Kaplan (25:39)

So you start writing these jingles for sports teams. You've got a great revenue model. You've got royalties this time from CD and DVD sales. And then with a guy named Kenny Dichter, you started. The company was called Alphabet City Sports Records. You sold the company for $4 million to a company called STX, a public company in stock and cash, which netted you $1.3 million after taxes. It was your first big payday. As you mentioned, you bought a Maserati, spent all of your money, and tried a bunch of things, all of which failed. Selling carrot and celery sticks door to door. Selling chicken, shrimp, and meat door to door. Starting a T shirt company. And if those weren't enough, your record label at the time dropped you as well. Those were five failures. As the failures kept piling up, what were you telling yourself? And what's your advice to people who have failed time and time again? How do they bounce back mentally? And what advice do you have for them to keep going? And at some point, is there a number of failures, 10, 15, 20, where they should say to themselves, hey, I should probably do something else with my life?

Jesse Itzler (26:46)

Yeah, all that's accurate. Except for the Maserati. I never had a Maserati. I've never had a fancy. I've never bought anything fancy like that, like a car or anything. No, the failures, I think I was. First of all, I was in my 20s, so the fact that I even had my own apartment and I was on my own and all my other friends were working, like, for someone else, reporting to someone else, you know, working really late hours. A lot of my friends gave up their 20s in their 20s, working really long jobs, hard jobs, trying to get promoted in two years, three years. That was the trajectory. And I. I had the freedom. So, like, I didn't care about the failures. I'm like, I can. I can go to Coney island and jump in the cold plunge, and they can't. Like, I could do. I could do all these things. So I was just so enthusiastic to be trying things until something hit big that the failure, the failures did not literally. I mean, it might sound crazy. They. They really didn't. They didn't sting. I was like, this is what I'm doing. I'm an entrepreneur. I'm trying things. Like, I didn't expect anything to work. I was like, oh, they're like 1 in 10. You know, things work or whatever. Like, all right, I'm on number seven. I got three more shots. Like, it didn't. Didn't phase me. And I was always doing projects that I just thought were fun, even when I was selling carrot and celery sticks door to door in New York City. I was like. And I was getting up at 5. I was getting the carrots and celery. I was chopping it up myself, making, dressing, packing them all, everything. I loved it. I loved it. And I was making negative money. Negative money. Like, it cost me more to, like, get on the subway. I mean, I was like. And I loved it. I didn't care. So I was just, like, I knew, look, as an entrepreneur, you got to believe in the end of your story. I knew it would work out for me. I was like, all right, it's not going to be carrots and celery, celery sticks. It's not going to be T shirts. It's not going to be cleaning kiddie pools. Like, what? But it's going to be something. I never thought it would be private jets. I never thought it would be coconut water. But I knew. I knew I was going to get. Get a hit. I knew it. You got to believe it, man. You don't have to know. Clearly, everyone's like, oh, you have to visualize. I didn't visualize what the product was or what the service was, but I visualized and knew that I was going to do something on my own. I didn't know how big it was going to be. I didn't know I would end up, you know, where I am in my life right now. But I knew, like, all right, strike one, strike two. You know. You know what's interesting about entrepreneurship that's different than baseball? Three strikes and you're not out. Three strikes and you're learning and rolling. So, like, those failures, I'm like, I'm killing it. I'm killing. I'm meeting everybody. I'm having fun. I just suck at what I'm doing right now, but I'm going to get good.

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Randall Kaplan (30:30)

It's so interesting because in the venture capital business, if you hit 3 out of 10, you're in the hall of fame. And what you're saying, it's very similar, except that there's an unlimited number just to keep going and going. But is there a limit where people should just say to themselves, I'm stopping. I'm just not good at this?

Jesse Itzler (30:53)

Is there a limit where people could say, I'm not good at this, and they just.

Randall Kaplan (30:56)

Meaning I failed 10, 15. Yeah, yeah, no, I get it.

Jesse Itzler (30:59)

I get it. Yeah. I mean, I love that because, I mean, I think most people think that there's a limit and that for me, that fortunately they do because it weeded out 97% of the competition. I think I am where I am just because I kept going despite the failures. If I were to stop. Look, when I was looking for a record deal after 10, let's say that was the limit. 10 nos. I would never have gotten a record deal. My book. 13 publishers passed on living with a seal. 14, number 14 gave me a deal. I went to multiple distributors, multiple people for coconut water. No, no, no, no, no, no. I mean, every single time, it's been the same thing. So I don't think there's a limit. The limit, I think, depends on what your tolerance is for embarrassment. But I never got embarrassed by my failures. Even today. Like, again, like, if I have a business right now that's not working and I were to shut it down, I could not care less what the. Like, the outside world were to think about that. Maybe that's because I'm a little bit older, but even when I was younger, I was like, I always. Like, it always made me laugh because the people that would be critical were the people that never had the courage to do it, or they were the people that never had the guts to do it, or they. The people that were miserable at their job. But, like, no entrepreneur came over to me and was like, oh, my God, like, you know, I can't believe you tried that and it didn't work. Like, I never got that from Warren Buffett's. Not running around to people, you know, scolding them for trying to have their own business. You know, that didn't work. But other. But the people that never did are.

Randall Kaplan (32:51)

So we all have different paths to success. We all have different ingredients that led to our own success. So let's switch gears and talk about the value of relationships. Can you tell us about your. Your first private jet flight, a man named Jim Jacobs, and getting his daughter on stage with Christy Aguilera at one of her concerts as a backup singer for Sweet 16 Warren Buffett. And finally, how and why your eight person focus group was 100 times more effective than any PowerPoint you could have created. And how you created a company in the industry you knew absolutely nothing about and grew it to $5 billion in sales in only 10 years.

Jesse Itzler (33:33)

Okay, yeah. I got exposed to private jets as it being a guest on a private plane and had an idea with my partner to start a private jet company because there was no, there was a void in the market for an opportunity for that. But we had no airplanes. So I got a meeting with again, get your foot in the door. Through a guy with a guy named Jim Jacobs that was the president of the largest private jet company in the world called NetJets owned by Warren Buffett, 650 planes in the fleet. The way I got the meeting was his daughter had a sweet 16 a year prior and someone had called me up and said that she had that he had a friend, Jim Jacobs daughter that was having a sweet 16 and was going to a concert of a famous singer and knew that I knew the manager and asked if I could do anything special for this guy's daughter. I'm a yes and person. I'm not a no person. So when someone asks me can I do something, it's always like yes and when do you need it done by. So no strings. I was able to do that. I got his daughter on stage with this famous singer as on at the concert as a backup singer with the mic off. The guy calls me up insane. The guy calls me up, he goes, I don't know who you are, I don't know what you do, but if you ever need anything, you know, here's my name and number. Well, a year later I needed 650 airplanes. He was the president of NetJets. So I called him up, I said, remember me? The guy with the daughter got me a meeting and we pitched him the idea for Marquee Jet, which was, which was a our idea for a private jet card company. We needed his airplanes. They threw us out of the room in about 15 minutes. They were like when I was 28, they're like, we're not giving two 28 year old kids our airplanes to do this crazy idea. But Jim had saw something in the meeting and said, you know what? I'm going to get you another shot, come back and repitch this, tweak it, whatever. And we came back a week later, but we brought our own focus group in rather than pitching him on a PowerPoint, we're like, we got to bring this to life. And anybody listening, if you're starting up and you have a big meeting and you have one chance, you got to make that meeting work. You have to bring it to life. You have to make it memorable. You have to stand out. You have to explain why you are, you are positioned, uniquely positioned to make your idea, product or service work. So we brought an own focus group who explained what we had, like Carl Banks from the Giants run from Run dmc, who's in this picture behind me, all the and one by one, they stood up and explained why our company would work. And we left with a deal. A year later, we were like bigger than netjets from a customer perspective, I think maybe Rev, I don't remember revenue customer. But anyway, we ended up building a $5 billion company. And yeah, so I mean, getting your foot in the door, like you said, being prepared, standing out, making people, it all goes back to everything we talked about in the last 30 minutes. Likability. They liked us in the meeting enough to be partners with us. We got our foot in a meeting in the door. We were prepared, we stood out, we took a chance. All those things happened and we left with a deal. And then we had to get good at what we did. And that took some time, but ultimately we got really good at it.

Randall Kaplan (37:05)

Thanks for listening to part one of my amazing conversation with Jesse Isler, one of the greatest entrepreneurs nerves of our day. Be sure to tune in next week for part two of my awesome conversation with Jesse.