In this conversation, Jesse Itzler reflects on how his approach to work and entrepreneurship has evolved from embracing high aggravation for high reward to now seeking low aggravation for any reward. He argues that sustainable success comes from doing the tasks others refuse, leveraging systems that minimize friction, and focusing on time and energy efficiency. Itzler shares anecdotes from his early career, including building Marquis Jet from a pool‑side job to a multibillion‑dollar enterprise, and highlights the importance of being willing to navigate regulatory hurdles that deter most competitors. He discusses market realities such as the saturation of podcasts—about two million total, with roughly 25% quitting after a single episode—and how persistence can capture a disproportionate share of the audience. He also cites statistics on company revenue tiers, noting only about 17,000 U.S. firms generate over $100 million annually, underscoring the rarity of large‑scale success. Throughout, Itzler critiques the myth of high valuations without cash, emphasizes the role of willpower amid betrayal and low‑integrity partners, and concludes that true fulfillment comes from aligning work with personal priorities rather than relentless hustle.
Chapters
When I was young, I could take high aggravation for high reward. I was willing to invest incredibly high aggravation, people work, meetings because the reward was potentially very high. Now if it's a super high reward, but it's high aggravation, it's a non starter, it's a no. I want low aggravation for any kind of reward. And that is business, that's people, that's everything. I want as low aggravation as I can get. Now that comes with a sacrifice. That comes with the ability to scale, maybe that comes with the ability to do it again. But I'm not competing with anybody and I've gotten to a spot where that's okay with me. So those factors come in. If someone said to me right now, Jesse, you could be in ground zero at Google, but you have to go, and we're going to go to Europe three times a year and blah, blah, blah, blah, I'm out, I'm out. I'd rather go to the football game, my kids football game.
What you're saying here is repellent to some people. Right, right. And some people saying that's impossible. You're only saying that because you've become successful. And I would have been one of those people in my 30s. I was very, I made 6 million bucks when I was 26 in the tech world, lost it when I was 28. So I same kind of thing, you know, we, we both did that. And I traded a lot of good stuff I should have done and traded some of my health for that for no good reason other than. But I know today I know at least a couple dozen people who are 30 or under who didn't do that and are quite successful, quite wealthy, and they're way happier and have better relationships and better friendships than other people. So there is no evidence that shows that hard work creates, creates results. Because we know lots of people work hard and don't get results. We know the ability to work hard is important to get results, but it doesn't mean doing it all the time is how you do it. In fact, doing it for brief periods of time with greater results seems to work better. And that's the goal you set when you're younger, is leverage your time, leverage your energy so that you can start these activities earlier and be a lot happier.
There's a famous speech by a guy, I forgot the guy's name, but I need a memory pill. Dave. The holidays send me something that will give me better retention. But I do remember reading that in the 1940s at Prudential Insurance. A guy gave a talk, a famous talk. I'll send you a copy of it because I have a paper copy of it. It's interesting where he studied what made people successful. And he wanted to distill it down to one thing because he had been told his whole life exactly that. You just said, if you work really hard, you have to work hard to be successful. If that's the case, everybody that worked hard would be the people that were successful. But he found people around them that weren't working that hard, that were mega successful. So he was like, well, what is it? So he did like a year of research and he gave this talk to Prudential, and he simplified it to one characteristic. And it sounds obvious and there's a lot of buildup, so it might be disappointing to the people listening, but it's something everybody can do. The people that were most successful did the things that other people weren't willing to do, didn't want to do. So, for example, they would come home and when everybody else went to happy hour, they didn't want to return all their calls or whatever. They did it. When everybody else was going to the football game, they drove two hours to see the client that changed their life or whatever there was. They were willing to do the things that other people just weren't willing to do. And that was. And that made sense to me when I look back on my journey, like I said earlier, like I was able to go to that point where we did people out. They weren't willing to go past mile 40 with the blisters and the tire. They weren't willing to go. Look, when we started Marquis Jet, I had no aviation. I was a kiddie pool attendant. A couple of years before it, I went from kiddie pool attendant in five years to starting a company that did 5 billion in sales. All right, when we started Marquis Jet, if they would have said to me. They did say to me, you're going to need FAA approval, Department of Transportation approval, raise money, buyers, higher sales. I'd be like, what? I was a kiddie pool attendant. What are you talking about? What's the first thing you said? I need Department of Transportation approval. There must be a lawyer that specializes in that. Let me get the lawyer that specializes in that. Okay, we got that. What's the second thing? Faa. There's got to be a guy. We got that. What's the third thing? Where the other people were like, we could never start a private jet company because we don't do that. I'M not willing. I don't. That's not what we do. I don't know anything about that. I'm not willing to go down that route. It weeded out 95,199% of the people. So now my competition pool is like, three companies.
Love it.
Let me tell you something. You know how many Apple podcasts there are? I think there's 2 million.
It's gotten a little bit crazy.
Right now there's 2 million podcasts. Did you know that? 500,000. I want to. I want to put an asterisk next to this because I want to double check my math, but I believe there's 2 million, and I believe that 500,000 of them, 25%, only do 1 episode of the podcast and then quit.
Exactly.
So if you're telling me that the state of the union is we can discredit 25% of anyone in our field or whatever, because, oh, the advertisers didn't come, this is too hard. I don't want to have what it takes to grow a following. Then I already like my chances. Because what I say at the very beginning of this conversation when you talked about is, why do you run the hundred mile races? Because it's a test of will. So if they're not willing to do that now, my field is only 75% of the market now. We get to 10 episodes, it gets to like 50. So all I got to do is stick in for 11 episodes and I'm in the top 50%.
It's. It's completely true. Same thing goes with companies. The vast majority of companies, something like 99 out of 100, don't make it past a million dollars in revenue. And then it happens again, going past 10 million and again going past 100 million. To the point there's 17,000 companies in the US doing north of $100 million in revenue, and I built one of them from scratch.
Wait, wait, what? You said there's 17. Say that again.
There's only 17,000 companies in the US doing north of $100 million a year in annual revenue.
Whoa.
So, and you've built companies that are the next tier above that. The billion dollar companies I never hit. I might have hit a billion dollars in valuation using fantasy math, but if you don't sell it for a billion dollars, it doesn't do anything.
Fantasy math is amazing when your head hits the pillow, but it doesn't do much for you.
Even when people say, elon's worth a trillion dollars. If you tried to sell all of his Tesla shares tomorrow, the price would drop precipitously. So it's not really worth a trillion dollars. And it's true for everyone who's a, you know, who's a kabillionaire. It's like they own assets that are worth a lot, but they don't really have that much money. But, so whatever. But, but to build a company, that much revenue, that's a hard number. So that it's the same thing with, with, you know, running. Do you have the willpower to stick out all the, you know, every entrepreneur has been betrayed. Everyone's, you know, had investors try to screw them over and had employees who, you know, absolutely didn't do the job and then turn around and, you know, try and sue for whatever they can get, for whatever reason they can make up just because they're low integrity people. And, you know, to go through all that, it's, it's rough. In fact, the guy who started Nvidia, did you see that interview?
I didn't, man.
He, they said if you had advice to yourself when you were 19 years old when you started Nvidia, what, what advice would you give yourself? And his advice was, don't do it. Like, no one can ever tell you how much you will suffer to become this successful. You will spend so much of your life. Wow, man, that's kind of dark. But he's not wrong. I don't regret anything I've done because I wasn't doing it to make money. You're listening to the Human Upgrade with Dave Asprey.
