Practical Optimism with Jesse Itzler

Jesse Itzler is a serial entrepreneur, recording artist, coach, co-owner of the NBA’s Atlanta Hawks, and the New York Times best-selling author of Living with a SEAL and Living with the Monks.

With so much information at our fingertips, we modern humans tend to overthink things. And when we do, our hard-wired negativity bias brings our focus to the risks and threats around us… Read the rest of this article on my Substack


00:00:00 In this episode…

00:00:13 Intro

00:02:12 Chapter 1: The Goals That Choose You

00:13:45 Chapter 2: Saying Yes By Saying No

00:25:22 Chapter 3: The Process of Achieving Goals

00:36:45 Chapter 4: Intuition and Purpose

00:46:38 Chapter 5: Dodging Arrows and Remembering Tomorrow

00:54:49 Chapter 6: Building A Life Resume

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Remembering Tomorrow, with Jesse Itzler




This is my conversation with serial entrepreneur, rapper, coach and best-selling author, Jesse Itzler.


Jesse’s one of the most infectiously positive and entrepreneurial people I’ve ever met.


I first discovered him at a Tony Robbins event, where he was on stage sharing his entrepreneurial war stories – how in his 20’s, he founded a private jet company he eventually sold to Warren Buffet even though he knew nothing about the jet industry, how he met David Goggins and eventually wrote a best-selling book about him, became part owner of an NBA franchise, and how he’s helped countless business owners build successful companies through all kinds of quirky ideas…


And I realized quickly – these stories were very different from the ones you’d get from professors in school or in the ranks of the corporate world.


They were adventures from a real human being – they didn’t follow the usual script of “learn the lessons first, then apply them” – they were about dreaming big, diving in, learning as you go, and grinding relentlessly when – not if – you get knocked down.


There’s always this high-energy, FUN vibe to everything Jesse does – a positivity that’s contagious but also realistic, and an antidote for all the negativity we have in the world today.


Jesse’s life philosophy teaches the value of listening to your heart, not negotiating with the big goals that really excite you, and building not just a career resume, but what he calls a life resume.


You see it in the way he prioritizes his wife and kids, the way he shows up for his friends, and in the sheer audacity of his goals …


I hope you all enjoy learning from this awesome human being as much as I did – this is Jesse Itzler.



Chapter 1: The Goals That Choose You


FRED: You started as a rap artist in the early nineties and had some early hits, including the pretty epic Shake It Like a White Girl under the artist name, Jesse James. You wrote a popular jingle for the Knicks Go, New York, Go, which reached number one on New York radio. I think they’re still using it at the Knicks, right, at MSG?


JESSE: Yeah, they are. They are.


FRED: Amazing. Amazing. You then founded Marquis Jet, which became one of the largest private jet companies in the world, which you eventually sold to Warren Buffett’s Berkshire Hathaway in 2009. You then married Sara Blakely, the founder of Spanx, a game-changing billion-dollar brand in women’s fashion. In 2015, you were part of a group that bought the NBA’s Atlanta Hawks, which we just talked about- the basketball stuff, love it. And, you then became a New York Times best-selling author, when you published Living with a SEAL, the story of you living and training with David Goggins for 30 days, and then later, Living with the Monks, more of a spiritual journey, which was also awesome and funny and super insightful. Today, you offer various programs and challenges, including Build Your Life Resume, and various running and endurance challenges. Your life and career, when I look at it, it seems like a wild ride, and in an amusement park, more than a kind of a linear journey that people typically have, you know, school, start a job, and then maybe start a business. There’s always this very upbeat, fun energy to like everything you do. But when we scratch the surface, even just a little bit, you see a completely different side also. You see kind of a savage, super consistent work ethic and discipline, and usually, we don’t see those qualities in the same person. Did you always have this kind of duality in you, or how did it take shape in you as you sort of grew and started engaging in your life journey?


JESSE: Yeah, I would just put an asterisk next to the work ethic thing. I mean, I have a good work ethic, but I wouldn’t say my work ethic is better than anyone else’s or- I’m not working 21-hour days. I’m not the person that- I have four kids, and I try to go to everything. But I do, when I have a goal, I do really hone in on that goal. So, I get incredibly out of balance when I have a big race or a big business thing. I’m – whatever, whatever the goal is- but I always bounce back to normal. So I wouldn’t say like, I don’t want to think of myself, Fred, I don’t think of myself as someone that’s, you know, this guy, this guy, Kobe’s always in the gym. I’m not that guy. But I get really when, again, when I have a goal, I sink my teeth into it, and then I’ll make sure I carve out the time, and I’ll obsess on it until I get it done.


FRED: Interesting.


JESSE: So, I’m all the way until it gets done, until you see it to fruition. But I don’t live, I’m not- you know… I hear that all the time, and I just, I’ve never lived my life like that. You know, like my Saturdays- I shut the phone off when I come home. I actually take three hours a day for myself. So I don’t, I don’t have that, you know, I’m not a 23-hour-a-day grind guy. I don’t, I really don’t always necessarily believe that- everyone’s different, but that’s me. So anyway, that’s for starters.


FRED: Okay. Right. So you’re really goal driven. Like, it’s the goal that excites you. It’s not like a general characteristic that you have, to like always be like waking up, grind, grind, grind, work, like, be super organized. It’s really the goal itself that gives you the energy that you then use to sort of get after it like, like obsessively.


JESSE: And I go in and out of it. So I go through weeks where I’m just, I’m not, I don’t have that same energy or drive, you know. Like right now, I’m a big, I like signing, I’m an endurance athlete. And I just completed a really big race called Ultraman, which is a 20- a 6.2-mile open water swim, 6.4-mile open water swim, a 261-mile bike ride and a 52.4-mile run. And once, since that is ended, I haven’t even really ran or anything. I don’t have anything else on my calendar. So I’m in between that right now. I went through like an intense period, training, whatever, and now I’m back to like, you know, not, not in that mode. So I go in and out of it. Yeah, I love the new in it, and I love challenges.


FRED: Do you approach that in-between time as like recovery time or is it just like you’re waiting for the next goal to come? Because you hear that a lot of peak performers really stress the importance of recovery. Like, they see it more as waves than as like just kind of like always grind, grind, grind. So do you approach that as, yeah?


JESSE: It’s less recovery for me, and more- I like big goals. You know, like, I have- and they take a lot out of me. So, and I’m not talking about physical. It’s even just the emotional of it. I’m still processing the whole race. What I got out of it, how did I do it, you know, the good, the bad… And I’m looking for something that will get me… My goals are based around enthusiasm. I was very enthusiastic about whether or not, seeing if I could complete this or not. And until I find something, business or personal that sparks that enthusiasm, especially now I’m in my fifties. I’m not- I really- I don’t do it, I don’t do it. So I’m not gonna have a goal to have a goal. But if I’m, I’m always looking for something that I’ll be very enthusiastic about. Fred, when you get a 980 on your S.A.T.s, you got an over-index in enthusiasm.


FRED: I love it. I love it. And that dopamine just kind of keeps driving you forward and towards that goal. And I guess you also have to be super authentic with yourself and in touch with yourself and your own emotions to kind of know yourself: if you pick the wrong goal, right, you’re not going to generate enough energy to actually get after it.


JESSE: And sometimes the goal chooses you, just chooses you. You know, my parents are elderly now. My dad passed away recently, and sometimes you get in the position where, wow, this wasn’t, this wasn’t what I’d expected to be putting my energy into. You know, you get put in a position where your- the goal chooses you. People think we always choose our goal, but very often, something happens in life, you get dealt something you weren’t expecting. Maybe your kids have a glitch. All of our kids have some kind of glitch. You have to deal with it, you know? So, I’ve been- that, that happens periodically, too, and that takes a lot of energy. I don’t have unlimited energy, so I have to choose the elective style goals based on enthusiasm.


FRED: That’s, that’s great. So when I look at the different goals that you’ve picked in your life, right, you’ve got this really strong artistic side, right? You started as a rapper. I mean, you’ve done a lot of stuff in the music industry, right? I’ve seen your career. I mean, you weren’t just dabbling in it, right? You actually went in, and you had a whole sort of, artistic career dealing with labels and so forth. And then, for me, like the most striking transition, when I look at all the different goals that you’ve picked in your life, is the one when you go from being essentially an artist, and I’ve worked with a lot of artists, a lot of recording artists, I kind of know the profile- You go from that to not just having a business idea, not just founding the private jet company, but actually building a private jet company that turned out to be, you know, one of the largest in the world that you eventually sold to Berkshire Hathaway. We know how, you know, demanding they are on their metrics and the management and the quality of the business. I mean, so, so I see this artistic side, and then I also see this really, like, building an amazing business as well. How did this transition come about in your life? How did you choose to go from a more, you know, artistically oriented goal, to a really hard-core business goal and actually seeing it through?


JESSE: Well, like most things in my life, it wasn’t planned. You know, I was a guest on a private airplane, and I saw an opportunity. My partner and I were like, saw an opportunity in that space. And we had no aviation experience. We had no airplanes. We didn’t have really much money or much access at that time, but we had an idea. And everybody’s just one idea away from changing their life. You know, we just, sometimes, we don’t see it, or we don’t think about it, or we think it’s impossible. And we had this one idea, and once we had the idea, it was very overwhelming. You know, we’re going to start this private jet company so we can fly private. I was 28 years old. And if they would have said to me in the beginning, Fred, like, “Well, you have to get FAA approval,” they did say this. “You have to get FAA approval, Department of Transportation approval, you have to build a sales team. You’re going have to raise money. You’re going to…” And I was like, I was a kiddy pool attendant four years before that, you know, like, what are you talking about? What was the first thing that you said we had to do? We had to get the Department of Transportation approval. Well, there’s got to be a lawyer that specializes in that, let’s get that cleared. And once we got that, we moved on to the next thing. So, you know, we took this gigantic obstacle or journey that we had, which it would be very, almost too intimidating for most people, and we started doing it just like doing Ultraman, you know, like, I didn’t know how to swim six months ago really. You start to attack it, bit by bit, chopping off the most important things. And for us, a lot of that was hiring, outsourcing. Like, I realized I didn’t have the skillset, nor did I have the time to learn how to- I call a plumber. Because I can’t- it will take me too long to appoint an electrician, because I’ll never be able to YouTube it and figure it out. And what… So I should call someone.


FRED: Right?


JESSE: So it was the same thing, a lot of my career has been like, I know what I’m good at, I’m good at sales, I’m an, I have good vision, I’m a good idea guy, I’m good at marketing, I’m good at enthusiasm, I’m good at culture. And those are the lanes that I stayed in. And when we could afford to hire people, and for the other positions we did, and that’s still the same today. I’m not a balance sheet guy. I’m not, you know, I’m not a lawyer, so I know my lane, and I try to stay in my lane.


FRED: It’s so amazing how, as you say, staying in your lane… It sounds like you’re making yourself smaller. It sounds like you’re restricting yourself. But in reality, that’s exactly what’s required to build something really big, right? Because you’re not going to excel at enough things, and there are people out there who do excel at those different lanes. So it’s almost like in order to transcend your own limitations, you need to first accept what they are.


JESSE: Yeah. And listen, I’ve seen people build amazing- You know, they have the bandwidth, the bandwidth to do that themselves. And my dad, on the plumbing supply house, I was never around business. I didn’t- I still am learning. You know, I’m constantly learning, but I really rely on people that are experts to help me. And even when I had nothing, you know, slowly but surely, they don’t happen at once, we would bring in people that could assist and, and that’s, that’s always been the same formula. Even today I haven’t bothered to learn, you know, a lot of the legal and the accounting side of things… enough, enough. But why? When I get high up in the company, I’m not doing it myself. I’m going to someone like you or someone that does transactions that can really help guide me. And I’m willing to pay that fee for that expertise as opposed to using the time, my time to try to learn it. But I’m never going to be as good as you at it, you know, because I have other things going on.




Chapter 2: Saying Yes By Saying No



FRED: Absolutely. No, that’s really wise. And you often stress the value of like, diving in, like not overthinking it, not… basically leading with action, right? In the Monk book, you write, for example, “Experience is overrated” because it just takes too long, right? If you waited until you had all of the credentials that, like some business academic would tell you, you need to start a private jet company, you would have never started a private jet company, right? So like, experience just takes too long. You dive in, and you, and you figure it out, your survival instinct kind of kicks in, and then you kind of energize, sort of, everything you do. And obviously, combined with that amazing ability to know what you’re good at, to know what your limitations are, and then kind of build a team around that. So this is obviously a super powerful approach, without a doubt. It could also come with a little bit of danger and risk, right? Definitely more danger and risk than people who go with a more deliberate approach, who want to play things a little bit more safe, or more connected to sort of all the different downsides that can happen… How do you decide, like when to dive in, and when not to dive in, right? You’ve got this big goal, there’s like… Are you aware of, do you apply that same sort of self-awareness of your role, do you apply that also in the selection of the actual goals or the actual ventures you’re going to get involved in?


JESSE: Yeah, I mean, first start- for starters, for many people, it’s really intimidating to not have experience. Experience is important if you’re a surgeon, but for what we’re talking about, I just didn’t have the time for most of the businesses to develop the skills. I mean, there would have been a million different businesses launched in the same space if I would have waited. And for a lot of people, not having the experience can be incredibly intimidating, and it could be a deterrent. But for me, it was always a big gift because it guaranteed that I would do things differently than everybody else. It guaranteed that I trust my- I would learn how to do it, you know, it would give me a different perspective, a fresh lens than everybody else in the industry. Most people in most industries follow the playbook that, that’s standard in that industry. And that’s not where innovation and disruption comes from. Innovation comes from newness, and being willing to do things: look different, and operate different, and treat your customers differently. And I’m constantly asking myself, how could I do this differently? You know, what makes me stand out? Is this the right thought? Is this- every element of that. And not just to be, just for the sake of being different, but authentically different. So, for me, that was the greatest gift because it meant Marquis Jet, we were going to average- we were going to do everything differently, and every business that I’ve had. So, that’s the first thing. When I was younger, in my twenties, I said “yes” to everything. Twenties are a great time to network, say “yes”, get out there. You’re building a foundation, and you want to create luck. You want to put yourself in an environment where you can attract luck. Who you meet, a possible sale, introduction… That doesn’t happen staying home. So you have to say “yes”. As I’ve gotten older, I’ve realized the importance of saying “no”. And a lot of people don’t want to say “no” because they don’t… You know, you don’t, you know what, Fred? “Fred’s a jerk. I asked him for 15 minutes, and he couldn’t even give me 15 minutes of his time.” You know, 15 minutes of your time- If you spend 15 minutes every day, and you would just, and just treat it like a throwaway, “I’ll give you 15 minutes.”  Because people always ask me- 15 minutes, it’s like the standard. 15 minutes- there’s something called the rule of a 100. The rule of a 100 is if you spend a 100 hours in the course of a year, it’s basically 15, 18 minutes a day. You’ll be better than, in any discipline that you choose to spend 15 minutes a day, you’ll be better than 95% of the world’s population in that discipline. It doesn’t mean you’ll be a Jiu-Jitsu master. It doesn’t mean you’ll be the best saxophone or violin player or chess player. But you’ll be better than 95% of the world’s population. If you spend…


FRED: Crazy.


JESSE: …15 minutes a day reading a book and you’re an average reader, you’ll read about 18 or 20 books a year. Think about what you can learn. So you can’t be casual with, with your little 15 minutes a day. In fact, you should be really deliberate, and carve out 15 to 30 minutes a day. When I was- I’m going to answer your question in a second, but when I was- I don’t know how many parents listen to this- but I remember before I even had kids, I was in my office at Marquis Jet, my friend came in. I asked him how the weekend went. He said it was good, I said, “What do you do?” He said, “I went to my son’s soccer game.” I said, “How’d he do?” Just making conversation? “How did he do?” He said, “He had seven goals.” I was like, “Seven goals? How old is he? Seven goals? You kidding me? He’s like, six.” I said, “Well, how did he get so good at soccer?” He said, “I spend five minutes a day with him.” I was like, “What are you talking about?” He goes, “It’s just five minutes a day. All the other kids they go to, they go to practice on Saturday. And, and then, they do their own thing and then they practice on Saturday. But my kid is getting an extra five minutes, an extra 30 minutes a day, an extra two hours a month.” And he goes, “That’s the difference.” And I didn’t even have kids. And I’m like- I never forgot that. And I started implementing the five-minute-a-day rule with my kids when they were young. Now it’s gone to like a 15, 20-minute rule a day. But those- that time is very valuable. It’s important that you structure your day and you leave time for yourself to learn. Gandhi said it best. “Live like you’re going to- live like you’ll die tomorrow. Learn like you’ll live forever.” You have to keep growing.


FRED: That’s a good one.


JESSE: … and mastering your skill, whatever your skill is. Before I did Ultraman, all right, I’ve never even done a sanctioned Iron Man in my life, and I jump into this like the granddaddy of all, of all these races. I dove into it every day. I learned how to swim on YouTube. I was, I mean, that’s when you talk about- in the beginning hard work. No, it’s an obsession, while you have your goal, on your, on your way to your goal, and then you go back to your regular life. And I told my family, I told my wife and kids, “I’m going to be… Dad’s going on his own island for three months, man, I got to knock this thing out, and then I’ll be back.” You know? So they knew, because I didn’t want them to resent me. I didn’t want to resent them. I didn’t want to feel guilty for- if they took away what I love to do. Going back to your question about choosing things on experience, and lack of experience: your twenties, you say “yes” to everything. And then, as you get older, you start to realize the importance of “no” and how to say “no”, which I can talk about in a minute if you want. But the way that I grade things now, as I get older and, you know, if you’re not in your fifties, you can think about this as you get older, is aggravation versus reward. You know, for me, I don’t want high aggravation in my- going into my sixties and seventies. In my twenties, I could handle high aggravation for high reward. It was that, that tradeoff was worth it for me. That, the aggravation was worth it because I had nothing. I wanted the rewards. But now, I want low, low aggravation, even if it’s low reward, but for the highest worth. It’s high aggravation- you know, someone says, “Hey, you want to start, want to co-found Google right now?” No, you couldn’t pay me a bazillion dollars to start Google because I have four kids. You know? I wouldn’t- that- it’s not- I wouldn’t trade that for that right now in my life: missing, and working 20- you know, I wouldn’t do that. So it’s aggravation versus reward. One thing I want to add: there is an art to saying “no”. And if you’re like me, you don’t like it, because you want to be liked. So you don’t want to say “no” to people, because you’re scared that they’re not going to like you. But there’s an art to saying- If you invite me, Fred, to go to dinner on Thursday night, this Thursday night, you’re like, “Jesse, we’re all five guys, man. We’re going out. We’d love for you to join.” First of all, you know, I would say, “Fred, I appreciate the invitation. I can’t do it on a Thursday.” I don’t need to explain why. I don’t need to give you an explanation when I say “no” of why I can’t go. I’m not- I’m not on the defensive. You invited me, and I can’t go. Now, you guys…


FRED: That’s big.


JESSE: The reason I don’t want to go is: I’m going to sit home and play baseball catch with my son this Thursday. Now, you guys, five guys are at the restaurant. I’ve already said “no”. And I do it myself. I don’t outsource my “no’s” usually. I do it myself. Let them know. I’ll call up the restaurant, “I’ve got my friend, Fred, my friend Fred is there. I want to pick up the bill. I want to send dessert. I want to buy a round of drinks. I want you to write this note, please: Fred. Thanks for the invite. I wish I was there with you guys. I love you, guys. Dessert on me. Enjoy.”


FRED: So you show, you show, like, love and appreciation. You don’t just say it.


JESSE: Right.


FRED: You also demonstrate it, and you’re, and you’re kind of part of the experience.


JESSE: And I’ve used it as an opportunity- I’m the hero of the dinner. I’m the hero of the dinner. “Like this guy’s … Look at this guy. He’s not even here. He sent this… He thought about us? I invited him five days ago. He remembered?”


FRED: Yeah, that’s really cool.


JESSE: “He’s thinking…” There’s a way to turn a “no” into an amazing opportunity.


FRED: That’s huge.


JESSE: … Think about all the time you’re going to save, the 15 minutes you’re going to save to master whatever it is you want to master, and think about, you know, how that’s going to have, you know, shockwaves throughout all those “no’s” that you say. And I’ve become really good at that, and I know it. I do show up for my friends. I do show up. I don’t say “no” to everything. But, I can’t say “yes” to everything. One more thing I want to say, warming up now… As you evolve, as you evolve, right, when I started Marquis, I didn’t have kids, I didn’t have a wife. I had time, you know? I would eat dinner at 11:00 at night. I’d still carve out time for myself during the day. I’d still run races. But I would like, I can do whatever I want, in and out of the office, weird hours, all that. At 54, my life looks very- I eat dinner at 5:30 now. So, your life system has to evolve as you evolve. You can’t, you can’t- And as I put more on my plate, running races that take, you know, it’s a 30-hour race, having kids and all this stuff, you have to say “no”, you can’t keep adding stuff without saying “no” to other things. So you have to get good at it.


FRED: I love how organic you are about these things. Like, you don’t have like a, like a perfect theoretical answer that you then try to measure, like that, you then try to sort of fit your life in. You have this very kind of like, organic, responsive almost approach, like, okay, what does my life look like today, right? It’s not the same as it was at 20, not the same as it was at 30. So you’re trying to make it fit in a broader sort of life experience.


JESSE: I don’t want to scare anybody on theory. I can only talk from what I- my life model, what I’ve experienced, what’s worked for me and what hasn’t. I can’t talk about theory. So either some of the things that we’ll talk about in the course of our conversation today will resonate, people will try it, or it won’t. But I have to only share from my experiences. I’m a big believer in the more you experience, the more you can offer. You know, I’ve lived with, with a Navy SEAL, I’ve lived in a monastery, been in the music business, I’ve written books, I’ve had businesses that work, businesses that fail, I’ve dealt with losing a parent, I have kids, you know… I feel like I can talk about a lot of different things, but only things that I’ve done.


FRED: Yeah. Yeah. And that’s why I think it resonates because we feel that authenticity, even in your writing style, it’s very authentic, it’s very direct: you’re not trying to make it sound like, like something, you’re not trying to make it sound like someone. It’s very clear that it comes from the heart and it comes from, from your actual experience.



Chapter 3: The Process of Achieving Goals


FRED: So, Living with a SEAL, that was a very, very- a lot of people read that book. A lot of people are into, you know, the whole- David Goggins Stay Hard movement. We love it. Gives us the inspiration, sometimes you need that little kick in the butt to wake up in the morning and go for that run. And living with him for 30 days, the question I have for you: does Goggins have a secret, friendly, soft side that we don’t know about and don’t see, or is it really, all like, stay hard all the time?


JESSE: Well, you know, I haven’t spoken to him in a while, so I don’t know what, what he is like now. But, you know, when I met him, I met him in 2006, so I met him 16 years ago. And he was a part of my life more than just 30 days, you know, we, we… I wrote about 30 days, but I’ve known him for a long time. And yeah, I mean, he, he has or had I should say, as far as, you know, when I was rolling with him more, in intensity that tracks still, I don’t think he’s ever going to lose. You got to ask him. But what I love about Goggins is- they always say surround yourself with like-minded people. But I always found like, why? Like, they do, they think like- I want to surround myself with people that aren’t like me so I can learn about them. And I love meeting people that are really great at what they do in fields that I’m interested in, like spirituality, the monks, mindset, you know, Goggins, business- I live with- my wife is an incredible entrepreneur- health and wellness. I seek out these people that are great at things that I’m interested in, and, and Goggins was one of them.


FRED: Amazing. A key lesson that really resonated with me, and it goes back to what you said about having these huge goals and then chunking it down, like starting with the, you know, you had to get the approval, and then it’s like, all right, now we’ve got to build a team, and now we’ve got to do all of these things that, that, right… We’ve got to find the right pieces around us. One thing you wrote about your experience with the SEAL is that your perspective on time changed. You learned how to control your mind, and in particular, you wrote that SEAL just wanted to get better tomorrow, right? That was his perspective. It wasn’t like, this big overwhelming idea. He just, it just, it was just focusing on getting better tomorrow. Why is it from your perspective, and to me, I see a clear theme, right? Like people who overthink or who make a big plan and then they try to measure up to that plan, get overwhelmed, right? You seem to be much more in the immediate, and it’s much easier to kind of persevere through the immediate. Why do you think from your perspective, that thinking too far ahead, and sometimes like overplanning, overthinking can be detrimental to actual, like perseverance and, you know, pushing through the grit?


JESSE: I think a lot- I think there’s a lot of ways to answer this. I think a lot of people shortchange the journey when they think too far ahead, you know, and they go, they go right to the end, then they eliminate, like, the steps. You know, so I’ll give you an example. It’s just- Ultraman, you know. It wasn’t a five-year ahead or big thing, but I had, I had a goal, but I was- I loved the workouts, I loved the process, the journey. If I was studying for the bar, I, you know, there’s a- you have to have a passion for the process, the actual late night. So, like, there has to be an appreciation for that, because everything requires that. You didn’t just take the bar and pass it, you had to stay up late to study, and it stunk, and you sacrificed and all that. Guess what? That’s the same with every single big goal that you have. There’s no way to get around that. And I love the process. So, the relationship with, your relationship- people think of relationships in terms of people. How’s your relationship Fred with your son or your parents or whatever. But they rarely think about their relationship with money, really understand their relationship with money. Why am I working? What do I want to do with it? What do I use my money for? You know? And time.


FRED: Yeah. What are the sacrifices, right? What did, like, the time sacrifices, the health sacrifices… I know so many people grinding for that money, sometimes I think they’re unaware of all the sacrifices they’re making along that, that sort of chase.


JESSE: Or they think they have forever to do it like, “Oh, I’ll do an Ultraman next year, I’ll take the bar next year.” I’m sure most everybody listening to this knows they’re going to die. There’s no one listening to this podcast that doesn’t think that. But I guarantee you that 99.9%, maybe yourself included, don’t have their graveyard plot picked out. They don’t have, even their passcodes to their significant other. “Here’s the key to my security box. You know, if something were to, God forbid, happen to me, here’s my Instagram pass-” Like, they haven’t done that. The reason is they know they’re going to die, but they don’t think it’s going to happen anytime soon. Because if you did, if you knew, if you knew definitively you had a week to live, you would have all that mapped out, right? So, we don’t think it’s even possible that something happens to us. We don’t think we could get in a car accident, or we could wake up with a diagnosis. It’s- we’re bulletproof because we- that happens to other people. Until you realize that, any day- I- my relationship with time is, I believe, so unique: I’m so aware of my mortality. I am so aware of every single day. I talk about it, I think about it, I talk to my wife about it. You know, I always say to my wife, like- both of our parents are alive, that’s not true anymore, but I used to say all the time, “Both of our parents are alive, our kids are healthy, knock on wood, you know, like, your job, your role with- how could life even get better?” And like, I’m always bringing her to like, where, like what it is. And I’m aware that it can all change. And it did change for me. As it will for almost everybody. I’m sure the people that got diagnosed with cancer didn’t think, most often, they were surprised, “I got this thing checked out. Oh my God.”


FRED: That you never think is going to happen to you, like, it’s the classic, right? Like, it’ll happen like, one day that’s so distant that I don’t really have to kind of think about it, how I’m living my life right now. It’s the Memento Mori thing, right? Like, remember that you are mortal. Like, we usually don’t live with that consciousness.


JESSE: If you’re not thinking of that, you know, I operate with- I’m almost manic. I operate with the most insane urgency. Everything is ready firing. I hear about Ultraman, I sign up for it. I don’t know where it is. I don’t know how cold the water is. I don’t know… I just, I’m in, and then I’m going to figure it out. Marquis Jet, great idea, I mean, there’s a little bit of research behind it, obviously, but I don’t have it all figured out. No one- I don’t have the time to wait to figure it out. If I have the enthusiasm, if I can see it in my mind’s eye, if I can see it, like, I could do this, in my heart, if my intuition is telling me that I can make this happen- again with no airplanes, not knowing anything- but I could see a path, and I, and I see what it looks like, I go, I go for it. I’m not-


FRED: It’s a very inspiring, it’s a very inspiring approach you have, I have to say. Like, I went more like, the sort of the school path and like, right, that, the planning everything out, and planning everything like 20 years in advance. And it took me a long time to sort of reconnect with my, my intuition, with my desires, right? And when I read your book, you wrote something about how, you know, an experience is like a deposit in a bank account. It’s something you can draw on. And it’s so true when you’ve had these amazing experiences. Anybody that’s had great experiences in their life, it’s something you can go back to with your memories, something that feeds you for your entire life. And you wrote this line. You wrote, you know, if you climb Mount Washington with someone, like, you’ll have an experience with them, like, you’ll have lifelong memories. And I have to, I have to confess, when, when I read that line, it struck a chord. I started sending out some texts, I’m like, “Guys, we’re climbing Mount Washington next year.” A few people think I’m crazy, but we’re doing it. We are doing it next year. It was inspired by a line in Living with the Monks, so I had to give you credit for that. That’s going to happen.


JESSE: Fred, when I when I shot Living with a SEAL, Living with a SEAL is my first book, I went to 14 publishers, and every publish- I wasn’t on Instagram. Maybe, maybe I was, maybe I had like 200, 700, something like 2,000, 700, something like that, like nothing, followers, and most of them like fraternity brothers, you know, my family, my coworkers… 14 publishers rejected it. I didn’t even get a meeting. I didn’t even get a face-to-face meeting with any of the publishers, all right. And then I went, knocked on the door of a small independent publisher called Center Street, which is a division of a bigger publisher called Hachette. And the editor Kate Hartson gave me a shot, okay? She gave me a shot. And the book became, you know, a huge hit, huge hit. New York Times bestseller, blah, blah, blah, blah. And the reason why I’m sharing this story is: it’s, it is the exact example of my journey. 14 people said “no”, and I kept going until I found the one “yes”. My- the only thing I’m good at, it’s like the only thing I’m good at is- not the only thing but- is not quitting until I find a path to success. That’s it. I could have easily been like… the book would have never came out, but I was going to exhaust every possible option. I would, I would exhaust every possible option from smaller publisher to smaller publisher, smaller publishers, self-publishing it. And ultimately, I would have, I would have found the way to put that book out, even if she said “no”. And that’s not a superpower, man. That is just, an un- an unwavering commitment to not negotiate your goal. And I have an unwavering commitment to that. And it doesn’t always work. But I’ve always found that there’s only two outcomes: success, or you’ve exhausted every possible option, and it didn’t work. And either one of those is okay, it’s okay to fail if… but not to quit. Not to quit. And there’s a big difference between failing and quitting. Quitting is like, “This sucks. I don’t have what it takes. I’m not, you know, I don’t want to go through this. I quit, I quit, I tap out, I’m done.” Failing is, “It didn’t work for me. I tried everything, and my product wasn’t right at the time. It just didn’t work.” And that’s okay too.


FRED: You can still have that self-respect knowing that you’ve exhausted all of your reasonable paths. You’ve done all the things, you’ve learned, maybe, probably some lessons along the way. But it wasn’t out of discouragement for the fact that it was hard.


JESSE: Or I don’t have enough experience or I’m not good enough.


FRED: Those excuses…


JESSE: that people use to fuel a story to the public, you know, ultimately of why it didn’t work.


FRED: Right. I love it. And this is, like such a great mindset for anybody trying to achieve anything in life and obviously, with your track record- speaks for itself.




Chapter 4: Intuition and Purpose


FRED: But then with Living with the Monks, you go through a different journey, a completely different journey. And just, first of all, it’s, it’s also a hilarious book, “laugh out loud” moments. First of all, like, the moment where you realize that it’s Christian monks. It’s true, we talk about monks, we think it’s going to be Buddhist monks, so like that, that sort of surprise. And then, you know, your driver getting there and says, “Oh my God, this is the boonies!” Your driver’s like, “This is the boonies.” “This is the loonies.” Right? So this is like really, really hilarious. And you write that you were looking for that feeling of accomplishment that you get from business, but you were looking for, you were looking for it permanently. So it was more like an inner quest, like a spiritual quest than an external quest of, of achievement. It’s clear that, like, all the stillness and the calm was kind of irritating you, if not driving you crazy at times. And you had this really interesting thought that kept coming back in the book, the thought that the one thing, one of the things you realized living with the monks is how modern life kind of constantly bombards us with information and overwhelms us. And we’re so constantly overwhelmed by everything: social media, kids, calendars, business appointments, workouts, all of the different things that in this mad scramble, it’s the first time I read it expressed quite that way, that we’ve lost our most significant asset, you write: the ability to think for ourselves. And you write that this mad scramble of modernity, one of the effects it has is you can start losing touch with your own intuition, your own gut feeling, which is really one of your secret weapons. Obviously, in your life, you’re beyond busy, your life appears, at least from a distance, to operate at warp speed sometimes. How do you deal with this challenge, this sort of information overload challenge on a day-to-day basis to make sure that you don’t lose touch with your intuition, your gut feelings, your authentic sort of connection with yourself?


JESSE: Yeah, again, I’m not a, I’m not a scientist, but, or a therapist, but I do believe, I stand by that, that, you know, the only- one of the only ways to stay in touch with your, our greatest power, which is our intuition, especially when we’re getting bombarded with social media, news, and this, and influence, and podcast, and all this stuff is to spend time alone. And it doesn’t mean you have to go to the Himalayan Mountains. Lay on a couch and sit, you know, and think for an hour and hours at a time. But it’s important to spend alone time. You know, you sharpen that muscle by spending alone. Intuitively, I’ve been doing that by running. You know, that’s my time to think, block everything out. I didn’t even realize it. But it’s important to spend time alone, and to do some thinking. If you look at a lot of the great leaders, great CEOs, I just saw on the Bill Gates special, you know, he goes on think retreats. My wife created a fake commute; work is two miles away, but she goes for a 40-minute commute so she can think in the morning. It’s important.


FRED: That’s cool.


JESSE: It’s important to spend a little time, and not ask Siri, and not Google things, and think about what it means to you, you know, and get in touch with your intuition. So, you said something earlier when you were introducing the Monk story, though, about feeling accomplished, and I’m just going to take a quick sidebar.


FRED: Yeah.


JESSE: To piggyback off that. When my wife sold Spanx recently, I asked her, like, you know, it was a big transaction, you know, about transactions. It was a big transaction.


FRED: Yes.


JESSE: And she was like, I asked her, you know, “Is there anything you want to do to celebrate this? Like you want, to want to buy, what do you want to buy, a yacht? Like, what do you want to do? You know?” And she didn’t, and she just said three words to me. She said, “I did it. I did it.” She had this feeling of accomplishment. She didn’t need a yacht, to, you know, she didn’t do it for the yacht. She didn’t do it for- She did it for the sense of accomplishment. And I could tell you from experience, I sold five companies, that if, so I have the right to say this: the, the feeling you get when you sell a company- maybe Sara’s was different because the transaction was bigger than, you know all five of mine combined- the, the same feeling you get when they send the wire to your bank account because you sold the company or they give you the check, it’s the same feeling you get, feeling, feeling, when you cross the finish line of a marathon, or you help an old lady across the street, or you do something that makes you feel accomplished and good. It’s the same, it’s the same exact feeling. And many of us, we spend our whole life trying to figure out that one Spanx moment when we sell the company, or that one big whatever, and we wait to get that. But the reality is, if you could, if you could figure out how to bottle those feelings every day, you know, you’ve really got one life, because those transactions are once every two decades, you know, in your life. But-


FRED: If ever, if ever. I mean, the vast majority of people, it’ll never happen, right?


JESSE: … but one person, helping someone, volunteering, doing this, doing something that makes you feel, it’s what we all have in common: we want to feel good, we want to feel accomplished. If you can figure out how to do that every day, you don’t need to climb Mount Everest to do that. If you can figure out how to get that in your life every day, you really are, have one. To me, that is the secret. It’s not- that is the number one secret because it’s a feeling. And I just, it struck me when she said that, when I put it into like, “Wow, you know, like, I’ve felt that I know what you mean, but I get that feeling all the time, sweetie.” She goes, “What are you talking about?” And I really do, on a day-to-day basis. I really do. Now, I have a coaching program, so I get, you know, my ROI, my return on investment isn’t a financial element of it, it’s the DMs that I get saying, you know, “Wow, you really impacted me today. I went to visit my mom. I would never have done that if you didn’t tell me more about time and this and that.” Even you as a transaction, you know, as a lawyer, as, as in all the things that you do, as a podcast host or whatever, the return on, the ROI should not only be financial, you know. It should be about the viewers and listeners that watch this, that benefit. It should be about, you know, the people, your clients that you help on the legal side. You’re still practicing law? Right, Fred?


FRED: Yeah, yeah, absolutely.


JESSE: Yeah, right. So I mean, just wanted to make sure you didn’t retire already or anything yesterday.


FRED: No, no, I’m still in the game. I’m still in the game.


JESSE: But the ROI should be more than just settlements and transactions. The ROI should be like, you know, how you influence your clients, how you interact with them, if they feel like they made a good decision on the lawyer that they chose, that they feel like they put their commitments and family matters in the hands of someone they can trust. Like these are the things that people get overshadowed by the dollars and cents. I’ve never built my career on that, man. I’ve never-


FRED: So true. No, it’s so true what you’re saying. I remember when I was younger, working in, like, bigger firms, and I was working in, like, complex transactions, complex, right, like working with bigger companies and so forth, and you get a lot of satisfaction from that. But then, I decided to try out, sort of practicing on my own more independently. And the biggest difference I felt initially was not, it was- had nothing to do with financial, right? People thought I was like, being an entrepreneur or whatever. It had nothing to do with that. The biggest difference was I could feel the positive impact I’m having on an entrepreneur’s life, like helping a human being, helping this person, helping this person, like making a difference in their lives and their business, in their family lives and so forth. That was really, I felt like, wow, what a source of energy I’m getting just from being closer to the client, helping actual human beings. That’s such a, an amazing source of energy.


JESSE: If you don’t have… You know, again, we’re having a conversation with friends. I haven’t, I haven’t thought about this stuff, but I- on the top of my head, if you don’t have that feeling as an entrepreneur or as a business owner, you’re probably in the wrong space, because they say you find your, your purpose at the intersection of three things. What is it you love to do? What is it you love to do? Providing a product or service that can help people, and getting good at it. If you can do those things, you really found your purpose. If you’re not, if you don’t feel like you’re helping people through- and I always did, even at Marquis Jet; I’m making your travel easier. I’m going to be the best customer service advocate rep I can for you. You know, I’m never going to not take a call. I’m going to get in front of my problems. Like all of that stuff. I really felt like I was providing a service first, you know, rather than just a transaction.


FRED: Right. It’s very clear that energy of purpose is very present in your life, like making an impact on people’s lives, helping people, making sure that you can have that impact, it’s very, very clear. And it’s so funny because, like, over the course of my, my own journey, I sort of became more and more obsessed with this concept of purpose. And I know you’ve written about, you know, Viktor Frankl writes about, you know, once you’ve found a purpose, once you’ve found something where you want to help people, you want to be part of something greater than you are, you create really strong imagery around it. I love the fact that you took that, that aspect of Viktor Frankl’s work, because again, it’s really practical, really tactile, right? Like create imagery around that, and then you kind of stay connected to it, and it really energizes you that, that’s the thing. It’s not like, it’s not like halo stuff, it’s not like you’re trying to prove that you’re a good person.


JESSE: Right.


FRED: It really does provide you with an unbelievable amount of energy that I believe, once you hit certain financial milestones, you just don’t get that, that same energy like going for more money, right?


JESSE: No. I agree. Yeah, I agree.




Chapter 5: Dodging Arrows and Remembering Tomorrow



FRED: It’s amazing. It’s amazing. So you’ve got these really cool little hacks that kind of like, work as like, almost like, and I took just a couple of them, like two or three-word expressions that kind of like, bring you like, focus you on, on a kind of key concept that can help you perform. One of them is “dodging arrows”, right? You talk about, and we talked a little bit about like dodging the distraction arrows, about how, you know, once you reach a certain level of activity in your life, might be after your twenties, maybe into your thirties, you’ve reached that level of energy. Now, it’s no longer just about adding stuff. It’s also about what are you going to remove, right? To have that focus, you need to eliminate certain things in your life, right? So, so do you have a process where you kind of take a look at your life like, “Okay, what can I eliminate? What do I want to focus on?” Do you build that? Do you schedule that into your actual day-to-day?


JESSE: Not so much that I schedule it into my day-to-day, but I’m aware of it. So if I’m going to- I  just took on a project All Day Running Company, I know that to take that on, I have to eliminate some of the other stuff that was on, that I was looking at. I had to make a decision. I can’t do everything. But the arrows that I talk about mostly are stuff that come at you without you even knowing, every day. And it could just be like, I need 15 minutes of your time. Or my son has to… It’s constant. It’s constant. Like today, you know, I had to do something for my son- his braces fell off- to the orthodontist… You’re just always getting… So, one thing that I do to kind of get in front of that is, I’m a big believing- believer in morning routines. I like to get early mornings, but I’m a much bigger believer in evening routines. I like to set my calendar for the day the night before. I don’t think anybody here listening is good enough to just wake up, and wing it. What am I going to do today? “Oh, let’s map out the day!” Like, no. The best CEOs in the world, they have, they have three assistants, they give them a thing, a schedule, and they say, “9:00, you’re here, 11 here, 12, I’m asking you to be here…” They follow the script. We don’t have three assistants.


FRED: Yeah.


JESSE: So you got to map it out the night before: most important stuff first, and then you go, and you try to execute on it. You just follow the script. So, you can avoid a lot of arrows when you’re, when you’re, when you’re playing offence. Most of us, I believe, play life on defence. Our calendars fill up with other people’s requests for our time: Zoom meetings, weddings… And we’re just “Yes, yes, yes.” And then all of a sudden our 52 weeks, weekends, and- they’re all filled, and we have no time for ourselves. And I flipped that model upside down. I play life, I play… Let me show you this, Fred. Check this out. Are we on video or just audio?


FRED: Video, too. Yeah.


JESSE: Check this out. So, this is my entire year. This is a calendar.


FRED: Oh, man.


JESSE: This is my entire year. You can see all these different things laid out.


FRED: That’s so cool.


JESSE: That’s a thing called the big-ass calendar that I have, and… But I lay out my whole year in advance. In advance. Ultraman- these things, they’re planned. And I follow the script. So when the arrows come at me, I get thrown off track, but the most important things, I try to get on my calendar, and play offence, so I don’t fill up my calendar with other people’s requests for time. And that, guess what? My 2022 was unbelievable. It was baked in December 2021. I’m just executing on it. My family trips-


FRED: You’ve just been executing it.


JESSE: One-on-one trips with my kids…


FRED: So, so you’re not dealing with all that overwhelm, and all the different, like, you know what you want to achieve, you know the goals that you’ve selected. It’s so funny because as a sports fan, the first time when we were talking about dodging arrows, I’m thinking like, “Oh, that’s great, you’re actually playing defence.” But it’s interesting how you frame that as playing offence, right? If you want to achieve the goals that you’re going to achieve, you’re not going to achieve them by getting hit by all the arrows, right? So, it’s actually part of playing offence.


JESSE: Sit around waiting, man, and then, you know, you just, then you lose, you lose control of your time.


FRED: Oh, it’s great. And another one that, that I love is “remember tomorrow”. I love that. Just, it’s just a little weird two-word statement, right? And it’s like whenever you get to a key decision, remember how it’s going to make you feel tomorrow, right? Like always, do it with an investment mindset of like, what’s the impact going to be tomorrow? What’s the impact going to be at the end of the year? And you kind of go back to that, I’m sure. It’s just a nice way to kind of phrase that.


JESSE: That, that in a nutshell, is, think about how your decision today will impact you tomorrow. So, if you want to drop out of the marathon at mile 18, that’s cool. But how will you feel tomorrow, when you have to wake up and be like, “I could have gutted it out”? You don’t want to make return on your calls, your clients, this and that prospects that call- you don’t want to go… That’s fine, but how will you feel tomorrow if someone else does it and gets the account? So, I always like to ask myself that question, like how will this decision, big or small, impact me tomorrow?


FRED: Yeah, the impact on the future. And part of that is also your investment mindset of like, you know, the 18 minutes a day, like, you do something seven minutes a day, eight minutes a day. It’s like, think about the compound interest of that practice over time. And a really great little hack that you shared on your Instagram, which is really filled with all kinds of super useful stuff that I really love: this idea of like, think of, like, I forgot what you said, like 10 or 20 or, however, whatever the number is, the people that can make the biggest impact in your life or your business, and like, once a quarter, just make sure that you’re kind of present in their life. And you just plant those little seeds, and it doesn’t take a lot of time, but you’re not focusing on like, one thing they can do for you. It’s not transactional. It’s more like you’re planting seeds, and you keep planting the seeds, some of them eventually are going to…


JESSE: I was on the way, I was on my way to pick up my son yesterday at school, he goes to school at like 40, 40-minute drive in traffic yesterday, and the first thing that came into my head is who are the people that I should call during these 40 minutes? Like, instead of listening to the radio, let me just, you know, knock out three or four seeds. Let me plant a couple of seeds. Let me hit a couple of people up, and just check in. And, you know, and I do, I do that. It’s second nature to me. But listen, here’s the thing. If you just do that three people a day, right? Take a minute. A minute. A minute.


FRED: Yeah.


JESSE: I text “Hi Fred. Thanks for the pod today. Great to meet you. Awesome chat and appreciate you.” Boom, sent. Three of those a day in a year. That’s 1,000. Three minutes a day equals 1,000 people. Now, they’re not all going to be customers or clients or best friends. But, one- what I said earlier, you need one. One idea, one “yes”, one referral, one anything. So I like the odds: if you go to a 1,000 people, that one of them is going to react or respond and be there when you need them. And I’ve been doing that.


FRED: It’s huge. It’s huge when you adopt that longer-term perspective, and investing in the future. One little habit like this, right, the one minute a day, could literally have a transformative- and then like, you do that for three years, that’s 3,000, right? So it’s like, it keeps adding up.


JESSE: Or in my case, 30 years. Yeah. And I call it the three-minute miracle. You just spend three minutes a day: you send a text, handwritten letter, DM, and the floodgates will open. I’ve never- Fred, I just want to say one thing- I’ve never seen anybody that’s invested a couple of minutes a day consistently, can’t do it for a week, but consistently, even a call a day, that has backfired. I’ve just never. And all those transactions, they’re one way. I’m not asking. “Hey, Fred, I need a favour.” I never do that. I don’t ask for favours, unless it’s like medical, or like, really important. You know? So, it’s all one way, man. “Fred, I know you’re into the Raptors. Check out this article on the Raptors.” I’m giving stuff. I’m not asking for stuff.


FRED: Yeah, and I love it. And it’s like, remember tomorrow and like, remember next year? Remember two years from now, right? So, keep planting those seeds, keep going forward with that, that investors mindset. It’s just a great way to look at it.




Chapter 6: Building A Life Resume


FRED: So for all the amazing things you’ve achieved, in some quarters you’re still known, and you refer to yourself even, as Mr. Sara Blakely. You spoke about the amazing transaction. You had some funny stories of women noticing you at a restaurant, and then coming up to you, and you think it’s- and it’s like, “Are you Sara Blakely’s husband?” Right? That’s what you’re kind of known as. And a lot of men feel insecure being with a successful woman. You hear this a lot when you talk to successful women, they’re like, “It’s a struggle because we just make men feel insecure.” And in today’s society, like, we’re, you know, men are supposed to be providers and protectors, so very few men will ever have a woman that’s as successful as yours has been, is. What advice or perspective can you share with men in this regard? How can they celebrate the power and beauty of powerful women, and not be made to feel insecure, or judged by how the culture sees them?


JESSE: I don’t know if I have the secret formula for that, Fred, but for me, when the, when the red light is on for Sara, I’m her biggest fan and cheerleader and vice-versa. And, I just feel like, I went through a period of insecurity. Like, I remember going into, pre-Sara, when I sold my first company, into meetings with the board and this and that, feeling like I’m definitely the least intelligent person in the room, the least qualified person. And I’ve gone through that. I know what that feels like. But now, when I look at my life and accomplishments, and I’m not talking about financial, just, in multiple buckets, I just don’t feel that way. So, I don’t know. I’ve never felt that way. I’m super proud of her, and… Yeah, I love when people come over to her. I love it. So, I just think, it’s a partnership, man.


FRED: Yeah.


JESSE: And she’s never made me feel like that, you know what I mean? Like, she’s so particular. She’s like, and Spanx is a small part of her success. You know, you’ve said very few people be as successful as her, maybe financially, but success has multiple buckets. So in, you know… Yeah.


FRED: Right. It’s the life resume approach, which I love. It’s one of the things I really love about your work. It’s the focus, not just on building a work resume, not just a focus on building a career resume, but building a life resume, building those life experiences, and not just focusing on one of the buckets. And you talk about, you know, some people have a bucket list, you also have a fuck-it list, like something you’re just going to do, just because, right, just because you feel like it, just because you want it. It’s going to bring energy in your life. So, talk a little bit about that. Like, first of all, like, how did sort of you approach this idea, and I know you’ve helped other people do that, of building a life resume, thinking of your life as experiences. And then, I’d like to know what’s a big thing coming up for you in your life resume or your fuck-it list building up into the future?


JESSE: Well, I just think the more you experience, the more you have to offer. I feel like there’s a huge wave of influencers about, talking about how to grind and push and work so hard or whatever and like, no shit? Did you go to Harvard to tell everybody that? Guess what everybody listening? You got to work hard. Like, that, that’s obvious. But what was lost in that message is the importance of not giving up your twenties, of not giving up. You know, they interviewed the wealthiest families in America- there was a, in a study where they, you know, liquid net worth of like 20, 25 million liquid or more, very wealthy families- and they asked them what their biggest regret was in getting all their money. And overwhelmingly, it was giving up what they had for what they wanted. They gave up what they already had.


FRED: Hmm.


JESSE: To get what they want. And, you know, again, you couldn’t- it’s easy for me to say now, but like, I have friends on a very, very modest salary that would say the same thing. You couldn’t pay them enough to miss a season of little league, you know. So, you can’t lose track of that. And your life resume is as important as your work resume. It’s, it’s the things you’ve done, how you show up, your adventures, your races, your, your art, whatever it is that you do. It’s that bucket. And it’s what makes you interesting. It might help you land a job. It’s what people want to talk about at lunch. It’s what customers, you know, it’s contagious, it’s infectious. And so, I really always encourage people, every year to do one-year defining thing. There’s an old Japanese ritual called the Misogi. And the notion around a Misogi is you do one big year-defining thing every year that you can really remember. So, if I were to ask you, Fred, like, what’d you do- you don’t have to answer me- 2015, 18, you know. You shouldn’t struggle to rattle it off. In 2016, I wrote a book. I launched a podcast in 18. I ran a marathon. I went through- I learned Chinese. I did- whatever. But, you should be able to- here’s a thing. If you’re 45 and listening to this, 45 years old, the average American lives to be 78. So, you live another thir- you know, you like to 80- you live another 35, 35 years. Imagine if every year, you did some kind of year-defining thing that you normally wouldn’t have done you know -this year, for me, it was Ultraman- and you had 35 Ultraman-type things on your life resume. Like, that’s a friggin’ un- and you did everything else. You had your law firm…


FRED: Yeah.


JESSE: You did everything else the same. That’s an unbelievable look back when you’re 85, and you look back. And I want to be able to rattle that on, and I can, you know. So, I, every year- I don’t know what 2023 will look like- but I just did a race that I’ll have forever. And that one day of suffering, man, that one-day investment of suffering will give me another 35-year return on investment if I live another 35 years, you know. Every single day I can talk about it. No one can take it away from me. I went through one day of suffering: for the rest of my life, I’ll have a memory and experience I can talk about. And by the way, I can, I could give a whole speech, I could write a book, we could spend five hours talking about the benefits: how I did the race, why I did the race, what I learned from the race, what changed, how I changed, how I benefited from the race, the friends I made from the race… I, like, I could go on, I could do a TED talk on it. Just, be- you want to know why? Because I did it. Just because I did it. So I really encourage people, while obviously, you have to build your business and pay your bills, you also don’t neglect the life resume side of your journey.


FRED: I love it. It’s such a full way of looking at life as a whole, right, as a whole. And then, you kind of build up these meaningful memories along the way and these amazing relationships and these stories you can tell. I also love the whole “the more you experience, the more you can give”, right, the more you can contribute to others. People will kind of benefit from that experience. And I mean, I find your work super refreshing and inspiring. Especially for, like, those of us who have gone through, like, the traditional, more like, the school system, the regular sort of, you know, career path, and we always kind of, make these great plans and then we try to measure up to the plan, and then like, right, like we inevitably, like, we don’t hit all of the goals that we have, and kind of like… You remind us, always go back to your experience, always go back to like, what excites you, what provides you with enthusiasm, what provides you with meaning and purpose, and don’t neglect that. And I just feel like it’s such an important message today to not lose sight of that, not lose sight of like, the bigger battle, right? And sacrifice it for an-


JESSE: You know what? Get off road a little bit, you know. You have to stay on the highway, on the road, but sometimes, it’s good to pull over a little bit, man, and just, and just shake it up. It makes the drive on the road less bumpy, you know what I mean? It just- I need that in my life. I need a distraction from just the work and the kids. I need something that’s for me, that makes me feel accomplished. I mean…


FRED: Yeah. So I’m, stake in the ground: I’m claiming the Mount Washington idea for 2023. What’s one big idea, one big element on the fuck-it list or on the life resume that you’re kind of dreaming of that, that might be next for you?


JESSE: You know, like I said, I just knocked one off so I’m not sure what the next thing is going to look like. But, I can tell you that it’s going to have the same characteristics or characteristics it will have: it all have an element- and you have them all in Mount Washington- it will have an element of challenge, like it won’t be easy. It’ll have an element of enthusiasm, like I’ll be really excited about it. It’ll have an element of fear, which I’m sure you’ll have when you get to Mount Washington. You can do it in the winter. And it’ll have a huge return on investment for me as a person. And those are the qualities that I always look for in those kind of challenges.


FRED: That’s awesome. That’s awesome. Jesse, thank you so much. This is super inspiring, super educational, super helpful in a practical way, not just in a sort of theoretical way. I think you have so much to give to, you know, entrepreneurs, young, young generations, older generations. Just keep, keep that perspective in mind of, that you’re building a life, you’re building experiences, you’re building relationships. I think your, your message is awesome, your content is awesome. I want to thank you for being you. Keep doing it. Keep crushing it. You inspire a lot of us. Jesse Itzler, thank you so much.


JESSE: Thank you, Fred. Thank you.