Wild Ideas Worth Living Transcript: Jesse Itlzer


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Shelby Stanger: This episode features author, entrepreneur and adventurer, Jesse Itzler.


Welcome to Wild Ideas Worth Living, an adventure podcast presented by REI Co-op, the brand who helps get you outside through gear, classes, and adventures. We talk to experts who’ve taken a wild a idea and made it a reality so you can too. From people who have climbed the tallest peaks, started thriving businesses, and even broken records. Some of the wildest ideas can lead to the most rewarding adventures. I’m your host, Shelby Stanger, and I hope you enjoy the show.

Jesse Itzler only eats fruit until noon, he loves Run-DMC and he enjoys living life out of the box. He’s the author of the New York Times bestseller, Living with a SEAL, a story where he literally hired a Navy SEAL to live with him and train him for a month. Then he wrote this book called Living with monks, where he lived with monks in upstate New York. Prior to being a bestselling and hilarious author, he co-founded Marquis Jet. It’s the world’s largest private jet card company which he and his partner sold to Berkshire Hathaway/NetJets. Jesse then partnered with Zico Coconut Water which he and his partner later sold to the Coca-Cola Company. He got his start as a rapper on MTV and he wrote and performed NBA’s Emmy Award-winning, I Love This Game music campaign, and the popular New York Knicks anthem, Go New York, Go.

Jesse is also a serious adventurer, which we get into a bit on this podcast. He’s an Ultra Marathon runner, and in the last few years, he launched this event called 29029 where participants literally go to a private mountain and they get 36 hours to hike 29,029 vertical feet, which is the equivalent of climbing Everest. They climb up, take the gondola down, repeat with awesome like-minded people, good ambiance and good food. On top of all of this, Jesse is the owner of the Atlanta Hawks, the basketball team.

He’s also married to Spanx founder, Sara Blakely, who by the way is a new shark on Shark Tank. He’s a father to four kids. I had Jesse on because it’s rare I read book cover to cover and then fight with my boyfriend about who gets to read his next book first. When I do, I reach out to them and try to have them on the podcast. I also discovered, from some good friends, that Jesse has a course going right now called How to Build Your Life Resume, and that name really struck out to me. As we get closer to the holiday, and the new year, and we’re setting goals, I really wanted to ask Jesse about this concept, because we could all build better life resumes.

We talk about all sorts of things, from goal-setting, to cold calling your heroes and how to do it, and how to have a better relationship and get real with time. I hope you enjoy this show.


Jesse, thank you so much for coming on this show. I pretty much told everyone how awesome you are in the intro, and I’m pumped. But rather than talking about your books and everything else, I wanted to start with what you’re doing now. Especially because the new year’s around the corner and people are setting goals, changing jobs, gearing up and you have this course, How to Build Your Life Resume. I’m really curious, why life resumes, not paper resumes?

Jesse Izler: First of all, I appreciate you having me. I don’t believe in resumes in the traditional sense. I really have always believed in building your life resume, your body of work and trying to accomplish as much in this lifetime as you can, squeezing everything out of life as possible. That’s always made me feel the most alive, made me feel better than sitting in an office or looking at a computer screen all day. Although I understand everyone needs to make a living, and I’m not suggesting you don’t, I’m just saying really emphasizing living life for a living, and that’s the things that’s always been what’s attracting me.

I read once that the average recruiter scans a resume for six seconds before he or she decides if an applicant is qualified or not. I was like, “Six seconds to decide if you get the job or don’t get the job?” I just felt like, “What if you could land the dream job? Or what of you could get the promotion? Or what if you could become so much more interesting through your experiences?” I flipped that model upside down and I focused on building my life resume, and the premise around it is simple. The more you experience, the more you have to offer. The more you have to offer the people, the more you have to offer yourself, and that’s how I live my life.

Shelby: I love that. When I was 21, I applied for the associated press, and my resume wasn’t big because I was in college, or just about to graduate college. I had surf instructor on my resume, and all the women wanted to talk about during the interview was surfing. Interesting.

Jesse: [laughs] It’s so true. When I was 21, I decided I was going to run to be mayor of DC.

Shelby: What?

Jesse: I went to school at American University, and all you needed was, I think it was like 5,000 signatures. I don’t remember the exact amount of signatures you needed. I’m like, “I can get 5,000 signatures. Even if I lose, that would be an amazing thing in my resume.” I decided to run for mayor. I didn’t actually run for mayor. I got a bunch of signatures but then I wanted to go out more than I wanted to acquire signatures, and then I never had a resume. The plan never came to fruition, but I did, at one minute in time, that was my focus, like, “I’m going to be the mayor of DC.”

Shelby: That’s really interesting that you did that. I love that. At 21 years old, that’s good practice. You probably learned a lot about politics. You have this course going on right now, and I imagine that a lot of people listening are gearing up to set new year’s resolutions or goals. Do you even believe in new year’s resolutions?

Jesse: What I don’t like about new year’s resolutions is that– I believe in them if you can accomplish them. I think only 3% of Americans actually have goals and write them down. Only less than 1% reviews them daily and changes them and modifies them. I think only 8% of people that even have goals complete them. I’m a believer in them if you have a system that allows you to accomplish them. I’m not a fan of just doing them to do them, but if you have a bullet proof system to accomplish the goals, I think it’s a great thing. You have to have goals, you got to dream big, but new year’s resolution usually fail.

Shelby: What advice do you usually give to people who are trying to set some sort of big goal or have a big adventure in mind or a big task they want to accomplish?

Jesse: A couple of things. For starters, I believe in smaller goals, mini goals. Accomplishing mini goals gives you a lot momentum towards a much bigger goal. I think having many people that do set goals have so many that they loose focus. Having one or two goals that are so big that if those are the only two things that you accomplished in the course of a year, it would still be a hell of a year. I think that’s really important. Very often, we live in a calendar year. 2019 and 2020, fiscal year. Everything is based on a year, and I like to shorten goals into quarters. First of all, you can accomplish more.

Imagine if you can accomplished a major goal every quarter, you would have four times the result as if you just had one big goal a year. I try to shorten the horizon. It makes it more manageable for me. For example, I’m working on a documentary, I haven’t started it yet, but instead of saying, “Most documentaries take a year or two to shoot, to edit, and to write, and this, and that.” I’m like, “Let’s do it in four months.” If we can focus our energy and create a great documentary in four months, it gives us another eight months, three-quarters of the year to go and attack the next major goal. That’s my approach, and how do you get your two year plan done in a year.

Shelby: I have so many questions. Can you share about the documentary? What it is?

Jesse: The documentary, the working title is called Cereal Killer. Cereal, like breakfast cereal. It’s a work in progress, the title might change. But it’s just something I’m very passionate about. The deception in the advertising, forgetting about the ingredients. That’s a another topic group which we will touch upon in the documentary, but more about the deception and trying to bring awareness and hopefully change some of the ridiculousness going on by these major food companies specifically targeting kids.

Shelby: I’ve seen a lot on your Instagram. Is it Fake Fri-

Jesse: Fake Friday, yes.

Shelby: Fake Friday, okay. Everybody check out Jesse Itzler’s Instagram, Fake Friday. He just divulges a lot of untruths that marketing companies do especially around kids cereal. You talked about condensing goals. You’ve had some really interesting, funny goals that you’ve condensed. Living with a Navy SEAL, hiring one to live with you. Not just any Navy SEAL, but David Goggins. He’s a pretty remarkable human being. Why at first did you hire him?

Jesse: That wasn’t a goal. That was just, when I meet someone I find to be inspiring or interesting, I very often try to become friends with that person, like a five-year old in class that passes a note like would you be my friend, check the box, yes or no.

In this particular case, it wasn’t a goal. I met Goggins at a race. I was doing a 24-hour running race as part of a relay team with four or five other people and he was doing it by himself, and he was, at that point, this is 2006, he wasn’t really well known. Outside of the endurance community, I think I didn’t know who Goggins was, or I didn’t know anything about the sport endurance racing in general. I just saw this guy that was 280 pounds or something like this running on tremendous will and drive, and I was just inspired by the determination that I saw from him.

So, I did a little research on who he was, on his background, and at that time, I don’t think he’d even ran a hundred-mile race. So other than he was a navy seal, there was no real information on him, so I cold called him. I cold called him and flew out to meet him, became friendly with him and asked him if he would come live with me because I saw something in him that I wanted. I’ve come across people in my life that have, whether bits and pieces of things that I like about someone that I want to incorporate into my life, and those people have become mentors to me. Some of them I’ve met like Goggins and invited them into my house or became friendly with them. And Harvey Diamond, is the guy who wrote Fit For Life, is another guy like that, and others have been virtual mentors that I follow on social media and I get little nuggets of wisdom that I try to apply to my life. In this particular case though, it wasn’t planned. I was doing this race, I didn’t set out for any other reason other than to participate in this crazy 24-hour running event, and from it, I ended up at the end of the race, reaching out to David.

Shelby: I think you wrote somewhere in the book that the guy only have like a bottle of water and a box of crackers.

Jesse: Yes. He weighed a lot during this race and he really struggled because of his weight and because he had no nutrition. There was no plan, he ate crackers with water, and he had exerted himself for I guess what, basically a hundred miles. He had broken some bones in his feet, he had kidney issues, he was peeing blood, he had all these issues yet he kept going. There was no award for this race. You finish it, you get a little pat on the tushie and you go home, and I was like man, what in the world is fueling this guy? That’s what kind of inspired me because I was like, if I could get a little bit more drive, if we all could get more drive, more passion, more persistence, more grit and incorporate it into our lives, we’d be better parents. If we could teach it to our employees, they’d be better employees, so how do you master that? And for me, it’s an ongoing search of mastery. I’m trying to master all the buckets in my life; not one, all of them, and that’s part of the journey, the constantly-learn-build-your-life resume, it’s about learning. It’s like as kids, we’re so thirsty for knowledge, we’re thirsty to learn new things: we want to learn how to ride our bike, we want to learn how to water ski, we want to learn how to whatever it is, fill in the blank. But as adults, we get caught in routine. It’s super hard to introduce newness into your life as an adult.

So, my journey, it’s never stopped, and I’m still thirsty for all those things. And when I see someone that I feel has a little bit of the secret sauce, I try to learn about it. And whether it’s Goggins or whether it’s Harvey Diamond or whether it’s you and surfing and whoever, if I have an interest in that lane, I recognize that my time on earth is short. I just turned 50, the average American lives to be 78, so if I was average and I knock on what I hope I’m not, I hope I’m only a third of the way of where I’m going. But if I was average, if I am average, if we are average, that would mean that I have 28 summers left, 28 years left, and that’s a super short window. So, what do I want to do? Do I want to live it in routine, or do I want to build my life resume and get out there and experience and try and fail and learn and get wet and get hot, and that’s what I want to do.

Shelby: What buckets do you focus on?

Jesse: I really only have four buckets. I have a wellness bucket, I have a family and friends bucket, I have a business bucket, and then I have like charity, causes, kind of miscellaneous bucket, and those are my focuses. Obviously, I have friends, I have other stuff going on in my life, but pretty much everything fits in one of those buckets, and if it doesn’t, I try to eliminate it.

This year, going into 2019, my biggest thing is efficiency. That’s where I struggle, and even though I’ve been able to accomplish a lot, I don’t think I’ve been able to accomplish nearly as much as I’m capable of, and it’s because as your life changes, your system has to change. I’m working with the same system that I had before I had four kids and a wife and other stuff in my life. My system hasn’t evolved that much, and I’ve been able to get away with it on some level. But to operate it the level that I want to operate, I need efficiencies, and my focus is on building a system. You talked about new year’s resolutions. Resolutions are important, but systems and winning habits and winning routines, to me, are the most important thing, and that’s where my focus is, building those efficiencies.

Shelby: It kind of reminds me of this old book, What Got You Here Won’t Get You There, you have to change how you get there. So, when it comes to starting, what do you tell– imagine you’re coaching thousands of people, hundreds of people, I have no idea, but I know already two people who are just in your course directly from around the world, so where do they start when it comes to just setting these goals and thinking about your life resumes? Where do you encourage them to start?

Jesse: I start with reestablishing everyone’s relationship with time, because I think when we think of relationships, we think in terms of relationships with our friends, our family, our parents, our kids, but very rarely do we focus on a relationship with time, and that is such a critical aspect. Once you understand and truly understand– I just crashed the surface on the 28 summers concept, but if I really broke it down and reversed engineered those 28 years and how the stuff you like to do like surfing, maybe climbing mountains, adventure races, whatever our listeners like to do, there’s not a tremendous amount of people climbing Mount Washington or some of these mountains that I like to do in their 70s. Your years of active, relevant, maximum potential, they shrink as you get older, as the percentage of your remaining years. So, I start with your relationship with time and understanding the urgency, and I think, for me, that’s been a good starting place for most people, because most people wait for the right time, wait until they have the right amount of experience. It’s never the right time. You can always get more experience. I’m encouraging people to start the journey and start the process without having all the answers figured out, and that’s the basis of the starting point of the course. It’s around time, urgency and your understanding and relationship of it, taking control of it.

Shelby: Because it’s the holidays and I remember reading this so profoundly in your book, Living With Monks, can you share the example of time when it comes to your relationship with your parents? Whether or not you enjoy hanging out with your family around the holidays, I think this is an important one.

Jesse: Well, again, it goes back to really understanding that relationship. So, as it relates to– well, I use parents as an example because as you get older, people tend to drift away from– I mean where do you live? Do you live in San Diego?

Shelby: I live in San Diego, and I’m really lucky my parents don’t live that far.

Jesse: Okay, and do you have brothers and sisters?

Shelby: Yes. I have sisters who live in LA and parents who live in LA/Pond Springs.

Jesse: Okay. Well, that’s a good thing. Very often, I bet if you ask some of the listeners here, where do your parents live, where do the people closest to you live, very often, they don’t live that close to you. I live in Atlanta, my parents live in Florida, my brother-in-law lives in San Diego, my in-laws live on the West Coast as well, 3,000 miles away. The people that we care about the most, we don’t see the most, at least that’s the case many times. So, this example strikes home I think very clearly like I now say to people, “How old are your parents?” and they’ll say, “Oh, I don’t know. My parents are 75,” I said, “Okay. How often do you see them?” “I see them two times a year.” “Great,” and well, let’s say they live to be 80, they’re 75 now. What I like to explain is you don’t have 5 years with them. You have 10 visits with them because you see them twice a year, you’re going to see him for five more years. That’s 10 visits.

When you start to look at things that way, and in through that lens, you start to reestablish how you want to prioritize that. Like, okay, well first of all, those 10 visits become super meaningful. They become way more important than maybe I should turn the football game off and actually have a conversation with my parents, and maybe I should not be on my phone checking emails and social media. I should shut it off and spend these two days that I have with my parents right now with them.

Or maybe I should have more visits scheduled. I like to reverse engineer my time. I like to reverse engineer it. That’s something I do a lot. I project out a lot. I use that and I use cumulative thinking as well. Let me give you an example of what I mean . Let’s say someone’s going to have an ice cream cone and they say, I have an ice cone every day. It’s not a big deal. That’s like my one vice– like over 10 years and you have 3,500 ice cream cones. It is a big deal. I like to think in terms of time as– what’s the term, compounds. Things compound over time. They build up, and that’s our starting point.

Shelby: Well, as soon as I read that, I booked a trip with my mom to Hawaii, no phones allowed, because our time is short. My fiancé’s mom has Alzheimer’s. We don’t know if her parents are going to get sick, and I just so appreciate that advice. When you do an adventure, you go all in. You don’t, living with a seal, living with monks for Halloween. I just saw that you’ve wrapped, you dressed up as Scooby doo, the whole family and you wrapped your, is it afford Ikano Line van? Family van.

Jesse: Yes.

Shelby: You wrapped it like the mystery machine.

Jesse: Yes.

Shelby: Talk to me about going all in, because right now, you have the resources to go all in, but you haven’t always had the resources to go all in and yet you always go all in.

Jesse: I don’t think it has anything to do with resources. When I was starting out in business trying to get a record deal, I was all in. I had no resources. I slept on 18 different couches, friends’ couches. During that journey I was still all in. I think you have two choices. You can go 80% in or you can go all in. Who in the world wants to go through life at 80%? Does that even make sense? You have one chance to live, why would you not approach something with 100%. I have only eaten fruit until noon. I eat fruit in the morning until twelve o’clock in the afternoon, pretty much every day.

There’s been a couple of days over the last 27 years where there’s been exceptions. Every year, there’s a handful of days where I want to have pancakes with my kids and this and that, but it’s been unwavering. Why wouldn’t it be? If that’s what I think gives me the most amount of energy, and I think that that is a staple to how I live my life, why won’t I be all in on that? Like why would it be, I’ll go home and do three days a week? No, if it works, I’m all in.

It doesn’t even make sense to me how you could even think about trying to live your life, the 80% version of yourself. At this stage of my life, I don’t understand that. At 19, 18, 20, I get that. All right. Yes, there’s distractions is this. I don’t have time to be distracted and be like, I’m 80% in, I’d rather not do it. If I’m going to sign up for a race and I just dropped out of a race. I signed up for a race in September, and because I couldn’t go give it 100% of what I thought I needed to do to get the best results that I had in me, not against anyone else’s scorecard, but my own. Look at myself in the mirror. Was I 100% committed to this? The answer was no. I said, I’d rather not do it. I’ll go do it next year.

Shelby: That’s smart. What race was it? Just out of curiosity.

Jesse: It’s called the last man standing. It’s a race that keeps going until only one person’s left.

Shelby: What? That sounds amazing. Where is this race?

Jesse: This particular one was in on the east coast, but they have them all– There’s not a ton of them, by the way. Not a lot of people want to keep running until only one person’s left running.

Shelby: It sounds horrible and awesome at the same time.

Jesse: I know. Listen, there are times where I want to do it even though I’m not trained or I just want to get my foot wet. I want to experience it, but I’m saying in general, we’re talking about being all in all the time. That is what it takes. There’s 7 billion people in this world. 7 billion. I’m sure a lot of them are surf coaches. A lot of them are in the coaching space. A lot of them are doing things that you and I are trying to do. If you’re not all in, someone else is, and I would bet on someone all in versus someone with amazing talent, 60% in all the time.


Shelby: We’re going to take a quick break to hear from previous guest, Semi-Rad’s Brendan Leonard, about some holiday tips, courtesy of REI.

Brendan: We all know how fun it can be trying to make the holidays perfect for everyone, and although your family probably loves the idea of you stressing out until you get sick or exhausted just as much as you do, maybe you don’t do that this year and get yourself a little something special. Some sanity. Instead of getting up at 5:00 AM to be first in line for a holiday sale, try getting up at 5:00 AM to get first chair, or instead of running yourself ragged trying to do everything, try going for a run and taking care of yourself. Maybe ditch last minute shopping for your loved ones and go last minute sledding or surfing with your loved ones instead, you know, outside. Wishing you simpler holidays from me and from REI.

Shelby: When you’re young, someone gave you advice. You were trying to make music and license it, and someone offered you money for 10% of your future earnings, and then you went to someone wiser and they give you really good advice.

Jesse: Well, during my journey of being on 18 different couches, I was writing theme songs for professional sports teams. I had done two successfully and now I was realized that there was a lane and I had a real business opportunity, but I didn’t have enough money to, all of the work that I needed to do was on Spec. So I had to go in the studio, record the songs, and then once they were recorded, traveled to the professional sports teams, like let’s say the San Diego Padres or the Chargers or whatever, and try to sell them this song that I had written. If they didn’t like it, I was out the money. I needed money to go make these demos.

I went to this guy who said he would give me $10,000 to go record the stuff– the money that I needed to record a bunch of these songs. In return, he wanted 10% of all my future earnings. He was a big money guy and bunny manager and he felt like he could open up all these doors for me. Aside from the 10 grand, at that time in my life at 22 years old, it was super compelling. I needed the money. I had no chance of doing anything without it. Plus he had connections. It was like 10%, and I was like sounds good. $10,000, all the money in the world.

I went to get a second opinion, and I went to a guy that was Uber successful. Father of a girl that I knew loosely. I went into the meeting, and the first thing is this guy, when I walked into this guy’s apartment was, I’d never seen wealth like this. I’d never seen a penthouse apartment in New York City with a swimming pool in it. It was like Annie, like daddy warbucks with all this artwork and people cooking. It was just remarkable.

I was intimidated. I was 22 years old. The first thing that the guy said to me, he said, “You know what?” As we started to talk, he interrupted me and said, “You know what, I would trade every single thing that I have for the one thing that you have.” I was like, “Me? I have $117 in my bank account. I’m sleeping on your daughter’s couch right now. What’s that?” He was like, “Youth. You have this whole playing field in front of you. You have the whole journey in front of you. When you have an appreciation for that journey, the good, the bad, these kinds of decisions right in front of you, take the $10,000 or not. I don’t have that anymore. I had that already”.

Shelby: He also asked you if you could make it happen, and you said, “Well, I can make it happen”. Then he said, “Will you make it happen?”

Jesse: Right. As we started to talk about my $10,000 dilemma, he said to me, “Do you believe in this business, and you’re willing to bet the farm on it?” Is what he said to me. I said, “I do”. He goes, “Will you make it happen? Will you take this opportunity? Are you going to make it happen?” I’m like, “Yes, I can make it happen. I can do this”. He’s like, “No, will you make this happen?” I’m like, “Yes”. He’s like, “Well, then go forget the 10 grand”.

Shelby That’s such good advice, and it’s really helped me in making good decisions. I’m curious, today you’re in a completely different spot.

How do you decide what to say yes to and what to say no to? Because I imagine, you get hit up for all sorts of things all day long. How do you say no more easily? Because that’s something I really struggle with and I’m sure listeners do too, saying no.


Jesse: I said yes to everything for 40 years of my life pretty much, but now I have four kids and a family. It’s not fair to them. There’s other reasons to say no. I also want to help everybody, athat’s why I set up my course, so I could reach a lot of people in the most efficient way. But if it doesn’t, in general, I have those buckets that I mentioned; my wellness bucket, my family bucket, my business bucket, et cetera. Unless something comes at me that fits into one of those buckets, if it doesn’t fit, it’s almost an automatic no. Not no like I don’t want to help people. Of course, I do. I do a lot of that, but I’m just saying needing-wise.

Human nature, I was thinking back to this. When I started out business and I called to try to get meetings and looking for mentors and this and that, very rarely, I can’t even really remember any time other than this one meeting that I have with this guy, literally, where it was one-sided, where I called up and I’m like, “I want to sit with you because I want to pick your brain and get all this stuff. I only want an hour of your time.”

Any time that I had a meeting, it was two ways. “Here’s why I think I can help you. Here’s what I can do. Here’s what I’m offering. I’ll do this for free.” It was never like a one-way ask. I feel like a lot of people now don’t really know the best way to ask for things, because human nature is the recipient. He or she is like, “What’s in it for me?” That’s just human nature. What’s in it for me? If you can’t answer that question, there’s a good chance you’re going to get a no. If you can answer that question, there’s a good chance you’re going to get a yes.

Shelby: No, I think that’s good. That’s why I’m offering you surf lessons, and we’re going to do it, I hope.

Jesse: There you go. That was compelling. I didn’t say no. It was super compelling.

Shelby: You have some bright lines and some great routines like fruit until noon. Do you still keep three hours a day to yourself every day?

Jesse: Yes.

Shelby: Awesome. What do you do in those three hours or maybe just some of the things you do?

Jesse: First of all, it’s cumulative, so I don’t just clock off 1:00 to 4:00 every day is for me. It’s cumulative. I have a list of things that are important to me in those three hours. It’s my time. I can do whatever I want to do I want to do in that time, and I have zero guilt when I’m doing it because I don’t want to resent my wife or my kids, anybody, my boss, for taking away things I like to do. I operate much better when I’m able to do the things that I love to do during the day. I’m better at work, I’m a better parent, I’m a better husband when I get my running. Take my run away from me, take my exercise away from me, take my hikes away from me, take my swims away from me, I’m resentful and angry. I’m just not the same.

It’s important to me to be able to carve out that time so I can be better in those other areas. Those three hours, again, they’re cumulative. It could be a 30-minute run in the morning, it could be reading, it could be sitting in the sauna. It could be doing nothing. The point of it is, it’s whatever I want to do. If I can’t prioritize 10% of the day for me, how unbalanced is that? If I loved making music and that’s all I wanted to do and I want to sit around and write songs all day, that would be enough. That would be fantastic. But there’s a lot of things that I want to do, so those three hours are really important to me.

Shelby: You talked about how you’re making a documentary right now, but I want to go back to your books because some people haven’t read them yet, Living with Monks, Living with a SEAL. Your books are really different than others that I’ve read. A lot of people listening have a wild idea to either do an adventure or write a book, and you basically combined the two of them together. You did something really out of your comfort zone for a period of time. The book was hilarious. I’m curious, for people who want to write a book, that’s their goal, any advice? A little bit of insight into your process, because I appreciated them. They’re page-turners.

Jesse: Well, I didn’t set out to write a book. In fact, the SEAL book came out more than five years after I met Goggins. I met Goggins in ’05. I think I met him in ’05. My book came out in 2015. I didn’t set out to write that book. I had no experience in writing a book. I think everybody’s process is different, but to me, the first step was to– My SEAL book started out as a blog, so I had a framework already. Once I had that framework, I had an outline. I outline the chapters. I wrote the chapter names, and then I started working on the actual, and as I got stalled during the process, which I think probably happens to a lot of people, you burn out or you get a little writer’s block or whatever, I would try to write two or three pages a day. That was it. It was like, “Let me just get two or three pages out.” I would write my stories down and figure out, “Where could I plug in these stories?”

Once I had an outline, that was the beginning of the process. I spent a tremendous amount of time. I don’t think there’s been a project in my life that I’ve committed to more than the SEAL book. That was the best book I was capable of writing. I really believe that at the time. I reread it, reread it, changed it, tweaked it, it’s not good enough, changed it, tweaked it, it’s not good enough. When I say not good enough, I mean not good enough for where I wanted it to be. I felt like I had more, you talk about all in, had more in me. Even when the publisher was like, “Hand it” and I’m like, “It’s not ready. It’s not ready” I would read it again, cover to cover and mark it up, then I would read it again, cover to cover.

The system is the same to anything. It’s taking it to the point where you can look at yourself in the mirror. I had plenty of times where I had not done this, many, more so than I have, where I can look at myself in the mirror and be like, “I gave this my all.” That project is one of those things that I can truly, honestly say that, and I have many that I can’t. It’s good enough, it’s 80%, and they don’t have the success that the ones that you went all-in usually do.

Shelby: What do you still carry from David Goggins and from living with monks today? I’m sure there’s a lot, but maybe you could just give us two nuggets.

Jesse: When you experience things like that or any kind of experience where you take note while it’s happening and you appreciate it and you actually recognize and retain certain things, they never go away. What happened to me in both living with the monks, living with Goggins, and multiple other experiences in my life, is they impact my grit meter, they impact my courage meter, they impact my awareness meter. They just enhance things that we all have that need to be exercised. I want to say that there are one or two things, there are, I could mention one or two things specifically for both, but at 30,000 feet, it just gave me the edge. It gave me an edge. It gave me an advantage in certain situations.

“Am I going to quit now when I go for a run?” Probably not. Thank you, David. “Am I going to be more patient with my kids?” Yes. Thank you, monks. “Am I going to set my goals bigger because of XYZ?” Yes. Thank you so and so. But you have to experience. You can’t read about it, you can’t watch it in a lecture, you can’t Google it and watch it on YouTube. You got to it. Again, building your life resumé, it’s about experiencing. It goes back to the first minute of this podcast. The more you experience, the more you have to offer, but you have to experience. I think was it Gandhi that said, “Learn like you’re going to live forever. Live like you’re going to die tomorrow.”? Something like that.

Shelby: It rings a bell.

Jesse: If that’s not it, it sounds good.

Shelby: It sounds great.

Jesse: If that’s not the exact quote, let’s make that a quote.

Shelby: It’s so funny, we ask all of our guests one question. If you could throw any party, who’s coming? What would you do? You just turned 50. It looks like you threw the party of a lifetime from your Instagram and you said you’re hiring 50 coaches to train you in 50 things that you want to learn.

Jesse: Yes.

Shelby: Talk to me about that. What are you learning?

Jesse: It’s a birthday present to myself. I made a list of 50 things that I always wanted how to do but never learned. I’m bringing in a coach to teach. There are 50 different coaches to teach me those things. Everything from DJing to freediving to wake surfing to backgammon to chess to ballroom dancing. I have a mechanic coming. I don’t know how to drive stick shift, all those things. That’s my gift to myself when I turn 50.

Shelby: Just so other people didn’t hear, you’ve once invited every rapper to dinner that you wanted to meet.

Jesse: Yes.

Shelby: How did you pull that off?

Jesse: I asked them.

Shelby: When was this? So, you just literally cold-called them.

Jesse: I went to a dinner party and they asked people to go around the table and say, “Name three people who are alive that you want to have dinner with”, and at the end of the party, I was like, that’s a really fun game to do at a dinner party, but I’m going to do that for real, so I invited the 10 most influential artists or 10 of the most influential artists in my life growing up as a kid in New York to my house for dinner, and I knew a couple of them, but not all of them, and they all came. Again, what’s in it for me? The ask wasn’t like, “Hey, I want to come and would you come and have dinner with me?” The ask was, we’re going to put together this amazing group of people. You guys probably haven’t seen a lot of you each other in a longtime. We’re going to go over some ideas on how we could all help each other in business. We’re going to have fun. It’s going to be interesting. It’s going to be different. It’ll be once in a lifetime and et cetera and they said, “I’m in.”

Shelby: I love that. What do you like doing with your family? You have a big family. What’s your favorite thing to do with your kids?

Jesse: Anything. My kids are four kids under 9, so just watching them being kids is so rewarding for me, but I made a promise to myself that if they asked me to do anything within reason-

Shelby: What’s you’re going to say? [laughs]

Jesse: – I wouldn’t say no. If my kids want to go swimming and it’s cold, I’m going in. They want to have a baseball catch, I’m going to go. They want to go, of course, there’s boundaries, of course, I say no. There’s discipline and all that stuff, but I don’t want, again, here we go, relationship with time. I don’t want to look back and be like, I missed 6 to 10. I don’t want to miss 6 to 10. I can never get it back, so a mega aware, I say to my wife all the time, just appreciate this. In 9 years, my son is going to be at in college. We only have 14 years of this before the kids are out of the house. That’s nothing. Zero. I don’t want to squander that, and I’m aware of it so, I like it all.

Shelby: What advice do you give them, if any? They’re under 9.

Jesse: Be doers, participate, try.

Shelby: I just want to touch on one thing, because we have a lot of female listeners and you’re married to one of the most badass women in the world, Sara Blakely. Any advice to men on dating really strong badass women?

Jesse: I think it’s important to let– When Sara star shines bright, her biggest fan and supporter and cheerleader, and I’ve never had a problem with that, and I think for a lot of people that could be challenging. I think it’s just to be as more supportive as you can, and you have to understand the animal. Miss Saras and Elaine, she’s a mom, she is a business owner. She’s a wife. She’s a daughter. That’s a lot of responsibility. My job is to support that. My job is to encourage, my job is to be a listener, and people understand. It’s two way responsibility, and it’s work.

Shelby: I appreciate. I just interviewed Gabby Reece who’s married to Laird Hamilton, and they’re another power couple and she gave pretty similar advice, respect, work and let the other one star shine. I like that. Jesse, I know, we’re getting short on time, but you’ve done a lot of rad adventures, and this podcast is sponsored by REI. I know you’ve mentioned them in your books, but gear, you have to love some pieces of gear, is there any gear that you really like, that you recommend to other people to have?

Jesse: First of all, I love going into REI. That’s my Willy Wanker. That’s the factory. I love trying everything. I love tents. I love sleeping bags. I love gear. I love product around outdoors, so anything outdoor gear related, I’m a fan of. I really just recently got into winter adventures, so I hiked Mount Washington and slept on the mountain in a -40 sleeping bag, and I just got introduced to all this new gear. I don’t have a favorite thing that I would just say, “Oh, I love this piece of gear. You have to say what’s your favorite running sneaker? What’s your favorite sleeping bag? What’s your favorite tent? What’s your favorite this? What’s your favorite that? I do have favorites. I use a king paddle board, which I like a lot. That’s custom made.

Shelby: Yes, they are my neighbors.

Jesse: They’re based right by you guys.

Shelby: I like them a lot.

Jesse: I like their boards, but I like other paddle boards too, so I wouldn’t say that I have something that pops into my head.

Shelby: Jesse, do you have any plans to go do something else pretty wild like this again, live with Elon Musk or Richard Branson, go to space, I don’t know?

Jesse: I’ll not go to space. I’m a land animal. But the adventures never stop, I have a list. Let me get past these 50 things, I’m trying to learn and I can go and convince my wife, try to convince my wife. I can go live with someone else.

Shelby: Is there anything out there that we wouldn’t expect to be on the list? I like the learning stick shift because I can’t drive stick at all. It was a nightmare when we went to New Zealand.

Jesse: Well, I’ll leave you with this. I had 49. I picked 49 of the 50 things and I allowed my wife to pick the last one and I’m like, what would the one thing you think I should learn or be interesting, and she chose an etiquette coach.

Shelby: I knew you’re going to say that. That’s amazing, and I bet when you’re in Atlanta, there’s a good one. So funny, I would like to have an etiquette coach too. Jesse, it’s been such a pleasure. I so appreciate it. Anything you can just challenge listeners to do next year?

Jesse: I just think, every year, you should have one thing on your calendar that is just massive, so my challenge would be like, we talked about bucket list but change the B in the beginning, drop the B and add an F. What’s the one thing on your effort list in 2019 that’s so big, so scary? You didn’t think you could do it that requires preparation, training, maybe failure and put something every year really big, one massive goal that defines the year on your calendar, and if you look back and be like, wow, in 2019, because I set this goal and I did it, and even if everything else didn’t come to fruition, if that happen, it would still be a remarkable year. That’s an amazing thing to work towards. Very few of us actually do that. We have a lot of many goals, and like I said, we spread ourselves out thin, but that would be something I would encourage people to try in 2019. What’s something you always wanted to do, and make it happen.

Shelby: Jesse, you’re a legend. Thank you so much. We’ll link it to your books and your website and your coaching class, How to build a life resume and the show notes?


Jesse, thank you so much for coming on this show. You rock, and your sound recorder, Jeff, did an awesome job. I totally appreciate it.

If you want to find more about Jesse, go to jesseitzler.com. That is J-E-S-S-E-I-TZ-L-E-R.com. You can sign up for his How to build your life resume course, or you can even sign up to go Everesting, which is to hike 29,029 feet in 36 hours. It sounds really fun. I’m interested, so I don’t know, we should look into it.

To my sister, Felicia Alexander, and her friend for linking Jesse and I up, I really appreciate it. Jesse, if you haven’t found a surf instructor, I’m pretty sure I could have you surfing in an hour, so let me know.

This year is coming to an end, and we’re starting to build next year’s shows. But before we talk about next year, I just wanted to say thank you. Thank you for listening to this show and for giving me feedback, telling me what you liked, what I could improve. I’m always looking to improve, so you can send feedback to me on the contact page at wildideasworthliving.com, or you can write a review on Apple podcast, iTunes, Stitcher, Spotify, wherever you’re listening to this show.

You can also find us on social media. We’re mostly on Instagram and Facebook at Wild Ideas Worth Living.

Thank you so much. I hope you’re all having a beautiful day wherever you are, and don’t forget, some of the best adventures often happen when you follow your wildest ideas.


[00:49:38] [END OF AUDIO]

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