Jesse Itzler: Crushing The Comfort Zone

Imagine this… You're an extremely successful entrepreneur with a string of mega-successes starting and selling amazing companies like Marquis Jet and Zico Coconut water after having success rapping on MTV and starting the “sports music” industry. Now imagine you're married to the self-made female billionaire Sara Blakely, founder and CEO of Spanx.

Life is good, right? You might even say “comfortable.” This was the life of Jesse Itzler. So why did he invite one of the toughest Navy SEALS alive to live with his family for a month and put him through the most excruciating mental and physical training imaginable?

Why is he obsessed with Crushing The Comfort Zone? And what did he discover about the 40% rule? He details it all in his bestselling book Living with a SEAL: 31 Days Training with the Toughest Man on the Planet and goes into even more detail in this episode.

Jesse is a true “entrepreneur's entrepreneur”. He is a genius at identifying and capitalizing on trends and nurturing relationships that can lead to multi-million dollar empires.

Learn more about his ways and hear his biggest takeaways as he reveals how his mind works and shares what the comfort zone means to him.

Some Topics We Discussed Include:

• How and why Jesse Itzler decided to live with a SEAL, which became the inspiration for his book.
• Why limitations are self-imposed
• Why doing things you’re uncomfortable with is part of an improvement
• How to get your foot through the door and figure out the rest later
• Why maintaining contact with people can build an organic and profitable network

To get to know Jesse deeper, visit his website at https://jesseitzler.com/.

About The Guest: Jesse Itzler

JESSE ITZLER only eats fruit 'til noon, loves Run-D.M.C., and enjoys living life “out of the box.” In fact, he doesn't even have a box. The author of the New York Times bestseller, Living with a Seal, cofounded Marquis Jet, 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 sold to The Coca-Cola Company.

He's a former rapper on MTV and wrote and performed the NBA's Emmy Award-winning “I Love This Game” music campaign and the popular New York Knicks anthem “Go NY Go.” When he's not running ultra-marathons, eating vegan food or being a dad to his four kids, Jesse can be found at the NBA's Atlanta Hawks games, where he's an owner of the team. He is married to Spanx founder Sara Blakely.

Jesse Itzler: Crushing The Comfort Zone

We all had this reserve tank. When we think we’re done, we have more in us. He would say three. He called it the 40% rule.

At the first time of indication of pain or discomfort, our brain immediately sends a signal for us to stop because it doesn’t want us to get hurt. That’s a tap on a shoulder that we have 60% more in us.

—

That was Jesse Itzler, billionaire, bestselling author, endurance athlete, world-class crazy man, you’ll see why, and a world-class entrepreneur. We are going to cover some cool ground in this short, but one of my favorite episodes so far.

It’s not often you get a billionaire to jump on the phone with you and chat with you about the things that he’s done. I was first introduced to Jesse when a friend of mine recommended that I read his book, Living with a SEAL: 31 Days Training with the Toughest Man on the Planet.

The author decided to get out of his comfort zone and hire a Navy SEAL to live with. He and his wife and child for 31 days and put him through the ringer. It’s a very inspirational book, very motivational and it’s about much more than just beating yourself down physically.

It is much of a business book as it is a book about life, discipline and determination. I didn’t realize this at the time but Jesse is also an impressive serial entrepreneur who has done everything from talking his way into a record deal by pretending to be somebody he’s not.

In essence he created an industry called sports music. He then cofounded Marquis Jet and sold it to Warren Buffett and NetJets. He then cofounded Zico Coconut Water before he sold it to Coca-Cola.

He married Spanx CEO, Sara Blakely who is also the world’s youngest female billionaire. This summer they purchased the Atlanta Hawks basketball team. Now, he’s talking to you and me.

One of the things I like most about Jesse is he’s down to earth, one of the guy’s persona. I listen to the audiobook and the entire time I was like, “I want to hang out with this guy. I want to meet him. He seems like somebody who would go get a beer with me.”

There’s no pretention about him. I was thrilled when I reached out and invited him to be on the show. He said yes. I was thrilled to be able to bring you. Jesse, welcome to the show. It’s great to have you here.

Thanks, Brad. I appreciate you thinking of me.

A friend of mine Ed O’Keefe said he was interviewing you on his show. I commented a Facebook. You saw that. I was excited to hear that you would come on the show. Literally that day I’d finished your book, Living With A SEAL.

It was hilarious, insightful and inspirational. The next day when I was in the gym I can hear both you and David Seal screaming to my ears. I pumped out, I did 200 pushups that day. It was more than I’ve ever done in one day. It also made me think you are crazy printing some of that stuff.

David would say if you did 200 you had 280 in you.

I want to get to the book. There’s so much I want to talk to you about. I could literally spend hours chatting. You brought up so many ideas and concepts. Tell me a bit more about the journey.

A lot of things that have happened to me in my life, this particular thing where I lived with Navy SEAL was not planned. I saw him at a race. It was a relay race that I was doing, 24 hours to run as many miles as you can.

I was part of a six-person team. We were rotating. Each guy would run a mile. This guy to my left had no team. He was running the entire race himself.

The race was self-supported. You had to bring all your own supplies. The race didn’t provide anything. We have bananas, Gatorade, tents and chairs. This guy who was about 270 pounds had a bottle of water, a bag of crackers and a foldup chair, that’s it.

I was so blown away by his size. He had nothing. He sat there. He looked angry. By mile 70 he’d broken all the small bones in both of his feet because of his weight. I watched this guy finish the last 30 miles. He ran a 100 on pure guts and just drive.

I was so inspired and intrigued that I wanted to learn more about his guy. I googled him. I learned he was a Navy SEAL. I cold call him and flew out to meet him. I sat with him for ten minutes. A thought popped into my head. My life would be so much better.

I’d be more disciplined. I could be more productive. I learned more about myself. All the buckets in my life would be better if a little of what he had rubbed off on me. I asked him out of nowhere to come live with me, my wife and my family for a month. That’s how it started.

Were you a bit scared going, “What am I getting myself into here?”

I didn’t have time to be scared because three days later he was at my breakfast table. To answer one of your questions in the beginning where was I in my life, I was in a great place in my life. I was happy. I was married, I still am. I sold a business. I had success but I was in a routine.

We all tend to go into autopilot at different times in our life. I don’t know what triggered it with me. I had a great routine. I was doing it the same thing every day. I wake up, run, workout, go to work, family, dinner, and repeat.

Routines are great but I wasn’t getting better. I was stuck. I was comfortable. I didn’t have the power to get out of it. I needed something like this to completely shake up my life.

Part of it was I wanted to get in great shape and I wanted to be pushed physically, but that was obvious. He’s a Navy SEAL and his backstory is unbelievable. He is an amazing endurance athlete but he wasn’t always like that. He weighed 300 pounds. He had low self-esteem as a kid at a high school.

He turned his life around. I wanted to get out of my routine. I wanted to get the psychological side of it. What makes a guy like this tick? Where was that drive that I saw at mile 70? Where did that come from?

Crushing The Comfort Zone: It’s one thing to read about inspiration, but it is another to live with inspiration.

How do I incorporate that into business deals, into training, into my personal life? That’s what I signed up for and I went in with no expectation other than hoping to find some answers.

How did it transpire, the stories and the journey that you took? I was with you the whole time but at the same time, I was so happy that I wasn’t doing it with you. If it was my book, I would have complained a lot more. I’m going to die. This guy has a pretty good attitude through all this.

It’s one thing to read about inspiration. I like to say, but to live with inspiration is such a different thing. Going back to his backstory, Navy SEAL twenty plus years. He’s done so much stuff for our country, been through so much.

He’s been through hell week, been deployed, been to the coldest water and the hottest temperatures, all that stuff. I’m going to complain like I can’t do 100 pushups, there was no wiggle room for that.

It puts it into perspective. How has it affected you now? This was a few years ago that you did this.

It was. I got out of it. That’s why I wrote the book because it started out as a blog. I wanted my friends to follow along what I thought would just be the training side of it. “Here’s the run we did, here’s the workout we did. Try to follow along or laugh at it.”

What was interesting was that whole psychological side. That was a takeaway for me. I got out of my routine. He gave me all this wisdom and nuggets. The biggest takeaway was I thought I was operating at a high level.

I was running a lot, I was focused. My business life was great. It was all good but I thought I was high level maxed out. He taught me that we all have so much more in us. The way he did it happened early on in our journey, literally the first ten minutes that he was there.

We went down to the gym and he wanted to see how many pull-ups I could do. I did eight. He said, “Drop down, wait 30 seconds and try it again.” I got maybe six. He said, “Wait 30 seconds and do it again.” I barely, kicking my legs, got three or four.

I was done. My arms hurt. He said to me, “We’re not leaving until you do 100 more.” I said to him, “You’re kidding, right? That’s physically impossible.” He said, “I’m going to show you how a lot of the limitations you’re putting on yourself, you’re setting those limitations.”

“I’m going to prove to you that a lot of this stuff is self-imposed.” I sat there. He goes, “I don’t care if you do it one at a time, go do 100.” Two hours later, whatever it was I finished. He proved to me three things, one, I convinced myself I couldn’t do it. It is self-imposed.

Two, we all have this reserve tank. When we think we’re done, we have so much more in us. He would say, three, he called it the 40% rule.

At the first time of indication of pain or discomfort, our brain immediately sends a signal for us to stop because it doesn’t want us to get hurt. That’s just a tap on the shoulder that we have 60% more in us.

That’s a quote in there that stuck with me, both when I’m in the gym and when I’m working. Maybe it’s midnight and my eyes are burning but I have stuff I’ve got to do. As an entrepreneur sometimes you have to push through and get things done.

It works. When I whisper that, that’s a theme song that runs through my head. It could be as simple as like I’m in traffic and I’m about to freak out because I can’t handle it. I’ll remind myself, “You know what and you have way more patience than this, Jesse.”

It goes everywhere. It’s not just how much endurance you have. It’s physically, it’s emotionally, too.

I use that a lot. I am forcing myself to do things I don’t want to do. I’m forcing myself to do things that make me uncomfortable in all areas of my life. That’s an important element to improving.

If you’re not willing to get uncomfortable, experience pain, failure or whatever, you’re never going to get better. Part of our routine was every day doing something that sucked. He would wake up and be like, “Every day we’re going to do something that sucks that you don’t want to do.”

What he was doing was he was resetting my set point. He was taking the baseline that I operated on as far as mental toughness. Every day he was raising it.

Also redefining your definition of what sucks. You may think, “I’ve got sit down and do some taxes.” That doesn’t suck. Running ten miles and doing 200 pushups, that sucks.

Right, but they both suck. We procrastinate, put stuff off. That doesn’t do us any good. Sometimes you got to step up and be like, “It sucks but I’m going to do it.” You feel better. That’s when you feel most alive. The harder the challenge, the more you’re doing stuff that you hate to do, the more rewarding it is.

You talked about some interesting ways of getting your foot in the door in your career. I would love for you to share some of those stories a bit more.

You were talking about when you first got your first deal. I heard you talk about the Marquis Jets deal a little bit. What to you is the biggest door you got your foot in, in your life?

It’s all been a process. It’s all been a ladder, one step leads to the next step, leads to the next step. I’m still going through doors that lead to new adventures and new journeys. The Marquis Jet was a big door for me financially. It was a bigger platform.

I wouldn’t have gotten there if I didn’t fiddle my way into the record executive’s rule to get a record deal. It’s all been a process.

It’s all interconnected, right?

It’s all interconnected. I’ve always had a movie in my head about where I wanted to be at the end of the day but I never had a script. I’ve always been filling in a script as I go along. I always knew I wanted to have independence, have a house, kids all that stuff. I’ve had some colds that I’ve had.

I have no idea how I was going to get there. I know the finish line, I had to fill in the script to get to the finish line. The common theme for me is that I’ve never had any past experience in anything that I’ve gone into. A lot of it hasn’t been planned.

I didn’t have past experience in aviation or living with a Navy SEAL and writing a book. It’s all been a process. It’s all been getting my foot in the door and calling audibles, figuring it out as I go to get to that finish line.

A lot of it has been, getting a tap on my shoulder from myself or from my gut and telling me that I’m a little bit off course. A lot of times I’ve been in it like music. I got a record deal when I was 22-years-old. I sent out 100 cassettes. When I grew up, it was cassettes.

I had sent out most people on those days, 100 cassettes to every record executive on the planet. I didn’t get one single call back. I realized I had to do it differently if this is going to work for me. I want to get into the music business.

I ended up calling a label out west called the Delicious Vinyl. I got the founder’s assistant or secretary on the line through a lot of confusion. She thought I was an artist that was out, a popular artist in hip-hop, and scheduled a meeting for me thinking that I was this artist.

That’s how I got my foot in the door. I went and met with this guy. He was confused. I continued to confuse him but I ended up getting a deal.

It sounds like you live by “Let’s ask forgiveness rather than permission,” motto that so many of us do. Let’s get in there and figure it out.

I ended up becoming great friends with this guy. That was my first foot in the door. A lot of what’s happened to me in my life has been getting my foot in the door and then getting a tap on my shoulder.

I didn’t do great in the music world. My record didn’t sell the way I thought it was. I couldn’t retire after putting out a record. In fact, I needed a job. I realized that I was off course a little bit.

I wanted to stay in music but maybe it wasn’t as a traditional artist. Maybe there’s a different lane for me to go. I changed course. I started doing jingles. I started doing sports theme songs for sports themes.

I opened a whole new world of opportunity. Intimately the next chapter of my life which was sports music. A category that I basically created and started the company around theme songs for teens and sold it to a public company. You never know where it’s going but you’ve got to get started.

I couldn’t agree more with you. I’ve thought of myself in the past. I would probably define you as an opporteneur. You realize and you see the opportunities abound and then you bring your entrepreneurial skills to that whether or not you’ve got experience or credentials in that area.

I’ve done a lot of the same thing. I’ve been involved in so many different businesses now. I’m not as motivated by money as I am by a challenge.

If I think it’s going to be fun and exciting to work in, and if it’s something that I can do well, whether or not I have any skills in that area, I’ll either develop them. I’ve come to realize that I don’t need to know everything as long as I know the people who do.

Relationships have been important to me in building those and nurturing those. I don’t know if this was in your book but I definitely read about it or heard about it in one of your podcasts either with Jordan or another one.

You’re intentional writing notes to people, staying in contact with your circle of influence. Can you touch on that a little bit more about what you did there? It didn’t just happen by accident, it doesn’t sound like.

In your 30s, the people are in positions of power. It was important for me to stay in contact with people in my 20s because on my 30s when I need stuff, my friends were the decision-makers.

The guys that worked in the mailroom are now the guys that control the board room. For me, I had a thing, I would always write. Every day I was writing ten personal letters that I would mail out to people to stay in contact, which is 3,000 people plus a year.

It could be anything from, “I appreciate what you did. It was so authentic.” It could just be a friend, “I appreciate what you did for me. I enjoyed going to the Knick game with you,” whatever it was. It helped me build this amazing authentic network.

That became important when we started Marquis Jet and we had to build our customer base. I had 3,000 people for X amount of years that I could tap into to spread the word. A lot of the stuff that I’ve done, I’ve been able to do organically through this network.

That’s absolutely brilliant. It shows that success is intentional. You didn’t put luck into this stuff. You put a lot of the work behind the scenes to make those relationships happen. They come back to serve you. I remember you talking about the story with 50 Cent that came back around.

50 Cent came into my office through a friend. He needed a job. I was writing sports theme songs for sports themes. He was helping me because there was so much to do. He had a partner named Kason.

They were doing rap stuff. I love Kason. I thought Kason was super talented. I signed Kason and then Curtis became 50 Cent.

You didn’t sign 50, did you?

I did not and obviously I don’t have a good ear for music talent that’s why I got out of that business. The cool part of the story is years later when he became a bestselling artist and all that stuff. I got a list of people.

Every day at Marquis Jet we would get a manifest of who is flying on the planes. I saw he was a guest on a plane so I sent them a note. I said, “50, you’re never going to believe this, it’s Jesse from Alphabet City,” which is the company that he interned with our company.

I said, “You’re on one of our planes. My partner and I started this company.” It’s a super cool way to turn around the story. The next day he added that he was only going to fly with Marquis Jet.

Living with a SEAL: 31 Days Training with the Toughest Man on the Planet

It shows you the power of loyalty that you never know who’s going to be whom or what’s going to be what. Do the right thing and the right thing comes back.

I read this on an interview that you did about you professionally, what you do. You said, “We find information about a niche and whether we start it ourselves or not, we’re bringing our entrepreneurial spirit and marketing savvy to those brands.”

I know you’ve got the 100-mile group and a lot of the different businesses that you work in, is that something you’re doing with companies? Whether it’s incubating them, advising them, investing in them, I’ve seen a lot. What can you tell me about what you’re doing professionally now?

I’ve always got my eyes out for stuff that I like. I look at the world, I go into a supermarket, and I study shelves. I like to see what’s trending, what’s new, what’s on the rise. I’m always looking for an opportunity.

I’m doing less of it now, I’ve got four kids and I’m trying to invest in my own projects like this book, stuff that I love to do. If something comes along that I’m a customer, I can help move the needle and accelerate it for the brand and I can get involved early on. I’m always interested.

Is there anything you’re doing besides promoting the book and playing with the kids, the marriage and all that you’re working on that you’re particularly excited about?

Nothing that’s launched, but one thing that I’m doing is in the past when I was younger I dove into stuff. Foot in the door first, figure it out later. Now I’m trying to take a little bit more time because I’m doing less. I have less time.

There are so many other things that I would love to ask and pick your brain on. One of them is, are you going to invite anybody else to live with you for a month in a challenge like that?

I am. I’m going to do this as a five-book series, so I can live with other interesting people. I have a couple of ideas. I want to live with the Rolling Stones. They don’t know that yet but that’s something on my radar.

I want to live with a monk. It would be cool. He can look at me and I can look at him and see what I learn about myself. I’m open to other suggestions.

It’s similar to what Morgan Spurlock did when he did Super Size Me. He did other things. I don’t know if you paid attention to his TV Series when he did that.

Of course.

This has been a blast. I can’t tell you how much fun I’ve had. I look forward to staying connected with you. Who knows, maybe there’s something, an opportunity that will turn up someday down the road between us. We’ll say, “It all started on this podcast,” because you never know.

That would be great. I appreciate it.

Living With A SEAL, you have to go get it and then follow him on Twitter and Instagram. Until next time, keep on tuning in to the show. Share it with your friends, and leave us a review on iTunes. I read every single one of them. Jesse, thank you.

I appreciate it, Brad. I’ll be in touch.

Important Links:

• Jesse Itzler
• Living with a SEAL: 31 Days Training with the Toughest Man on the Planet
• Marquis Jet
• Spanx
• Ed O’Keefe
• Twitter – Jesse Itzler
• Instagram – Jesse Itzler
• Bacon Wrapped Business on iTunes

About The Guest: Jesse Itzler

JESSE ITZLER only eats fruit 'til noon, loves Run-D.M.C., and enjoys living life “out of the box.” In fact, he doesn't even have a box. The author of the New York Times bestseller, Living with a Seal, cofounded Marquis Jet, 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 sold to The Coca-Cola Company.

He's a former rapper on MTV and wrote and performed the NBA's Emmy Award-winning “I Love This Game” music campaign and the popular New York Knicks anthem “Go NY Go.” When he's not running ultra-marathons, eating vegan food or being a dad to his four kids, Jesse can be found at the NBA's Atlanta Hawks games, where he's an owner of the team. He is married to Spanx founder Sara Blakely.

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