Jesse Itzler had a singular focus in college. While his contemporaries were struggling to secure internships, Jesse launched his hip hop career in his dorm room. He eventually won an Emmy for “I Love This Game” and his New York Knicks’ theme song, “Go NY Go,” became a fan favorite.
In 2001, he co-founded Marquis Jet, which he built into a multi-billion dollar company before selling it to Berkshire Hathaway in 2009. Always highly athletic, Jesse has completed 100-mile ultra-marathons and wrote the New York Times bestseller, Living With a Seal: 31 Days Training With the Toughest Man on the Planet.
In 2017 he founded 29029everesting, which hosts events in which participants ascend the height of Mount Everest, by repeatedly hiking, walking or running up a mountain until they reach the combined height of 29,029 feet (the height of Mount Everest).
Nothing In My Life Has Really Been Planned
John Greathouse: What led to you launching a music career – were you writing songs and performing while in college? If so, when did you know you weren’t going to follow a conventional path? (Note: Jesse’s remarks have been lightly edited for brevity and readability.)
Jesse Itzler: I grew up in the early 1980’s in New York when hip hop was exploding on the scene. While all my friends in high school were going out at night to parties … I was going to the roller skating rink in Queens for break dance battles. That love for hip hop stayed with me in college.
I went to school (in Washington D.C.) and started competing in open mic nights and local events. I got discovered by a producer my freshman year and we recorded a demo in my dorm room. All through college I worked on music and while all my roommates were busy working on their resume and interning at local offices… I was out trying to get a record deal. That was my only focus. When they were like, “Why aren’t you out building your resume up to get a job”… I would say, “Why do I need a resume if I’m going to get a record deal?”
Greathouse: I love your singular focus, which is typical of successful entrepreneurs. What did you enjoy more, performing, writing or recording?
Itzler: I like performing the best. Even today, I think my favorite thing is giving live speeches, as once you get the bug… it’s hard to get rid of it.
Greathouse: You won an Emmy for the NBA theme song, “I Love This Game.” You also scored big with the Knicks’ “Go NY Go.” Was your evolution from hip hop to Arena Anthems by design or the result of random events? Were you sitting at a game saying, “This music sucks?”
Itzler: Nothing in my life has really been planned. I have always tried to jump on the circumstances and opportunities that I see. The shift in my music career was no different. I got dropped from my label after my first album and that hurt. However, my passion was music and sports, so I decided to marry those two things and wrote a theme song for the NY Knicks.
I thought that a theme song could really be big and something the city could rally around. I did the song on spec and played it for the Knicks. It became the number one most requested song on NY radio and then I realized that a whole new category (sports music) had opened up.
Greathouse: Looking back on your music career, do you feel you drew upon your musical experiences once you left the business and founded Marquis Jet? What motivated you to going into the aircraft business – lousy private air service while you were running your record label?
Itzler: Most great ideas are born by solving a problem or filling a void. I was a guest on a private plane at 27 years old and when I walked on the plane it was like the scene in the Wizard Of Oz when everything turns from black and white to color. I couldn’t believe that people flew like this. My partner and I were like, “We want to fly like this!”
We realized there were no good options for folks that only want to take a few private flights a year on the best planes… and that started our journey into providing a solution. Marquis Jet was born a year later with no aviation experience and no airplanes. We grew it to well over $5 billion in sales.
Greathouse: Marquis was eventually acquired by NetJets’ for a ton of money. How did you differentiate Marquis’ approach and beat your legacy incumbent?
Itzler: Marquis Jet simplified all the private jet options at the time. We didn’t require huge commitments or upfront payments. You purchased 25 hours of flight time and it worked like a debit card. You fly 2 hours and you have 23 hours left. When the hours are done you can walk away or renew. For my generation that had trouble with “commitment,” this was amazing. It allowed you to fly on the world’s best fleet without having to own a fraction of the plane, which was very expensive. It worked.
Greathouse: I love that you and Sara (Blakely, Founder of Spanx) are both phenomenally successful, yet hugely supportive of each other’s careers. Traditionally, it seems that power couples’ lifespans are relatively short, due to the tension… energy required for each spouse to stay on top of their fields and the jealously that can screw up the best of relationships. Do you have any words of wisdom for young couples with children on the front-end of their demanding careers?
Itzler: The answer is…we work on it. We make sure that we prioritize our relationship and take time for ourselves. We also got married later in life – I was 40 and Sara was 37 – so we both waited for the right time. There are only 3 scenarios for marriage: 1) right girl… wrong time, doesn’t work, 2) wrong girl… right time, doesn’t work, or 3) right girl… right time. She was the right girl at the right time.
Greathouse: And I guess you were the right guy as well… timing is everything in life.
You’re an exceptional speaker. How did you hone your craft – is it an extension of your hip hop performance days? What advice do you have for folks who want to become more effective public speakers?
Itzler: Thank you. Public speaking is so important as almost everything revolves around it – sales, meetings, pitches, etc. I like to incorporate four elements: 1) Open with a good story or icebreaker. I try and use humor right away, 2) Tell the audience what it is you will be speaking about. The audience likes to know what to expect and it makes it easier to follow along, 3) deliver on your promise, and 4) leave the audience with immediate actionable takeaways.
Greathouse: What are some actions you encourage your audience to take , after attending one of your motivational talks?
Itzler: I obviously want people to leave inspired, but more important, I want people to take action. To start the process. A lot of my message is about building your life resume. We tend to obsess on our traditional resume, but our life resume is so much more important. I always try to give suggestions around things that have worked for me, as far as having winning habits, winning routines and a winning mindset.
Itzler: I was frustrated with the current options available on the market. I love endurance events and wanted others to experience the feeling and lessons I get from participating in them. Being outside, learning about yourself, pushing you limits. However, most events required you to be a good swimmer or biker… or, they required you to do obstacles that I don’t like doing. 29029 allows folks to experience an amazing challenge… outdoors… and anyone can do it if they have the will and resolve.
Greathouse: How can folks learn about upcoming events, speaking gigs or Everesting events?
Greathouse: When you’re a senior citizen, with your grandkids surrounding you, what do you want your professional legacy to be?
Itzler: I’m way less concerned about my professional legacy then my personal legacy. I always say you should be able to write your life story in six words or less. I want mine to read “Blessed with adventure, friends and family.”
You can follow John on Twitter: @johngreathouse.