Episode 43

Published on:

16th May 2018

Ep. 43 - Lessons Learned as a Rapper Turned Entrepreneur - with Jesse Itzler

Jesse Itzler is a rapper turned entrepreneur. It might seem like an odd transition, music to private aviation (and beyond), but Jesse wasn’t exactly following a plan – he was following his love for doing something new and different.


After some success with his first entrepreneurial ventures, Jesse found himself a guest on a private jet. He enjoyed the experience, predictably, and figured other people would like that experience too.


So Jesse transitioned out of music and co-founded Marquis Jets, one of the largest private jet companies in the world, which has since been acquired by Berkshire Hathaway.


Jesse has been hustling on quite a few projects since then – including writing the New York Times bestseller Living With a SEAL: 31 Days Training With the Toughest Man on the Planet – and he has learned that there are some constants, in every industry:


  • Things take time. Creating anything worth having takes a large investment of time and energy.
  • Focus on the product, and differentiate yourself by being the best; make yourself irreplaceable.
  • Be authentic. What makes you different? Through trial and error, build a winning formula for yourself.
  • Try a lot of things, especially while you’re young! After you learn what you like, you can perfect it and then cash in on it (with time, of course).
  • Don’t take the easy route, and don’t be afraid to take risks while you’re young.



Show artwork for Trendsetters with Jesse Kay

About the Podcast

Trendsetters with Jesse Kay
Jesse Kay interviews the entrepreneurs of Generation Z, all in their 20s or younger, who are making a game-changing impact in business.