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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.



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