Ep. 17: A Saxophonist Busks NYC Subways & Overcomes Drug Habit

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Jake Dester is an American musician based in New York City whose expertise lies in jazz saxophone and composition. Dester is also a songwriter, entrepreneur, arranger, music producer, singer, guitar player, graphic designer, marketer, and video editor.

He comprises one half of the "darling duo" Sydney & Jake, a partnership with vocalist/guitarist Sydney McNulty (aka Syd Caldera) that specializes in performing classic songs in a 1940s-50s style for weddings and corporate events.

Recently, he has been focusing largely on his songwriting pursuits and has taken up the moniker Pretty Mutant to encompass his role as singer-songwriter. He is in the process of writing, recording, and producing a 13-song album.

He is also known by the alias Sax On A Train (@saxonatrain) whose aim is to place jazz in the context of pop hits on subway train cars and platforms throughout NYC.

His transcriptions of legendary saxophonist Charlie Parker's solo work are uniquely detailed, and his unparalleled approach to teaching authentic bebop articulation has led to his creation of some of the most-viewed YouTube lessons on the subject.

A graduate of The University of North Texas' world-renowned Jazz Studies program, has studied with many of the world's greatest jazz educators and had the opportunity to meet and learn from legends and masters of the art form.

In today's interview we cover:

  • $5,000 in credit card debt
  • Living in NYC
  • Growing up singing and playing clarinet
  • Declining a college scholarship
  • Establishing residency in Texas of in-state tuition
  • Obstacles of the music education system
  • Writing and composing for a 9-piece ensemble
  • Promoting shows using guerilla marketing
  • Freelance gigging around Denton/Dallas/Ft. Worth
  • Teaching private music lessons
  • Confronting a student parent and the repercussions
  • Busking rules and difficulties in Chicago
  • Selling all of his horns
  • Buying a one-way ticket to NYC
  • A 3 week cooking stint that led him back to saxophone
  • Playing saxophone on subway trains
  • Building a business playing weddings and corporate events
  • Living in a rehearsal space only to have it flood
  • Coping with drug dependency
  • “Who am I when I’m not on drugs?”
  • The interconnectedness of drug use and the music community
  • Developing a relationship with money through family and scouting
  • Credit card debt 101
  • The importance of financial literacy
  • The dangers of stigmatizing money
  • Making money with music
  • “If you’re not playing the game you are being played by the game”
  • The importance of reading books with an open mind

Resources and names mentioned:

Connect with Jake:



Thanks for listening and keep thriving!


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