The Best Job I've Ever Had with Alex Lobert

The Grind & Groove of Chicago Jazz: Andy Brown Beyond the Green Mill


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What’s it really like to make a living in jazz? 🎸

In this episode, I sit down with Chicago Jazz guitarist Andy Brown to talk about the reality behind the Green Mill stage — the late nights, the mentors who shaped him, the mistakes that taught him, and the gamble that brought him from Cincinnati to Chicago.

We explore:

  • Why moving to Chicago was the pivotal decision of Andy’s career
  • The grind and joys of being a working jazz musician today
  • How mentors, community, and mistakes shaped his unique sound
  • What jazz teaches us about work, growth, and resilience

Whether you’re a musician, a fan of Chicago’s jazz scene, or someone curious about turning passion into a career, Andy’s story will inspire and challenge the way you think about work and art.

Links from the show:

  • Andy's Website: https://andybrownguitar.com/
  • The Green Mill: https://greenmilljazz.com/
  • The Jazz showcase: https://www.jazzshowcase.com/
  • Andy's Club: https://andysjazzclub.com/
  • The Best Job I've Ever Had: bestjobever.org
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The Best Job I've Ever Had with Alex LobertBy Alex Lobert