Building a Lasting Music Career w/ Jason Miles

In this episode, I’m joined by Grammy-winning keyboardist, composer, producer, and arranger Jason Miles - an artist whose legacy spans decades of music-making across jazz, R&B, and beyond, and whose work has helped define the sound and direction of multiple musical eras, working alongside some of the most influential voices in modern music like Miles Davis, Luther Vandross, Grover Washington Jr., David Sanborn and Marcus Miller, to name a few.

No less than Roberta Flack said about him, “Jason Miles has raised the level of excellence for the musicians who have had the good fortune of working with him, myself included. He has enriched the lives of millions of people.” And Miles Davis, in his 1991 autobiography, labelled Jason a genius - not a term he threw around!

Jason and I met here in Lisbon, and what started as a conversation became a very honest and enriching exchange for me. I’m grateful to have had the opportunity to sit down with him.

This podcast explores the journey behind the music - the decisions, mindset, and lessons that shape a sustainable creative life, especially in today’s DIY landscape. We begin our interview by talking about what Luther Vandross understood about music that most musicians never quite grasp.

From there, Jason shares the biggest lessons he’s learned across his outstanding career — we explore creative decision-making, trust on the business side of music, and his perspective on today’s jazz landscape compared to the past, as well as Jason's 2026 musical projects.

This conversation is about practises that still guide artists today. If you’re an independent musician looking for clarity and perspective, I am sure you’ll find a lot of inspiration in hearing Jason's stories, reflections and guiding principles.

Jason Miles - Links:

Website

The Extraordinary Journey of Jason Miles

Bandcamp

Table of contents:

00:00 Intro
03:29 Luther Vandross's integrity & intention
14:26 Advice for DIY artists: listen & learn
21:16 Why decision-making matters
22:19 Trust in the business side of music
23:11 Dealing with rejection
26:11 Today’s jazz landscape
28:27 Jason Miles’ 2026 projects

As you listened, what reflection stayed with you the most?

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