ABOUT CHAOTIC GOOD JAZZ

Black background with yellow handwritten text reading 'and Alex Lester'.

Chaotic Good Jazz brings together the things I care most about: listening deeply, sharing discoveries, and helping artists share their music. It’s a weekly newsletter for music exploration as well as a radio show on Shady Pines Radio and Freeform Portland.

Chaotic Good Jazz is built to keep music moving freely, with fewer barriers and more connections. Whether you’re an artist, a label, or a listener, you’re welcome to tune in, subscribe, and be part of the community. Prepare to discover something different.

A yellow compact disc with a brown center on top of a yellow case, with headphones and a yellow cable inside the case.
A colorful, abstract, geometric pattern consisting of blue outlines, yellow rectangles, and small red squares on a white background.
Silhouettes of four musicians performing on stage against a blue curtain, with one holding a double bass, another with a microphone, one on drums, and another raising a hand.

WHY MUSIC?

Music has always been central for me. I played tuba on a college scholarship, and today I run Chaotic Good Jazz because I believe music deserves amplification and I enjoy building community around a shared love of discovering something different.

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WHO I AM

I’m Alex, a Jazz broadcaster and host with 10+ years building audiences across radio, editorial, and social platforms. Before launching CGJ, I spent a decade building content systems, leading branding projects, and helping teams streamline how they work. Along the way, I co-founded a food media company that was acquired in 2023, co-authored a cookbook, and even taught middle-school science.

When I’m not running CGJ or working with clients, you’ll probably find me climbing Pacific Northwest trails, cooking plants (vegan 6 years strong 🌱 ), or digging for the next thing I can’t stop listening to. → Check out my creative portfolio.

A MacBook Air laptop displaying a webpage about jazz music, placed on a wooden table with a smartphone in front of it.

WHY I WRITE CGJ

Music (especially jazz) has always been therapeutic for me. A good groove is meditative, grounding, and just the right amount of chaotic. I spend hours digging through new releases, hidden gems, and under-the-radar deep cuts to find the stuff that feels fresh, funky, or totally off-the-wall and CGJ is my way of sharing the best of it.

If you’re into acid jazz, ethio-jazz, experimental fusion, spiritual jazz, or artists who aren’t afraid to break the mold, your next favorite album might just be an issue or show away.

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BEHIND THE NAME

Chaotic Good Jazz refers to jazz that is rebellious, free-spirited, not bound by any set of rules and making positive change in the world. Or it might just be a record filled with chaotic drum breaks and screaming sax solos, you decide.

Collection of album or music-related posters with waveforms, diagrams, and graphics.

BEHIND THE DOODLES

I’ve always loved finding ways to make music a visual experience. As a lifelong doodler, this project started as a meditative practice while listening and notating the parts where I found my head bobbing, toe tapping, and brain exploding. It’s all the parts I would be excited about sharing with friends in person.

This is my way of saying, “Hey, check this out!” in the most visual way possible. I publish doodles as part of my monthly and yearly round-ups of my favorite albums in the CGJ newsletter. Subscribe to get full access to the newsletter, playlists and archives.

Stats (August 2026):

Substack - 900+ subscribers / 1.25k followers / 4.5k 30d views

Instagram - 1k+ followers / 13k views 30d views

ARTISTS INTERVIEWED ON AIR:

BrandonLee Cierley

PoiKilo

Negative Concord

Bendrethegiant

Cochemea

Brandon Woody

Reed Wallsmith (Blue Cranes)

Jeremy Famà

No Soap, Radio

BrandonLee Cierley PoiKilo Negative Concord Bendrethegiant Cochemea Brandon Woody Reed Wallsmith (Blue Cranes) Jeremy Famà No Soap, Radio

RECOGNITION

“Curated playlists from the adventurous edges
of modern jazz.”

— American Jazz Museum

“Great weekly jazz recommendations.”

— Matt, Sonic Explorations

“Great weekly deep dive into an enormous amount of new music. Well designed graphics and thoughtful presentation.”

— Jonas Jacobs, Penguin Jazz A-Z

“Alex has really made this Substack and his radio show something special with his energy and enthusiasm and taste.”

— Adam Sieff, Jazz on the Beach

NEVER MISS A POST OR A PLAYLIST

Listen Live on Shady Pines

Every Friday from 10–12 PT, I host Chaotic Good Jazz Radio live on Shady Pines Radio. It’s a show built for deep listening and background head-nods. Expect spiritual grooves, noisy breakdowns, funky detours, and plenty of sax solos. It’s messy, soulful, and the best way I know to start the weekend. 

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Listen Live on 90.3/98.3 fm

Tune in on Freeform Portland for New Music Monday's every other week starting April 6th, 2026 for two hours of off-the-rails drum solos, mind-blowing saxophoning, and oh so groovy modern jazz. Listen locally on 90.3/98.3 fm, and around the world at freeformportland.org.

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