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 thrive. It’s a weekly newsletter for music exploration, a radio show on Portland’s Shady Pines Radio, and a platform where I offer support with web presence, promotion, and the systems that make creative work sustainable.

It’s also a gathering spot for the wider scene — a place to find local shows, essential albums, and the occasional piece of merch. 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 and be part of it.

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 platforms as bold as the art itself. From writing liner notes and building websites and brand identities for artists, to curating playlists and hosting a radio show, I care about helping music reach people — and giving musicians the tools to make that happen without burning out.

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WHO I AM

I’m Alex — a creative strategist, operations consultant, and jazz enthusiast. 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.

Now I put those skills to work in the music world: building websites for artists, developing promotional assets, and helping labels and nonprofits find clarity and cohesion online.

When I’m not running CGJ or working with clients, you’ll probably find me climbing Pacific Northwest trails, cooking plants (vegan 5 years strong 🌱 ), or digging for the next thing I can’t stop listening to.

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 like I mentioned above. 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 this newsletter 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 email 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.

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.

NEVER MISS A POST OR A PLAYLIST

Listen Live

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. 

Promotional poster for a radio show titled "Chaotic Good Jazz" hosted by Alex Lester, airing Fridays from 10 am to noon on Shady Pines Radio, with a vibrant blue background and yellow 3D text.

WAYS TO GET INVOLVED OR WORK WITH CGJ

If you’re a listener — subscribe and tune in.

If you’re an artist — check out my services or submit your work for a possible feature in the newsletter or on the radio show.

Chaotic Good Jazz is one hub with many doors. Step through whichever one’s yours.