What a 66-Year-Old Jazz Record Teaches Us About Navigating the AI Shift

In 1959, John Coltrane walked into Atlantic Studios in New York with a composition that would break some of the best musicians on the planet. The song was called "Giant Steps."

Transparently, I used to work at the record label that released it. Before I built software companies, before the startups and exits — I ran digital for Verve Music Group, a division of Universal Music. Verve is home to some of the most iconic recordings in American music: Ella Fitzgerald. Billie Holiday. Charlie Parker. Oscar Peterson. Antonio Carlos Jobim. And through its Impulse! Records imprint, the entire spiritual jazz canon — including the later work of John Coltrane.

I also play bass — upright and electric. I've spent enough time inside harmony to get what Coltrane was doing on a gut level, not just an academic one. So when I tell you that "Giant Steps" is the best lens I've found for what's happening in technology right now, I'm not reaching for a clever metaphor. I'm describing something I've lived from both sides.

What Coltrane Actually Did.

Here's the short version for non-musicians: Before "Giant Steps," jazz harmony moved in predictable circles. Songs resolved in familiar patterns. If you were a skilled player, you could learn the vocabulary — the scales, the patterns, the licks — and navigate almost any tune. The better your vocabulary, the better you sounded.

Coltrane changed the rules. "Giant Steps" cycles through three key centers — B, G, and Eb — a major third apart, dividing the octave into three equal slices. The chords move so fast (roughly 290 beats per minute, two chords per bar) that the existing vocabulary simply doesn't work. You can't run your bebop scales. You can't fall back on muscle memory. The structure shifted underneath you. He didn't write a harder version of what came before. He wrote something that required a fundamentally different way of hearing.

The Flanagan Moment.

Tommy Flanagan was the pianist on that 1959 recording session. He was not some amateur. He was one of the most respected jazz pianists alive — the kind of musician other musicians called when they needed the best. And if you listen to the original take, you can hear him stumble. Not because he lacked talent. Not because he wasn't prepared. But because the changes were moving through territory his vocabulary wasn't built for. His fingers knew where to go on a standard tune. This wasn't a standard tune anymore.

I think about Tommy Flanagan constantly right now. Because I'm watching the same thing happen across every industry I touch.

Three Key Centers.

When I was at Verve, the music industry was going through its own Giant Steps. The key centers were shifting from physical CDs to digital downloads to streaming, and the tempo was relentless. I watched brilliant executives — people who had built careers on deep expertise — stumble. Not because they were wrong about music. Because the harmonic structure of the business had changed underneath them, and their vocabulary hadn't caught up.

The playbook that worked for selling CDs didn't translate to iTunes. iTunes didn't translate to Spotify. Each shift wasn't an evolution of the previous model — it was a new key center entirely.

I left music and spent the next fifteen years building digital and technology companies through similar transitions. Social media, programmatic advertising, the platform economy — each one a new key center that rendered last cycle's expertise partially obsolete. Now I'm building in AI. And the tempo is faster than anything I've seen.

Everyone Is Tommy Flanagan Right Now.

Here's what I've noticed: the people struggling most with AI aren't the ones who lack skill. They're the ones whose skill is deeply optimized for the previous key center. The senior developer who writes impeccable code but can't articulate what to build — because the value is shifting from execution to judgment. The marketing executive whose media buying expertise is being compressed into a prompt. The startup founder who spent two years building a feature that an API call now handles in seconds. These aren't failures of intelligence. They're Flanagan Moments. The changes moved, and the vocabulary didn't.

That gap — between technical execution and contextual understanding — is exactly where AI lives right now. It can play the notes. It doesn't always hear the music.

Coltrane's Solution (And Ours).

Here's the part of the story people miss: Coltrane didn't solve Giant Steps by playing more notes. He solved it by finding pentatonic cells — small, efficient melodic patterns (1-2-3-5) that could be transposed cleanly across all three key centers. Simple building blocks, endlessly adaptable.

That's the playbook for navigating what's happening now. The people thriving aren't the ones who've mastered every AI tool. They're the ones who've developed transferable mental models — frameworks for thinking about problems that work regardless of which key center they're in. Product judgment. Systems thinking. The ability to ask "what is this actually for?" before writing a single line of code or crafting a single prompt.

I've been lucky enough to practice this across music, digital media, social, and now AI. Each transition forced me to rebuild my vocabulary while keeping the underlying instinct intact. The notes change. The ear doesn't.

From Giant Steps to A Love Supreme.

There's one more part of the Coltrane story that matters. After "Giant Steps" — after pushing harmonic complexity to its absolute limit — Coltrane pivoted. He moved to modal jazz. Long, open forms. Fewer chords. More space. A Love Supreme isn't a showcase of technical mastery. It's a meditation. He didn't retreat from complexity. He passed through it and came out the other side with something simpler and more profound.

I wonder if technology is approaching a similar inflection. We're in the Giant Steps phase right now — maximum complexity, maximum speed, everyone scrambling to keep up with the changes. But the history of every paradigm shift I've lived through suggests that what follows isn't more complexity. It's clarity.

The companies that will matter in five years won't be the ones that played the most notes. They'll be the ones that found the melody.

The Recording.

Go listen to the original 1959 take of "Giant Steps." Listen to Flanagan stumble, and listen to Coltrane soar. Not because one was better than the other — Flanagan was a genius. But because in that moment, one of them had a vocabulary built for where the music was going, and the other had a vocabulary built for where it had been.

Then ask yourself: in your industry, in your career, in the work you're doing right now — which one are you? The changes are moving. The only question is whether your ear is moving with them.