Every Monday morning, John Nastos enters the Portland airport a jazz artist. A short flight later, he emerges in San Francisco a software engineer.

By Wednesday night, he’ll be back in Portland, performing, rehearsing, or recording in town while still working remotely as an engineer, until the next Monday when he does it all again. One of the city’s top woodwind players, he’s staying as busy musically as he was before he took the full-time job three-and-a-half years ago that led to his current position with OpenAI.  

He’s loving both careers.

“I feel lucky to be doing everything I’m doing,” the Portland native says. “I really enjoy both music and software engineering. If given a big sum of money right now, I wouldn’t stop doing either one of them.”

And why should he? For the past dozen years, he’s been on more than 10 notable jazz recordings by the city’s top bandleaders. He’s also been part of the classical scene, playing with the Oregon Symphony and contemporary chamber ensembles 45th Parallel and Third Angle.

In fact, a 2023 Third Angle performance of Phillip Glass’s 1,000 Airplanes on the Roof, he says, “was one of the coolest musical experiences I’ve ever been a part of. The performance was beneath the Spruce Goose, and it was an unbelievable multimedia show.”

A recording of that performance will be out in 2026, as will an album by Darrell Grant that includes Nastos. He’s also performed with Pink Martini in addition to touring with Grammy-winners Diane Schuur and esperanza spalding.

And though they may appear poles apart, playing music may not be all that different from his work as a software engineer. 

Jazz and software

In his youth, Nastos was able to keep both left-and-right brain activities going at once.

“I’ve been interested in computers pretty much forever,” he explains, “but in middle and high school, I also became very interested in music. So when it came time to apply for colleges, I applied to half computer science programs and half conservatories.”

Then he had to make a choice.

“I talked to my family, I talked to musicians, and I decided that I’d take advantage of the momentum I had in music. I had a lot at that time, and I thought, ‘I can always go back and get another degree later if I want to do computer science, but it’s going to be really hard to gain this momentum back in music.’”

So off he went to the Manhattan School of Music, and he’s been working as a musician ever since. In 2007, when he returned to his hometown, he found that Portland was a good place for a jazz artist.

“I’m very glad I spent some time in New York City,” he says. “For myself and a lot of jazz musicians, it’s important to be there at some point — almost like a pilgrimage. Because it was economically viable to make a good living playing in Portland, and since I wasn’t enjoying the non-arts aspects of New York City much, it made sense to move back.”

Besides, he missed the trees.

He never did get a computer science degree, but late at night, after the gigs, he began to teach himself how to develop apps for his personal practice routines.

First he built Metronomics.

“It came out in 2009, and it was a very long project,” he recalls. “Most of it was written between 11:00 pm and 3:00 am. It was a big learning process. But I’m glad I did it.” 

And then he created three more: Harmonomics, an ear-training app; PitchCenter, a tuner; and LessonKeeper, lesson management software for students and teachers. And so he built up his software engineering chops — just as he worked on his growth as a musician.

At the heart of the action

A product of Portland’s nurturing music ecosystem, Nastos took advantage of the many educational opportunities available to aspiring jazz and classical musicians, from summer music camps and school bands to private lessons with top professionals. 

He became a member of the Mel Brown Septet, and a few years later  he emerged on recordings by that group (Gordon Lee with the Mel Brown Septet: Tuesday Night), as well as albums by the Ezra Weiss Sextet (Before You Know It), The Chuck Israels Jazz Orchestra (Second Wind), and Darrell Grant (The Territory), to mention just a few.

He later taught as an adjunct at Portland State University and Mt. Hood Community College, positions he gave up to pursue software engineering full-time. He also authored two method books: An Improvisation Overview and Pentatonic Patterns.

And all the while he was working with a variety of musicians. But some of those associations were more impactful than others.

“In just sheer number of gigs and the invaluable experience I’ve gotten from them, Mel Brown’s Septet and Christopher Brown’s Quartet are at the top of the list,” he says. “Both bands contributed significantly to how I developed my sound, my conception of playing with others, and even my musical taste.” 

The Mel Brown Septet was one of three bands the storied drummer led at Jimmy Mak’s, Portland’s top jazz room for more than a decade in the late 1990s and 2000s. The ensemble’s book contained hard bop classics and originals by band members. Modeled after Art Blakey’s Jazz Messengers, the Septet, like all of Brown’s groups, was tight and polished. 

If you count the award-winning Sextet that was the precursor to his seven-piece group, it could be argued that Brown’s bands were the epitome of jazz in Portland for nearly 20 years. And for some of that time, Nastos was at the heart of the action.

Passionate and industrious

His talent was evident from an early age, according to Septet pianist Gordon Lee, who first met the then teen-aged saxophonist when Lee taught at the Mel Brown Summer Jazz Workshop. And since Nastos had been studying with Warren Rand, the original alto player in Brown’s Septet, it was a natural step for the young artist to take over his mentor’s chair when Rand moved away.

“John had already been sitting in with the band,” Lee says, “so we all knew him, and Mel really liked his playing. And he also became a teacher at the Jazz Workshop — we only had a couple people like that. 

“He’s a very industrious man who works really hard at everything he does,” Lee continues. “But what I love is he plays very passionately. And on top of that he can sight-read anything. I wrote ‘Change Your Dreams’ (on the album Tuesday Night) for John and he grabbed it. That’s one of the things I love about him as a musician: he figures out what I want him to do without me having to tell him.” Lee laughs. 

He found a similar reception in the Christopher Brown Quartet, where Mel’s son Christopher has given Nastos a prominent voice on the new album by his Quartet, Sole City. He has been in the younger Brown’s band since 2012.

“What John brings to the Quartet is a really high level of professionalism and consistency with his preparedness,” says Brown, “and a very deep knowledge of jazz. I like that muscular alto sound that basically sounds like a tenor player playing alto. John has that. So he has what I like and what I need.”

And it hasn’t been the full-time software job that has changed the woodwind player’s approach to jazz, Brown observes, but the natural outcome of gaining maturity.

“This is maybe par for the course for a lot of us, but it’s his use of space that has changed. When we’re younger we play a lot of notes, but as you get older, you start thinking about the emotional impact of music, you start to realize that, for that to happen, you have to use more space — because emotion happens after the sound stops.”

In recent years, despite his full-time job as a software engineer, Nastos has kept up a steady recording and performing schedule. It appears that, at age 39, he has the best of both worlds. And they may not be as distant as they seem.

AI

Since he was keeping both passions alive, it was fitting that he was recruited for his first software engineering job by a former musician. The company was ReMotion, and two years later, when it was acquired by OpenAI, Nastos was hired to work on the applied product side of the company.

His work for OpenAI has nothing to do with music directly, but similarities to playing jazz are there.

“You [an improvising musician] are usually trying to come up with a solution to a problem,” he explains. “It’s a funny thing to frame playing a solo as a problem, but in a way it is. And you don’t have a prescriptive way of solving that problem. That is the engineering aspect of it: how do I design a system that will fit within the constraints I’m dealing with, that will solve the issue? That may be a kind of mechanical way of describing what a jazz solo is, but it’s also pretty accurate. And it’s certainly accurate for being a software engineer.”

Christopher Brown also notes a parallel: “The most obvious way he’s brought the engineering side of his mind to the music is his ability to put things together. John is a ‘systems thinker.’” 

A recent OpenAI video may give you an idea of what kind of work Nastos does for that company. At the end, he brings out the alto sax he keeps in San Francisco — a rare occasion, but it reveals how the musician in him is never far from the office. 

Now I’m not qualified to comment on whether AI may or may not benefit society in general or even certain fields where results have so far been promising, such as medical research. Much of what I read focuses on potential dangers and current problems with a technology that nearly everyone agrees will shape (some say will determine) our future. One recent poll showed that 43% of Americans think AI will harm them, while only 24% think it will help.

That unease appears to come from a feeling that the future is something that is happening to us, not something we have a hand in building. Some are worried about the data centers that are predicted to drain local water and energy supplies. Others are concerned about job losses, declining cognitive skills, and our increasing inability to identify AI-generated images. Folks fear that “truth” will become even harder to find, or that Large Language Models built on data from an unequal society will replicate and amplify that inequality.

But Nastos sees many benefits of AI tools.

“I think they’re super interesting,” he says. “If you want to know something about a musician, this is a great way to do it. If you’re self-employed and need help organizing your finances at the end of the year, then these tools are amazing. It also opens up the potential to be much more efficient than you have been before. That’s what’s exciting to me. I’m hopeful these things will be extremely important for frontier scientific research, if for no other reason than they are tireless and they can work at incredible scale. And that’s the future I’m most interested in.

“It’s very similar to the dawn of the internet,” he continues. “Who should learn to use the internet? Probably everyone. And it’s not to say that someone can’t get along without them. It’s just that you want to take advantage of the tools that are available.

“I don’t think there is a prescriptive use for any of these things,” he concludes. “But I do think they have increasingly impressive abilities in a wide variety of areas.”

Learning to live with them won’t be easy. We are resistant to change, and AI tools will require us to learn new ways of doing our work. As Nastos says, however, “It’s incredibly important to stay curious and on the forefront of what’s happening.”

Like plumbing

So, as it appears to this barely-informed writer, the main difference between his work on AI and on the bandstand is that jazz artists probably aren’t changing the world in the way software engineers are these days.

And yet, I want to believe there’s truth and joy in music that cannot be found in a machine, and that it’s possible to say that the arts — using jazz as our shining example — offer just the kind of skill set you need to deal with the new world order. 

Because jazz is built for uncertainty and change. Within the parameters of a composition, the possible actions and reactions are infinite. So improvising jazz players must navigate the kinetic movement of an ensemble that never plays a tune the same way twice. Sounds like good training for just about anything, doesn’t it?

“Playing jazz is like plumbing,” the bassist Glen Moore once said. “Except there’s already water in the pipes.”

A few upcoming performances

• December 14 — The Chris Lee Quintet at Burlingame Space
• December 19 — The Cyrus Nabipoor Quintet at the Jack London Revue
• January 6 — Morgan Freeman’s Symphonic Blues Experience with The Oregon Symphony
• January 7 — The Christopher Brown Quartet at the 1905
• January 8 — The Gordon Lee Quintet at the 1905