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Under the yellowing fall leaves of Christmas-light-wrapped trees, John Sterling is playing his saxophone as darkness falls in downtown Greenville.
He plays the blues — the notes light and swinging, then deeper, more melancholy.
His black-and-white Boston terrier, Poppy, settles down at his feet as a small group of women and a little girl approach.
Some of the women film him on their cellphones. The little girl runs up and drops a tip in his saxophone case, then skips away, smiling.
Sterling, a Greenville native, doesn't play for the money. In 2006, he sold the company he helped launch to success, Datastream Systems, which serviced the majority of Fortune 500 companies.
Instead, Sterling plays to make people happy.
"It's a combination of really enjoying mixing it up, playing for people, having those little positive interactions," he said.
Swapping basketball for saxophone
The first time Sterling thought about playing the saxophone, he was in Charleston in 1982. He had what he describes as "a vision" when he spotted a small doorway — the perfect spot for an outside performance.
"I thought it would be so cool to go over there and play the saxophone, be out there playing, people listening, making people happy," he said.
The odd thing was that he'd never played an instrument before. Sterling was a basketball player, not a musician. He played at Christ Church Episcopal School and then later at The Citadel, where he graduated college.
He even played a season of basketball in Ireland before entering the business world, he said.
But Sterling continued on with his life after the vision without picking up a sax. He got into the tech business and worked in Silicone Valley for a while before moving back to Greenville, marrying and having children.
He was an early investor in a company, Datastream Systems, which grew to provide management software and services to more than 60% of Fortune 500 companies, according to a press release. Sterling served as executive vice president of global sales.
He gradually stopped playing basketball, and eventually, he decided to pick up music.
"I just decided to pick it up as a hobby, really, just out of the blue," he said.
He bought a saxophone, found a teacher and began learning. He started a small band and played around Greenville.
But life got busy, and he was traveling for work. For several years, he stopped playing.
In 2006, Sterling and his business partners sold Datastream to Infor, a global software provider, for $10.26 per share in cash, "a fair price," Sterling said.
The decision was based on industry trends at the time, he said. It was risky to be a relatively small public company, and regulatory red tape was causing a lot of headaches. The sale brought him relief — and more time to spare.
After selling the company, Sterling spent his time investing in other businesses, doing professional development coaching and traveling, he said.
He also picked up music again.
COVID-19 pandemic helped Sterling with his music
In 2019, Sterling and his wife, Jennifer, moved to a condo in downtown Greenville. During the pandemic shutdown in 2020, Sterling worked with Craig Shields, a producer and musician in Charleston, who gave Sterling music lessons over video calls.
"The internet and the shutdown actually helped me with this music," Sterling said.
Sterling used to practice in his condo, where he thought no one could hear him. But one day, at a neighbor's kindly worded request, he was prompted to move outside.
"I'm telling you, I'm a big man and done a lot of things, but I was a little scared to go out there," he said.
It was a Tuesday around 10 a.m. There was hardly anyone on the street.
"I said, 'I have nothing on my schedule. John, if you don't get out there and open this thing and play one song, then just forget it,'" he said.
So he went down to the underpass on S. Main Street, and he began to play.
A man and his girlfriend strolled by. They looked at him; Sterling couldn't read their faces.
The man walked toward him. Sterling's mind raced. What would the man say?
"Can I put a dollar in there?" the man asked him, gesturing to his case.
Sterling advocates for the city of Greenville
Since that day in 2019, Sterling has played outside for an hour and a half almost every day when the weather is good.
He plays jazz and blues and Disney favorites.
"Someday my prince will come."
Two years later, Sterling has become a sort-of impromptu advocate for Greenville. While the performances are great practice, what's more rewarding are the little moments Sterling has with the people who stop to listen.
He has regulars, like the dog walkers and the runners he sees often.
Whiny children will hear the music and stop crying.
Tourists from all over — Buffalo, Seattle, Austin — ask him questions. "What's it like to live here? Where's the best spot to eat?"
"I wish I could play the saxophone," some people will tell Sterling wistfully. "I wish I didn't stop taking piano lessons."
But Sterling doesn't dismiss them.
"They can all play the saxophone," he said. "Everyone can."
Sterling plans to release a CD of performances
He's gotten to know other musicians who play downtown, too. Sterling figures there's about 75 of them licensed by the city to perform on the streets. Sometimes they'll sit down together and play a few songs.
Jennifer, their children and young grandchildren sometimes come and listen to him play, too. Poppy, his Boston terrier, comes with him often.
Sterling is working on a CD, which he hopes to release in the next three to six months. It will have the same kind of music he plays outside. He'd also like to get a steady, laid-back gig somewhere local, where he could play once a week or so.
But while Sterling has those goals in mind, he isn't putting pressure on himself or his music. He just wants to enjoy it.
"Playing outside for me isn't a means to an end," he said. "I intend to do this the rest of my life, as long as I can play."
Macon Atkinson is the city watchdog reporter for The Greenville News. She's powered by long runs and strong coffee. Follow her on Twitter @maconatkinson.
This article originally appeared on Greenville News: Greenville man sold his tech company, now plays saxophone on streets