WINSTON RIDER WAS THIRTEEN WHEN HE FIRST HEARD SHAWN MENDES’S BREACKOUT ACOUSTIC ALBUM HANDWRITTEN. IT WAS A PIVOTAL MOMENT FOR THE GREENWICH-BORN TEEN, WHO HAD JUST STARTED PLAYING THE GUITAR: “WHEN I WAS THAT YOUNG, I’D NEVER WRITTEN A SONG BEFORE,” HE SAYS. “BUT IN MY HEAD, I THOUGHT I CAN DO THAT. IT SPARKED SOMETHING.”
Winston spent the next four years focused on his craft, writing songs and playing his guitar every day—in his room at home in between classes at Brunswick. In the fall of 2021, he entered a contest for high schoolers sponsored by Z100 Radio for a chance to kick off the Z100 Jingle Ball in New York City. A few weeks later, he was coming home from a hockey game on the team bus when his phone rang. It was a New York area code he didn’t recognize. “I was like, I don’t know, I’ll just pick up,” he says. “That whole month I was picking up calls, which I don’t normally do.”
Good decision. It was the folks from Z100 inviting Winston to be the opening act for the Jingle Ball preshow at the All-Access Lounge at the Hammerstein Ballroom, before the main event at Madison Square Garden. (It was around that time that he dropped his surname “Mock” from his stage name.) Winston got to play four original songs in front of a live audience, as well as for the millions of Z100 radio fans throughout the metro area. “It was the first time I got validation outside my friends and family that my songs were any good,” he says.
Winston’s career has since been on a steady upward trajectory. In 2022 he was one of four local musicians to play on the town stage at the Greenwich Town Party (the year Billy Joel headlined). Although primarily a solo artist, the Brunswick grad called in his pals drummer Tom Seguso and bass guitarist Ron Haney to form a band for the day.
For GTP music producer Ken Hays, Winston’s sound was a natural fit for the Memorial Day celebration. “His songwriting touches the heart,” Hays says. “To put him on the stage in front of 8,000 people and hear him and what he brings to the table was really impressive.”
He has also performed twice at the country’s biggest music festival, Summerfest, in Milwau- kee; did a marathon two-and-a-half-hour set at South Farms in Litchfield in June; played a gig at Rimrock’s Tavern in Stowe in July; opened for the Pat McGee Band at Porch Fest in Milford in September and was one of four opening acts at
the Bedford Music Festival last month.
“He’s the real deal,” says Sherri Owles, one of the producers for the festival that’s now in its second year. The Bedford resident and music industry veteran knew she had to find artists that would complement the headliners, the Wailers. A songwriter friend, Sam Hollander, suggested she consider Winston. “When I first heard his demo, I was like, ‘Oh my God, this kid could go all the way. I have a great feeling about him.’ It’s very rare for me to get goosebumps,” she adds.
Sam Hollander isn’t just any songwriter. He’s a multiplatinum songwriter and music producer, who has collaborated with everyone from Panic! At the Disco and One Direction to Fritz and the Tantrums, Weezer, Katy Perry and blink-182, to name just a few. Among his most recent hits is “Someone To You” by Banners. He first met Winston when he was doing a reading and signing of his 2022 memoir, at botanical wellness shop oHHo in Bedford.
“He was there with his parents and came up to ask some questions, and I was impressed by his vibe,” Hollander recalls. “He was such a sweet and curiously intellectual kid. You could see in his eyes that he had a ton of passion for his art. He reminded me of an infinitely more polished version of myself at that age.”
They made a coffee date and Hollander invited his friend Shep Goodman to join them. Goodman is another music industry powerhouse—multiplatinum producer, songwriter and musician who has worked with artists such as American Authors, Rob Thomas and Hall & Oates. He is also co-owner of Dirty Canvas Productions, which focuses on artist development.
“I immediately thought, this kid has a cool presence,” Goodman recalls. “I liked his vibe overall. I loved how he handled himself in the meeting, taking notes, not just yessing and blowing it off. He seemed engaged. When I left, I heard one or two of his songs and thought this kid is really talented.” He and Winston started following each other on Instagram. “I gave him three or four things that I use marketing-wise. I figured I would follow him on IG and watch how he developed and the progress he made.”
He liked what he saw.
In July, Goodman and his creative partner, Aaron Accetta, invited Winston and his dad in for a meeting. “He played a couple of songs and we talked. We may get in the studio and write together soon,” says Goodman.
Todd Glassman is another music industry insider who has taken an interest in Winston. “He reached out via LinkedIn,” says Glassman, president of Collateral Damage Promotion & Marketing and former executive VP of Epic Records.“Iwantedto reciprocateand meet him in his environment. From the moment I walked into his studio and he startedplaying, I was blown away. It was mature, sophisticated and all self-taught. He was a true artist, not your typical TikTok artist.”
Glassman’s first move was to connect Winston with one of the top executives at A&R records, Paul Pontius. “I wanted to surround him with an experienced team who could foster and expand his growth,” he says.
As for the rest—in an age of rampant social media, Glassman is taking a cautious approach. “I want Winston to stay true to himself and his artistic value. He should have fun. He doesn’t have to depend on it [social media] like others to build his career. His music will ultimately take him anywhere he wants to go and most important enable him to control his own path. That’s extremely rare in our industry.”
ALWAYS A STUDENT OF MUSIC
Winston first picked up a guitar when he was ten during a family vacation in Nantucket. That was when his dad, Bradley Mock, rented a guitar and hired a local musician from the Community Music Center to come to the house and give his kids lessons. The first day, Winston and his three sisters had a fifteen-minute lesson each. The second day, it was just Winston and his younger sister. By day three, Winston was on his own. He took an hour lesson once a day for two weeks.
“I needed someone to show me the basic techniques when I was very young,” he recalls. “For some reason, it just stuck with me. The rest I learned on the internet and YouTube.”
Songwriting came next. It was a couple of years before he felt confident enough to show anyone his work. “Art can be a very subjective thing,” he says. “It’s hard to trust feedback.”
Bradley Mock remembers the day his son came downstairs and told his family he wanted to play a song for them. “He was in middle school and had been writing and playing quietly for a long time, and when he finally showed us what he was doing, I could see it wasn’t at a beginner level,” says Mock. “He understood how to build and layer a song, how to write and play a song, how to record and produce.”
From that point on, Winston was comfortable sharing his music with his family, especially his dad. “We’d play a new song through the house speaker. He would very carefully listen to everything I had to say, and I’d give him my honest opinion, and he’d listen and take it back to his studio. Now he’s taken it to a level that’s well beyond my feedback.”
Winston can often be found most in his music studio in the cupola-topped barn a short walk from the family home in backcountry Greenwich. It’s a peaceful spot with a generous tree-shaded yard and a chicken coop with six hens. An American flag hangs from a window outside. Inside, on the second floor, the walls are lined with posters and albums of some of his favorite musicians: Bruce Springsteen, Bob Dylan, John Mayer, Jackson Brown and Jeff Buckley. There’s a piano in one corner, a couch and area rug in another, a desk that holds the computer equipment and software for producing and mixing his songs. There’s a stool set in front of a black sheet draped with tiny white lights, which serves as a backdrop when he records himself. A mirror helps him work on different postures and poses.
“Just from watching other people perform in videos and at concerts, you can see when they go into different parts of a song, they do this or they move with the guitar. It’s the small things that people in the audience don’t really notice; they’re just seeing it as one big package. So, I look at it, like how can I make myself better
at that aspect of playing live.”
As he talks, it’s easy to see why people gravitate to him. At just nineteen, he has that certain something—an aura, a feel, yes, a vibe—that has “future pop star” written all over it. Dressed in a black T-shirt, indigo-blue jeans and black boots, Winston seems comfortable in his own skin. His smile is warm and inviting, his hair just the perfect amount of slightly tousled. There’s not a tattoo or piercing in sight.
“He’s a throwback,” says Hollander. “At the end of the day, it just warms my heart that there are kids who still care about the art. He’s a traditionalist and studies the songbook. There’s so little of that left. Kids can manufacture tracks within seconds now, but nothing supersedes the ability to study the work and know your history. I think that’s going to give him an edge.”
For Winston, playing guitar is a transcendent experience. “I pick up my guitar, and four hours later, I realize I need to go to sleep,” he says with a laugh. “The way I get lost in music—as a musician there’s no better feeling.” It’s also given him a way to navigate the stress and anxiety that comes with being a teenager. “If I’ve had a bad day, I come home and play the guitar.” This has given him insight into the healing power of music, and when the time came to take a community service commitment at Brunswick, he picked an organization that provides guitar lessons to veterans suffering from PTSD.
“I was in ninth grade, and I discovered Guitars 4 Vets through an ad. I got in contact with the cofounder, Pattrick Nettesheim—he’s a good friend now—and through him I’ve been able to set up fundraisers in my school and community.” Winston has raised more than $10,000 for the organization—enough to pay for fifty guitars for program graduates.
“I remember when my development director came to me and said, ‘Have you seen this kid on the East Coast who’s raising money for us?’” Nettesheim says. “I reached out to him and one thing led to another.” He invited Winston to play a set at Summerfest two years ago on the Guitars 4 Vets stage. Last summer, he gave Winston one of the prime 6 p.m. spots. “His star will truly continue to rise.”
This past September, Winston started his freshman year at the Berklee College of Music in Boston “I’ve spent so many hours by myself working on my craft, I’m so excited to open up to other people who are the same as me. And I’m so ready to collaborate with people.”
Winston has set high sights high. He wants to be not just a good singer/songwriter—“there are lots of those,” he says—but a great one. He points to his idols such as John Mayer, Ed Sheeran and Shawn Mendes as people he most admires. He studies their music, their songwriting and, most important, their technique, with one goal in mind: to find his own voice and pave his own way. “I think I’m on a good path with the kind of music I make and what
I want to make more of,” he says.
“All of the stuff I’ve done so far is to play solo. It’s the most stripped down and the hardest way of doing it. When I’m on stage, if I’m not playing, nothing is happening,” he says. But he thrives on the challenge. “When I’m in my room playing by myself, I close my eyes and pretend I’m playing in front of people. And when I’m playing live, I close my eyes and pretend I’m playing by myself.” winstonrider.com