ARDMORE, Pa. —The last mid-amateur standing at Merion this week had a bigger goal than hoisting the Havemeyer Trophy. Something that has everything to do with golf, but nothing to do with how well he gets the ball in the hole.
Christian Cavaliere wants to sell you something.
“It’s a refined look that you would see at a high-end country club,” Cavaliere told GOLF on Thursday evening at the U.S. Amateur. “We see it. We know it. When we make something, we want to make something that we would appreciate and we would use.”
What is it? The answer was everywhere this week at Merion as Cavaliere advanced to match play for the first time in five U.S. Amateur starts. It was on his head, on his clubs and in his back pocket as he bounced Boston Bracken 3&2 in the Round of 64 and when he rolled over Canadian amateur Dawson Lew to advance to the Round of 16. It was in the Merion clubhouse as fans and players raided the shop.
Christian Cavaliere once planned to walk the brutal path of pro golf, set to grind his way up a ladder that few can climb. Then, he decided on a different, albeit equally perilous, path of building his own golf start-up company: Tremont Sporting Co.
“They are both very uncertain paths,” Cavaliere, 28, said on Thursday night as the sun started to set over Merion East. “But I always wanted to do something big like that. It was kind of like choose whichever one you want to jump into. … Pro golf, that road is really tough. The entrepreneurial road is horrifying, and I wouldn’t recommend it to anyone, but that’s the same way people feel about pro golf. It’s a grind.”
That grind started in 2020, when Cavaliere, an accomplished collegiate golfer with pro aspirations, was starring at Boston College, looking toward pro golf on the horizon. As is often the case with talented golfers, Cavaliere has a creative side. He started sewing on his mom’s sewing machine when he was 10 and took to the craft. He started making custom hats for the golf team at BC, and soon other teams at BC wanted his hats too. It was a side hustle that padded his wallet, but Cavaliere still planned to pursue pro golf.
Then, the COVID-19 pandemic hit during the spring semester of his senior season, and Cavaliere moved the side hustle to his parents’ house in Katonah, N.Y., and expanded to custom head covers. During the summer of 2020, Cavaliere put the word out about his products through his golf network, and the sales surprised him. Thus, PinPoint Custom Studio was born and soon became Tremont Sporting Co., a company specializing in custom headcovers, hats, and other golf-related leather goods, including yardage books and dop kits.
With Q School canceled due to the pandemic, Cavaliere had time to grow the business a little bit while still contemplating whether he wanted to be a start-up CEO or a pro golf hopeful. He moved to Florida and lived with two roommates who were trying to walk the pro golf path. After “simulating” tour life by going from amateur event to amateur event in 2021, Cavaliere decided to take the entrepreneurial route and say goodbye to his pro golf aspirations. Tremont quickly grew from a small business that had Cavaliere, his mother, and a few high school friends up to their necks in sewing and embroidery to a blossoming company that now has deals with over 500 golf courses, including this week’s host.
As Cavaliere has grown Tremont Sporting Co., he has also re-entered the competitive golf ring, building a successful mid-am career that includes wins at the 2025 Azalea Invitational and the New York State Open. He also made it to the semifinals of last year’s U.S. Mid-Am Championship before losing to eventual winner Brandon Holtz and qualified for the 2023 U.S. Open at Los Angeles Country Club. Building a business has helped Cavaliere’s golf because he’s always thinking about the brainchild born in his Chestnut Hill dorm room six years ago, not about the need to go low. Whatever happens on the course, happens. Regardless if he makes a birdie or a bogey, he still has work to do.
“I think it’s just taken the need to play well all the time out of my head,” Cavaliere said. “It’s more of something I do because I really enjoy it. It’s changed my focus, which has obviously helped me play well, because I’m doing this because I want to, not because it’s a career or because I need to. That definitely has changed the frame. It’s less important than maybe it is to some other people. I’m on the course thinking about work stuff that is obviously important for my livelihood and for the company and my employees.”
The success of Tremont and Cavaliere’s budding mid-am career can be explained by the same thing if you ask the CEO.
“I’m mentally disturbed. I’m definitely sick in the head,” Cavaliere said with a laugh outside the Merion clubhouse.
That manifests itself as an obsessive need to fix things and find ways to get better. That’s something he can’t turn off. It has been key to his entrepreneurial success but also a plague on the golf course during times like Thursday afternoon’s Round of 16 match, when Cavaliere constantly found himself in tough spots in a 4&3 loss to Florida State’s Jack Whaley that ended his Merion run.
“I was saying to my caddie in one of my fits of anger on the course, ‘What’s the point? Why do I do this? Why do I come out here and stress myself out?’” Cavaliere said after his loss. “I do the same thing at work. My life is very stressful, but I prefer that. I prefer to try things and try to achieve something rather than not. It’s kind of a curse for sure, trying to be a perfectionist and high achiever. But I don’t know any different. All I think about is playing good golf and trying to build my business. Really, whatever I do, I feel like I need to be a perfectionist at it. It’s definitely a curse.”
Cavaliere knows he needs to find room to soak in big successes and let the stress wash away. But that’s a hard place for him to be. It’s antithetical to his wiring. He’s all gas toward his goals. But this week at Merion, during a dream run, he tried as best he could to see the bigger picture.
“I’m still trying to figure that out. I don’t do a good enough job of enjoying the moment and looking around and taking it in,” Cavaliere said. “I’ve really tried to focus on that the last few years. I think sometimes it’s so stressful, and you’re in the moment so many times with competitive golf and the business, that it’s hard to kind of take yourself out of it and see the good. But I don’t know. You just keep trying and keep doing things. I try not to be too introspective because I don’t even know if that’s a productive path. Just keep trying things, and one day you’ll wake up and be like, Wow, I made some great memories.”
Maybe one day Christian Cavaliere will be able to set the unattainable chase for perfection aside and relish what he’s built. It was there Thursday at Merion in a maroon hat with a mouse swinging a club and in the leather head covers adorning the clubs that marched him into the final 16 at Merion. Those are Tremont products, similar to those found in the Merion pro shop.
One day, Christian Cavaliere will wake up and be amazed by the success he has found on an “uncertain path.” But that’s not Thursday, not even after a hard-fought loss in the Round of 16 at the U.S. Amateur. He still has miles to go.
“The work starts right now. Ihave a lot of work to do after I get out of here,” Cavaliere said with a smile. “I got to go get to it.”
