Plan A is the goal. Always.
But when Plan A fails to come to fruition, the opportunity to pivot and pursue Plan B and make that a rousing success is far more than a consolation prize; it’s a testament to your embrace of a passion. Especially when Plan B is in the same family of Plan A.
Consider that a segue into a story on Christian Cavaliere, a young man whose thirst for competitive golf has been quenched on numerous occasions – at the recent U.S. Amateur and last summer’s U.S. Mid-Amateur – but whose desire to be engrained in the golf world with creative juices and intrepid thinking are to be admired.
More later on his recent success at Merion and last summer at Sand Valley, but the story of this lad from Katonah, N.Y., weaves from Westchester County to Montauk on the edge of Long Island to a wonderful four-year stay at Boston College and is enchanting and so rich in golf flavor.
“His mind was always working,” said Drew Kayser the men’s and women’s golf coach at Boston College. “On the golf course he was always so analytical, just the way he thinks his way around the golf course. But he was in the Carroll School of Management (at Boston College) which is numbers and science oriented so I’m not surprised by his business success.”
That success is the Tremont Sporting Co., which Cavaliere founded in 2022, two years after graduating from BC. With an emphasis on leather goods that primarily began with head covers but has grown to include an array of other accessories – pouches, toiletry bags, pennants, ball markers etc. – the company still sells a lot of hats, which is only fitting.
That’s because hats sort of got Cavaliere going.
“I learned a lot from a summer job with Greyson (a high-end golf apparel company), which was just getting off the ground,” said the Class of ’20 grad. “I started making custom hats in my dorm room, a small side business.”
When in the spring of 2020 his college golf got cancelled by the COVID pandemic, Cavaliere went home to Katonah to face this unsure world.
“No school, no golf.”
But with such a creative mind and a relentless love of golf, Cavaliere got busy making head covers. First, it was on a whim. Then, “I got so many requests,” laughed Cavaliere. “It was pretty hilarious, the organic growth steamrolled.”
Like every other college athlete back then, Cavaliere was granted a fifth year of eligibility and he toyed with the idea of transferring to Notre Dame where he could play golf and pursue a graduate degree.
“Christian was really bright and he told me he just didn’t want to go to school anymore,” said Keyser.
He just wasn’t a hundred percent sure what he wanted to do, except that it would involve golf. “It felt like I was in purgatory,” said Cavaliere of that 2020 period. “Should I turn pro? Just work? I just didn’t know.”
When he moved to Florida to be around a lot of his friends, Cavaliere was still mapping out a plan to turn pro in 2022. He continued to fulfill the many requests he had for his leather head covers and the incredible creative juices that leaned on him for new club logos.
Along the way, Cavaliere reached out to another former BC golf teammate and Patrick Hallisey (Class of ’18) didn’t need much convincing. He had seen his friend’s work with the hats out of a dorm room, with his videography, with the sketchbook he always had with him.
“So creative. I just said, ‘Hey, how can I help you?’ ”
The first thing Cavaliere and Hallisey agree on was a new name. Pin Point Custom studio was out; Tremont Sporting Co. was in.
“We liked it. It was an ode to Boston,” said Hallisey and Cavaliere clearly proves that he’s deeper into the history of Boston than most of us. “It was a city of three hills, Trimountain (often spelled Trimountaine),” said Cavaliere and “three of us from BC were involved.”
That third BC friend didn’t pursue the Tremont Sporting Co. journey and while Hallisey is still a co-founder of the company he acknowledges that “Christian is the one who got it all going.”
There are clean and vibrant information platforms for Cavaliere’s products – tremontsportingco.com on the web; @tremontsportingco on Instagram – and for a deeper look into the engaging personality that is Christian Cavaliere there is a gentleman named Mac Webster. He, too, played golf at Boston College (Class of ’22) and he is the creative force behind the Milky Golf Instagram page.
(Imagine coach Kayer at a tournament being asked about “Milky Golf and this kid selling hats” and nodding his head while laughing. “Yeah, they’re both on my team. They love this game.”
Anyway, one of the social media postings made by Webster was a tribute to his former BC teammate. You need to scroll down to the second tweet where Webster talks about “The End Club.” It’s lovely. Pretty cool, too – https://x.com/_macwebster – especially if you know of, or have been to, Montauk, and you get a true sense of Cavaliere’s inner soul and how it connects to golf.
They were teammates at Boston College; now they're business partners at Tremont Sporting Co.
Roll all of this together, then toss in the fact that Tremont Sporting Co. has doubled its sales year after year and is 97 percent wholesale to country clubs and golf clubs, with many of them in the Top 100. Next, consider how the 28-year-old Christian Cavaliere has been on a roll the last two years in the highest level of amateur golf.
Last summer he defeated the heralded Stewart Hagestad in the Round of 16 before losing in the semifinals of the U.S. Mid-Amateur Championship at Sand Valley.
Just a few weeks ago at vaunted Merion Golf Club, Cavaliere shot 69-72 to make it into match play at the U.S. Amateur. He recorded a pair of 3-and-2 wins before being ousted in the Round of 16, but it took the eventual winner, Jack Whaley, to knock him out.
“Such a great property, an amazing place,” said Christian about Merion.
When you factor in the 2022 U.S. Open at Los Angeles CC’s North Course, which Cavaliere qualified for, he’s now played in 13 USGA championships, including six U.S Ams, though Merion was his first match play experience.
All of it makes Hallisey gush about his friend and business partner. “He’s been able to find that space where he can totally pursue both goals simultaneously,” said Hallisey.
“There’s sort of a flywheel effect here. The more he plays high-ed amateur golf, the more connections he’ll make in the golf world and the more business he can generate.”
None of which surprises Kayser, who is quick to remind that at the time COVID hit, Cavaliere was coming off a fall schedule in which he had a stroke average of 69.5 and “there was no doubt in my mind he was going to earn a spot in the NCAA Championship.”
Cavaliere still owns some BC scoring marks and it’s in the record books how he won three times, including the Clemson Invitational.
Pretty cool, all of this, and Cavaliere is humbled by every positive step he’s made since discovering a love of this game.
“I’m overwhelmed by all of it,” he said. “I’m trying to take it all in. This mid-am world is amazing, so great, and I pinch myself all the time.”
