Before Flynn Ryan, the owner of the Millerton Driving Range, moved from Arizona to Lakeville as a high school freshman in early 2020, he had only a passing interest in golf. He was a football guy in Arizona, but when he found out practice for the Housatonic Valley Regional High School athletes was an hour away, he joined the golf team.
A couple of years later, while working on a school assignment to improve the community, Ryan noticed the old driving range. The weeds and grass were up to his eyes. With no connections and no experience, he walked into Talk of the Towne Deli next door, asked for the landowner’s number and called him right there from the parking lot.
What he got was one heck of a deal.
The owner, who didn’t like seeing the range fall into disrepair, was thrilled that a local kid wanted to revitalize the business. He gave Flynn the first year rent-free, use of all his equipment, a little knowhow and, just like that, the high school junior became a business owner.
That’s where it stopped being easy.
At first, Flynn wasn’t very good at golf. But his personality compels him to dive deep into his interests and make himself an expert. It’s the same drive that pushed him to learn how to trade stocks, futures and cryptocurrency as a teen, spending years failing before turning a profit. That first year on the golf team, he earned the honor of most improved.
The Driving Range is located at 138 Route 44 in Millerton.D.H. Callahan
If you’ve ever been to the range, you know how wonderfully casual it is. It’s the kind of place where nobody cares how good you are. Where people intimidated by the sport can pick up a club and have a great time right next to a seasoned pro. Classic rock pumps through the speakers. There are chairs and a coffee table for people who bring their own picnics and parties. A ragtag collection of clubs invites you to try them out for size. The balls come out of a vending machine. The place is the definition of laid-back.
Flynn’s job seems like the easiest in the world. It is not.
During the warmer months, Flynn gets to the range at 6 a.m., picking up balls in his golf cart. Of course, the back field, where the long balls end up, has to be picked up by hand, one ball at a time. On busy days, that can mean as many as 6,000 balls. Once a week, he mows the whole thing.
It might not sound like all that much, but consider that for most of the year Flynn is working toward a business degree at Old Dominion University in Virginia. When he’s away, his family picks up the slack. His mother, Jennifer, chips balls into the center of the field with a pitching wedge before gathering them up, and his father, Michael, takes care of the mowing. Flynn keeps offering to hire workers, but his parents seem to love working for their entrepreneurial son.
While there’s nothing solid on the books, Flynn dreams of expanding his business with more ranges in the future, as well as hosting events on the Millerton grounds. Until then, he’ll keep the Zeppelin pumping, the ball machine loaded and the grass nicely shorn.
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