Cassette Composer. Perennial Prepster. Tennis Trickster. Kick back for a morning on the porch with Boast president, John Dowling.

Like its owner, John Dowling’s home on quiet Columbia Place in Brooklyn Heights is in a sort of calculated disarray. Painter’s tape is stuck to light fixtures, a pair of ladders sits propped against the living room wall, the final stages of renovation are in full swing. “I was living with just a card table and my cats for two years,” he laughs, a collegiate grin on his face, his sandy hair a mess. “It was time to get my act together.”

There isn’t much deviation between John and the quirky company he bought and runs—Boast. After seven years, Boast has become John. And John was kind of always Boast. He played tennis. He attended prestigious boarding schools. His life had all the stampings of East Coast WASPdom—Groton, Harvard—but enough irreverent spikes—NYU Tisch Film and a stint in Hollywood as an editor and producer—qualify him to handle the reins of Boast’s particular breed of off-axis-prep. John first discovered Boast at tennis camp at age 11. 25 years later, he charmed Boast founder Bill St. John into selling the rights to it and now, as we said, he carries the torch.

“I’m not exactly Mr. Rogers,” John says. “I kind of wake up when I wake up, toss on a dirty pair of jeans and walk across the street for coffee.” He pops his foot in and out of his flip-flop, feeds his meowing cats, Scout and Fool. The cats came East with John when he moved back to New York from Los Angeles in 2012.

Across the street, the dual storefront of Iris Café/Willowtown Store #7 is bustling even at the early hour. At the counter, John orders coffee, a biscuit with butter and honey, and holds up a New York Times as if to say ‘This too’. “Everyone in the neighborhood comes through [here] on a given day,” he says. “There’s no WiFi, no laptops, I have a running tab with the brothers who own it. It’s that kind of spot.”

“I kind of wake up when I wake up, toss on a dirty pair of jeans and walk across the street for coffee.”

John eats his biscuit on his front porch with the paper. Then he sits in the sunlight of the back patio and clips his fingernails. “If you think this is disgusting,” he says and shrugs, “I once tried to clip my nails in the back of an Uber.”

In an upstairs office, John shuffles to the desk to attend to emails. On his left: a signed copy of Bret Easton Ellis’s Rules of Attraction. On his right: a framed photograph of his grandfather at a summer home in Maine—sporting white bucks and a fisherman’s sweater. “I just love how effortless he looks,” John grins and cups his bowl of Peanut Butter Captain Crunch. He showers, and slips into his favorite threadbare Boast polo shirt and a pair of Stan Smith sneakers. A canvas tote bag sags with the girth of tennis balls, a laptop computer and extra shoes. “I like to exercise at night,” he says. “I’m meeting a buddy to hit around in the Park after work.”

Before walking to the garage where his station wagon is kept, John makes two final stops—first to the refrigerator for a bottle of orange Gatorade, then to a tucked away compartment to select from his massive collection of cassette tapes. “I like to pick something to listen to each day. I have mixes, bootlegs, things that can’t be recreated,” he says. “I’ve lost pretty much everything over the years—fancy watches, things I’m supposed to care about—but I’ve managed to keep these cassettes. I don’t know, some things just stick with you.” He smiles and slings the tennis bag over his shoulder and bounces down the front steps.

“I like to pick something to listen to each day. I have mixes, bootlegs, things that can’t be recreated…”