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A Trucker's Hat and Many More

Tue, 10/17/2023 - 09:38
Ryan Sherman was captured in his native habitat on the grounds of the Art Center at Duck Creek in Springs.
Jennifer Landes

There is growing unease as the families who have provided generations of productive citizens of the South Fork, who have contributed to its support, safety, services, and creative output, are dying out or moving away. For the younger generations who remain, or who came back after sojourns elsewhere, their resolve to stay and continue that tradition seems all the more unyielding.

Consider Ryan Sherman part of this trend. A Springs native who has spent time in New Hampshire, Colorado, Hawaii, Europe, and California, he has returned to his parents' home, not in defeat but with a firm commitment to the area and his generation of Bonackers and other locals who are just as resilient and determined.

"I feel like this town has not been protected for the last 10 years and it's killing me." While he understands that the area needs the people and businesses that "come from away" in summer and on weekends, "I'm seeing my friends and their businesses struggle to pay this crazy amount in rent. I'm seeing them have to eat $5,000 mortgages to live in a 1,000-square-foot dump ranch. It's asinine. And the argument from the older generation of, 'If you want to stay in paradise, you have to make it work.' Okay, buddy. It was a lot easier to make it work when you were my age."

In a lived-in T-shirt and shorts, his long red hair kept away from his face with a backward trucker hat, Mr. Sherman apologized for his attire, offering some of the forthrightness that marks his conversation. "I'm not going to dress up fancy. I've never done that in my life, why would I do it now?" Since the meeting place was a picnic table at Duck Creek in Springs, he blended into the surroundings as seamlessly as generations of farmers, tradesmen, and artists have before him. 

He is a man of many hats -- photographer, podcaster, media consultant, musician -- and has worked in sales, marketing, operations, and the food service industry. These days, he switches from vocation to avocation frequently, doing whatever is called for to succeed as a local presence. This year, with Zakk Waleko, he formed Three Mile Media, an umbrella company of his various initiatives, which also offers branding, identity, visuals, broadcasting, and digital advertising services. They have worked with Hampton Water, the Clubhouse, 3 Moms Organics, and other companies, bands, and venues with a focus on creativity.

That focus came naturally to him growing up in Springs. "I had a teacher early on who encouraged creative interest, Irene Tully. She was a big influence when I was younger." She also made sure Mr. Sherman, who has Tourette's syndrome, wasn't made fun of by his classmates.

As his classmates and peers now try to find their way as entrepreneurs and artists here, Mr. Sherman wants to help. His "Highly Educated" podcast showcases them and their ventures, like Ruby Honerkamp's Encore canned cocktails, Travis Beckmann's journey from professional surfer to Montauk real estate broker, and Brittany Rivkind's Thriftknd retail consignment and thrift store in Sag Harbor. The pod also features local teachers with side gigs, athletes, skaters, and creative types living on the East End or from it.

He said he wants the local kid who is at home thinking, "I don't know what I'm doing. I feel lost. Nothing here is for me," to listen as he interviews someone who "started from here and is doing something passionate. . . . I want them to hear that . . . and be inspired by what we're creating."

Mr. Sherman cross-pollinates the podcast with events that include clients' brands, social media, websites, and other means of promotion. He said he wants to do everything he can to help his peers succeed, including showing them how they can have their own podcast (he learned from YouTube videos) and offering attractive rates for those with young businesses. 

"I want them to feel comfortable reaching out to me first, before some firm from the city, up the Island, or online," he said. A number of overseas "tech farms pump out work and it's cheap, but that's not supporting the community. That's not supporting the art and creative spirit of who we are. And if you're from this town, it's built within you, whether you want it to be or not. Art is around you every day."

"Ditch at Dusk" captures some of the natural beauty of the area. Ryan Sherman

Mostly self-taught as a photographer, Mr. Sherman did take a class in high school to learn the mechanics. But early in his adult years, he said, he was overwhelmed by the natural beauty of places he lived and visited, including here. He now sells his prints of local scenes and subjects online at Bonac Print Shop, and still takes photos on assignment for weddings, performances, and events for private or promotional use. 

He lived on the South Fork after he received his degree in history, but a dream to make it in the film or music industry sent him to Los Angeles. It was 2014 and he was working at Peloton in East Hampton. He had become friendly with John Foley, the founder and former chief executive officer of the company. ("I had started at the company when they had under $1 million in funding and left when they had $300 million.") 

When he told Mr. Foley he wanted to move to L.A., he lined up a job for him to be a West Coast representative and gave him a three months unpaid leave of absence. Mr. Sherman went to Europe. "He set me up to be very comfortable out there and not stressing out about how much money I was spending" while he was traveling. "That gave me the freedom to go out and take all these incredible photos and ignite my passion for photography even further," he recalled. 

In L.A. he lived in Venice Beach and also stayed in Santa Barbara, rooming with surfers. He ended up doing surf photography and working long hours for Peloton. He said the five years he spent in California "got me out of the small scope of the Springs-East Hampton mentality. It's what opened my mind to explore different avenues and different things. When you're from here, it's extremely tough to break out of the box, especially if you have some kind of family business. My dad's a builder, and that's what he probably wished I did."

Instead, Mr. Sherman's variety of activities this year included playing drums at Westlake Fish House with the band No Sailor, serving on the board of the Offshore Art and Film Festival (which took place in Montauk in September and had fashion shows during the summer), producing two podcasts -- "Highly Educated" and "Good Lies Golf" ("lifestyle related to golf") -- and the occasional photography assignment, all while building his business. On the weekend of Nov. 11, he'll have a exhibition of 15-20 artists at Ashawagh Hall, an effort he started last year. This year it will benefit the recovery fund of Jeff Yusko, an East Hampton father who got hit by a car near Townline BBQ. 

He said everyone he has spoken with since he started these ventures has been "nothing but positive, receptive. . . . It's almost like they're getting passionate about what I'm doing too. That to me was so cool that people in my community were understanding and respected what I was doing just as an artist and a creative. I figure if people keep seeing me put the energy in and being consistent, not letting up, not taking my foot off the pedal, that's what's going to shine through everything."

This article has been altered from its original and print version to emphasize that Mr. Sherman's leave from his position at Peloton was unpaid. 

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