Ryan Sherman’s first job was picking up cigarette butts outside the restaurant where his mom worked. He was 12. A year later he started changing kegs and polishing silverware. “I was a hustler,” he said. “I always worked hard.”
So did the people around him. While his mother managed restaurants, his father built single-family homes. Most of his friends had two working parents, and most of his friends worked — summers, after school, whatever they could squeeze in. “Everybody who lives in this town is hardworking,” he said. “You have to be.”
But for Mr. Sherman and many like him who grew up in East Hampton, N.Y., hard work is rarely enough to make it in their hometown.
“Everybody’s getting eaten alive by that same monster that is the housing beast,” he said. “This is the struggle for everyone trying to make it out here. I don’t care if you’re in construction, landscaping, retail — whatever it is, you’re not making enough money to live here.”
Mr. Sherman moved back in 2019. After living on the West Coast and traveling throughout Europe, he wanted to reconnect with the place that had shaped him: “I missed home and wanted to experience it again.”
But it was already a different place. Sure, there had been changes throughout his childhood: 9/11 brought many families from New York City, and a few years later the reality television boom popularized the area in a way that Mr. Sherman hadn’t ever seen. Celebrities like the Kardashians and cast member from Bravo’s “Real Housewives” franchise started paying visits, playing up the seasonal glamour of the Hamptons, he said. “That’s when the population really started to shift,” he said. “Full-time, year-rounders realized they could sell their homes for a lot of money and get out of here. And now, here’s a new influx of people who are not from the community.”
But nothing compared to the changes that came with the Covid pandemic. “It was like a giant bomb went off and the housing market erupted out here,” Mr. Sherman said.
By the end of 2023, the average home price in East Hampton was $2.5 million, more than a 40 percent increase from the previous year. “I have a father who worked hard for more than 40 straight years, bagging nails,” he said. “But my generation can’t afford the same path that our parents could afford.”
$1,200 | East Hampton, N.Y.
Ryan Sherman, 32
Occupation: Media specialist and podcast host of “Highly Educated”
On self-direction: Mr. Sherman didn’t have any experience in podcasting when he jumped in. “I was doing this all from scratch — square one,” he said. His informal education involved more YouTube videos than he can remember, and he’s had a learning curve over time. “It’s been a long journey from the first episode,” he said. “I do a good job at editing and I take great pride in that.”
On making money: While most of his income comes from consulting various businesses on media strategies, Mr. Sherman has only made modest income from the podcast so far — but that’s changing. “This is the first year my company is going to produce a revenue and I can pay myself a salary,” he said. “It feels good to get there.”
The rental market in the Hamptons doesn’t provide viable options either. Many property owners opt to rent to visitors for warm weather premium rates, rather than accept the lower returns of an annual lease to a full-time resident.
The scant rental housing that is available is often out of sync with wages. “A one-bedroom rental is at least $2,500,” Mr. Sherman said. “People easily pay 50 percent of their income on rent out here.”
The most realistic option for many is paying rent to friends or family who have room to spare. A 2018 survey found that 41 percent of young adults between the ages of 18 and 34on greater Long Island lived with their parents or other relatives. “That’s probably doubled by now,” Mr. Sherman said.
He fits squarely in this statistical space, living in his family home with his parents. It allows him to pay a more manageable rent which, over time, has fluctuated between $1,000 and $1,200. “I used to feel awkward thinking, ‘Oh, I’m almost 33-years-old and I’m paying rent to my parents,’” he said. “But I came to realize it’s very common.”
Like many full-time residents, Mr. Sherman makes a living with a few different streams of income. “Most people I know have two or three jobs,” he said.
He’s always been drawn to artistic endeavors and makes most of his income with photography, videography and media consulting jobs. He originally studied history, earning a Bachelor of Arts degree from Hunter College, driven by an innate curiosity — not just about the past but also about different perspectives in the world today. So, in 2021, he started “Highly Educated,” a podcast.
“The whole shtick of the show is that every guest I bring on is going to make me more educated — and all of my listeners,” he said. “I want to be like a sponge. I’ve always been that way.”
His brings on a range of guests, each of whom offers a perspective that reveals the Hamptons — and, in some ways, the world at large — in a new way. He’s interviewed artists and police officers, DJs and environmentalists. “All of the first guests I brought on were navigating the waters of trying to make a living here,” he said.
One episode features Eiji Shiga, a barman telling stories from decades past; another is a conversation with Freddie Smith, a real estate broker who tries to make sense of the housing market. The podcast is all about processing how the Hamptons have changed and how they might continue to change.
“When I see a good family that’s done everything right, trying to make it work, it hurts me,” Mr. Sherman said. “I feel bad for the guys who are working all day, trying to save up for a house they can’t afford, and they have to go home and take care of their kids. That’s when it hurts me as a Long Islander. I think, damn, our parents didn’t have to face that.”
Many of the people he grew up with, or he’s interviewed, are the kind of workers who, despite the long hours, can’t afford to engage the service industries (in which they are sometimes employed). So, weekends are defined by chores that look a lot like the work that’s done all week: laundry, scrubbing, weeds.
“Maybe in the summer, wow, you get two beach days,” Mr. Sherman said. “And all we talk about is how beautiful it is to live here and how fortunate we are. But we don’t have any time to enjoy, to embrace the place where we live. Every day is about pulling yourself up by the bootstraps.”
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