Shelter Island profile: Jonathan Russo, a life afloat

In Genesis when new things were created, they got named. Jonathan Russo, advertising executive, talent developer, entrepreneur, sailor and long-time Shelter Island resident is really good at naming things.

For example, at the Shingle-style home in Shelter Island Heights he shares with his wife Deborah Grayson, Jonathan recounted, “I woke up one morning in January, and saw two sleeping foxes in the snow, spooning together. After that we named the house “Sleeping Foxes.”

Born in Brooklyn to Jack and Miriam Russo, Jonathan grew up in Roslyn with his brother, Seth, and sister, Emily. In 1957, his father brought five-year-old Jonathan to Shelter Island for a boys’ weekend at the Chequit that included a motorboat outing in Dering Harbor. It would take Jonathan a couple of decades to return, but when he did, it was boating that lured him.

In his 30s, with little sailing experience, Jonathan decided, “sailing would be my passion in life.” He bought a boat and christened it Wu wei for the Taoist principle that translates, “Go with the wind and go with the flow.” He is now on his fourth boat, Sachem.

Jonathan graduated from Roslyn High School, but just barely. From the age of six, he was plagued with what he termed “fairly severe learning disabilities,” including attention deficit disorder, for which he took medication. Numbers were not his forte, but words and reading books were his retreat.

While many of his high school friends went off to Ivy League schools, Jonathan enrolled at Suffolk University in Boston, driving a cab at night to help support himself. He also learned out of necessity to cook and feed himself, since his college had no dorms or dining hall, and credits this experience with initiating what would be a life-long fascination with meal preparation, wine and farmers markets.

“In 1969, the markets in Boston were frequented by Portuguese and Italian people, “who would not eat crappy processed food,” Jonathan said. “It was for immigrants, but I was down there every week buying food for me and my friends.”

After graduating in 1972, Jonathan came back to New York. “The call of business was very powerful,” he said. “My father was a businessman.”

From 1973 to 1978 Jonathan was in the thick of the New York advertising world just past the height of its power and licentiousness, but close enough for the 23-year-old to experience the three-martini lunch more than once. An account executive at Foote Cone and Belding, he moved to legendary BBDO and finally to the giant InterPublic firm. “I recognize Mad Men very closely,” he said.

Itching to get away from working conditions he saw as too corporate, Jonathan left advertising in 1978 to represent the brothers Albert and David Maysles, documentary filmmakers whose films, “Grey Gardens” and “Gimme Shelter” had brought them acclaim. Six months later, the business relationship ended in total failure.

“I had no prospects. I was backed into a corner,” he said. “I couldn’t believe that this was happening to me, but it was happening.”

Jonathan said the experience changed his approach to work and life. “I never assume I can’t have a setback,” he said. “I was taught the bitter lesson that sometimes things just don’t work out and you can be punished for that, and I was.”

He landed at William Morris, an agency he called, “the heartbeat of show business,” and where he worked until 1983, leaving to start Artists Agency, Inc. with a partner.

At Artists Agency, Jonathan said, they purposefully concentrated on soap operas and reality TV shows such as “Inside Edition,” “Current Affair,” “Hard Copy” and “Judge Judy” rather than scripted television, which was mainly produced in Los Angeles as a strategy for keeping the business in New York. As soap operas faded from television, the agency shifted to developing programming for the Food Network including Sandra Lee, Paula Dean and “The Chew” with Mario Batali.

“We are still at it,” Jonathan said, although “it’s not appropriate for me to sell television shows anymore because everybody buying them is 28. They say, ‘Grandpa is here to sell something?’”

Jonathan’s learning disabilities affected him in an obvious way when he was a kid in school. More subtle was the effect on the kind of work he chose to do as an adult. “I’m not in a fact-based industry,” he said. “I was able to use my intelligence and gift of people skills, insight into human nature and business acumen in a way that is entrepreneurial rather than structured because I couldn’t compete with people with real defined skill sets. I left the factual, brilliant part of the world to my wife.”

Deborah Grayson and Jonathan met in the early 1980s when Deborah was between jobs, working at a company Jonathan was doing business with.

“I couldn’t believe she was the new receptionist, she was only there for a week. We fell in lust,” he said. “Later it turned to love.” They have been married for 26 years.

Deborah is a hospice nutritionist for Visiting Nurse Service in New York and is an active supporter of East End Hospice through fundraising and writing about EEH services to raise awareness of the good work it does.

Jonathan and Deborah started to come to Shelter Island regularly around the time he was starting his business. “We were so poor, I had to drive to my parents’ house to sleep at night in Roslyn,” he remembered. “The next year I did a little better and we could afford to stay in Greenport for $29 a night at the Greenporter, and the next year we did a little better and stayed at the Ram’s Head.”

Next, they upgraded to a one-bedroom cottage on Fresh Pond, where they stayed five months of the year for 14 years, until they built the house in the Heights in 2000.

“I came here to go sailing, and I’m on the water every single minute that I can,” he said.

At Coecles Harbor for almost 20 years and the Shelter Island Yacht Club for the past 16, he credits Coecles Harbor and Steve Corkery with turning him into a sailor. “They taught me everything I know,” he said.
Jonathan calls Coecles Harbor “a fair trade marina.”

To him, that means fair pay for the skilled workers and craftsmen that build, repair and preserve the boats. He points out that the mechanics, carpenters and electricians all have pensions and healthcare.

We’ve all heard of community involvement, also known as giving back. The ad man in Jonathan shows itself when he labeled the give-and-take between him and Shelter Island, “The immediacy of the community.”

For example, Jonathan wrote a boating column called “The Float” for the Reporter for many years. When Amanda Clark became an Olympic champion, he asked to interview her and “the next thing I knew, I was interviewing her and working on her fundraiser.”

Immediacy of the community is also when, in the days before 1991’s Hurricane Bob, Jonathan and Deborah worked to protect their boat, as well as the boats of others, at the Coecles Harbor Marina, volunteering to help in any way they could. It was all hands on deck as the marina prepared for the storm and Deborah and Jonathan were with them, tying lines and getting supplies.

Jonathan described how he and Deborah, with four other families in 2002, helped to preserve Hampshire Farms as a rural horse farm by purchasing the property in a deal that was part of the Open Space initiative with Peconic Land Trust.

In March, Jonathan funded a new benefit called “Honoring the Hands” for Hudson River Healthcare, a network of healthcare service providers that works with the poor and uninsured — people who in Suffolk County are very likely to be farm workers, maids and child care workers. The very first event raised about $70,000 to support the health of these workers.

“I wasn’t particularly religious when I came here, but I am religious now. I’ve become an animist,” he said, referring to the belief that was characteristic of many Native American cultures, believing there are spirits in nature. “In October I watch the sunset while I’m swimming, or I sail around the Island and I feel like I’ve had an epiphany,” he said.

“I can’t believe how lucky I am that in my early 60s , I have a dozen friends I’ve made since I’ve lived here, adult friendships,” he said. “There are so many people here who are interesting and talented. I am so blessed.”