One of Craig Wood’s first jobs stands out among his childhood memories, and not in a good way.
“I did not like manure day,” he said, referring to the task of cleaning out the barn on his family’s upstate farm. The fact that manure day was a particular day — meaning they only shoveled when the pile reached a tipping-point — made the task even more memorable.
Craig’s work history is eclectic and unlikely, from farming, fishing and landscaping with enormous rocks, to writing computer code and starting and running a successful high-tech company. His diverse experience turns out to be a great preparation for his latest job as a Shelter Island Town Assessor, a position to which he was appointed and then elected this past November.
When Craig was 15, his family, including his older sister and younger brother, moved to Hong Kong from their farm near the Finger Lakes when Craig’s father, who worked at I.B.M., was transferred. Craig recalls being stunned for the first six months, as he struggled to adjust to life in a megacity with completely new languages, foods and culture.
“I couldn’t adapt quickly,” he said, “but it opened my mind to the shocking realization that we are not alone. I saw that there was a whole world out there.”
Craig lived in Hong Kong in the late 1980s, until he graduated from high school and moved back to the United States for college. He still sees that three-year experience as one that shaped his worldview.
At Cornell University, Craig met Carrie Hopler, a fellow student in the landscape architecture program. At the homecoming football game, the pair never made it out of the parking lot, opting to sit out the game on a tailgate and talk. Cornell was defeated, but it was a good game for Craig and Carrie.
Carrie told Craig about her parents, Ray and Lorraine Hopler, and their home on Shelter Island, where her family had summered since 1958, and beginning in 1987, lived year-round.
Craig visited the Island for the first time when he and Carrie came for her parent’s 40th wedding anniversary celebration at St. Gabriel’s. Craig and Carrie were married at St. Gabriel’s in 1993.
At first, he had a business in Ithaca, New York building walls from locally-quarried stone. The work was physically taxing, and he realized he needed to change direction when his landlord told him, “If I had my life to do over, I’d use my brain and not my body.”
Building on an interest in the emerging field of computer programming, Craig began to create custom websites for individuals and small businesses, and went on to write large scale programs for companies needing specialized applications.
Finding satisfaction in this work was hit or miss. “After finishing an application, I asked when my program would go live and they said, ‘Oh we decided to scrap the entire project,’” he recalled. “I spent all this effort and time. I got paid, but my work was never used.”
After 10 years of working in pay-per-click advertising management for a business that did search engine-based marketing, Craig started his own company in 2007. Called Crowd Fusion, it was a content management system geared to large scale media outlets at the very time when social media was blowing up.
The company looked promising, got the attention of investors, and in 2012 Craig sold his interest and stepped off the corporate treadmill.
“I was missing my kids,” he said.
Craig and Carrie bought their own home on Shelter Island in 2001, and after renting it for many summers, decided to go full-time. Their daughter, Audrey, is now a 10th grader at the Shelter Island School and 11-year old Owen is in 6th grade at the Hayground School. “The most important thing in my life is taking this seven years I have while the kids are in my house,” said Craig. “I’m going to look back and say I want that moment.”
Soon after he was on the Island full-time, he was back at work, but now he’s devoting his talents to improving his new home. “I started going to Town Board meetings. I was outspoken about short-term rentals,” he said. He also didn’t like walking through the forest and seeing no undergrowth, and has been a voice in favor of culling the local deer herd.
He’s not satisfied with the retail environment on Shelter Island, finding it much too hard for a small business to make a go of it here. “I’m missing Fedi’s,” he said. “The site plan review we passed makes it even more difficult to start something new.”
Craig was attending a Town Board meeting when he learned that the town would have to find a new assessor. “Maps, math, computers, all the boxes checked as something I would be interested in,” he said.
He was appointed, and subsequently elected to fill out the remaining two-year term in the November voting.
Over the years, Carrie’s parents, Ray and Lorraine, had introduced Craig to all of their friends, including Toots Clark who, in his early 90s, took it upon himself to teach Craig the fine points of clamming and scalloping.
“After Ray passed away, Toots didn’t have any one to go fishing with,” Craig said.” I figured he called me because there was no one else to go out with him.”
Toot’s fishing lessons were hands-on and specific. “He’d edge the boat up to a rock and say, ‘When you feel the boat bump, cast on the other side of the rock.’ I love being on the water,”
Craig said. “But now that I’m assessor, it’s kind of eating into my scalloping.”
What do you always have with you? My wedding band. I’ll never forget my wedding at St. Gabriel’s.
Favorite place on Shelter Island? My garden.
Favorite place not on Shelter Island? The Thousand Islands.
Last time you were elated? Yesterday. Seeing my kids do something right makes me so happy.
What exasperates you? Working with someone who denies a fact or a proven truth.
Last time you were afraid? I was afraid on Friday that I would hold up the mailing of tax bills when the computer was not working.
Best day of the year on Shelter Island? The winter solstice — after that the days start getting longer.
Favorite movie? “The Princess Bride.”
Favorite food? Pork.
Most respected elected official? Tom Wheeler, former chairman of the FCC. He decided to go after the cable companies to enforce net neutrality even though he was an insider before he was appointed.