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Middlebury College Junior Balances Business and Books as Overeasy CEO

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Sophie Snowdon Hiland wearing a HoodE - CALEB KENNA
  • Caleb Kenna
  • Sophie Snowdon Hiland wearing a HoodE

In this crazy, confounding coronavirus economy, every CEO has felt the strain of keeping operations running, and Sophie Snowden Hiland is no different. Overeasy, the company she runs, makes a wearable called a HoodE — a puffy, faux-fur scarf that can stretch cobra-like over your hat or ski helmet to provide added warmth. Sales have been brisk, but the company lost out on a huge marketing opportunity at the FIS Alpine Ski World Cup at Killington Resort in November when fierce winds wiped out the first day's racing.

If you live by the weather...

Hiland had little time to dwell on the lost sales and exposure — the demands of her other job awaited. She's a junior at Middlebury College, and those 10-page American studies papers have to get written, even when she's also juggling calls from her production manager at Herkimer Industries in upstate New York.

"Not too many college kids have adults calling them about shipping deadlines," Hiland acknowledged.

A bifurcated life requires weighing "what deadlines are hard and which are bendy ... It's a constant cost-benefit analysis," she continued. "Which isn't to say that schoolwork ever comes last just because it doesn't have the financial benefits of business."

True that. But professors are more likely to excuse a late paper for "I had to meet my company's shipping deadlines" than for "My ferret ate the assignment."

Overeasy is headquartered in the Old Stone Mill Annex on the Middlebury campus, a five-minute walk from Hiland's Atwater Hall dorm. Just as Apple guru Steve Jobs had his garage, would-be startup entrepreneurs such as Hiland and company founder/owner Eva Shaw have space at the annex to work on business plans and seek guidance from the Vermont Center for Emerging Technologies.

Vermont is not awash in venture capital compared with states such as California and Massachusetts. But VCET is an incubator with benefits, including coaching, coworking and mentorship.

Skida — Swedish for "ski" — is a well-known VCET success story. The company was founded by Corinne Prevot, a Nordic racer at Burke Mountain Academy who developed stretchy ski hats for her teammates and later built a company while at Middlebury.

Another success story is SheFly, apparel designed by a group of Middlebury College women seeking urination parity with the flyboys. SheFly pants are a cunning zipper away from all-access.

Vermont's entrepreneurs have long capitalized on a reliable natural resource: cold weather. And snow. It was the latter that played a major role in Hiland's unlikely ascension to CEO-dom. That and a willingness to put herself in the path of good fortune.

Eva Shaw, of the celebrated Shaw family of Vermont ski racers, had a promising career ahead of her when injuries forced her off the slopes. With time on her hands and sewing skills acquired in a seventh-grade home economics class, the teenage Shaw came up with a stylish solution to the original brain freeze: a hybrid scarf/head cover that she named the HoodE. Shaw sewed — and sold — the first 200 HoodEs herself in 2016.

"I wanted something fuzzy and warm that also looked good to go skiing in," Shaw said in a 2019 interview on WCAX-TV. "I couldn't buy it, so I made it myself."

She got advice from members of her family, which boasts more Olympic athletes than some countries. Father Gale "Tiger" Shaw, a two-time Olympian who just completed an eight-year stint as head of U.S. Ski & Snowboard, urged his daughter to go for it. Uncle Andrew "Beach" Shaw, a marketing guru, introduced her to Vermont retailers. Her cousin Linley Shaw, Beach's daughter, supplied the company name as she and Eva rode the popular Over Easy gondola to Spruce Peak at Stowe Mountain Resort. Her logic, according to Beach: "It goes over your head easy, so why not call it that?"

Eva Shaw borrowed money, pitched benefactors while at Middlebury and contracted with Vermont Teddy Bear in Shelburne to sew raw HoodEs. But Shaw is no teddy bear when it comes to finances.

"I've never given away equity in the company, so I still own 100 percent," she told Seven Days. Perhaps that business sense is why she's now working at Goldman Sachs.

One thing Shaw couldn't borrow or buy, however, was extra time to run Overeasy. By the summer of 2020, she was working remotely in an investment banking internship and needed someone to help out with her enterprise. Enter Hiland.

The then-sophomore approached Shaw at a party as fall semester began, praising the HoodE and inquiring about working for her. After a couple of get-to-know-you bike rides, the two women began discussing a working relationship.

In September 2020, Shaw hired Hiland conditionally to handle social media and marketing. "Two weeks after that, Eva said, 'OK, how about operations, you ready for that?'" Hiland recounted. Next came wholesale account management, then finance.

"Eva was sort of showing me the ropes," Hiland said. "And by early November, she said, 'OK, so I've got a big job to go off to ... How about I have you take it over?'"

Hiland wasn't shocked; she expected the on-the-job training to lead somewhere. Confident in her responsibilities and expectations with the company, and not too worried about ... uh ... college, she took over the day-to-day operations of Overeasy in January 2021. Champagne was in order — she'd become drink-legal four months earlier.

"Sophie did such a good job as an intern, so I asked her to run the company, and she was super excited," Shaw said. "I'm there as an adviser. We reach out on the weekends, but she is driving the company."

And Overeasy is picking up speed. Hiland estimates that 20,000 HoodEs have sold at $65 a pop, producing total revenue in "six figures." The product is now sold online and in more than 30 local and national retail outlets.

Overeasy has been an easy sell at mysa in Shelburne, a boutique specializing in local craft and luxury goods, almost all produced by women or women-run companies.

"People come to us looking for things that are soft and cozy," mysa co-owner Jen Whalen said. "And I think, with COVID, people want to be outside more. Everyone's feeling very cooped up. So to be able to have something that's fun and warm is not a bad thing."

Whalen said sales of the HoodE were "exploding," adding that she'd ordered 60 for 2022 — twice as many as last year.

Like Shaw, Hiland has Vermont roots. Her father, Chris, went to Middlebury and met her mother while both were graduate students at the Bread Loaf School of English. Her aunt Becky Dayton owns the Vermont Book Shop in Middlebury; her grandfather is a management consultant in Cornwall.

Hiland's twin brother, Owen, was the one with an early entrepreneurial bent, Chris said. As a boy, he would collect Lego sets, exhaust their permutations, and then repackage and sell them. He used the proceeds to purchase a guitar. By contrast, Sophie was a relationship builder. "Her ability as a kid to connect with adults was uncanny," Chris said.

Before taking on Overeasy, Hiland interned for Lisa Lynn, whose company Addison Press publishes Vermont Sports and VT Ski + Ride. Lynn said Hiland demonstrated maturity and confidence that belied her youth.

"She loves to learn," Lynn said. "She not only takes on projects, but she looks beyond them and is always sort of thinking about what the next step should be."

At Lynn's urging, Hiland joined the Vermont Outdoor Business Alliance, a business association of mostly big-name recreation companies in the state. Lynn said: "I told Bruce Hiland — Sophie's grandfather — that whatever she's doing, I'd invest in it."

Still, what prepares you to be a CEO at age 21? Hiland freely admitted that there are days when she'd rather have to worry only about a term paper assignment in her inbox.

"We're by no means past the point of being a startup or a small business," she said. Recently, while working on a spreadsheet, she came close to tears "because I couldn't get all the cells to add up right.

"We've had a lot of growth these past couple of years," Hiland added. "But when it comes down to it, I'm doing a lot of googling."

The thrill of receiving compliments when she's wearing a HoodE and being asked where she got it is a great psychic reward, though. Not to mention seeing her products in TikTok videos.

Hiland has two more semesters before graduation, which raises the question of how long she'll stick with the company.

"I think we're doing one step at a time, with a lot of dreaming and goal setting," she said of her discussions with Shaw about the future. "At this point, I cannot wrap my mind around not being involved with Overeasy.

"It's been such an incredible experience and exciting thing to grow and be a part of," Hiland continued. "I'm immensely grateful to Eva for seeing some promise in a random kid who offered her help one afternoon."

The original print version of this article was headlined "Overeasy Does It"