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 He used to get a few requests for such work years ago, but the num- ber grew quickly and profoundly after he got into the sock business. “I’ve been in business for 17 years, nine full-time, but I guess, for
whatever reason, socks are more provocative or sexy or interesting,” he said with a laugh and a shrug of his shoulders, adding that his calendar is getting even busier as photo assignments come back and requests to partner on initiatives involving his socks arrive with greater frequency.
Overall, this is an intriguing success story already — on many levels. Equally intriguing is where all this could go, especially Upscale Socks. At the moment, it is mostly a regional phenomenon, although the socks are sold online and in outlets in other parts of the country. But Underwood is looking to go next level.
“I’m hoping to attend some conventions and trade shows so I can get in more stores throughout other parts of the country,” he said. “I’ve done pretty well organically; a number of stores have reached out to me — they discover me on social media and they reach out because they’re interested — but I know that, if I want to expand into larger markets and places I’ve never heard of, I
need to get in more stores and make more
For this issue, BusinessWest talked at length with Underwood — about socks, pho- tography, entrepreneurship, mentorship, that full calendar of his, and how it’s all become an adventure unto itself.
Dream Weaver
By now, most people know the story; Underwood has told it many, many times.
Upscale Socks is a dream come true. Quite literally.
Many have a
purpose behind them, and others are more artistic or wacky or funky, as some people call them.
  He said it was probably seven years ago
that he had a dream that he started a company making and selling socks. He said he usually doesn’t remember his dreams, and he didn’t recall all of this one. Just the main theme.
“It was really vague,” he recalled. “I just remember being the owner of this business and selling socks; the dream wasn’t to have a store, but just to have them available in stores and online as well. And that was it.”
He ran the concept by the friend who auditioned with him for Wheel of Fortune, and they agreed it was an idea with merit and poten- tial. But there was a lot of learning to do and hurdles to clear.
“I knew nothing about retail,” he acknowledged. “I didn’t do any- thing for maybe a year but toy with the idea and do some light search- ing on social media. Nothing really materialized.”
Eventually, he connected with Paul Silva, then-director of Valley Venture Mentors (VVM), who steered him to SPARK (now EforAll) in Holyoke. Mentors at that agency helped take the concept from the fuzzy dream stage to reality, he told BusinessWest, by compelling him to ask the hard questions, conduct customer discovery, and work to determine if there was a real market for the product.
“They held me accountable to look for manufacturing, so I researched probably 30 around the world,” he recalled. “They gave me more insight on numbers and data to work with; it was very helpful.”
The venture started slowly, but it has taken off. The socks, now seen on the feet of a number of area business and civic leaders, have become a fashion statement — but, as noted earlier, perhaps the real key to success has been that these socks often have a purpose well beyond comfort and fashion.
“Many have a purpose behind them, and others are more artistic or wacky or funky, as some people call them,” he noted, adding that many of his socks are attached to causes.
As an example, Underwood held up a pink sock designed to bring attention to breast cancer and Breast Cancer Awareness Month (Octo- ber). He’s also working on one focused on AIDS awareness. Another initiative, undertaken in conjunction with the Mental Health Assoc., was the creation of socks designed to bring awareness to mental- health issues during Mental Health Awareness Month in May and help remove the stigmas attached to seeking help for mental illness.
“They’re very purposeful,” he said of his socks, adding that his rela- tionships with area nonprofits and organizations, elected officials, and visitors’ bureaus bring many benefits. They create awareness for his products, but they also put a face — or a sock, to be more precise — on many of the issues of the day.
Overall, he has more than 75 current styles, and the number contin- ues to grow, as with that Massachusetts sock. There are seasonal socks, for Halloween and Christmas, for example, and products for children — with matching styles for their parents.
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