Page 9 - BusinessWest October 13, 2021
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 Lenny Underwood says Upscale Socks now has more than 75 designs, and many of them have a “purpose.”
thing from entertainment to fashion design to literature.
“I still try to break away on a weekday if I can,” he said. “I like art, and I gain inspiration from hearing their stories — their life and how they were able to attain success and grow their business.”
As an example, he mentioned meeting Ruth
“It’s a cool experience to share my experience and offer some advice on how to obtain success with whatever they’re looking to do.”
Carter, the Oscar-winning costume designer who grew up in Springfield. “I gave her a pair of my socks, and we talked about business and designs,” he recalled. “Those are really good networking opportunities — and learning experiences.”
While listening to and learning from others, Underwood is passing on what he’s learned to others as a mentor, teacher, and advisor.
He told BusinessWest he’s been doing much more of this work in recent years, especially within the minority community and with groups like VVM and EforAll. He said it’s been a mission of sorts to not only talk about entrepreneurship and all that comes with choosing that route, but
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     “I hope to grow that collection in the future,” he told BusinessWest. “When I first started the children’s collection in 2016, I didn’t do as much field work to really discover what children like and dislike, so they’re not as colorful and fun as the adult socks; that’s a line I really want to grow, and I think there’s a lot of potential there.”
At present, he said he’s selling perhaps as many as 15,000 pairs a year through his web- site, the stores he’s in, and the many partner- ship efforts he’s made with nonprofits and other agencies.
When asked what that number could be someday, Underwood said the sky’s the limit —
“as long as I remain authentic to what I’m offer- ing,” he added, noting that the business plan is being continuously revised, and he’s working to create new partnerships and new avenues for vis- ibility and growth.
Getting His Foot in the Door
While his businesses keep him busy — too busy to fly out to California on a moment’s notice to tape an episode of Wheel of Fortune, for exam- ple — Underwood says he tries to make time to do the occasional book signing and meet those who have forged successful careers in every-
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