Cover Story

Lenny Underwood Is Making an Entrepreneurial Fashion Statement

Portrait of the Artist

 

When he was in college and developing his skills as a photographer, Lenny Underwood recalls being told to ‘get a real job.’ He thought he already had one, and eventually built a successful business. A decade or so later, he created another one, Upscale Socks, which is turning heads with its products while also helping to bring attention to everything from breast cancer to mental-health issues. These days, while growing his two ventures, Underwood is also passing on what he’s learned and doing important work to encourage entrepreneurship, especially among young people.

 

MAKING QUICK WORK OF IT.

That was the puzzle Lenny Underwood had to solve when he advanced to the bonus round of an episode of Wheel of Fortune that aired in May 2018 — three years after he first auditioned to be on the popular show.

With the few letters that had been revealed — Underwood doesn’t remember which ones they were (he could choose three consonants and a vowel) — he wasn’t able to come up with the phrase. But he noted that he wasn’t familiar with it and had never used it himself, so he was at a real disadvantage. (He also failed to solve another puzzle — WKRP IN CINCINNATI — claiming he’s too young to recall the late-’70s sitcom.)

But, overall, his appearance — he and a good friend competed together — was a success on many levels. He did win a trip to Guatemala for advancing to the bonus round, along with some press — both before the show and after it — and some fond memories from the experience, which came at a point in his life (the audition part, anyway) when he had much more time and inclination for such escapades.

“We did a lot of things like that — we were interested in adventures,” he told BusinessWest. “Things like skydiving, being audience members for TV shows, meeting celebrities, going to book signings … things that were interesting. We would say, ‘let’s audition for this,’ or ‘maybe The Amazing Race,’ things I could add to the arsenal of things that I enjoy doing.

“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.”

“But that was before Upscale Socks,” he went on, referring to what would be described as his latest entrepreneurial venture. It is, as that name indicates, a sock venture, but one with some distinctive artistic and philanthropic flares to it.

Indeed, since launching his line, he has designed sock patterns that do everything from identifying many of Springfield’s many ‘firsts’ — basketball and the monkey wrench are on that list — to drawing attention to breast cancer and mental-health issues. His latest design — he’s planning a press conference to announce it — is what he calls a ‘Massachusetts sock,’ complete with many symbols of the state, including mountains, cranberries, the mayflower, and art connoting higher education.

There is far less time now for things like Wheel of Fortune as Underwood continues to adjust the business plan for both his sock venture and his photography studio, another artistic enterprise he launched 17 years ago, one that suffered greatly during the pandemic, as all such businesses did, but has bounced back in 2021 as the world returns to normal — in most respects.

Meanwhile, there are other matters competing for hours in the day, he noted, listing a growing number of mentoring initiatives with young entrepreneurs, including many aspiring photographers; involvement with Valley Venture Mentors, EforAll Holyoke (he recently judged a final competition among participants in its latest accelerator cohort), and other agencies working with entrepreneurs; and teaching assignments within the broad spectrum of business and entrepreneurship. He’s also writing a children’s book on entrepreneurship.

He used to get a few requests for such work years ago, but the number 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.

Lenny Underwood, seen here talking with a UMass Amherst student

Lenny Underwood, seen here talking with a UMass Amherst student at a pitch contest he judged, has become a mentor to many aspiring entrepreneurs.

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 connections.”

For this issue, BusinessWest talked at length with Underwood — about socks, photography, 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.

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 potential. But there was a lot of learning to do and hurdles to clear.

“Many have a purpose behind them, and others are more artistic or wacky or funky, as some people call them.”

“I knew nothing about retail,” he acknowledged. “I didn’t do anything for maybe a year but toy with the idea and do some light searching 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 (October). 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 relationships 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.

Lenny Underwood says Upscale Socks now has more than 75 designs, and many of them have a “purpose.”

Lenny Underwood says Upscale Socks now has more than 75 designs, and many of them have a “purpose.”

Overall, he has more than 75 current styles, and the number continues 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.

“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 website, the stores he’s in, and the many partnership 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 offering,” he added, noting that the business plan is being continuously revised, and he’s working to create new partnerships and new avenues for visibility 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 example — Underwood says he tries to make time to do the occasional book signing and meet those who have forged successful careers in everything 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.”

Lenny Underwood, seen here donating 200 pairs of his socks to Square One

Lenny Underwood, seen here donating 200 pairs of his socks to Square One, has long made philanthropy and working with area nonprofits to help advance their causes part of his business plan.

As an example, he mentioned meeting Ruth 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 encouraging it as a career option as well.

“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,” he said, adding that, over this past summer, he was one of several invited to teach business to middle- and high-school students in Springfield. He’s also been part of programs at the college level, at Springfield College, the Berthiaume Center for Entrepreneurship at UMass Amherst, and other schools.

He finds it rewarding on many levels to pass on what he knows and to try and inspire others to get started with their own ventures or get over the hump and to the proverbial next level, just as he is doing in many ways.

And then, there’s the children’s book. He’s still finalizing a title, but the work is essentially done.

“It’s about teaching children how to become entrepreneurs at a young age,” he explained. “There will be key words throughout the book and definitions, so when they hear the word ‘entrepreneur’ or ‘branding’ or ‘prototype,’ they’ll be familiar with that language, and they’ll have the confidence, hopefully, to embark on something.”

Imparting such lessons is important, he said, noting that he didn’t have that kind of encouragement when he was younger.

“When I was a child, I tried a lemonade stand and tried to sell things like Blow Pops and water balloons in the summer months, but I didn’t think that was a business, and it wasn’t instilled in me to start a business,” he recalled. “Even in college, when I was doing photography, I was told, ‘get a real job — that’s just something you do for fun; that’s not something you can do as a career.’”

 

Developing Story

If Underwood had solved that puzzle in the bonus round of Wheel of Fortune, he would have won a pair of Mini Coopers. Looking back, he can say with hindsight that he’s not sure what he would have done with them — probably sell them.

It’s a moot point because, as he said at the top, he wasn’t familiar with the phrase in question and certainly couldn’t nail it with the few letters at his disposal.

As for the ongoing puzzle of entrepreneurship that he’s currently trying to solve … it’s equally difficult in some respects, but he has a better handle on the answer. And it has nothing to do with making quick work of anything. Instead, it’s about handling myriad challenges, pivoting when necessary, and, in the case of socks, having designs on success — in every respect. u

 

George O’Brien can be reached at [email protected]

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