Page 7 - BusinessWest October 13, 2021

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.
“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 dis- tinctive artistic and philanthropic flares to it.
Indeed, since launching his line, he has designed sock pat- terns that do everything from identifying many of Springfield’s
Lenny Underwood, seen here talking with a UMass Amherst student at a pitch contest he judged, has become a mentor to many aspiring entrepreneurs.
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, cranber- ries, 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 enter-
“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.”
prise 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 initia- tives with young entrepreneurs, including many aspiring photog- raphers; involvement with Valley Venture Mentors, EforAll Holy- oke (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 spec- trum of business and entrepreneurship. He’s also writing a chil- dren’s book on entrepreneurship.
Richard F. Burkhart, CPA and Salvatore J. Pizzanelli, CPA, JD, PFS
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