Page 6 - BusinessWest October 13, 2021
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 6 OCTOBER 13, 2021
 Portrait Artist
Lenny Underwood Is Making an Entrepreneurial
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.
MBy George O’Brien
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 popu- lar 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 anoth- er 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

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