40 Under 40 Class of 2020

Lenny Underwood

Owner, Underwood Photography and Upscale Socks; Age 36; Education: American International College (BA, MPA)

Underwood has owned Underwood Photography for 15 years and Upscale Socks for three years. Through his charity work with Upscale Socks, 220 pairs of socks were donated to Springfield elementary schools, and 150 pairs were donated to Square One. He also established a $500 scholarship for a student at Springfield Central High School. Meanwhile, Underwood has received several awards, including the 2019 Game Changer Award from the Springfield Thunderbirds, the 2019 Changemaker Award from Martin Luther King Jr. Family Services, and the 2017 100 Men of Color Award in Hartford, Conn. He is a deacon at St. John’s Congregational Church, a board member with Way Finders, and serves on the Brianna Fund for Children with Physical Disabilities steering committee and the Love Fusion Singles & Couples Conference planning committee.

Lenny Underwood

What did you want to be when you grew up? An attorney — until I worked in the litigation department one summer at MassMutual as a 10th-grader. It was an eye-opening experience that made me rethink my life plans.

What three words best describe you? Creative, motivated, focused.

What’s been your biggest professional accomplishment so far in your career? Recently, I have been invited to guest speak in various spaces, judge competitions, offer consultation to aspiring small businesses, receive prestigious awards (like this one), and also compete and win on Wheel of Fortune with my friend in 2018.

What are you passionate about? Health and wellness. In addition to my businesses, I am also a certified personal trainer.

What do you do for fun? In my photography business, I have the priviliege to work at many fun events over the course of the week. There is usually great food, great people, and great music!

How do you relieve stress? Prayer and meditation, exercising, and, recently the sauna.

What person, past or present, would you like to have lunch with, and why? Probably Dr. Martin Luther King Jr. He accomplished so much at such a young age, and he is still widely celebrated across the world.