A Company with Sole
TAGS: Alumni Story

Most people don’t have dreams about starting sock companies, but Lenny Underwood ’04, ’05 MPA did—and he had the drive to turn that dream into reality.

Start-up companies usually begin with an aspiring entrepreneur having an interest in a particular industry. Through careful consideration, hard work, determination, and varying amounts of risk and luck, he or she develops that interest into an idea for a certain product or service. Over the course of months or years, a company is born, shaped, and grown.

Lenny Underwood ’04, ’05 MPA approached his business a little differently.

“I had a dream one night that I started a sock company,”  he says as he displays the first seventeen products that launched his new company, Upscale Socks. “It wasn’t a dream about starting a clothing line or creating other types of accessories or anything else. The dream I had was specifically about starting a sock company. So that’s exactly what I did.”

The Road Less Traveled

Lenny in socks sitting on steps
Lenny Underwood models a pair of socks from his collection.

If it seems somewhat unbelievable to start a company in that manner, you have to get to know Lenny Underwood a little better. His story starts out like a lot of AIC students: born and raised in Springfield, Massachusetts, he attended AIC because of its relaxed atmosphere and sense of community—but that’s where many of the similarities end. Unlike some college graduates who take the path of least resistance when entering into one career or another, Underwood always made sure to let his passions guide his life choices.

It was this inclination that led him to begin substitute teaching in the Springfield public school system while still a sophomore at AIC, and to begin teaching photography at the Holyoke Street School in Holyoke, Massachusetts, during his senior year. In addition, it was at AIC where Underwood began to hone his professional photography skills, shooting events for various offices around campus. This led to his first business venture, Underwood Photo, which he began in 2004, a few months before he graduated with a degree in public administration and a minor in business.

Like most of the paths in his life, though, it wasn’t that simple.

“I was having a breakfast meeting one morning about a month before completing my undergraduate degree and someone broke into my car and stole all of my camera equipment,” explains Underwood.

“I went to church that evening and met someone who was getting married that Saturday over Thanksgiving weekend, and she asked if I wanted to do photography at the wedding. I explained that my equipment had been stolen, but she insisted that if I could get a camera in the next few days, she would love to have me shoot it. My mom was able to help me get a camera on Black Friday. Of course, I wasn’t really familiar with the camera so there was a lot of pressure, but I did the wedding and the client was happy. That kind of sparked my confidence that I could do photography full time.”

Underwood took on as many photo shoots as he could over the next several years, building his business through word of mouth, cold calling clients, and networking. Slowly, he grew his portfolio, all while continuing to substitute teach and becoming a certified personal trainer in 2008.

Teacher, photographer, personal trainer—to say that Underwood keeps himself busy would be an understatement. For most people, having three pursuits in life would be enough, but then there was that dream. And Lenny Underwood is never one to ignore a dream.

 Following Your Dreams (Literally)

“I almost never remember my dreams,” explains Underwood. “So when a dream of mine is really vivid and stays in my head for a long time, I truly believe that it means something.”

Underwood embraces this idea fully, getting LASIK eye surgery a few months after dreaming that he’d had the procedure. His sock dream, however, took a little longer to develop. After having the dream in the summer of 2014, he wrote down his initial thoughts but waited a full year before taking his first steps toward turning his ideas into a concrete plan.

“The idea for the company stayed with me, but I didn’t know anything about manufacturing or retail, or where to even start the process of learning what I needed to know. So last summer I reached out to Valley Venture Mentors, a local organization that puts young entrepreneurs in contact with community business leaders.”

Underwood went to one of the organization’s “Ask An Expert” events, and from there was put in touch with SPARK Holyoke, a local partnership that offers entrepreneurship education for local area start-ups. He went through SPARK’s Launch Program in late 2015, all while designing his first sock and researching over thirty manufacturers to find the one that could give him the best quality at the best price. Once he settled on a company out of China, he was up and running. Even the name came easy to him—the “U” for Underwood and “scale” for Libra, his astrological sign. Upscale Socks was born.

“I started manufacturing with one sock so I could be sure of the feel and look of the product. I was really happy with the results, and started slowly building the initial line out to seventeen products. I’m now in talks with some stores in the Springfield area, as well as some small  boutiques in Northampton. I’ll also be selling through my Website, upscalesocks.com.

“The dream I had was specifically about starting a sock company. So that’s exactly what I did.”

Underwood is currently Upscale’s only employee, though he does work with a graphic designer for some of the sock designs. He also created a sock design contest with students at the Roger L. Putnam Vocational-Technical Academy in Springfield. Over 100 students submitted designs, with the top three winners receiving a pair of the socks they designed and a gift card. Approaches like this, says Underwood, are part of the joy of starting a company.

“It’s already starting to grow faster than I thought it would, but I’m just trying to have fun throughout the process and let things happen naturally. That’s my real goal now— just grow the company slowly and steadily and continue to enjoy it all each step of the way.”

Finding Balance

Underwood is uncannily relaxed for a person just starting his own business, but he explains that his attitude is less nonchalance and more even-tempered confidence.

“I’ve had a lot of support throughout my life. There’s my mom, of course. And people at AIC like Naomi White-Innis (former head of multicultural affairs), who was always very encouraging of everything I was doing, and Bruce Johnson, a professor who helped me build the people skills that are so crucial when starting and maintaining business relationships.”

He also mentions the organizations in the Springfield area that helped get Upscale Socks started. “This is a very supportive community for young businesses. There are a lot of programs and funding and grant money. Small businesses are really the engine for this economy, so there’s a lot of potential, but you have to get out there and talk to people, learn all you can, and take advantage of those opportunities.”

As for the future, Underwood is determined to continue to grow his company at a steady pace, in part to keep costs down and in part so he can keep the venture a solo project, though he admits that the latter may not be possible if the company takes off. For now, though, he’s following the advice he gives other young men and women thinking of starting their own businesses.

“Go slow, don’t rush, be patient, and stay diligent. There’s nothing worth losing sleep over. You need to have a work-life balance. Don’t burn yourself out, but also enjoy the journey. Maybe that’s the Libra in me—balanced. I do work hard, but for me it’s more about working smart.”

And above all, he says, don’t ignore your dreams.

“My mom and grandmother would sometimes say, ‘You went to college and you have these degrees, so when are you going to get a real job?’” He smiles. “But I knew myself well enough to know what would make me happy. And so that’s exactly what I did.”


-By Michael Reid