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Meet Leonard (Lenny) Underwood of Upscale Socks & Underwood Photography

Today we’d like to introduce you to Leonard (Lenny) Underwood.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I began taking photos in high school. You would often find me with my film camera around the school capturing different events and activities taking place as well as family and social events. Something I probably started doing because of my mom.

Growing up, this was her hobby with creating photo albums. When I went to college, I started taking my love for photography more seriously by photographing campus events like fashion shows, homecoming dances and photo shoots as well as various events in the community.

This morphed into a business in 2004 when I was asked to photograph my first wedding Thanksgiving weekend of that year. It’s been an awesome journey. We now capture many corporate events, offer photo booth services, slideshows, digital equipment rentals just to name a few. It has turned into a full-time business.

Summer of 2014, I had a dream one night that I owned a sock line. I woke up the next morning, told a friend and we both thought it might be a cool idea but the negatives seemed to outweigh the positives. For a year, I toiled with the idea of stepping out on faith to pursue this dream because I never worked in retail, nobody seemed to really have any answers to my questions, my time was limited, feared failure etc.

In 2015, I was told about a 10-week business development workshop for new or existing businesses for free (at the time). It really gave me more confidence and direction to continue to lay the foundation for this new entrepreneurial endeavor. It took me another year to create a buzz, come up with concepts, develop a website, create a following (or alert my current following) seek advice from wise counsel and really takes my time strategizing for launching.

In December 2016, the launch party was held for Upscale Socks. Our socks are fun, funky, funny, colorful and vibrant. They are for the entire family, starting at age one. Most of the children’s sock styles has an adult sock that matches. So far, the journey and support has been great.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
For the most part, the road has been relatively smooth. There have been some bumped along the way, like with any business venture but I see them as learning experiences and character development. Nothing that I’ve encountered throughout my journey has set me back or caused me to lose momentum or hope.

So let’s switch gears a bit and go into the Upscale Socks & Underwood Photography story. Tell us more about the business.
I think I covered details about what my businesses do but I would say my photography business is known for reliability, good, quality, professional service with a quick turn around time. The final results are high quality and second to none.

I am most proud of sustaining the business throughout all of the ups and downs that life can bring and being able to garner great relationships and partnerships with other local small and major companies.

The same goes for the sock line. We are still in the infancy stage but there has been really good support and ideas that have been birthed.

Has luck played a meaningful role in your life and business?
It has played a pivotal role. Sometimes it has been “being at the right place, at the right time” or knowing the right people to support my business ventures. I have experienced bad luck but I can’t let it stop or slow me down from where I am going or plan to go.

We have to remember that we are much greater than one or sometimes a few bad situations. We can always use our roadblock and make them our stepping stones.


  • Photography services are usually $100/hour and wedding packages range on average $899-$1999
  • Socks range for from $5.99 (for children) to $14.99 for adults. There are various price points to choose from

Contact Info:

Image Credit:
Brenton Jenkins, Daryl Moss, Jonathan Rosemond, Chris Marion

Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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