Entrepreneur Lenny Underwood’s story is a literal example of a dream come true. After dreaming one night of owning a sock line business, he followed his intuition and just a few years later, Upscale Socks was born! 

Already an established photographer since 2004, Underwood launched this new venture in 2016, and Zydalis Bauer spoke with him to learn more about his pathway to entrepreneurship.   

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Zydalis Bauer, Connecting Point: Entrepreneur Lenny Underwood’s story is a literal example of a dream come true. After dreaming one night of owning a sock line business, he followed his intuition, and just a few years later, upscale socks was born.

Already an established photographer since 2004, Underwood launched this new venture in 2016, and I spoke with him to learn more about his pathway to entrepreneurship.

Lenny Underwood, Entrepreneur: So, when I had that dream in the summer of 2014, you know, I woke up, told a friend about it. We both thought it was a great idea, but neither of us ever worked in retail before, and so for a whole year bugged me on how to get started, how to formalize the idea.

But something in me said it was never the perfect time. I knew that eventually I would find resources that would be able to help me be a human resources or financial resources, or just bootstrap the whole business myself, which I ended up doing.

But, what made it so compelling was — just I enjoy fashion and it was another aspect of me expressing my creative side through fashion, and just something I’ve never had the opportunity to do as a business.

Zydalis Bauer: Now, speaking of businesses, before upscale socks you were already an established photographer with your photography company, Underwood Photography. You started that back in college, and so you’ve been doing photography for almost 20 years now.

What is it about entrepreneurship that has always intrigued you? Why was that the line, the career pathway that you decided to take?

Lenny Underwood: I would say it was by accident because when I was doing photography – even in high school, it was more of a hobby. It wasn’t anything that I thought it would turn into a long term career.

My family would encourage me to get a real job that that was just a hobby and nothing that would make me — I would end up being a starving artist or I would need that support. I just knew that, you know, creating my own pathway and way to find financial wealth and, and even mentoring other businesses along the way and being that example for my community and others around me was compelling and great in itself, and it’s been wonderful just to see it all blossom.

Zydalis Bauer: You are a native of Springfield, born and raised, and that is something that’s really prevalent in upscale stocks. You have given donations to Square One, have started scholarships, Friends of the Homeless.

What is it about giving back to your community that that you really connect with? Why is that so important to you?

Lenny Underwood: Yeah, well, to whom much is given, much is required. So,  feel as though it’s my duty to, in whatever fashion that may be, contribute back to the community in a — in a kind of financial way.

When I had the vision for Upscale Socks, I want to make sure I had an arm that was philanthropic as well. And so it’s called “Suit Your Soles”, where we do just that — suit the soles of those in the community and and beyond.

Zydalis Bauer: So, let’s talk about the designs and the creativity aspect of the business. You design some special socks for certain causes and you have everything from classic argyle, cotton candy leopard, and even you pay homage to the city of Springfield as the City of Firsts.

So, what’s the process, the creativity process that goes in behind designing the socks? What does that look like for you?

Lenny Underwood: So, a lot of what you have said comes from different inspiration that I may see within the area, or someone may share an idea with me, or I may dream about an idea.

So, they come in several different forms, and so, I may go back and forth on what colors or what I should include in that design.

Zydalis Bauer: Now, I know this is probably one of the most challenging questions to answer, but do you have a favorite design that you’ve created, or is there something that you haven’t created yet that’s been on your mind?

Lenny Underwood: Great question. So, one of my favorite — well, my favorite color is blue. I really like argyle socks, it has blues and green, as well as I like to see a first sock because it’s representing where I’m from — and the feedback has been really great and I think that’s been my number one seller over the last three years.

So, those are, I would say, the ones that stick out in my head for now and have quite a bit of styles coming out in the near future that are more theme based, as well as contributing to the cause community, as well.

Zydalis Bauer: Having been an entrepreneur for so long now, you’ve experienced the ups and the downs that come with this career. What has been the most rewarding part of owning your own two businesses?

Lenny Underwood: Most rewarding…would be the reception, I would say, from the community when it comes to, you know, someone hires me for their wedding or for their birthday party and seeing their happiness when they receive their photos, or return customers utilize me for their maybe their baby shower, then they’re having other like first birthday or fifth. And so, you’re a part of their life for so many years.

And so, with upscale socks, people ordering from all over the country, that’s been really gratifying, and how they read about what I’m doing or they see how it is bigger than just the profit arm of the business, but seeing how I’m about the community and really want to contribute to those around me.

Zydalis Bauer: Lenny, you have two businesses that heavily rely on the consumers, right? And so, you’re with photography, you rely on the people and then the retail industry. Both have been hit really hard during this pandemic.

So, how have you managed to stay afloat during these really trying times and what have you learned?

Lenny Underwood: Yeah, I’ve learned that I wasn’t in this journey by myself and we had to rely on other people around us for that moral support and my faith. So prayer and just really believing in that, we’re going to get through this together and I just have to be patient, do my part as well.

So, applying for grants locally or nationally, statewide, those resources are still available. So, tapping into those as much as possible, being creative about how you can approach sales.

So, utilizing my social media, many of the models that you have seen on my page never met before until I started reaching out for them to see their interest. So, that allowed me to get creative in how I approach, you know, marketing of Upscale Socks.

Zydalis Bauer: Now, you talked about having resources. What are — what local resources have been available to you to help support your entrepreneurship journey?

Lenny Underwood: So, when I had the idea for Upscale Socks in 2014 and 2015, I was the second cohort for at the time it was called SPARK Holyoke now called E for All out of Holyoke and they were really supportive and helpful in me getting the footing for Upscale Socks.

Not necessarily give me the the answers to all of my questions, but it gave me direction so that I knew okay, well, I can survey 100 individuals in the community and get feedback on what kind of styles or colors that they like when they shop for socks.

So, it certainly has been a wonderful resource in the Greater Springfield community amongst so many others that are available. And Valley Venture mentors being another one, where if you’re a small business or even if you’re in college, they have the summer collegiate program through UMass as well. So, tapping into those local incubators or startup business programs is vital.

Zydalis Bauer: That brings me to my, my last question. What advice would you give to others, young people, people of all ages, really, who may be thinking about starting a business or having an interest? What would you like to share with them?

Lenny Underwood: One thing is to be consistent. So, it’s oftentimes we’ll start something and we may stop for a break or things may come up in our life. But I think it’s important that if you get started, just continue to go get those, get that support from those around you that can help you to stay afloat — stay committed to what you’re called to do and rely on those resources that, that I mentioned as well outside of the community.

And they can always contact me as well if I could be of any source of support.