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.
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.
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?
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.
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?
Yeah, well, to whom much is given, much is required.
So I feel as though it's my duty to, in whatever fashion
that may be, contribute back to the community in a --
in-kind or 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.
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 First.
So what's the process, the creativity process that goes in
behind designing the socks?
What does that look like for you?
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.
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?
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.
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?
Most rewarding? Would be the reception, I would say, from
the community when it comes to, you know, someone hire 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.
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?
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 scale socks.
Now, you talked about having resources.
What are -- what local resources have been available to you
to help support your entrepreneurship journey?
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 SPARC
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.
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?
One thing is to be consistent.
So is 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.