Who The Hell Am I?

I am fueled by the act of creating. In my experience, the success of a business isn’t in hitting sales goals, becoming a social influencer or even being the best...

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Jessie Kaye Bio Pic in E Smith Mercantile

I am fueled by the act of creating. In my experience, the success of a business isn’t in hitting sales goals, becoming a social influencer or even being the best at something, success is creating something beautiful in the world that solves a problem, and makes an impact. I believe success is honoring what makes you feel good, and creating a space for others to live in that with you. 

Around the age of 7 my entrepreneurial bug started itching. First, I cataloged our basement book collection into a library that I coerced my family into “checking out” and then charged late fees. Next, about a year later, I placed flowers on my bedside table, a mint on each pillow, and much to my mother’s agitation, mailed an invoice to our out-of-town guests for staying in my room. As I reached my teens I taught myself to sew. I named and branded my first business, “Osira Designs,” a mail order catalog with printed pages pasted together from my dad’s fax machine, emblazoned with a clip art dragon.

Like most 18 year olds facing the end of their schooling, I was at a loss of where to go next, or who I should be. I had always had a love of fashion. I remember walking up to the large map that hung in the school hallway starring at all the names and universities my peers were attending next year. I wanted to manifest the dream I had just discovered of going to fashion school in New York. I walked up to the map, and sunk a small red pin with my name and "F.I.T." into the city of that never sleeps.

But I wasn't ready for New York, and was not accepted. Instead I followed some other artist friends to Cornish and spent four years in what I lovingly referred to as "grownup Kindergarten," exploring my creativity and lavishing in the opportunity to just make. As the statistics will tell you, after four years of play I entered the workforce still needing skills. I spent another two years earning a technical education in apparel design, and even spent a summer living in New York for an internship. Dreams really do come true. That work led to an insightful, yet challenging few years in corporate design.

Creative freedom came calling. Overcome with a longing to be more meaningful, and make a greater impact than choosing buttons and thread colors that were a part of someone else's grand design, the foundation of what was next crept into the extra spaces of my time. Between meetings, after work, every weekend, I would make brand boards and gather supplier info and test cocktails.  

My, perhaps, overly generous parents used their inheritance to partner with me for my first brick-and-mortar business, E. Smith Mercantile (named for my great-grandfather). A hybrid business, before that was considered the norm, with a throw-back general store in the front and a craft cocktail bar in the back. I consider it now my 5-year Masters in Business. Not a success by the traditional definition, but with less than 100k in start up capital, for 5 years we maintained a profitable retail and restaurant business. 

E Smith Mercantile full of shoppers

 

I had over 10 years of working in retail under my belt, but had never worked professionally in a restaurant. Within the first year I was on the cover of a local magazine, bartending. We were written up in global publications like Monocle, Condé Nast Traveler and Sunset Magazine. But even with everything we did right, sometimes things go wrong. 

In order to keep up with the ever-increasing expenses of a growing business, we continued to add new sales channels, new product, more services. We expanded to events, taught classes, held over 30 monthly chef dinners, developed a private label collection offered by a good handful of National retailers, and employed up to 12 other creatives at a time.

Jessie bartends at E Smith Mercantile Heritage Room, photo from Conde Nast Traveler

 

Our tight margins made me feel that I had to do it all on my own. Finding justification to outsource things like bookkeeping and employee management, both things that I was fine at, but nowhere near good at, felt impossible. I wanted to be able. I was so attached to what we had built, that I was afraid of losing control of the big picture. I felt that by giving away what I should be capable of doing (but wasn’t), that I was admitting defeat. Like the scene from Friends where Joey puts on every piece of clothing in Chandler’s closet, I’d squeezed into too many layers, and was feeling the heat.

Our under populated neighborhood couldn’t sustain consistent sales, our landlords didn’t support us, the city tore into the main street in front of us, and on top of that, demanded too big a chunk of our overhead. When we decided to close I was surprised to feel equal parts heartbroken and relieved.

With some hindsight I’ve been able to look back at what we achieved and redefine what success looks like for me, both professionally and personally. My biggest fear was that I would be a disappointment to those people who supported me. It’s still something I struggle with: how to let the small, deep, internal voice that knows only how to love and uplift me, be the loudest one?, the only one I let guide me. How do I quiet my mind and my ego to find the joyful sound my soul, so naturally, creates? The hindsight is 20/20 and I’d like to share that clarity of vision with you.

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