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Voices of Gatsby: Betting on Myself is the Only Bet on the Table

Jess Watson
September 9th, 2020

On some days it feels like the world is ending. 

I have trouble falling asleep, or I wake up panicked with the minute details of days that have not yet come to pass and maybe never will. This is a characteristic of being at the forefront of my own livelihood. I eat what I kill in a landscape where some parts are constantly changing while others remain always the same. As a Black business owner of 10 years in tech, my existence in this space sometimes equates to an anomaly. Only recently, as our country is forced to more publicly reckon with a past of systemic racism and do the uncomfortable work of shining light on what keeps us divided, have I realized that maybe what I’ve accepted as normal all these years should in fact be challenged. Daily.

Shortly after our country exploded in protests following the death of George Floyd, I was seated in the lounge of my coworking office. My shoulders, already heavy with the weight of navigating a small business through the turbulent seas of COVID-19, were now further burdened with the dark ominous clouds of our racial past. A perfect storm. A fellow Black business owner in tech sat down nearby and our eyes locked. We exchanged the kind of glance where everything was said in our silence. 

Eventually, he spoke. “I want to do something about all this,” he said with earnest conviction. “It seems like our country is looking for answers, for solutions. Maybe tech is what helps us solve it.”

I nodded along, agreeing that something should absolutely be done…and notably hesitant about who was responsible for what. But then he asked a question that required a response.

“Where do you see your company in five years?” The query was simple enough, very similar to what one might hear at a job interview, and an open invitation to dream.

But my answer was grounded in reality instead of dreams. Without missing a beat, I replied “People like me, and companies like mine, are not supposed to survive.”


How Am I Still Here?

The most likely outcome of having a business is failure. Data from the Bureau of Labor Statistics shows that approximately 20% of new businesses fail during their first two years, and 65% during the first ten. How am I still here? 

According to Fundable, fewer than 1% of startups are funded by angel investors, and less than 0.1% are funded by VCs. At the same time, a 2018 survey by Guidant Financial and LendingClub Corporation shows that Minority-owned businesses receive lower loan amounts. This means they are forced to leverage their own cash when financing their businesses, making it difficult to plan and sustain future growth. Add to this the homogenous tech environment and the color of my skin, and over time I arrive simply at survival.

Author James Baldwin wrote in a letter to his editor in 1979, “A journey is called that because you cannot know what you will discover … what you will do with what you find, or what you find will do to you.” The journey of being a Black woman, a business owner, and operating in tech is an endlessly repeating journey of walking into rooms — conference rooms, coworking offices, networking socials, tech incubators — and being the only person of color. Despite the fact that all of these rooms are in Baltimore, a city that is 62.8% Black. Every time, I put on my armor and I walk in with confidence, but I walk in alone. 

Being me in tech is also being underestimated. It’s my company being thought of as too small or too young to handle a challenge. It’s being pulled aside and given advice that I never asked for. It’s being told time and time again that my company’s prices are too high when our research puts them as on par for our market and size, and even in some instances less than what they should be. I’ve been told “You’re too expensive” so many times that on some days I’ve believed it, even though I’m immensely aware of the quality of the work my company provides. (This mentality of “I can get it done cheaper somewhere else” has always undermined the foundation of what good businesses are building).

Being me in tech is an ongoing internal dialogue of wondering “Am I doing this right?” “Are they laughing at me?” and “Am I enough?” Holding those questions even knowing that friends and family members are so proud that I’ve taken the leap to start a business. They are counting on me to be the one that makes it. They see the sunshine on the horizon line, and not the mountains blocking the view. I’m left publicly saying, “Everything is going great,” but privately losing sleep and falling short with work-life balance. The contrast between the behind the scenes of business ownership and the romanticized lure of entrepreneurship makes for isolation and some lonely nights. 

Now, in my late thirties, there are days I question if I still have the rosy demeanor that accompanied me when I first filed for that LLC ten years ago. Or have I, weathered by all these storms, become so jaded by the reality of what is that I am no longer dreaming of what could be — even when a colleague directly invites me to envision where I will be in five years?

But those same ten years have also given me something else. Being deeply committed to this business, and to tech, for this past decade has let me bear witness to grassroots change. I have seen it coming slowly but surely, in people like Arlan Hamilton and Lolita Taub, in groups like Baltimore Womxn in Tech and Bunch of Founders, in companies like Fearless, organizations like B360, and coworking offices like Spark. There is a groundswell and I’m part of it. I still, even on days of defeat, have hope. 

Recently I saw a Black woman proudly sporting a shirt that read I am my ancestors’ wildest dreams and it made me smile. It makes me think that, even though there have been struggles, owning a business — rising each morning to do something I’m very passionate about — that is truly something. Something that, in and of itself, could even be called thriving. 

I want to get to a place where I am no longer on autopilot with default set to simple survival. A place where, the next time someone asks me where I see myself in five years, my immediate response — without missing a beat, without even thinking — is, “Thriving.”

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Founder and CEO of Points North Studio, Jess is also co-founder of Baltimore Womxn in Tech, a pioneer of working remotely, and always in search of good tacos.

Follow Jess Watson on Twitter

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