Outside Looking In: A Black Entrepreneur Story

Greg X Willis
4 min readApr 29, 2021

I’ve always found it more interesting to observe first before taking action.

To listen, before speaking one’s mind on a topic.

And I’ve done a lot of listening and observing in my life so far, and it’s apparent I must be an anomaly or not searching in the right place for the voices of aspiration. Aspirations that share a pigment like mines, but don’t rely on a scapegoat to proclaim our failures or success.

Its obvious advertising is created for demographics of specific race, color, creed, and interests. A prime example is Netflix’s Luke Cage, a demographic being catered to in a world lacking diversity in the superhero spectrum of entertainment. Let’s be honest though, without a show like Luke Cage, beyond the already established fandom base who would know about Luke Cage the character?

These ventures do not garner more sales for their comic book counterparts. Let alone push the topic forward of creating more diverse worlds, and characters for entertainment. With each demographic feeling under represented they create their own “shell” of distribution platforms to represent them and their audience of nationality. I’m at odds with this method of business development, cause as much as I admire Tyler Perry’s hustle from his days of stage shows to his production empire now. His product has never really been for me.

That brings me to the subject of my piece. The lack of diversity and black entrepreneurs in general in the entertainment, and tech world.

Only 15 black executives have ever made it to the Chairman or CEO position of a “Fortune 500” listed company. Of these 15 executives, there are currently 5 active, representing 1% of the Fortune 500 top leadership.*

*source: https://www.blackentrepreneurprofile.com/fortune-500-ceos/

It’s not surprising to see so few in these type of positions, because what we are instilled from birth to adulthood is to be more consumer-centric than creators. That was not just a blanket statement I declared also. The aspirations to be entrepreneurs in the tech industry are never a common topic we present to ourselves or our families. Being an entrepreneur or founding a startup I know is not for everyone, and everyone is not interested in the lack of possible comfort or work involved to be a part of one.

The attributes for why people don’t aspire vary, but as an anecdote my reason was fear. I had a lot of ambition growing up with varying concepts, but I feared my ambition was not tameable. As they say “ideas are like…”, and so I focused more on being the best flash developer, the best creative, then just the best developer for who employed me. Then reality struck at first my two paying gigs that paid nicely, but I had a sour taste from the lack of vision these companies had. I always considered strong leaders to have strong visions and can steer a company through thick and thin. So this monster, ambition, again grew in me from what I observed. I came across black entrepreneurs, but they looked down on me like we were not one and the same. Maybe because I was more tech and entertainment focused in my endeavors than traditional. Maybe because our education was different. Even so, I yearned for others with aspirations as my ambition grew.

What I learned, is trust is an expensive and alluring commodity we don’t even realize we’re buying or selling it on a daily basis. Trust metamorphs cultures, ideas, and people. It’s not distributed in equal portions in communities, and it depreciates with each seller. As I feared my ambition I realized I didn’t trust it, because it was not part of my DNA. Role models are not needed, but examples are always welcomed. The idea of “making it” is not just a placeholder for black communities, but all underprivileged areas of the world. People unaware or fearful of their ambition.

I always believe education, and knowledge are not one and the same when you look beyond its surface. You can be educated in what you need to know, and knowledgeable of the things you perceive, discuss, and discover.

The idea of “making it” is not just a placeholder for black communities, but all under-privileged areas of the world. People unaware or fearful of their ambition.

The End

I apologize, but I just saw this again in my medium profile. An article I wrote over 4 years ago that I never published. I had a lot more to say then and was figuring out a nice way to discuss a few pain points and wrap them into a conclusion, but that’s not the case anymore reading this today.

It’s not that my ambitions or perspectives have changed drastically it’s that the world itself has not changed much in regards to the topic even from a younger version of myself.

I’ll publish this as is, and let it inspire, infuriate, or make the reader in-different to my POV.

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