No one can prepare you for a racially biased altercation with the police — even one that ends with you alive. It steals away the magic that makes you special, your light. It’s not the death of a thousand cuts. It’s one big fucking chunk of your soul stolen. One single evening, one altercation, robbed me of my hitherto unshakeable confidence in my own abilities. I ended up beaten and arrested for doing the same thing that hundreds of other students and alumni were doing. Except they didn’t look like me.

If it was this easy for them to steal my power then did I really have any power in the first place?

I’m sitting at a nexus of contradictions. I am equal parts hood and Harvard, working class upbringing with moments of privilege, having seen poverty and wealth firsthand. I’m born and raised in NYC and have been here all my life with my last 25 years in Harlem. I hate seeing the local bodega morph into yet another hipster coffee house, but I’ll happily order a horchata latte. I’m Black, yet light-skinned and unlike coffee, the dilution doesn’t seem to weaken my flavor.

With contradictions, come “choices” and my whole life was built on making the “right” ones. I graduated from an Ivy League school, and worked at two top banks. I had opportunities that others didn’t. And when I was 27, I was assaulted by the police. When I say “assaulted” I mean “beaten into unconsciousness”. Neither my light AF complexion nor my Harvard degree saved me that night.

I’m lucky to be alive.

In any decade — let alone today — I could be killed by the very people that are supposed to protect me. Instead, I spent three days in jail, and got 13 stitches to close the gash in my head caused by a police baton. I still have the pictures of the long bat shaped bruises covering my entire upper body.

You never forget a moment like that and this is the reality I’ve lived with for the last 22 years. It has impacted every aspect of my life: my personal relationships, my development as a professional, how I view founders and their companies, and colored every single interaction that I have had with law enforcement. Full stop.

I was released on bail, with multiple assault charges leveled against me as the aggressor. I spent the next year fighting these charges. Though the two white friends I was with were absolved, I was never cleared. Facing four counts of aggravated assault (one for each officer I allegedly beat up in this altercation) and in what I now realize was the biggest mistake of my life, I took an 11th-hour plea deal rather than risk going to trial.

I was, after all, a young, Black, Harvard graduate with a promising future, and everyone I spoke to told me that this was the smart move. So I plead guilty to assaulting the officers who had assaulted me, and in the process lost a part of what made me special. Fun fact, the judge in my case would later gain fame as the judge in Meek Mill’s case. Read up on the Meek Mill sitch. That about sums up my experience.

This was my litmus test. It showed me that my privilege didn’t exempt me from this most negative and all too common of Black experiences. The police saw me as a big black man. A threat. They didn’t care that I had never been arrested in the previous 26 years. They didn’t care that I had gone to college.

It was a binary decision: Black =dangerous, white =safe. Through this interaction, it became crystal clear that there were elements in the justice system, the same system that we had all been taught to believe was part of the bedrock of American fairness and equality, that were actively working against me and those like me, not on the strength of anything we did, but based on the color of our skin.

If being beaten instead of protected by the police stole my light, being innocent and never vindicated ensured that my light, my certainty, my righteousness, would forever remain peppered with seeds of doubt in who I was and how I show up.

It made me feel less special and less certain of my uniqueness and of my vision. It made it much harder to accomplish my goals and near impossible to articulate a contrarian vision with passion and conviction. It also made it harder to be a successful founder and took me years longer to get to a position where I could help companies succeed on my own terms. Losing your light is something you never fully recover from.

Experiencing police brutality, is like addiction; your recovery is a constant state, a constant battle where ground is gained and lost, day by day.

I moved on with my life. I transitioned into tech, becoming a product manager, a strategist and a developer of alliances and partnerships. I took my love of tech into music, film and media. This eventually led me to graduate school, where the economic climate of 2009 dragged me kicking and screaming back into financial services ( “signing bonus”…say it with me), and then into other, less stifling opportunities. I tried to raise a media technology fund in 2010. Fail. Not epic, but fail nonetheless. Too early, not wrong. I did another stint in banking. In 2015, I finally found my work family, and ended up building humble ventures with friends who are more like brothers.

By most yardsticks, I’ve done well. Today, I work with companies helm-ed by diverse founders and those building solutions for diverse audiences. The companies I enjoy working with the most, are advancing elements of social justice, health, and health equity through their mission.

But I feel like I have to fight everyday to get my light back.

My friends, those who’ve known me longest, and those, like my business partners, who met me later in life, get to experience the best version of me. They see the errant rays of sunlight fighting to shine through the clouds.

Occasionally the companies that I work with see it: the light that I lost shines down in those moments when a young company makes a breakthrough in how to tell their story and communicate their value, when they raise a round or win an important new contract. These are the few, fleeting moments when others see and realize the potential that I’ve had all along.

Photo by Nathan Dumlao on Unsplash

Those moments are few and far between. It’s the founder’s dilemma writ large — we see something that others don’t (yet) see. To succeed, we need to articulate that vision. For a white, male founder, it’s already really hard to convince a group of others that your vision is the right one — that it’s early, but not wrong. We are taught that if (and only if) you’ve gone to the right schools and come from the right families it’s possible. Sometimes. If you look different or sound different, then it’s much harder to walk into the same rooms and articulate a vision that only YOU can see. Hell, it’s much harder to even get in those rooms in the first place.

For Black people in corporate America, it’s hard to even maintain a positive self image amidst all that’s happening to us outside the corporate walls, let alone articulate a vision for a part of said corporation that only you can see. Now try it if you’ve had your liberty taken from you by the very people that your tax dollars subsidize. See how well you can articulate and sell a vision that differs from that of the majority.

My corporate life, like that of many of my Black and brown peers was filled with these Cassandra-esque moments of structural racism. There’s a little bit of you that dies inside every time you speak truth to power and are told that you’re wrong. You’ve heard it so often that you want to be wrong just so the system, the meritocracy, will make sense, instead of having your freshness tamped down on specious grounds, but you already know how this movie is gonna end. In my case, being beaten and incarcerated, however temporarily, stole my conviction that I was smart enough and insightful enough to see something that others didn’t.

For those of us still climbing the ladder in the corporate world, they have a little bit of their light stolen from them every day in meetings, on Zoom calls, and in Slack channels where their views aren’t validated because of how they show up to the majority world. Fight to retain what makes you special. I fight every day for my light…to reclaim the passionate belief in myself that I had at 26.

My mother is white and my father is Black, yet I grew up in NYC with both of my parents and absolutely no dissonance about who I was and how I would be viewed. I thank them every day for this gift of certainty in an uncertain world. They named me “Kayode”, which in Yoruba means “He brought joy” when they could have named me Anthony, after my Grandfather. I was a Black boy and I grew up to be a Black man. I’m hella light skinned, and I’m sure that’s provided me with many advantages in life, but that night it didn’t save me from a policing system that saw me as a threat.

Ah, But YOU Went to “HAHVAHD”

Before we go down the “Oh, you’re so privileged” rabbit hole, let me clear some shit up: I’m a first-generation college graduate. My father was a veteran, honorably discharged from the Army and the Navy (where he enlisted at 15 with a fake birth certificate, because it was the south and well, racism.) He was a mechanic and a short-haul truck driver until the day he died.

My mother was an artist, a singer, and an all around bad-ass who worked in the restaurant industry and later in corporate, to ensure that she could provide healthcare and sustenance for her family after my dad died.

We weren’t well off. I remember times when we had food stamps (the paper kind) and the old school blocks of orange WIC cheese (you know the shit that’s terrible on sandwiches, but marginally acceptable if hidden in Mac & cheese). It wasn’t all the time, but it wasn’t just one time either. We were an average working class family. Neither of my parents finished college. I bought the first blazer I ever owned for my Harvard Interview, and how I ended up there is a story for another day (It’s a good-ass story, trust me).

I went from city kid to Ivy League and back, only to really experience structural racism at its worst as an adult. If I look back on my experiences, the clues were always there. I just didn’t know how to put them in context:

Illustration by Aurélia Durand

I remember vividly the time when a white VP at my bank came by my cube and literally patted me on the head for a job well done, without any shame or historical context on how this action would be received by a black man. There was absolutely no sense of the fingernails scraping the chalkboard wrongness of her action.

This was the type of stuff that didn’t even get reported to HR in the 90’s. As Black professionals. we recognized the slights and maybe bitched to our close friends of color, but the mantra was keep it moving and “catch that check”.

The clash between structural inequality and financial services catalyzed by the events of the last few months is unraveling decades of corporate assimilation programming among Black and brown professionals. When my generation came in, we played the game because that was our only way forward. Those that played well excelled in the traditional sense. Those that played less-well left to go do other things (raises hand), but regardless of how they did at places like Morgan, Goldman, Bain or McKinsey, these places remained the gold standard. In order to be successful there, we needed to become even more adept at code switching than we had been earlier in life. While not exclusive to Black and brown folk, code switching has traditionally been part of the Black professional playbook.

According to the HBR article, The Costs of Code Switching, the authors highlight code-switching as one of the key dilemmas that Black employees face around race at work. While it is frequently seen as crucial for professional advancement, code-switching often comes at a great psychological cost.

One late night at work, while we were putting together a set of books for some client (shit seemed super important at the time, but now I can’t even remember which client. Funny how that works), a fellow analyst overheard a phone conversation that I was having with a longtime friend. Her comment to me was “I couldn’t even understand what you were saying, it sounded like you were speaking a different language” (for the record it was hood English, heavy with metaphor).

Part of me wished that I hadn’t taken the personal call that night, because it was a window into who I was when I wasn’t being “tight booty, I-Banking me”. Part of me reveled in the fact that I could communicate with my people in plain sight and then effortlessly tighten my sphincter back up and switch back to work mode. Sigh. The me that reveled in that duality of context is long gone. Code switching is what we did to get ahead, but it cost us, all of us, more than we will ever acknowledge.

Here I am, standing at the intersection.

Of corporate and hood.

Of minority and majority.

Of vision and myopia.

Of founder and Black founder.

Of VC and Black VC.

Of Victim and Oppressor.

Trying not to engage because the PTSD is fucking overwhelming.

Yet, while I sit on the sidelines, the conversation continues. Punches land on both sides, but at the end of the day, nothing really changes. I listened to a fireside chat with a prominent VC recently, and he’s convinced that now the industry is really reckoning with the dearth of Black and brown representation. His comments left me experiencing yet another Groundhog Day moment in a year that has been chock full of them. I thought “damn, I’ve heard this song somewhere before…” Then I remembered that this is the remix. These promises sound eerily similar to promises made in the past, and if history is any judge they will slowly (or quickly) fade into the ether, taking with them any unrequited protestations of commitment and fidelity to change, because the requirements of “diversity theater” will have been satisfied.

Please don’t misunderstand me. I believe that people are sincere in their belief that this feels different, but as someone who’s read the book, seen the movie, and bought the tee shirt, it’s really hard to see how any of the moves in corporate or venture will do anything more than benefit those who are already set to benefit (basically folks like me). We need to expand the funnel. We need to do better.

Unless you know what it’s like to have your rights violated, to have your very existence on this earth threatened based on the color of your skin, to have your identity snatched from you in an instant, and then to spend the rest of your life trying to get back the light that was stolen from you, it might be hard to understand why the corporate statements accompanying the capital allocation discussion today feel like such a farce.

So let me state it plainly.

While we dither, making the case for a bigger slice of the pie (or a bigger pie altogether), People are dying. Every day, lives are snuffed out of existence as a result of how our law enforcers see (or choose not to see) us. And against this backdrop of the murder of Black lives, what’s our idea of action? Of moving the needle? Fortune 500 companies making heartfelt statements? C-suites wringing their hands wondering if they’ve said and done enough? VCs feigning ignorance, discovering Black founders the same way Columbus discovered America, and allowing them entree into their newly constructed kiddie pools?

People. Are. Dying.

They have been for the last 400 years and they will continue to unless we fix our system. That’s bigger than capital providers circling the wagons, bigger than the Black and brown players in VC moving from PBS to prime time, even bigger than the Black and brown ‘made men’s” conspicuous silence. In the face of all of this, how do our current actions stack up? So please, let’s all grow the fuck up and find a way to fix the real issue at play: Systemic, structural racism. Until we acknowledge and develop real-world strategies to counteract its effects, nothing else really matters.

I thought long and hard about telling this story. The truth is, even the people I call friends don’t know the details of what went down and how it affected me. I do a pretty good job of keeping it together and pushing forward despite all of my own baggage. Then we had a global pandemic, whose aftershocks will likely trigger an economic depression, combined with a very public murder of a black man at the hands of law enforcement. Again. This kicked off seventeen different tweet storms from a multitude of voices and perspectives. A cacophony of sound and fury that was so loud, I couldn’t even think. So I had to write, and after much thought I decided that my silence would only serve to perpetuate the system that stole my light. All I lost was a few days of liberty and my pride, and that has shaken me to my very core for two decades. Many others have their very existence cut short in similar altercations. This is where our energy needs to be directed. In the face of what we see, and what we have seen, over the last twenty-some odd years, the lack of progress makes everything else feel pretty meaningless. Fuck a statement. Fuck a twitter rant. Fuck a medium post (mine included). Do something to change the status quo other than talking about changing the status quo. Here’s what I’m doing along with my partners at humble ventures:

1. Helping amazing underrepresented founders/folks build companies to eliminate inequities in our systems. We do lots of work in health/SDoH but that’s not the only space we work in. We do this for no fee and no equity from founders.
2. Health is inextricably linked to social justice and equality. We can’t have one without the other. I’ve felt a more powerful pull towards these founders over the past few years. That pull was accelerated by my own experience surviving COVID19 hospitalization, and the attendant acceleration of digital health in the wake of our country-wide quarantine. We are working with partners to bring innovation, commercial attention, and capital to these important spaces.
3. We are speaking to students and student athletes about structural racism and implicit bias. Please check out the work of Maryland Lacrosse alumni Harry and Thomas Alford here and here.
4. We are serving as resources for a larger network of allies who want to know more and do better.

I rock with people that believe what I believe. That’s enough for me. This is important work that needs to be done. So we do it.

To founders and future founders: Protect your light. Nothing in this world is as important as your insight and your conviction. Yes, You gotta be great at what you do, but you also need to maintain and protect your passion in the face of a world that often feels aligned against you.

To my majority peers: Show up for Black and brown founders. Show up for the men and women inside and outside of your companies who look and think differently. Show up for those that come from communities that look and act differently than those that you came from. You will be surprised by the results of these small steps.

To my BIPOC peers: Share your stories. Let those around you know what you’ve been through and what it’s taken to protect your light from being extinguished. Only by sharing these stories will every part of your network come to see, and call out structural racism for what it is, systematic unfairness eclipsing your ability to shine brightly.

What happens to a dream deferred?

Does it dry up

like a raisin in the sun?

Or fester like a sore —

And then run?

Does it stink like rotten meat?

Or crust and sugar over —

like a syrupy sweet?

Maybe it just sags

like a heavy load.

Or does it explode?

Harlem

BY LANGSTON HUGHES

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