Hooded in America
A reflection on my journey from Harlem to Wall Street and Silicon Valley as a black male
When I was 12, my mother told me that I was forbidden from wearing the hood up on my sweatshirts. It was 1996 and my sister and I had just immigrated from St. Lucia to the U.S. to join our mother in Harlem. At the time, she was working as a nanny for a family that lived on the Upper East Side while she went to school part-time to earn an associate’s degree. Hyper-aware of racism and her children’s safety, she wanted my sister and me to appear as non-threatening as possible. We were not allowed to wear hoods as my mother feared it would make others nervous. We had to take our hands out of our pockets before entering any store, so nobody thought we were trying to steal. Even when it was cold out, we weren’t allowed to put our hands in our pockets because someone could think we were holding a weapon. So much of what we learned was to ensure that others around us were comfortable with our existence, even if it made us feel uncomfortable. We couldn’t let anyone assume the worst and call the cops or harm us themselves. Of course, tragically my mother’s fears turned out to be founded, both in 1999 when 23-year-old Amadou Diallo was shot 41 times, his hand emerging from his pocket holding nothing but his wallet, and in 2012 when 17-year-old Trayvon Martin was murdered after being thought too suspicious for merely wearing a hoodie. Botham Jean’s killing in 2018 was especially surreal for me — we were both born on the same day on the same island. It felt like the only difference between us was that he ended up in Dallas and I in New York City. The cop who killed Botham entered into his apartment thinking it was her own. The situations could have easily been reversed, and that could have been me.
Hoodies are comfortable and practical, especially for children moving between leisure and activity. White children probably don’t think twice about putting one on. Meanwhile, as children of color, many of us are told not to wear them, or, at least to don them in such a way as to ensure white people don’t feel nervous. In some sense, the inability of black and brown children to wear hoodies represents one of the many ways that children of color have their childhood taken from them. Whether that’s through the literal loss of life, as was the case for Trayvon, or the traumatic experiences so many of us live through, black and brown children are forced to grow up with an adult-type of awareness of our own mortality that no child should have to experience.
I think about how jarring it was to launch my career as a tech entrepreneur, as so many of my peers wore jeans, hoodies, and sneakers. Casual dress is practically a uniform in Silicon Valley, and venture capitalist Peter Thiel even says he won’t invest in CEOs if they show up dressed in a suit. I can understand the appeal of leaning into this look: it’s cozy and functional, particularly when sitting at a computer all day. But I don’t think people in the tech industry or in other increasingly casual workplaces realize the levels of anxiety associated with wearing the hooded sweatshirt for so many young professionals of color. While for white men, this aesthetic of extended adolescence furthers their image of grown-ups tinkering with technology toys, for people like me, we worry that we won’t be taken seriously or, worse, that we are making ourselves look threatening and are therefore at risk for violence.
In the context of not being taken seriously, black entrepreneurs already receive markedly less funding than our white counterparts. A 2018 study from the Partnership for New York City showed that black people made up 12% of the labor force but only comprised 0.4% of VC-backed entrepreneurs. This is compared to 63% of white people constituting the labor force and 80% of VC-backed entrepreneurs. To put it more bluntly: if we don’t dress the way Peter Thiel wants us to, our companies might die. If we do, then we might.
If we don’t dress the way Peter Thiel wants us to, our companies might die. If we do, then we might.
Believe it or not, I still have genuine hope that better days will come. My mother and sister were integral in my life and we’ve all shared successes. My mother went on to earn her master’s degree in social work from NYU’s Silver School of Social Work. Since the beginning of this global pandemic, she’s been a frontline worker at a hospital in Brooklyn, providing support to patients with diabetes in a neighborhood that has also been hit hard by COVID-19. My sister recently completed medical school with an MD-PhD and she too will be joining the front lines as a doctor at a renowned hospital in Manhattan. I myself had a successful career on Wall Street and went on to found the tech startup CariClub, which is all about empowering individuals and corporations to develop the leaders that our society needs and deserves. As proud as I am about what my mother and sister have accomplished, it is not lost on me that our story represents more of an exception than the norm when it comes to low-income families and the lack of access to quality education, healthcare, housing, justice, nutrition, and employment. Our story could have gone down an entirely different path had it not been for the interventions of nonprofits like the aptly named, Sponsors for Educational Opportunity and Prep for Prep, that helped to close the opportunity gap. It’s why I decided to reorient my previous career in finance towards the work I currently do through CariClub, and why that work continues to keep me hopeful and motivated to help bring about a future where a hooded sweatshirt is just a hooded sweatshirt, regardless of who’s wearing it. The fear of being in the wrong place at the wrong time as a black male has never gone away and I doubt it ever will, but I will never allow that fear to defeat me.
The fear of being in the wrong place at the wrong time as a black male has never gone away and I doubt it ever will, but I will never allow that fear to defeat me.
I am very proud of the business that we have built at CariClub — it feels much more like a calling than just a company. We have an impressive and growing roster of clients including some of the most respected, forward-thinking firms in the corporate world. I thank them for sharing and supporting my vision on how to help their emerging leaders channel their passion and talents towards the many worthwhile nonprofits in need of their support — a need that has only become greater since the pandemic hit. My thanks extend to the early angel investors, including a pair of venture pioneers, Paul Raether and Henry Kravis, who early on took a risk in me and my vision. As I turn to the institutional VC community to help CariClub with the next leg of its evolution, I will hold VCs to the standard of evaluating me, and CariClub, on our track record of sustainable growth and adding value to society.
Lastly, I’m heartened to see companies begin to make statements of solidarity with the protesting of police brutality and violence against black and brown people in this country. Given the immense influence that companies have on economic and public policy, I believe that it’s necessary that those companies are led by enlightened leaders who are allies invested in working towards solving some of the more intractable challenges that we have failed to solve. While I appreciate the symbolism behind sharing a post or black square on social media in solidarity, that symbolism will be reduced to mere hypocrisy if not backed by well-funded, concrete action. I implore these engaged leaders to put their money where their mouth is. So if building a more equitable society is important to you and you’re interested in being a part of our movement at CariClub, either as an employee, corporate client, investor, or nonprofit, let’s talk and take action.