John Henry
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Instagram: @johnhenrystyle

How long have you lived in Harlem and how does it inspire you?

I started by anchoring my business here in 2012 and then moved here. It inspires me as a beautiful infusion of people, style, culture, eclecticness and vibrancy. Harlem has a neighborhood feel that hasn’t resonated with me any other place as much as it does here.

Was it a conscious decision to align your career with making Harlem a better place?

I’m a native Manhattanite but spent my teen years in Florida. When I came back I had some rediscovery of neighborhoods to do. As I mentioned, businesses sprouted organically for me in Harlem and I fell in love. It is the kind of place that lends itself naturally to community. I had a physical storefront and got to know owners of other businesses then joined a local merchant group and became more involved in the business community. Before I exited my first company, a couple of friends and I had the idea for Cofound Harlem, which was way less strategic than it sounds now. We were all working Uptown and thought it’d be cool to put together a meetup for people who were interested in startups. Around the time of the exit, I noticed I was spending a lot more time thinking about the idea and soon after we added a business model to make it sustainable. We created an incubator out of it which grew into being more embedded in the Harlem community. It has not been a thing I’ve tactfully thought through. The spirit of an entrepreneur is to go with what feels right. And Harlem always felt right.

Taking a step back, how did you arrive at the decision to become a full-time entrepreneur at 18?

If I were to reflect on it honestly, my first generation immigrant upbringing ties strongly to the school decision. I recall when the college application process started. Other kid’s parents were deeply invested and as they had been through it before, able to help them. My parents cared about school of course, but  working several jobs made it harder for them to be more pro-actively involved. Thus, when I first got back to New York, I was in community college and working full-time as a doorman with every intention of going onto a four-year college. Doormaning gave me access to all different types of people that were living their dream and doing what they love at a very high level. That quickly became much more interesting than the classroom. When someone came to me with the opportunity to start what would become my business, I didn’t even know the word entrepreneur. However, as it grew the more I realized the value of my time and that something has got to give. The first thing that went for me was school. I never formally dropped out. I just stopped going. Eventually I got fired from my job because I was not paying enough attention with the business always on my mind. People talk about taking a leap of faith but in reality, life pushed me off the edge.

Many entrepreneurs are working towards the day when their businesses are acquired. What factors weighed into your exit?

When people hear that I exited, many think that I went about it in the calculated way associated with entrepreneurship today. Remember though that I didn't even know the word ‘entrepreneur’ when I started. I knew I liked the freedom of being able to generate income for myself, not having to answer to anyone and the challenge of building something. My passion was in the growing of businesses, not cleaning people’s laundry. It’s a really fascinating and intense process. There were days I woke up bleeding from my nose because of stress, but everyday I felt fully alive. At some point I realized I had grown a business valuable enough that someone was willing to pay for it. I was initially reluctant but became very excited by the potential to start new. With the skillbase I had developed and my true passion for business made clear, I wanted to see where focusing on Cofound Harlem would take me.

As you transitioned into the world of incubators and venture capital, how did you make up for the gap in formal training?

From the outside looking in, it often looks like the barriers to entry are higher than they really are. Darwinism definitely weeds out those who don’t have the willpower to put in the time to gain knowledge. But once you break through, you find that irrespective of the interest - art, business, whatever - the common denominator is your perspective. The more you hone the specific way that you think about and do things, the more valuable you are. The technical can be learned. It really comes down to how you are going to apply it in a fresh way. That’s what I think people should spend more time on.

People that studied formally may have an advantage in technical proficiency, but their creative application is often limited in a way that is not the case for people who aren’t bound by those rules.

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What attracted you to join Harlem Capital just over a year ago?

At the same time that I was operating from an entrepreneurial perspective incubating companies, the guys at Harlem Capital were just getting started investing . The original purpose was to put pool capital and put it to work. It was over time as we became more and more exposed to the VC ecosystem, that we realized that there’s not only a glaring diversity problem amongst founders - but investors especially.

How did you evaluate the partnership aspect of joining Harlem Capital?

My partners come from a more traditional background; went the banking route, developed an interest for putting capital to work then gravitated to each other as men of color. We had the chance to meet, and in that first meeting it was evident to me that this was a team of young and bright minds. Everytime I interacted with them, my confidence in the team grew and that’s exactly what I look for. Continued confidence is usually tied to passion, commitment and being the right team for the problem.

You mentioned on your Instagram story recently that you are more of a producer of content than a consumer. What impact do you think that has had on you and your presence?

When I was high school I fell in love with playing guitar. I wanted to be the best jazz guitarist you could ever think of. It became super clear to me then that TV was a big time suck. I made a personal commitment to spend as much time as possible, not on leisure, but on something that would move the needle with my craft. It has had a massive impact on my career and I think content creation is the more interesting side of the equation. You’re putting things out there of value, its comes back around and eventually people pay you to be yourself, as my homie, Julian Mitchell, a writer at Forbes, says. That frees up more time to produce more and before you know it, you’re releasing books, podcasts, TV shows, etc. All of these can generate income, which enables you to build a team to keep going. While consumption more easily leads to spending, creation more directly ties to earning. As I’m working on this TV project, I’m seeing the value in being an executive producer. Our community needs more of that. We’re such exporters of culture but don’t own nearly enough IP.

I’m not sure how much you can share, but what are you most excited about in stepping into the TV space?

I’ve watched in fascination as what seems to be a organizing principle sprout in my career and careers of others. The things that you seed, grow. Back when I was starting Cofound Harlem, I saw value in filming the meetups. I’ve made a few half-assed attempts since then at creating content but didn’t have the infrastructure in place to stay consistent with it. I still kept gravitating towards content, then eventually took social more seriously and invested in the vlog. It wasn’t until I started producing content that the potential was sparked for other opportunities in that style. I went through a few opportunities before landing upon one that resonated and decided to explore where it went. We’re still in the exploration phase for now.

You’ve had a podcast for a few years when they just became mainstream in 2017. How do you position yourself to stay on the cutting edge of an ever evolving landscape?

I was fortunate because I landed a podcast with Gimlet, the best in the business - but I was not seeking out podcasts. They reached out to me. I think the most important consideration is making sure you’re active in the discussion and bring something meaningful and distinct to it. That happens by doing cool shit. The reason Cofound Harlem received so much earned media from publications like Techcrunch, Business Insider, Inc., BET and more is not because we had a PR strategy, but because it was just a fascinating project. That kept me in the conversation and when you’re kept in the conversation, the likelihood is increased that when folks are seeking new messengers for new mediums, you’ll come to mind.

What is on the horizon for you in 2018?

I still experience doubt and fear but I believe that as your reach and influence grow, so does your responsibility. If you’re blessed enough to have these opportunities, you must expose more people to the possibilities. So, my big focus for this year is focus. It’s the best measure of how much you revere your opportunities.

How do you stay motivated as you strive to achieve your goals?

Motivation comes and goes for me. That’s why it’s important to be rooted in doing something that I seriously believe in. Then it’s more about how one weathers through the inevitable periods of low motivation. I want others to not be alarmed. The journey comes with ups and downs. The key is to stay cool and even as the pendulum swings. The motivation will come back around. Sometimes a conversation sparks it or perhaps a break is needed to fall back in love.

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