Tell me a bit about your early years and where you come from.

I was born in South Africa. I was born in Soweto, which is a township in the Johannesburg area. And I was born there in the ’80s which was a very tumultuous time to be born there. The height of the armed resistance against Apartheid. My mom went to Soweto to have me from Botswana, which was where she was living with my father. My father was in exile at the time and so he couldn’t come in to South Africa. So the first couple of weeks of my life it was just me, mom and the grandparents. But then ended up going back to Botswana and was there for a little bit. But the circumstances worsened quite precipitously and it got very violent and a number of people were killed in our immediate circle, and my parents decided that we needed to leave, so we came to the United States.

Wow. Where’d you land?

New York City. JFK [chuckles].

What was that like for you?

I don’t know.

You were still tiny?

I was tiny. But it was a rough-and-tumble couple of months there. It was a thousand bucks, and the Hebrew International Aid Society was an organization that took us. They and New York Association for New Americans had been taking refuges obviously for quite some time, and they were just great to us. They saved us. We lived in the Latham Hotel, which was a homeless shelter. We were on food stamps, and jobless and penniless, and all that. My mom ended up getting a job as an ESL teacher at Fashion Institute of Technology, and my dad got a job as a cashier and coat checker at the Museum of Natural History. That was actually 30 years ago. 30 years ago in April is when we landed. Then my dad eventually became a teacher at a public school in Queens. And my mom became a permanent substitute at an elementary school. They were both teachers, and we eventually got an apartment in south Bronx near Jerome Avenue. You could hear Yankee stadium. Dad didn’t know what a baseball was, but he loved cricket, so we ultimately ended up going to some baseball games. We even saw the Yankees coming out of the stadium once, when  after a game and my dad met Reggie Jackson was the Yankee at the time. He ended up getting the tickets, so he’s a lifelong very big Yankees fan.

What was it like being raised in New York but in a family that’s not from New York or not from America?

That’s a good question, but it makes me realize I should tell more of the story. My parents were both trained as educators and they’ve been teachers in Botswana and in South Africa with my mom. They ultimately had heard from a fellow teacher at Maru-A-Pula in Botswana about a school called Milton Academy in Boston. My dad was doing some research and he ended up applying for a job at a school called Phillips Academy in Andover, Massachusetts. We drove up together, the whole family. They offered him the job, and we made the move. So I grow up in Andover, on an idyllic tree lined, prep-school campus as the son of a chemistry teacher.

Wow. That’s a change.

So maybe the question that you haven’t asked that is the interesting one to answer is, What’s it like going to and growing up on a fancy prep school campus while being eminently unfancy?

Yes.

I don’t know what it would be like not doing that. So I can’t really answer the counterfactual to it. But it was really wonderful. I learned English in preschool and I had learned Spanish in New York. Spanish was actually my first language. And then Xhosa, which is my sort of family language, was my second language. So I was speaking this very odd mix of the three when I got to preschool. The teachers were like, “Wow, it sounds like Spanish but he’s clicking.” It was funny. It was wonderful. I was the only black person in my class often. Sometimes there were two. So I learned to translate. I got really used to people wanting to play with my hair. Wanting me to, “Say your last name. Say it again. Say it again. Say it again.” And and I became fluent in the language of suburban affluent white America, but fluent in it knowing that I was never part of it. So I remember there was a moment when I was probably six or seven, where I was thinking about Ronald Reagan, because he had just been President. I had a panic moment because I was like, “Ronald Reagan was President and I don’t think I can be President because I’m black and because I wasn’t born here and because I have a funny name [chuckles].”Two out of those three are no longer thoughts that a six-year-old would have in those circumstances, which is pretty great. I had numbers of moments like that where I was just like, “Wow, I’m really not one of them.” And so it was always a little bit disorientated, especially because my parents being activists and civil rights activists particularly, always instilled in us a very, very strong sense of self and a very acute and intimate sensitivity to racism. So it was something I was always thinking about, and it was ever present. When I got to college and people like, “Oh. You went to Andover?” And it’s like, I’m a lot preppier than you think because I actually grew up on the campus but I’m a lot less preppy than you could ever understand, because of all the other stuff. And so, it’s just weird to be a third rail kid. To have a foot on both sides of the ocean.

Yeah. That’s interesting. What did you think you were going to be when you grew up? And did you have family pointing you in any particular direction?

I thought I was going to be the president until I was six. And then I thought, “You know what? I might still be able to.”

And then, later, I wanted to be a lawyer. And then I wanted to be a diplomat because my—I have diplomats in my family. So, I knew about it—I learned about it early. And they’re like, “Speaking multiple languages helps.” And I went, “Okay. Great.”

When I got to college, however, I wanted to be a chemical engineer. My dad was a chemistry teacher. I was his student in chemistry. I was a very disciplined and conscientious chemistry student. And so, when I—and I even weighed the quality of the chemical engineering as part of the decision matrix for choosing my college. So, I really wanted to be a chemical engineer, or so I thought.

Yeah. When did that turn?

When I hated college passionately.

Me too.

Really? Hooray! I hated college so much. There were a couple of reasons. One thing I always say somewhat jokingly is if you are a drop out of Harvard or Stanford you must be a genius, but if you’re a drop out of a community college you must be emotionally compromised somehow. I was actually just emotionally compromised, not a genius. I hated college because it was very lonely. I was black but not black American in the sense that I didn’t have the shared history and I didn’t grow up in a black American home. I grew up in a black home in a America. So that was a very strange thing that I couldn’t navigate and so finding my people was a little disorienting on that basis. I was preppy but not wealthy. I was African but not Nigerian. That was just from the social side I was very isolated. Academically, I hated engineering and I had gotten about half way through it and then I just stopped. I switched to philosophy, and thought that philosophy would be a very purely intellectually stimulating pursuit, and I was sorely disappointed by that too. I ended up dropping out and it was a pretty shameful dropout, but I remember that—I realized that most of the people who were at school were highly intrinsically motivated self-starters with working parents with graduate degrees and per capita incomes of $250K and greater, and so they needed Stanford degrees. The notion of it being the best school was really that they selected people who were already going to be okay, and I found that also to be really distasteful – like it was such a—it felt like it was finishing school for the already successful, which  got me really depressed.

So, I dropped out.

What happened after that?

We did a startup, naturally. That’s the thing about Stanford. I will say, 2003, four, five, startups were, compared to now, they weren’t on anybody’s radar. But a guy at the business school was working on a project out of this class, Formation of New Ventures, which was taught by a VC and, you know? And he and I crossed paths and he was like, “You should come work for me on this.” And he asked me to do it because I had a lot of Facebook friends and, at that time, that actually meant something [laughter].

And so, and he was working on a product that was oriented towards the demographic that I had the connection to which is the young professional types. And so, I agreed to work for him. And so, I came on as a very early employee and in very short order we raised some capital and I was launched into the tech world.

I’m curious what your impressions were, or maybe even preconceptions of Silicon Valley, and whether or not they lived up to your expectations.

I didn’t have a ton because I was interested in science and engineering, so not really in technology per say. Certainly not in business innovation, and so I didn’t come in with any sort of presumptions particularly. What I will say I was surprised by, and only recently I was stopped being surprised by the fact that it’s a human capital business. It’s a people business and people tend to have insular networks. It’s very much a people business with a lot of instinct and gut and those types of things tied to people. It’s not that accessible surprisingly. I would have thought, and there was a brief period where I did think it was ridiculously accessible. It’s funny because it should be the most accessible place in the world. That is, I think, a preconception that I was disabused of. The other piece is venture is even more intensely that way… Times a thousand

Walk me through the startup chapter of your life when you were in it as an employee.

Oh, boy. I think we accidentally picked up the anti-startup handbook [chuckles]. We were building in PHP. I think we were building in PHP because Facebook was but no other real reason. All of the engineers we knew wanted to build on the Ruby framework or rails framework and we hired a series of executives and we outsourced to Russia non-thoughtfully. We had a hierarchical culture that emerged relatively quickly. We’re dealing with some intense cultural stuff. It was chaotic. It was intensely chaotic. In retrospect we were on the verge of going out of business for six months and I was naive and didn’t quite realize it at the time because it is a momentum thing. When the momentum was good you feel awesome even though you’re spending other people’s money and you’re lighting it on fire, basically. That was intense. The high highs and frequent lows were also a feature in that chapter of startup life. In part because I was also just not in a very good state. It felt like I had failed, in fact. I think it’s safe to say I had failed, in the sense that my parents were deeply disappointed and concerned about my state of being, and my peer group didn’t really understand me, and they thought I was sort of flailing in the wind, and I felt a little bit like I was. And this cult of failure that people celebrate here is  because failure just sucks a lot.

There’s plenty of failure out there. It’s not hard to find. And when people here talk about failure, they’re actually talking about success, and they’re talking about overcoming failure, which is all well and good but celebrating failure is something that is a pet peeve of mine because of having felt like I was fully failed. And we were able to sort of land the plane on the startup and get an outcome for it, and exit the business in a way that we were licking our wounds a bit, but it’s still alive. But it felt like a failure, and these outcomes feel so binary here, where if you’re not on the, “Oh, my god, this is it crushing it” track, you have failed. And that just really hurts. It’s so defeating. It’s so de-motivating. And the piece that I find motivating is not when I’ve failed, but it’s believing that there’s a chance that I can eventually succeed [chuckles]. A promise of success is what’s motivating me. So that period I try not to think about that much, and I’ve managed just like we all have to retroactively tell the story very neatly. Like, “Oh, like 300,000 users and a Series A!” But the truth is the matter is I was just sort of lost and confused, and we were making not excellent decisions with this startup, and I didn’t know my ass from my elbow, and so it’s been clear to me, if I even was value add, even though the founder kept me on—so it was not recommended. People have asked me. It’s like, “Oh, should I drop out of school, because you did?” “Don’t. Please don’t.” It sucks. It’s so lonely, and it’s discouraging and it’s so embarrassing and shameful. Don’t do it, you know? And not enough people, I think, are talking about that, so.

You touched on otherness growing up. Not feeling like you fit in with white kids. Not feeling like you fit in with American black kids. Did you feel that otherness when you worked in startup land?

Oh, yeah. The otherness–if I had to characterize the feeling in one word, it would be poor [laughter]. And I hear people say, “Just boot strap it.” It’s like what does that mean, you know? My credit score got crushed because I wasn’t sophisticated about that and my parents, they didn’t know a ton about that stuff. And so, they hadn’t really given me all the lessons. I didn’t have a nest egg. I didn’t have savings to speak of. I didn’t have aunts and uncles who could float me five, ten K to say nothing of the 50, hundred K’s that people get. And yes, of course, there’s cultural stuff. And there is gas lighting and feelings of invisible racism and other isms that are manifesting in conversations and manifesting in the challenges I encounter when I access certain networks but when the truth—when push comes to shove, not having as much money as everybody else around me was by far the biggest feeling of othering or otherness.

Me too. Yeah. I remember going—and no one knew this but going to all of my friends’ millionaire houses and partying with them and then going home and eating my pocket ramen like every night and being like, “Fuck. Am I the only one in tech living like this?” 

And poverty’s expensive, you know? It kicks you—it has a cognitive toll and a physical toll and it’s really hard to keep pace in a fast-moving environment when you’re also trying to navigate your personal finances. And it’s hard to do that I remember, I said to somebody that I’ve never been to SXSW, because when I was a broke, startup person, whether I was an early employee, or later a founder, I just didn’t have the money to fly there. That’s why I didn’t go. Now it’s like, “I didn’t go, because I’m way too cool for it.” No, I just was poor, and you were not, because your aunt gave you money. People might be surprised by how often people outside of the dominant demographic just don’t have financial access. Just disproportionately, don’t have financial access, and therefore, our risk calculus and the way we navigate this world, and how we spend our time, has to be different, because there’s some stuff we can’t afford to do. Ski week? Fuck off.

Yeah. That tweet storm that went around yesterday, the YC guy, I was looking at the replies, and I saw one guy’s reply just be like, “Did you ever consider not taking funding?” I’m like, what a silly assumption. To assume that it’s possible for him to just bootstrap it. With what money?

Now that I’m on this side of the table, I’m guilty of this too. Come back to us when you have some traction. Why don’t you raise a friends or family or an angel round. a.k.a I assume that you are in your first degree connections, in a world of millionaires. Which is a horrible and stupid assumption, and is incorrect and is wrong.

I make the same assumptions, even as someone who wasn’t a rich person here. I still assume that everybody else is.

There’s also this weird duck syndrome thing too, where we’re part of your credibility and your ability to make moves in this network is fundamentally tied to a money thing. You have to hang and so you have to fake it. There are plenty of people I know, and I was one of these who were furiously paddling under the surface just to cruise. Just to have the right clothes, just to have the right gadgets. I was on a dumb phone for too long because I couldn’t afford a smartphone because my parents weren’t rich. We came here with nothing. In America, where people of color are disproportionately in less wealthy networks, that just means that money is a barrier. Period.

If you want to touch on being a founder, we can do that, but walk me through, from that first experience, to getting into VC. Did you have any idea that that would be the path?

No, I’m on record all over the place, saying I’d never be in a VC. I had a view of VC, that they were just … Also deep down, I felt too poor to ever become a VC, so that was also driving it. I also just had a view of VC as Menlo Park, khakis, Princeton, MBA. I didn’t feel like that was the person I was growing into. Turns out, that’s what VC’s are, which is fine. At some point, I worked for Obama’s campaign. He was my people obviously and I was so drawn to him spiritually and then politically and culturally. That was a defining experience for me, maybe the defining professional experience for me because I remembered that I came from a line of people who were very politically motivated, not in the sense of ambitious in elected office, but who were civil rights activists and from my father to my mom’s father and my father’s grandfather and it’s all an investment in the future — in mine and my generation’s lives. I felt like that was something that was important to me that I had forgotten in the rat race of Churn and MRR and valuations and tech conferences and shit and so it reminded me that the only work that I really felt was worth doing over the very long term had to have some political point of view and had to be positive social results and that stuck with me since and has changed the way I felt about business. And that deepens the more I learn about our economy and my view of capitalism. So that was awesome, like, introducing Michelle Obama on election eve, which was just wild. Then, after working on some startups, I realized that I wanted to repair the relationship with my parents and then went back to school.

At this point, were they super stressed about you?

Yeah, they were used to it, but there was a constant hum of stress that had been following them for years. I knew it, and I could hear it, too, so I had it, too.

What was it like, going back to school?

Best decision of my life. I met my wife. I met my wife, and I also got involved with the d. school, and started really enjoying some of the philosophy work I was doing —actually continued into graduate classes and began a thesis on the theory of intention, which I still find fascinating.  But instead of finishing a Master’s, I ended up dropping out again to join Collaborative Fund. But it was great to be, you know, learning environment, having lived, having done a couple startups, and been in different parts of the world, and been around poverty, and been around extreme wealth, and just seeing stuff, you know?

What have been some of the toughest parts of your work?

Toughest parts of the work. Well, VC is not–being a VC is one of the best jobs in the world so it’s hard to complain about it. I truly love it. And, on some level, it doesn’t feel right to complain about it but if I see fifteen hundred companies in a year I usually make six investments. And so, I’m in the business of saying no. And I’m a dream crusher. That’s my job. And “you are what you repeatedly do”, it’s been said, right? And so I crush dreams. And that is trying. It never gets easier. And because somebody will have such an amazing story. You can just see blood, sweat, and tears all over their product and you can see that they’re just hungry – physically and spiritually – and you have to say, “I don’t like your brand. it’s just so crappy. The hardest part about that, too, at the earliest stage, because there’s no data, is, I can’t say it’s not personal. It’s personal. That’s all it is. It’s not just, really hurt the people. I totally understand it, and some people get really offended, and take it personally, as they rightfully should. Doing that every day, just doesn’t feel good. Having to find a way to do that while also maintaining one’s reputation, because as a VC, your personal belief in your firm’s brand is all you have. If we have to disappoint people all day every day, and still maintain a good reputation, that’s a tough nut to crack. Finding ways to say no to people, such that they’ll say nice things, is a weird thing to have to do every day.

In this project the idea has come up that VCs are interested in investing only in problems that they can relate to. What are your thoughts?

Yeah, well, one of the things that I’ve caught myself doing, and I’m ashamed of, and I don’t do it anymore, or at least I try not to do it anymore is I’ll see a feminine hygeine product, and I’ll think, oh I don’t know anything about that market. But then I’ll see a construction management software, and I’ll think oh, that’s interesting. Which is crazy behavior and is deeply sexist behavior. And probably misogynistic behavior because tied to that is: I don’t want to know anything about X, Y, or Z. And that is dark. And I’ve caught myself doing that. And I’ve caught myself, also, meeting with an entrepreneur from Paducah, Kentucky and, on the basis of that person’s accent, making judgments about their likelihood of being an effective engineer. I’ve caught myself evaluating somebody’s watch or effective—maybe Spanish was their first language and they have slightly darker skin and then discounting the quality of the design of their product. Just stuff like that. And–

Interesting considering Spanish was your first language.

I know, right? Yeah [laughter]. And I am somebody who’s trying my hardest to actively avoid these unconscious biases. And so, Lord help the rest of the industry. And yeah. Lord help the rest of the industry. It’s so tough. And there’s so many companies that, if you are a 26-year-old heterosexual white male living in a city, you are their target customer. And one thing that’s funny about VC is most VCs are old, too, and don’t live in cities. And so, that’s not even their experience.

And I think it’s we invest in people who we recognize. And because ultimately this is a human capital business and the signals are instinct and gut driven and your networks are insular and stuff. So, if somebody uses the right language or communication—body language, physical language, et cetera, and makes you feel like you’re in home space, then, I think, that is a criteria that loosens the strings. And so, I think that means that I, conceivably, have an advantage investing in people of color, and that a woman should have an advantage investing in products that serve half of the population that has been underserved – in theory. In practice it’s hard because—this author Richard Wright talks about this phenomenon called the beast in the skull, where he says that the effect of racism—racism twists the psychology and the consciousness of the racist, and of the receiver of said racism. So I’m as awful as a so-called racist is,and so I don’t trust my instincts sometimes because I’m wracked with my own level of guilt about my own biases, and about stuff that I’ve internalized that I know has been fed to me and I really don’t want, but that I have. I get all twisted up about it myself, and that is tragic. I don’t really know what to do about that.

Let’s come back here for a second. How do you—we touched on this quite a bit, but how do you feel about the state of Tech in 2016? Like what is really exciting to you? What frustrates you?

What’s really exciting to me is the unrelenting optimism. I really do feel like Tech as an industry is a very supportive culture once you’re on the inside of it. And it’s a very collaborative culture and some people are always co-conspirators and stuff. And even though there are—yeah, so there’s that. And then the piece that troubles me a little bit is this thread, or this belief in the hero culture and the cult of the founder and these sycophants, you know? You know, Jobs didn’t change the world alone, obviously. And so it’s scary to think about that because I think of that makes it harder to build, really inclusive and ultimately resilient culture – that hero culture thing. And it’s also not true of the best of tech. The best of tech is very collaborative, and it’s very open to criticism and is constantly adjusting and is swim or die, and so it’s always moving, and the best of tech feels like a hip hop world – you’re only as good as your last hit, and you’re always trying to get on somebody else’s single, and there’s beefs, but you’re all in this together and ultimately you’re trying to lift—you’re trying to push the whole culture forward, and you’re remixing the past and you’re constantly sampling and you know your history and you’re tied to this optimism through generations. And I think these are really wonderful features of this industry and they’re poorly understood by people outside of it, and then a lot of newcomers, which scares me a little bit. I’m cautiously optimistic now.

Where do you see yourself in five or ten years? Think you’ll still be in tech land?

Yes. A VC said something beautiful the day before yesterday. She was talking about feedback cycles and how some are longer and some are shorter. And in VC, the feedback cycle is so long that it looks like a straight line because it just takes forever to—it takes six, seven years to learn because that’s when whatever comes to fruition when you seeded the company. When it’s outcome has started to play out. And so, I don’t even know if I’m good at this yet. I know, now, that I can have a career in it but I don’t know if I’m going to get in it yet. And so, I think I need another three to five years to just know that. So, maybe ask me in three to five years but I suspect I’ll be doing this for 20 years.

My last question for you would be: what advice would you have for people from similar backgrounds who are hoping to get into tech or VC?

Number one would be to save money. Because if you have personal runway then you are structurally more like most of the people who have succeeded. That’s one and that’s not an easy thing to do, but save money. The second would be to try and divide the world of startups, especially in early stage setups, into two functions that constitute a startup. One is building the product. The other one is selling the product. And so figure out if you’re a builder or a seller and don’t be afraid of sales if you are a seller. Choose the one that you have the best chance at. By keeping it simple that way you can maybe orient and organize your activities around one of those two frameworks. Then, the third would be that who you know can be the difference maker, who you know is not whose cellphone and email address you have. It’s who is going to go into bat for you. A lot of people wrongly think that collecting a Rolodex is productive networking, and I think but that’s only 1% of it and I think that probably 60% of it is effective follow-up so I can’t tell you the number of times I’ve said, reach out to me and somebody reaches out. We have a nice first conversation. I don’t hear from them for a while and they reach out asking for something. At that point you’re like asking a stranger for something. What’s that going to do for you? Add value before you extract it. Be thoughtful and followup. Treat people well, meet them where they’re at. Be curious about other’s lives and learn about them. Listen to others and then use that to build your network.