escribblings

On a warm afternoon in early May, I sat at a cafe in the Crown Heights neighborhood of Brooklyn with a self-proclaimed hacker. The cafe was “Cotton Bean,” one of the many spouting up in the Nostrand Ave. corridor catering to a new influx of young professionals in the area. The hacker was Evan Stites-Clayton, former founder of Teespring, an e-commerce platform that was once considered a golden child of the Silicon Valley tech scene, commanding valuations approaching one billion dollars. Now, he was at the outset of a new venture, one that found a nest in Backend Capital’s Hacker Fellowship, a 10-week program that took place in a 23-bedroom brownstone a few blocks from where we now sat. 

“For you, it’s 1:15 EST. For me, it’s 4.65 hacker time,” Evan remarked, “As soon as I leave this meeting, my autopilot will tell me exactly what I need to do next.”

There was a clear feeling that even though Evan and I were sitting across from each other at the same cafe, in the same year 2020, his experience was driven by a technology that planted him firmly in the future. It was this technology which he had built initial prototypes of during the fellowship.

“The investors at first didn’t understand the concept — we had to let them take it home so they could experience it for themselves.

“We think of this as an Operating System for humans. By default we run "software" that results in greed, disharmony, and unhappiness. Ultimately it heats up the planet and destroys Earth's ecosystem.

“Our technology is an OS for humans that allows us to run different software, and thereby get different results.

“We expect most early users to think of it as a self-help or productivity tool, but really it’s much more than that.”

I was a little taken aback by what Evan was telling me, and even more surprised that he already had investors lined up to give his team over a million dollars in funding. Almost on cue, he gave me a knowing look. He pushed a stack of devices across the small table to me — a bluetooth headset, a fit-bit, and a cheap android phone. 

“The hardware solution is a bit of a hack at this point, but trust me, when you try it at home, you’ll get it.”

[ This piece was written as a part of an exercise at the Hacker Fellowship in which we were asked to envision an optimistic future vision of a reporter meeting with us a few months after the program. It was written on Friday March 6, before we realized fully what was about to happen. ]

If you’ve ever shared a drink with me it’s likely that you’ve heard me freestyle. In a certain state of mind non-lyricised conversation starts to feel trivial to me and the urge to flow bubbles up to the surface. So after listening to a couple of my late night verses in early 2018 my friend Albert said, “Hey I know this rap battle in Oakland that’s open to the public and you could easily win. You have to come battle.”

“It’s called Tourette’s Without Regrets” 

So the following Thursday, I went to “Tourette’s” with Albert and some friends, and two expectations were shattered. First of all, Tourette’s was much more than a rap battle: I watched audience volunteers fling mayonaise covered hot dogs at one another’s bared asses and a woman stick needles through her cheeks. Secondly, I could NOT easily win the rap battle. 

It was one thing to spit amusing verses while jamming with a friend at 2am in my own living room, and something totally different to be on a smoke-filled stage in front of a fired up audience, microphone in hand, with 30 seconds to insult another human being as much as possible over a beat I could not prepare for. I’m generally pretty comfortable getting up in front of people and I’ve done plenty of public speaking but this was another level of challenge. 

Not only did I lose that first battle, I lost resoundingly, barely getting in a single insult to my opponent, stumbling over lines I tried to prepare in the 30 minutes before the battle, and receiving zero votes out of five from the judges in the crowd. 

Afterward Albert said “It’s ok, you were great, you had a hard opponent.” It was true that my opponent was really good and he ended up winning it all that night (the rap battle is structured as a single elimination tournament between 8-16 people). I lost but had gotten a taste, and I was determined that I would go back and win a round. 

So I kept going back to the monthly event, whenever my schedule lined up such that I was in the Bay Area on the first Thursday of the month. Each time I had the same results: losing in the first round. 

That Fall when I heard that my friend Erik, another freestyle enthusiast, was going to be attending an 8 week freestyle rap training course in New York City - I decided to use it as a reason to move to NYC and attend the program. I was freestyling a ton to try to improve my game: in workshops, at parties, and at the end of every shower I took (waiting until I had spit a clean four-liner before turning off the cold water). 

In the new year, with all of that training behind me, I made my way back to Oakland and Tourettes. I had a new approach - less trying to plan out verses ahead of time, more being in the moment, focus on connecting with the crowd, staying on beat, and rapping out relevant things. 

I lost again. I went back the following month and lost again. 

At this point I started to wonder if winning a rap battle was actually something I could - or even should accomplish. As a (mostly) white dude from the Oakland Hills, why should I be trying to compete in a Hip-Hop art form? What was I trying to prove? Were there not more important things like saving the ecosystem from climate change that I could be working on? Was I even good at rapping at all?

In spite of those doubts I had a rule for myself: if I’m in Oakland on the first Thursday of the month, I’m going to Tourette’s and I’m going to compete — no exceptions. Plus I always felt encouraged by the battle organizer Asher to keep trying no matter how many times I lost. With my 0-6 record in December 2019 he enthusiastically welcomed me to come back and compete again. 

My first rap battle win started with winning a roshambo (rock-paper-scissors for my east coast friends). Before a each rap battle, a roshambo determines who will rap first. It’s much better to rap second because it allows you to give a rebuttal to whatever your opponent used to insult you. My opponent was the same person who I had gone up against the last time, and I remembered him throwing “paper.” So I went with scissors on my roshambo. Sure enough he threw “paper” again and I secured being second. 

Going into the battle my focus was to be as present as possible. I wanted to try to maintain eye contact with my opponent and an energetic connection with the audience. Because I was going second, my goal was to respond to my opponent’s verse. In his verse, he said something about me looking like Keanu Reeves. So when I started my rap I responded with:

“So I’m gonna say this, and you’re gonna hate this
I took the red pill and you’re still inside the Matrix”

After that round, the host decided that it was inconclusive and called for a second round (usually judging happens after just one back and forth, 30 seconds each). In my second round I started with a line inspired by my attempt to stay present and maintain an eye contact with my partner. 

“Let me tell you how we make it happen
He can’t even look at me in the eyes when I’m rappin’”

My opponent had a good flow, but none of his punch lines landed as hard as my rebuttals, in part because he was in the disadvantaged place of having to go before me in the rounds, and also because I had the support of three old friends standing in front who would scream every time I landed a line. Ultimately, when the judges raised their whiteboards three votes were in my favor and two went for him.

I went on to lose definitively in the next round, bringing my record to a triumphant 1-7.