Drag Racing, Gun Violence, The biggest Thursday of my Career & a Meditation Retreat

An Eventful Two Weeks

Trigger Warning: Graphic Content & Gun Violence

For those of you who don't know me well, stumbled upon my glorious substack, and suddenly are enlightened by the life of a venture capitalist tangled in so many projects that his identity has fallen deep into an unrecoverable abyss, I say, Welcome. You've joined for a pretty chaotic edition of my life, and just to set expectations, this is not a "work" newsletter; it's a John newsletter because, however you know me, you will learn a new side of me here.

It was about two weeks ago, on a Thursday evening, I sat in my loft, listening to James Taylor, taking in a pleasant spring breeze, and firing off a few late-night emails before waking up in 8 hours to shoot a mini-documentary on Drag Racing with my friend Ian Handler. We planned three days on-location, and I had just returned from a chaotic run to Target for some last-minute SD cards. As I began to ease into the back half of my evening, a car backfired; I thought, "I've lived in this city long enough to know the difference between gunfire and backfire.", I, apparently, have not trained my ear well enough, as moments later James Taylor's peace was torn apart by automatic weapon fire. I stuck my head out the window, ducked down so as not to catch a bullet, and watched a man scream out in terror that he'd be shot. Chaos continued to unfold as the man sprinted out of frame, holding the remaining part of his torso and drenching the sidewalk in blood. Moments later, an MPD office in an SUV went full speed the wrong way down a one-way, jumped out of the vehicle, and followed the trail of blood, one hand on his weapon, the other hanging free as he propelled himself in a full sprint. 

In classic DC fashion, nobody was caught, and one tweet was sent out by MPD about a shooting investigation, which was the last I heard of it. Not feeling safe, having watched a man bleed out from automatic gunfire in front of my apartment, I decided to retreat to my childhood home 20 min away in Bethesda, shot hoops in the driveway at midnight, and tried to bring myself back to a manageable reality. 

The following morning, I returned to my apartment to grab the film gear and prepare for three days on location. I was ready to move on from the night before, determined not to let last night's events take me out of my groove. As I pulled up to my apartment, I hopped out of my 2010 Acura MDX and immediately stepped into a dried puddle of blood. I proceeded to dry heave my way to my apartment as I grabbed my film gear. (Don't worry; that is the end of the graphic descriptions in this article.)

I did my best to pull myself together as I would have to drive 3 hours and be on camera, winning favor with race car drivers who already were not particularly excited about a film crew from DC and New York getting all up in their shit; we city dwellers were viewed with suspicion from the first moments at the track. Many warmed up to us over the following three days, and we secured an invite to a farm in West Virginia. I did my best over the 3 days to stay present while interviewing folks about drag racing and simultaneously replaying a man's probable last moments in my mind. In the few moments between racing thoughts and racing cars, another VC friend called me with a weekend fire drill, they were trying to come to conviction on a highly technical AI/ML infrastructure deal and wanted my take. I spent about an hour in my car getting up to date on the literature in this specific sub-domain of AI/ML infra, meeting with the founders the next AM, and sending my raw thoughts to the VC. 

As I dealt with a weekend fire drill, race car documentary, and shooting, a call came in from my own portfolio, where a founder was dealing with one of the most critical moments in the company's history and needed me to step up and advise on the matter at hand, I took the call from the woods behind the drag racing track, hunched behind a fence to try and block out the 4,000 horsepower engines. After that matter finished, a second portoco call rolled in right after, leaving me baking in the sun behind the drag strip, balancing my many lives one phone call at a time.

As I went home that night, I could not sleep, so I booked a 5-day silent meditation retreat in the hills of West Virginia for the following Thursday, ready to fuck off from DC, startups, and all the recent stress. As I pulled into the retreat center on Thursday evening, it was clear that this Thursday, of all days in the last 10 years, was the most important of my career; hundreds of millions of value across multiple companies were moving around me, and I was advising on the strategy behind much of it. As meditation retreat volunteers smiled and waved me in, I gave the founders my final flight instructions for the next 5 days, then turned off my phone, retreating into silence.

The retreat deserves a more fun and juicy write-up. I'll just say it was dope, and I only broke my silence when I said "Hot Sauce" on day five. We were eating burrito bowls, and I had gone through quite a bit of suffering in the previous week, but I absolutely would not suffer through a burrito without some semblance of seasoning, spice, and heat. 

I got back to my DC apartment recently, and it turns out that a few hours after I left for my meditation retreat, someone else was shot on my block again. You may wonder, John, do you live in the fucking hood? Dude, move....? The answer is no, not really; I live in a beautiful 394 sf studio overlooking a park in one of the most expensive neighborhoods in the city. There's nowhere to go but the burbs, and I may be pushing thirty, however, I still have some life left in me. One day, the highlight of my week may be cutting my grass before the other dads in the cul-de-sac on a Saturday morning. Until then, I'll be advising founders, meditating, producing documentaries, and writing furious letters to my useless DC city council.