Why I woke up one day and drove 5,000+ Miles with the clothes on my back
Hello San Fransisco
Ripping and rolling, beeping and bopping across America, I got a few strongly worded texts saying to "return the car immediately." - you see when I left DC on that Friday three weeks ago for a long drive that turned into a 5,000-mile road trip, I actually was not in my car, I was in my parents "extra" / beat up old Audi, driving it for the day to a meeting because it had been sitting so long we wanted to make sure it still ran well. My 2010 Acura MDX was in the driveway in DC; I even had the MDX key, expecting to be home in a few hours. Well, my parents were quite unhappy that I may or may not have broken a handful of federal and state laws by going 112 mph through the desert with their car, I was pretty directly told that they wanted their convertible back, so I dropped it off in Phoenix at a condo they have out there. I swapped it out for a massive Ram 1500 full-size pickup I rented (having lived out of what I consider a high-power lunchbox on wheels, I was done with the Audi and ready for a bit more room on the road.) It was with my mustache grown long, my clothes mainly from a border town Walmart, and sitting in a truck the size of a European flat that I can confidently say I felt like a man genuinely exploring America.
As I roared across the American Southwest, I got caught in a dust storm and stranded on the side of the interstate at a Love's gas station (the marketing is true: great bathrooms). As I lay in the back of the car, I stared into the dust, wondering how many more days I'd have to wait for the dust to die down. It took about 36 hours, but I finally got back on the road, watching trucks teater with 80 mph winds whipping through mountain passes and dust clouds billowing; I lowered the windows and played the Waylon Jennings just that much louder. The more ground I covered and the deeper I got into the South West, the more rural it was; often, I would cover 60 miles without even seeing a gas station.
I was hustling from southern Texas all the way down from Mcallen to San Diego, "them is some rough parts," as some might say. My cell tower pinged Mexico every few days, and the border towns were often less safe than I would have liked; I picked up a small knife at Walmart and kept it on my belt until I got to California. Sleeping in the back of my car at rest stops or small motels, alternating work calls, naps, coffees, and pool halls, I felt quite far from home, and indeed, I was.
But John, I thought this was a happy story...no...it’s, a real story, happy, sad, frightening and exhausting, it the story of real-life, one lived when what you "should" do has been thrown out the window. With the guidance of Joseph Cambell, my favorite mythologist, I followed my bliss, a state of being free, dropping what one should do and following what one wants to do, and I wanted to drive. And drive I did, nearly 5,000 miles later, I saw a newish friend (Nader's sister Natalie) in San Deigo, got a coffee & turkey sandwich, then ripped it to LA, where I stayed with a good friend I had not seen in years, Steve Page. Steve was a great host; he invited me to crash on this couch, we had a dinner party, and he let me drive his mini-motor bike down Venice Beach. Cruising around, I accidentally joined the mini-motor bike group ride/parade. I was flying down Venice Beach, music bumping, mustache dripping to the sides, and a hilarious blacked-out bucket helmet; I looked like a '70s coke dealer and villain from Miami Vice, pushing 30 mph down the boardwalk at sunset.
The next day, I made it to SF, crashed with a childhood friend, Lane, and his boyfriend Andrew, and then the next night, I jumped to my buddy Alec's, where I nailed what I can only dub "a back-to-back bed night." You see, most of the time I stay with a friend, I get a couch. A couch is fantastic, especially in a big city, but in SF, I got a spare bedroom with Lane and an entire spare bedroom with Alec.
With a back-to-back bed night under my belt, I hosted my work dinner, where I rented out a section of a restaurant and invited some friends, portfolio founders, and VCs I've gotten to know, all to mix, have a few glasses of wine, and eat Italian food. As we sat at a dinner that I planned from rural highways of the southwest, my 45-liter backpack lay in the corner, and I knew I did not have a "normal life," something that, to me, is a blessing. Reading back, the narrative in this article is much less clear than the older articles; it does not flow smooth, it's a bit choppy, and the language is rough, but I like it; it's how I feel; I'm making my way, it can be bumpy, but I ain't going to change how my article reads or how my life flows, at least, not today - bumpy and choppy is expected when you're headed in a new direction.
As I spoke to a friend and portfolio CEO in SF, I told him that I didn't want to work as a Partner at one of the big West Coast VC funds even though I'm well positioned to be a partner leading AI/ML investments. The reason is that I probably could not keep slinging hot fire on my substack; I value my ability to write and write what I want, when I want. Ready to turn down any senior roles at major funds, he stopped me with a great line - "Nah, you just have not found the right one yet." He may be right, or maybe.... I'll just start my own.
