Alex Roy’s Hero’s Journey
Equal parts rogue and idealist, who is the enigmatic character Alex Roy?
Alex Roy is not what I expected.
Walking into our interview I braced myself for a comic book villain, at best an anti hero. This is the public persona that Alex Roy has cultivated. I expected a Negroni of a man, equal parts street racer, playboy, and raconteur; definitely a bitter acquired taste.
What I got, surprisingly, was a friendly and disarming first impression. I was ordering a coffee at Miami’s Imperial Moto cafe ahead of our discussion when he approached. I didn’t recognize Roy, his trademark shaved head was covered by a baseball cap and he wasn’t wearing any leather. Alex seemed more of an earnest enthusiast, not an enigmatic bad boy. People are complicated, so I wondered if there are two sides to this character, and which one was “real”?
Alex Roy first entered the public sphere as a contestant in, then winner of, the early 2000s British reality TV show the Ultimate Playboy. While he initially went on the show because they’d pay his way to the South of France, Alex says the other contestants galvanized his will to win. As a fan of reality TV he realized “the only way I could stay on the show was to be a villain.”
He displayed a similar persona during his street racing days, entering multiple Gumball car rallies with a BMW M5 decked out in German Polizei livery. Channeling a ruthless Stasi street cop does not automatically cast one as the hero.
Later Roy took the bad boy vibe underground, setting the illegal Cannonball cross country driving record in 2006. Going on Letterman, he was officially a celebrity, an aughties anti-hero, a real Tyler Durden. The first rule of Cannonball, don’t talk about Cannonball (At least until the speeding statute of limitations runs out).
When we met up for the second time, we discussed the essential elements of a good story. Alex Roy has constructed such a great character I listened closely. According to Roy, every story must introduce the hero, the hero must face a challenge, and there must be a conclusion. Seems easy, but like everything it's all about the execution.
As Alex tells his personal story, I begin to wonder where he’s in his own narrative arc? The origin myth has been established and more than a couple journeys embarked upon. Right now he’s passionate about his work in autonomous vehicles, has a 3 year old daughter, and is enjoying a new life in Miami. It was not easy for him to get here. This may seem like an end, but somehow I hate to call it a conclusion.
Using his own framework, lets break down Alex Roy’s story, like all good tales the best part is the struggle.
Alex Roy’s Origin Story
When I asked about his childhood, the first thing he told me was that he’s the child of immigrants. Talking about his youth, Roy says “I grew up rather privileged and lucky, I’m the child of immigrants who came to the country with nothing. In New York City Alex “was surrounded by snarky and sarcastic people who always had everything given to them yet always found something to complain about.”
Attending the elite Private school Horace Mann, levels of Manhattan snark must have been off the charts. More uncommon for a city kid was his love of cars.
Roy’s father founded Europe by Car, a rental agency that catered to Americans traveling to Europe. His father also imported exotic European cars like Citroen and Porsche to the United States.
When I met up with Roy he was driving around in the 1987 Porsche 911 Targa that belonged to his father before he passed away. The first thing that struck me was how original the car was, it even had the stock targa top. The second thing was how generous Alex was, he let me drive the car which is incredible considering the sentimental value it must have for him. No villainous behavior, very Rutger Bregman.
This could be a pretty common tale, a second generation carrying on a first generation immigrants legacy. Alex Roy’s journey, however, was just beginning. Driven by an unfulfilled wish from his father, it was time to go Cannonballing.
The Cannonball Period: Crossing the Threshold
The Cannonball Run is an illegal challenge to set the fastest driving time from New York to Los Angeles. Roy broke the record from 1983 in 2006 with a blistering 31 hour time in his stealth 2000 BMW M5. But what inspired him?
“I was young and immature, I had something to prove, my father talked about doing these things and he didn’t” Roy reflected when asked about his motivation.
The morality around this is ambiguous at best, something Roy still struggles with. Looking back, Roy believes “It cannot be argued that doing something like that will save a life, but it’s easily argued that it is very selfish and at best has some mythology value.” There are indeed dangers involved and there’s something antisocial and roguish about devoting one’s life to an outlaw street race.
On the other hand, mythology is important in people's lives, something Roy, as a natural storyteller, understands. When pressed, Roy says “the only good consequence is that I have gotten emails from people saying it inspired them to do something they thought was impossible”.
The inspiration is real, I wouldn’t be writing this without it. I first encountered Roy through his book The Driver: My Dangerous Pursuit of Speed and Truth in the Outlaw Racing World. In 2019 the documentary film Apex: The Secret Race Across America was released chronicling his Cannonball adventure. The artwork for the film is telling, Roy in the dark from behind, dressed in a sinister leather duster with the collar popped. The villain persona is seen once again.
As I spoke with Roy, It seemed the real battle during this period was not against the clock, but with his personal priorities. While his family business atrophied, a kernel of Roy’s future was emerging. The mapping technology he innovated for the race caught the eye of Italian motorcycle maker Piaggio. Roy started a business helping the company integrate early online maps and video into its websites.
While flirting with technology, Roy regrets not committing himself fully. He says “All the technology we used to get across the country around that same time was used on a different path, a much more noble one”. This all happened around the time Google started hiring people from DARPA (Defense Advanced Research Projects Agency) To start the development of self-driving cars.
Roy says he “didn’t learn the lessons that I should have, so instead I went into the media business”. Not to say that wasn’t a success. In 2011 he was part of the team that started The Drive, an irreverent online car blog. Still he had the lingering suspicion his talents could be better used elsewhere.
It took another four years before he began to see his future path. He realized that Tesla, driver assistance, and autonomous vehicles were on the horizon. His interest was sparked in opposition to more traditional views, ”No one else I knew in the automotive enthusiast community felt the same way. They all had the same point of view, electric vehicles are soulless, driver assistance is soulless, autonomous vehicles will never work, and that’s when I knew they were the future”.
This is the future, at least in Roy’s personal story. Bringing us to the third, and questionably final act.
Miami, Argo, and Autonomous Vehicles
Now let’s talk about the Alex Roy I met at the coffee shop, not the outlaw racer or comic book villain. What the new Roy and old Roy have in common is optimism. Roy says he has “always been a big optimist, that extends from my old street racing days to what I work on now, for every single thing someone said is impossible, someone figured it out, you can’t look at history and not be an optimist”.
Going to work for Argo AI, the big optimistic challenge he is now taking on is bringing autonomous vehicles to the masses. The writing is on the wall, and he sees self driving cars as an inevitability. For Roy, this change will be good for society as a whole, “I have a daughter, she is 3 and I want her to learn to ride a bike, I would feel much safer if the critical mass of vehicles were autonomous than the driver’s I see right now”.
This is an interesting perspective for a former street racer, but Roy see’s no contradiction. Speaking about driver assistance, he believes “people think of it in zero sum terms, you increase automation and you remove the human”. Not so, he argues, “the parallel is automation that augments your choices” giving you greater freedom.
The driver can control the car when it suits them, but automation can kick in around congested places like New York City or Miami Beach. Roy asks the rhetorical question, is the driver free when stuck in traffic? Would he be liberated if he could do something else with his time?
Miami Beach is a testing ground for the Argo self-driving cars. All around the beach you see white Fords, sprouting LiDAR mushrooms from the roof, taking passengers for a ride. When you see this the future feels much closer.
Working for Argo brought Roy to Miami, but he sees himself staying for the culture. For Alex, In Miami “you see diversity in the best possible sense. There are people from all over the world, who come to certain cities and stay because it's like a flywheel effect of creativity and kismet”.
Alex Roy grew up in the glory days of New York, when Andy Warhol and Basquiat dined at Mr. Chows, nightlife pulsed, and the city was alive with creative energy. Alex sees parallels between the 80s and 90s in NYC and Today’s Miami, where the cultural moment is “clearly now”.
Finally we arrive at the present, but somehow have not answered our original question, who is Alex Roy and what is the end of the story?
Who is Alex Roy?
It took me some time to wrap my head around him. His tale has a lot of tangents, successes, false starts, and interesting adventures. He is at once a rogue and an idealist. Looking at the blank page, I struggled to tell the story of these two characters.
To do it, I have to resort to armchair psychology. Alex Roy’s story is essentially Jungian, the battle to integrate the shadow self into the core being. For a long time it seemed like his two sides were at odds, with the shadow often winning the internal argument. Now, however, I get the sense he has come to terms with, but not stifled, his inner villain.
If you read Carl Jung, integration is the ultimate state of being. Alex seems to have achieved this, perhaps it’s the final scene of our film. Is Alex at his “end of history” moment?
I doubt it, there seems to be more adventures to come. The Hollywood movie might end here, but perhaps the sequel is just beginning.
Thoughtful and thorough, Andrew <3