Craigslist, the simple (often too simple) online listings service. Some claim it has single-handedly annihilated the American newspaper business model. But in so many ways, it has innovated and built on that old model of newspaper listings.

Take for example the Rideshare listings, found under the “community” section. For anybody who’s picked up Kerouac’s On The Road, whether you love it or hate it, you could see ride-sharing services existed even in the 50’s. However, they had the disadvantage of being analog (maybe telephonic), rather than digital and available over a big, big network of computers and mobile devices.

On a rideshare I took from Los Angeles to the Bay Area this week, the driver mentioned he had been giving and taking rides for five years. After I scratched my head and counted a few fingers, I figured out I too had been doing rides on Craigslist for five years! What a nice chunk of time. We published a story  by Evan Winchester about the rideshare experience a few years ago in a magazine I co-founded called The Gutenberg. Evan has taken many rides between the Bay Area and Sacramento, and more than having a few stories, he has the wit and thoughtfulness to try to make sense of the whole experience, in a way that is introspective and true.

My most recent ride includes our driver, Mauricio, a front-seat passenger Zach, and my fellow back-seater Francois. Mauricio’s van is packed full of stuff–he tells me he’s moving up North after I step in from a Jack in the Box parking lot in Canoga Park, close the door and take a seat. He failed to mention this, along with the state of his van (running well, but visually suspect) as we talked and texted on the phone, coordinating pick-up and travel plans a few days prior. But I’m not upset, and I like Mauricio very much. He studied mathematics in school, like me, and now designs sustainable fixtures (solar, water, etc) for low-income families through a Bay Area non-profit. Zach is visiting his girlfriend in San Francisco, though he works in LA doing mobile app development for museums and the like. Francois goes to UC Berkeley and was visiting family in LA, though he’s from Maryland, and is now returning to Berkeley for summer school.

The San Juaquin Valley brings on a swelter. We sleep, chat about this and that, adjust our bodies, joke around, and swap ridesharing stories. Mauricio has given tons of rides, the only bad one was picking up a kid getting out of Humboldt back to Berkeley who lied about not having money and forced Mauricio to drive the kid to two different friends’ houses just to get the gas money he owed. Every other ride was fine, including one extraordinary ride in which Mauricio and several of his friends slept on a giant mattress in the back of a converted school bus. At one point, the driver had to make a detour to Ventura or somewhere and got in an argument with a Storage Facility Security Guard trying to hide a book in a bush for somebody else to pick up later, all while wearing nothing but a tiny, tight pair of tie-die underwear.

But most rides were pretty normal for Mauricio, including this one. Zach mentions a time a passenger smoked out the car (driver excluded), which was by far the most comfortable 6-hour drive he’s taken. Zach also described a far-out story where he, his friend, and his friend’s father got into an argument with a German submarine as their 20′ boat tried to pass through secured waters on their way to a German port, on a long boating trip. The submarine surfaced right in front of them, but after much threatening and American Military talk from Zach’s friend’s father, they were let through, and went to port.

Francois does not have too many exciting travel stories, especially since this is only his second rideshare–the first being his ride from Berkeley to LA for the very visit he is now concluding. The ride down, he says, was insane. The driver barreled down the 5 and made dangerous lane-changes. Francois was left disconcerted; he thought there was no such need to hurry. He brings up that many of his friends think he’s nuts for taking this ride. I echo the sentiments of my mother and her twin sister–recollections of their high school classmate who was killed while hitchhiking. Zach also knows more than a handful of skeptics. We all stretch, smile, and lean back. We feel comfortable, like part of a club, the members of which made a brief leap and landed softly, or at least softly enough to be here, in a van, on the highway, in the heat, heading North.

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