The First Cars of CarGurus

It could be a Pink Cadillac or a ‘69 Chevy (with a 396, Fuelie heads, and a Hurst on the floor). Cars have long been associated with independence and the open road, and no car epitomizes newfound freedom quite like your first car. Contrary to popular belief, not everyone at CarGurus is a gearhead—although some certainly fit the description. Our team covers a wide range of responsibilities, from software engineering to business development, and recruiting to… well, somebody has to edit this blog, right? Simply put, if owning a garage filled with Pininfarina was a prerequisite for employment, we’d have a much harder time growing our staff.

Our Gurus run the gamut, which means our cars do, too. And like most of the population, even our biggest car fanatics had to start somewhere.

One of CarGurus’ earliest team members, Pat’s a dedicated music fan, traveling near and far to catch the next show. But his first car, a 1989 Saab 900, nearly didn’t make it onto the road. “After having sat in my parents’ driveway for a few months, waiting for me to get my license,” Pat explained, “a family of bats took up residence under the hood. Naturally, once it was back on the road, we called it the Batmobile.” We can’t say for certain how the bat family managed their life during exodus, but it’s safe to say Pat enjoyed following his favorite bands’ tours.

Madeline wins the prize for oldest first car, with a 1976 Volkswagen Beetle Cabriolet. Long before she started recruiting engineers for CarGurus, however, she had to strike a deal with her father just to get behind the wheel. “I have fond memories of driving it down the PCH all the time in California. My father found it for sale for $6,000—we met the seller at a sushi bar. I paid $3,000, and my father picked up the rest. He sort of owed me, considering that’s how much I spent on mechanic bills when I was driving his Datsun.”

Jake is the man behind (the man behind) the camera for many of CarGurus’ videos, be they test drive reviews, impressions, roundups, standups (or screw-ups). Living in New Hampshire, a car was an absolute necessity for any semblance of a social life. Shortly after getting his license, he started driving a 1998 Volvo V70 station wagon, and as he remembers it, “My dad bought it, and we called it the silver bullet. It wasn’t the R trim… but that didn’t stop me from totaling it when I rear-ended my classmate’s mother.”

Alyssa is a true Car Guru, in more ways than one. Not only has her code helped build much of our website, but her current BMW 135i earns the jealousy of plenty of resident enthusiasts. Of course, things weren’t always so rear-wheel-drive: “I bought it myself, but I have no fun stories about my first car, a 2009 Scion xD… They get you in the door with mix CDs and promises of sweet LEDs, but they don’t tell you the car is actually pretty boring to drive. It did have a big hatch, however—we once transported a big chair ‘in’ it—about two-thirds was hanging out the back. I owned it for 3 years before I realized Miata is always the answer.”

At least until BMW becomes the answer, I guess.

Finally, there’s Kaylin. If you needed proof that not all CarGurus are gearheads, look no further than her first car: a 1993 Buick Century Wagon, complete with wood paneling and maroon velvet upholstery. “After a guy totaled my mom’s car, I paid for my Buick with a $500 check I received from his insurance company. I used to drive it around town with all of my friends sitting on the front bench seat with me—one of those friends actually works for CarGurus now. It had wood paneling outside and a maroon velvet interior. I once rolled up to soccer practice in it. When my coach saw it, his mouth dropped open and he rolled his eyes. It drove like a boat, started shaking around 60 mph, and my elder brother drove it across the country from Connecticut to California in 2013. In all likelihood, it lives in pieces somewhere in Tijuana. That’s not a joke.”

Actually, that sounds like a pretty great car to me.

What do you remember most clearly about your first car? What kind of car was it?

-Matt Smith

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