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For Luxury Car Collectors, McKeel Hagerty Is the Insurer to Know

Whether in a Ferrari or a Chevy, McKeel Hagerty has a plan to preserve the analog thrill of driving.


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For a guy whose first experience behind the wheel was at age 11, driving a ’33 Ford pickup his father had been restoring since before he could walk, McKeel Hagerty spends a lot of time thinking about the future: AI, autonomous cars, the sharing economy, and a not-so-distant future when the only cars we drive are not the Bluetooth-enabled, four-door cocoons that dutifully transport us to and from work, but the ones we drive for the primal satisfaction of accelerating, cornering, and feeling the mechanical extension of ourselves. Hagerty sees a day when— because of congestion, climate change, and rapid urbanization—we don’t drive private cars to get to the mall or the office, but we might still want to carve S-turns on the weekend in an old MG and that the right to do so will require defending.

“I get that for tens of millions of people the experience of driving is to sit on the 405, and it sucks,” he tells me. “We’re not trying to preserve that. But just a few miles up the coast is Highway 1, an all-time epic driving route. And as long as there are people, there are people who will want to drive it.”

Related: The World’s Most Iconic Vintage Car Races

We’re sitting in Hagerty’s expansive office in Traverse City, Michigan, where he presides over the family business. The room is filled with guitars and an endless supply of auto-related memorabilia. Hagerty was in seminary school in the early ’90s, when his parents were considering retirement. He came back to Traverse City to run the family insurance company with his two sisters. At the time, the business was quietly humming along, with 35 or 40 employees, and insuring about 25,000 classic cars and boats. Today Hagerty insures close to 2 million. For the people who are passionate about collectible cars, Hagerty is trying to be their everything: their content provider, community organizer, and source for market values. “We’re going to build a whole world around people who love owning and driving old cars,” he says.

So imagine you’re thinking about that classic British coupe—the one whose make (Jaguar) and model (E-type) and year (1966) you just typed into a Google search with the words “for sale.” This is where Hagerty comes in. With the Hagerty Price Guide, which has the most comprehensive price information, you can shop with a level of authority once reserved for collectors and other obsessed motorheads. Then, when you finally pull the trigger, that transaction will be entered into Hagerty’s growing database.

Now that you’ve landed your dream car, Hagerty wants to come along for the ride. The company offers roadside assistance and weekend driving tours. If you want to put your car through the paces, there are actual racetracks. There are also ways you can merely flaunt it. In fact, last summer, Hagerty bought the Greenwich Grand Concours d’Elegance, one of the country’s most extraordinary car shows, where guests can admire, and even bid on, rare finds like a ’49 Alfa Romeo Super Sport Cabriolet for $400,000.

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His parents, Frank and Louise Hagerty, founded Hagerty Motors in 1984 specifically to insure wooden boats and classic cars that other conventional insurance outfits misunderstood. They offered fewer restrictions than other collectible insurers, encouraging owners to actually drive their classics, and they understood the economics of classic cars, so they insured cars based on agreed value (what you and the insurer agree a car or boat is worth), not on actual cash value. For example, a 1970 Datsun 240Z is not treated like an import that retailed at $4,000 and has been depreciating for 50 years. It’s valued for its worth, which, because of its current cult status, can easily reach into six figures.

Over the past decade, Hagerty has invested millions of dollars in tech talent to build a database of classic-car data. Essentially, the team found a way to match and decode existing DMV information, credit agency records, and its own transaction and search data to create a clear picture of the market for cars built before 1982. (Trackable, registered VINs weren’t required before then.) They now know who owns which collectible cars, where they are, and how much they’re worth.
The results are revolutionary for car fans. “The number of pre-1982 cars out there is way bigger than we thought,” Hagerty says. And if you separate the “crapped-out old cars that aren’t driven or owned in any kind of collectible fashion” from the cars that they know people search for, there are roughly 19 million desirable vintage cars in America alone. Hagerty wants every one of the people who own, dream of owning, or just want to spend a weekend driving one of them to be in the Hagerty community.

The company’s app-based, Airbnb-style service, DriveShare, which launched last year, seems to be a win-win for both owners and renters. It connects classic-car owners with people who want to rent their cars for a day or a weekend or a week. It lets prospective buyers test-drive cars that haven’t been on a dealer lot in decades, and it gives owners a way to defray expenses like maintenance and insurance. In a sense, it’s Hagerty paying for Hagerty. Arizona-based car nut Jared White explains that it’s been a great way for him to offset some of the costs of his ’52 Dodge and his ’64 Cadillac DeVille. “You see, I have this habit,”he says,“butIalsohaveawife.And this helps me justify it.” On a recent weekend he rented out the DeVille to a New York couple. White isn’t uptight about lending out his DeVille. “There’s always a scare factor,” he says. “But the renters are the kind of people who appreciate the cars and take care of them.”

Hagerty recently hired a chief strategy officer, Kelly Smith, who helped create the Starbucks China mobile app, because he sees the power of data, not just in customer touch points but also in community. “Car people want to share information about their cars,” Smith says. “What if you had a Hagerty sticker with a QR code on your car window, and all someone would have to do is open an app on their phone, scan the code, and they’d get whatever story you wanted to tell about it—the history, what you’ve done to it, the paint color codes. It would all be right there.”

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There are more plans, more ideas. He continues to tell them to me as we take a tour of the company’s private car collection. It is a fully staffed, climate-controlled hangar stocked with many millions of dollars’ worth of automobiles. There’s a Jaguar E-type whose leather interior seems to have achieved peak patina; a Jeep that landed at Normandy; even the Ford pickup his father restored and let him drive as an 11-year-old. “If you wanted to be with my dad,” says Hagerty, “you had to hang out in the garage.” He shows me the Dune car, a ’48 Ford convertible Frank drove one summer when he was hired to take tourists on rides near Lake Michigan. The younger Hagerty found one of the handful of Dune cars, made an offer, and returned the car to Michigan, and to his father, a few years before he passed away. You sense that it was the smartest car purchase the younger McKeel ever made.

“One thing technology doesn’t do is take into account the human satisfaction of certain tasks,” he says. “Like grating cheese. Sure there’s an easier way to do it, but I don’t need it to be more efficient. Just like I don’t want to call an Uber to take me out for a drive.”


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