A homegrown Traverse City billion-dollar businessman is out to save the American driving experience. From Hagerty Drivers Club to specialty insurance for classic cars, boats and motorcycles, here’s the vision of the man behind the wheel: McKeel Hagerty.

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A grandfather sits with his grandson curbside at an ice cream joint on Woodward Avenue. The two work feverishly to keep vanilla-orange twist cones from leaking down their wrists. In the humid haze of an August evening, the nearby intersection’s street lights wink in their dance of green, yellow, red, welcoming in a new batch of cars with each cycle.

“What’s that one, Papa?”
“A nineteen-seventy Dodge Challenger.”
“That one?”
“Fifty-nine Ford.”
“How do you know this! That one?”
“That’s a Volkswagen Thing.”
A McLaren Spider.
A 1960 Cadillac.
1957 Porsche Speedster.

As the cars slow to a stop at the light, the air vibrates. Each car is an instrument, its engine’s sound a product of pipe diameters, exhaust layout, body shell, insulation, the combustion in each cylinder rising in waves. RPMs surge and fall as the drivers gun their engines, waiting for the light to turn.

The swelling ranks of cool cars and car lovers on Woodward Avenue tonight, during Detroit’s annual Dream Cruise, is part fantasy, part retrospective, part museum, part drag strip—a parade of hot rods, classics, one-of-a-kinds, collectibles and eye-popping luxury cars, but also just ordinary people driving vehicles they love. Each year, the fest draws 1.5 million people and 40,000 classic cars from around the globe, from as far away as New Zealand, Australia and Japan, for a week of shows, parades, live bands and nightly cruising, making it the single largest car-related event in the world.

During the last few years of the Woodward Dream Cruise, devoted car lovers could even do a drive-up renewal of their wedding vows, courtesy of Hagerty, the Traverse City–born insurance company-turned-automotive-lifestyle company. Dozens of car geeks roll up in their beloved rides to a backdrop that reads “As Long as We Both Shall Cruise,” where they’re provided bow ties and veils, cupcakes and sparkling apple cider and a chance to reaffirm their love. For each other or their wheels? Either might apply.

After all, car love runs deep. It’s a sentiment Hagerty as an institution is deeply in touch with, and one CEO McKeel Hagerty has inherited, intuited and used to transform a family niche business into a global phenomenon—one with a surprising mission to preserve a disappearing aspect of American culture.

Boys dusting off car covered in snow

Photo by Courtesy of McKeel Hagerty

Boy next to a car covered in snow

Photo by Courtesy of McKeel Hagerty

The Hagerty Cinderella story is well known to many, both in Northern Michigan and within the car community. Although the company began in 1984, the seeds of it were sown much earlier.

Frank and Louise Hagerty were insurance agents by trade, but their shared passion was their collection of classic cars and boats. “Cars were where it was at for my Dad,” McKeel Hagerty says. “We had a car workshop attached to the house. My earliest memories are when I was around two years old, sitting in a truck he was restoring.”

That passion was a given that shaped the family dynamics. “If you wanted to spend time with Dad, you were in the garage with him,” Hagerty says. “I had the [car] bug early, but it was [about] connection with him.”

A Hagerty family ritual: Each child, at the age of 13, chose a car as a project to restore with Frank. “These were cool cars, but not big fancy collectibles … it didn’t matter how valuable,” Hagerty says. “Even when I was eight, nine years old, I knew my time was coming to pick a car out.”

The two used to watch James Bond movies together, so Hagerty’s first wish was for an Aston Martin. But it was a snow bank that turned out to hold the seed of a restoration project that would result in a dream car for the ages.

Frank and McKeel knew a local body shop owner who had two old Porsches sitting in the foundation of an unbuilt garage on Old Mission Peninsula’s Bluff Road; from age 11, McKeel started visiting with his dad, nudging the guy, making offers on the decrepit 1967 911S (the “S” stands for sport, an enhanced version with a more powerful engine). At last, for $500, the deal was made and father and son dug it out of the snow and brought it into their workshop, where it began a slow and steady transformation.

The fire-engine red 911 is still in Hagerty’s possession. “This is one of the most sought-after Porsches, one of the Holy Grails,” he says. In mint condition, the car is worth $368,000; to McKeel, it’s priceless.

Headshot of McKeel Hagerty

Photo by Courtesy of McKeel Hagerty

It’s in keeping with the family’s ingrained passion, the one serving as the genesis for the family business that goes far beyond cars themselves and instead taps into the human attachment to them.

Hagerty Insurance launched in 1984, when Frank and Louise Hagerty faced a personal frustration: they couldn’t find insurance for their own classic boats and cars. Hagerty Insurance began in their basement as they created policies for hard-to-value/insure classic boats; within a few years, half of all classic-boat owners were Hagerty clients.

By 1991, the company was ready to expand to classic cars and introduced a specialty auto policy. Not long after, in 1995, two of the family’s grown children, McKeel and his sister Kim, returned home to Northern Michigan to run the family business.

“Very few businesses succeed by creating some new human need,” McKeel Hagerty says. “They identify a need or emotion that was there and tap into it in a way that hasn’t been done before. We tapped into the emotion that is in our members, and certainly was in my family.”

The love of cars is a widespread enough emotion: According to statistics, 69 million Americans identify as car enthusiasts and 43 million American vehicles fall into “car of interest” categories—sports cars, vintage cars, collectibles, something a step beyond the family SUV. The numbers are powerful enough to continue to skyrocket Hagerty’s growth; in 2021, the company reported a 24 percent year-over-year revenue increase, to $619 million, and bills itself as “an automotive enthusiast brand offering a specialty automotive insurance platform.” Last year, Hagerty merged with Aldel Financial Inc. and went public, its pro forma value skyrocketing to $3.1 billion.

It’s most definitely a story of local family makes good—very good. But beyond that, it’s about love.

The Hagerty mothership in downtown Traverse City is an elegant brick-and-glass building perched in the heart of Old Towne. At the front, a cylindrical three-story glass showroom holds a rotating collection of classic cars that gleam in the slanting light of the morning sun, as do the cars that pull up to it for the Friday morning Cars and Caffeine event Hagerty hosts. Here, an introduction is easy, and includes the most musical words a collector can hear: “Tell me about your car.” Enthusiasts park side by side, pop hoods and work in quick bites of complimentary donuts as they make small talk, field questions and admire each other’s wheels.

Similar events have caught fire around the country, drawing car people to nerd out and chat to the point that often the big silver carafes of coffee don’t get a lot of action—it’s all about the cars. As friendly as these get togethers are, they’re easy to write off as a nice-for-them klatch for obsessives, not the rest of us, but McKeel Hagerty has a response to people who tell him they’re “not car people.”

“I’ve developed my own sort of Maslow’s hierarchy of needs, when it comes to cars,” he says. “At the bottom is transportation value—the need to get from point A to point B.” Up a level? The much more interesting social value, “comparing one car versus another as a signaling device,” he says. (Think campaigns such as “Love: It’s what makes a Subaru a Subaru.”) The highest level is what Hagerty describes as “transformational value through driving and exploration.” This, he adds, is what Henry Ford intended when he built a car that an ordinary person could, as Ford said, “enjoy with his family the blessing of hours of pleasure in God’s great open spaces.”

Hagerty claims that a lot more of us fall among the loftier emotional levels of the car-ownership hierarchy than we’d admit, with few Americans feeling simply “meh” about their cars. Why else would we choose our colors and option packages so carefully, add the pine-shaped air fresheners and thoughtfully curated bumper stickers? Who hasn’t flown down a beautiful stretch of road, music cranked, windows down, feeling the blessing of those hours of pleasure?

Most of us have. Some of us feel that pleasure intensely and often. We are, Hagerty insists, just like their clientele—people who love a car or cars for reasons of nostalgia, curiosity, appreciation or to make a statement. Maybe our car is in fact a car of interest—that convertible we garage until summer, the high-performing German luxury ride, the midlife crisis sports car, the old muscle car. The best thing that happens to anyone who owns a car they deem special is the shot of joy and validation when a passerby eyes their wheels and gives them a thumbs up. (The worst? When they visibly, publicly break down by the side of the road. “Total thumbs down,” says Hagerty.)

And then, there are those who center their lives around the pursuit of extraordinary cars—the realm of race-team ownership and multi-million-dollar auctions and museum-like garages. These are among some of Hagerty’s most fascinating clients.

Red car driving down road

Photo by Courtesy of McKeel Hagerty

“The lengths people will go to in order to get great cars is unreal,” Hagerty says. He admits to knowing a collector who purposely married into a family with an enviable stable of cars. He also knows someone who created a submarine for an early attempt to reach the RMS Titanic in order to recover the fabled 1912 Renault Type CB Coupé de Ville—accurately referenced in James Cameron’s movie—known to have gone down with the wreck. It was never found, but the attempt says everything about what revs the engines of the car obsessed.

Cars hold value for countless reasons, but the ones that interest Hagerty personally, he says, are sports and racing cars from the mid-1950s through 1970, explaining that the most valuable cars tend to fall in that range with only a couple of exceptions. “Part of it, for me, is the cars from that era are simply beautiful,” he says. He falls hard for those that have some recognizable history. “When I see a car connected with an event, a famous race or a great driver, that kind of moves me … I like to take the mental leap of ‘what would that have been like?’”

His dream ride is the famous Mercedes 300 SLR raced by Sir Stirling Moss, one of the greatest drivers in the history of motorsports, who set the record in 1955’s legendary Mille Miglia (1,000-mile) race in Italy. “Most people would tell you it was the greatest day of driving, ever,” Hagerty says. And here, Hagerty’s CEO polish turns to a bit of schoolboy crush; he admits he’s actually seen the car a couple of times, the one enthusiasts simply call “722,” the numbers painted on the side of it representing Moss’s 7:22 a.m. start time.

What gave him chills, he says, was the last time the car was in Monterey, California—at the Pebble Beach Concours d’Elegance, one of the most prestigious car events in the world, where collectible cars are judged for authenticity, function, history and style.

“The head of marketing for Mercedes called me and said, ‘Hey dude, come over to the trailer—we’re about to start 722.’” And so, a small group gathered as the ignition was turned and the sound, Hagerty says, was “extraordinary … it’s difficult to explain. Not loud … but not quiet. It was literally like a rocket ship running on four wheels.”

His own best moment behind the wheel of a car was when history, driving greatness and car love converged in one magical afternoon. “I was at an event in Sante Fe driving a Jaguar D type—this beautiful multimillion-dollar car,” he says. “I spent the entire afternoon chasing Stirling Moss, who was driving a brand-new Mercedes, through the mountains. When we stopped for lunch, he came over and said, ‘Wherever did you find your D type, and how long did you have it?’ I said, ‘It’s not mine, but I think you raced against it once in Cuba.’”

Based on that shining moment outside of Santa Fe, if there is a summit to the triangular mountain that is Hagerty’s hierarchy of car needs, he has reached it—at least personally. But professionally, his concerns lie with the future as much as with his love of the past. A future in which the art of driving could soon disappear.

Hagerty Insurance could have stayed a thriving and profitable niche insurance company. But as McKeel Hagerty says, “you don’t find a lot of emotional attachment to a company that just sends you a bill once or twice a year.” Instead, under his guidance, it became something entirely new: an automotive lifestyle brand with a mission and a community.

A car person finds their way to Hagerty.com and soon finds not only practical products—like insurance and valuation tools—but also a membership experience with multiple layers. Former Road & Track editor-in-chief Larry Webster helms a richly designed bimonthly magazine, Hagerty Drivers Club, that mails to all members. Popular videos, such as their “Barn Find Hunter” series, have a sturdy fan-base as well, with more than 100 episodes chronicling the discovery of under-the-tarp treasures not unlike Hagerty’s 911S.

Members also receive industry discounts, VIP access to Hagerty-branded events and car shows, and roadside assistance—but most important, they find each other. “Car people live in this community,” Hagerty says. “And the purpose of it is to save driving and car culture for future generations.”

Because Hagerty believes that the culture of American driving does, in fact, need to be saved.

Americans are driving less in recent years—the pandemic and then the soaring gas prices have diminished the number of miles we put on our cars these days. Consider too the changing culture of Uber, Lyft and all things deliverable, as well as the shift in demographics: Boomers and Gen Xers saw driving as fun and offering a sense of freedom; Millennials and Gen Z see cars more negatively, as expensive, burdensome, even ecologically uncool. According to data from Jerry car insurance, while 70 percent of Baby Boomers and 66 percent of Generation X got their licenses as soon as they could, only 53 percent of Generation Z and 54 percent of Millennials said the same.

The feel of driving is changing exponentially as well—gasoline combustion engines are likely on their way out as energy and global warming concerns are addressed, and AI and driverless cars may render driving skills less of a must-have and more of a nice-to-have in the not too distant future.

“We need to create a lot of on ramps to the car world—to make it approachable, friendly,” Hagerty says. And although the company has scooped up ownership of numerous high-end Concours d’Elegance events, they also champion interaction that’s less velvet rope, more hands-on.

Steering wheel of car

In 2021, Hagerty created the Hagerty Drivers Foundation, which provides scholarships for students in the automotive field of education, offers financial support for automotive startups and grants for business ideas, and continues to build the National Historic Vehicle Register, which documents the history of America’s significant automobiles, preserving their information for future generations in perpetuity at the Library of Congress.

The company also offers various hands-on driving opportunities like the Hagerty Driving Experience, a two-hour session that puts drivers behind the wheel of classic cars and teaches the basics of starting, operating and driving a manual transmission. Club track days, a racing school and a platform for helping people rent out and experience old cars all create opportunities for ordinary drivers to get hooked on vintage vehicles. And there is, of course, the weekly Cars and Caffeine from late spring until fall each year.

Internally, every Hagerty employee can learn about repair and restoration, and the staff spend hundreds of hours collectively restoring a single car each year through the Employee Restoration Program. Recent completed restorations include a 1930 Ford Model A Deluxe Roadster, 1969 Chevrolet Camaro SS, 1964 1/2 Ford Mustang Coupe and a 1967 Sunbeam Tiger Mark I.

One of the gaps Hagerty hopes to bridge is the perception that special interest cars are the domain of the rich. “It’s not about wealthy people,” he insists. “This is a much more down-to-earth activity. People with very different educational and socioeconomic backgrounds can understand and appreciate [cars]. I can park a really cool Camero next to a really cool Ferrari and we can both acknowledge each car for what it is,” he says. “It’s not a complicated discussion.”

The other is generational. “It used to be you had to be pretty mechanically inclined—forty years ago if you were into classic cars or restoring vehicles, you had to work on cars too, which filtered people out,” he adds. And quite frankly, one of the current challenges in maintaining a car culture is that the next generation of drivers doesn’t really know how to use tools, never mind how to change a flat tire or tame a squealing drive belt. Perhaps the chance of falling in love with a car can reverse the trend; and cultivating that love is what McKeel Hagerty is banking on.

Classic cars lined up

As the evening grows dark, the light on Woodward blinks green once more and tires squeal, sending the smell of rubber and exhaust rising into the dusky night. The ice cream is long gone, only a sticky memory as grandfather and grandson spend just one more moment, one more light cycle watching the parade pass by.

Together, the cars are an orchestra, their shockwaves of sound vibrating through the chests of thousands of onlookers who line the fabled cruising strip. By now people have gathered on medians, perched on tailgates, popped open camp chairs and are peering over restaurant railings and rooftop decks, all to take in a spectacle born from the American love affair with the automobile.

In the midst of such an outpouring of car love, it seems hard to imagine a different future, one where quiet electric cars glide under the guidance of artificial intelligence, one where a kid never falls in love with a dream car, never knows the pleasure of clean white wall or polished chrome or tinkering under the hood until the engine purrs.

That’s a future Hagerty is willing to re-imagine. “We’ll need to be a bridge generation between this and electric vehicles,” he says. “That’s the call we have to answer to. We want to position ourselves in the evolution.”

In the meantime, he’ll continue to push the parameters of their work—in media, with events, in educating drivers and creating and preserving culture. And at the end of the day, he’ll hit the road home through the sinuous curves of Center Road, cruising north on Old Mission Peninsula in a fiery red 1967 Porsche 911S, the only car, he says, that he’ll never sell.

“We’ll grow old together. And that’s how it will be.”

Cara McDonald is executive editor of MyNorth Media and Traverse, Northern Michigan’s Magazine. She is a car person.

Photo(s) by Courtesy of McKeel Hagerty