How I Got Here

Trupanion’s Founder Went from Selling Cigars to Insuring Pets

Darryl Rawlings hatched the idea for his pet insurance company while living in a tent on a beach in Mexico for three months.

By Darren Davis December 8, 2015 Published in the December 2015 issue of Seattle Met

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Photo courtesy Trupanion

Sixty-five percent of U.S. households are home to at least one pet, and in 2015 pet owners will spend nearly $16 billion caring for their furry friends. Yet far less than 10 percent of cats and dogs have health insurance. In 1999, Darryl Rawlings set out to provide a reliable insurance option for pet owners, and after going public in 2014 Trupanion has become one of the fastest-growing providers in North America. With a new 228,000-square-foot Georgetown office set to open in 2016, Rawlings looks back on his winding path from cigar salesman to CEO.

1978: Loss in the Family

When Mitsy, the family poodle, came down with a serious but treatable stomach issue, 14-year-old Rawlings sat in a Vancouver, BC, veterinarian’s office and watched his parents run out of options: The vet could fix Mitsy’s twisted stomach, but the surgery was too expensive. Just like that, a beloved member of the family with a treatable condition had to be put down. “A horrible outcome,” Rawlings remembers. “For the dog, for a teenager to see this happen, for my anxious parents, and for the vet who wanted nothing more than to save our pet.”

1989–1992: Escape to Mexico

After graduating with a marketing and technology degree from British Columbia Institute of Technology, Rawlings spent his early 20s traveling—300 days a year to more than 50 countries—selling emerging tech to cellular providers. Soon he became disenchanted with the industry, however, and did what many young people only dream of: For three months Rawlings lived in a tent in Mexico, surfing every day and “doing the proverbial what-am-I-going-to-do-when-I-grow-up bit.” 

1993–1998: A Car Full of Cigars

Returning to America with about $150 to his name, Rawlings decided to sell cigars. So he maxed out his credit card on 10 humidors and $2,500 worth of cigars, loaded his inventory (and his dog) into his car, and drove around western Canada. Four years later he had a retail location and an online store, and his products were in 500 bars, restaurants, and golf courses in BC and Alberta. But it still didn’t feel right. “I had this dog that smelled like cigars,” he says, which reminded him that he should be doing something he was passionate about.

1999–2004: Cats and Dogs

Rawlings sold his cigar company for half a million dollars and used the capital to buy a boat, prepay two years of moorage on Granville Island in Vancouver, move in with his future wife, and start developing a pet insurance company. He admits to not knowing what he was doing, so he started talking to the medical community to identify the most common roadblocks in paying for veterinary care. “After all, I’d have to meet the needs of not only the pet owners but the vets as well.” By 2000 he sold his first policy in Canada, and four years later Trupanion was the first profitable insurance provider for cats and dogs in North America.

2005–Present: Time to Go Public

Following another soul-searching trip in Mexico, this time with his wife and infant son in tow, Rawlings decided to expand to the U.S. He spent two years raising $22 million—much of it from Howard Schultz’s venture capital firm, Maveron—and in 2007 moved his family to Seattle, where he eventually opened up a new office in Ballard. Seven years later, in July 2014, Rawlings took the company public. “We rang the bell at the stock exchange,” he says. Now, as he preps for the move to Georgetown, he’s hiring 15 to 25 people per month—or around one employee for every 500 new pets insured. That’s a lot of cats and dogs that won’t have to meet the same fate as Mitsy.

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