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Illustration: Ryan Snook

Most teens are into partying, sports or music. But when Jason Smith was 14, he just wanted a job. With a knack for math and a drive for making money, Smith went door to door in his hometown of Aurora, Ont., asking businesses to let him work for free. An insurance brokerage took him in, and Smith ended up coding a program to track sales leads. His boss was impressed and recruited Smith to build a similar system for real estate leads. And with that, Smith launched a career in the dull but profitable business of processing real estate transactions.

Now, nearly 30 years later, Smith is at the helm of Real Matters, which facilitates mortgage appraisals, insurance inspections and title searches. The company developed a platform that, for a fee, connects lenders to a network of appraisers and other professionals, which are ranked based on user ratings. Smith, who founded the company in 2004, feels no shame in Real Matter’s utter lack of sex appeal. In fact, he credits it as one of the driving forces behind the company’s success. “It’s a big industry with not a lot of smart minds looking at it,” says Smith. “Applying the technology to the processes just excited me as an opportunity to actually get something done versus going after the big thing of the moment.” Smith was right to trust his hunch: The company, enjoying a five-year streak of 50% annual growth, is now the second largest appraisal management firm in North America. From its headquarters in Markham, Ont., Real Matters handles one in 10 U.S. mortgages.

Smith hatched the idea after consulting with banks in Canada, the U.S. and the U.K., which griped that appraisals were the biggest expense, after salaries. “They didn’t like their vendors and complained about slow [turnaround] times,” Smith says. He decided to build an online platform to provide cheaper, faster and more convenient service. Owning the technology also means Real Matters doesn’t pay licensing fees and can pass on the savings to the appraisers and inspectors in its network. His strategy has paid off: Smith has raised $200 million for Real Matters, propelling its value to more than $650 million.

He was originally drawn to the mortgage industry for the money. In 1996, Smith created a website for borrowers to review mortgage offerings and complete loan applications, which evolved into Basis100, a company he sold for $33 million in 2004. At 30 years old, with millions in the bank, Smith moved with his family to British Columbia, where he would spend the rest of his days on perpetual vacation—or so he thought. “I realized that was such a misplaced goal,” he says. After nine months of fly-fishing, Smith was back in the mortgage game.

He talks about appraisal processing like it’s his calling—“I didn’t choose it; it chose me,” he says multiple times during an interview. The intense sense of duty has helped him avoid the shiny allure of other, perhaps more hip, opportunities in tech. “I can see 20 problems in mortgages,” he says. The next step, Smith says, is taking Real Matters public and turning it into a “$10-billion great Canadian tech company.” At 42, he does not plan to retire any time soon. “I’ve realized that fly-fishing is only fun when you have something to escape from every once in a while.”

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