Jason Goldsmith had found the car he wanted: a used, black 1996 Jaguar XK convertible with a V-12 engine.
But it was in Portland, Ore., and he'd found it on eBay, so he wanted a second set of eyes. He found a local prepurchase auto inspector online and hired the company to take a look. The inspector called him back and told him the car had been painted — a detail the owner had left out.
When similar incidents happened with the next three used cars he tried to buy online, Goldsmith said, he saw an opportunity.
"It just saved me from buying four cars that I would have otherwise purchased," he said.
He called the inspection company back and offered to buy the company instead.
"Nobody was doing anything where you could get a prepurchase inspection," Goldsmith said. "You couldn't get eyes on the vehicle to know the history before you were buying it. … Nobody was seeing the car over these longer distances."
It was 2003, and the company, Carchex, was a regional firm with 25 inspectors.
Goldsmith was four months away from selling his own company, TheLoanPage.com, one of the original online mortgage lead marketplaces.
Carchex now has 1,100 inspectors and expects to bring in $100 million in revenue this year, and Goldsmith has expanded the business to focus more on vehicle protection plans for car buyers.
The 40-year-old car enthusiast never got that '96 Jaguar.
He drives a black Jeep Cherokee SRT8 regularly, and has a collection of vintage "toys."
Those include a 1987 BMW 325is, with a 1996 M3 motor in it (he calls it a "Frankenstein" car because of the mismatched parts); a 1987 Porsche 944 turbo; and a 1965 Cadillac Coupe de Ville his father-in-law gave him.
All of them, Goldsmith said, are white with a black interior.
"Right now, I'm in that phase," he said.
Goldsmith, who graduated from Towson University with a degree in psychology, said he spends his free time skiing, hanging out with his family and mentoring entrepreneurs.
He infuses the workplace with his "eat strategy for breakfast" mentality. The 105 employees at Carchex's headquarters at Hunt Valley Towne Centre have access to boot camps, yoga, meditation, healthy vending and a company director of wellness.
"What I get excited about is the culture," he said.
Title: Co-founder, CEO, chairman of Carchex
Education: Towson University '97, psychology degree
Family: married, with two daughters
Hobbies: Skiing, spending time with family, mentoring entrepreneurs