The Super Bowl Pivot

It was supposed to be the culmination of Jeff Klee’s young entrepreneurial career: a trip to the 1988 Super Bowl. The 18-year-old had been earning $10 a ticket scalping hard-to-get Dodgers seats for what eventually became their World Series-winning season. The die-hard Broncos fan saved all season with the faith his team would play at Jack Murphy Stadium in that year’s Super Bowl—and they did. And they lost 42-10.

“That was the worst day of my life,” Klee told Portfolio.com

But it was also the season that inspired what would eventually become CheapAir, an American-based, "locally employed" airline-ticketing company, employing over 50 “travel enthusiasts” and selling roughly $150,000 in tickets every day.

“I never thought I’d go into the travel business,” Klee, now the CEO of CheapAir, told Portfolio.com. But in those early days, the aspirations were very modest. “We weren’t selling a lot, but it didn’t take much to make more than we could delivering pizza.”

In the late 1980s Klee made a modest living purchasing classified adds in the local paper for $10 a week and offering Dodger baseball tickets on the back of their star pitcher Fernando Valenzuela's skyrocketing popularity. But after the mild success (and ensuing heartbreak) of earning enough money to go to the Super Bowl, Klee’s business model pivoted to meet the demands of his close college friends—and friends of those friends. In other words, he began organizing trips to Europe for Spring Break, this time, including airfare.

(Read more about how friends can influence a startup.)

Now earning $150 a week in commissions, the recent college grad, still living at home, had no bills to pay and invested everything he earned back into his growing company. He admits that maybe a bit of the earnings purchased the occasional beer, but also said his lifestyle only improved once his business began to improve.

Klee’s big idea back in those pre-Internet days? Ordering an airline ticket without leaving home. He would mail them to you. Revolutionary!

But it kind of was, and it worked. With a bit of scrimping and saving, the startup pieced together $2,000 for what would become its first major investment, a designer phone number. And from that purchase, the company at last had its name, CheapAir.

In today’s travel market, where tickets are often bundled with all-purpose packages including hotel, travel, and entertainment, Klee’s company sets itself apart by offering “airfare intelligence” options such as selecting flights with WiFi, live television, and other amenities not often part of bigger companies search algorithms, according to Klee.

To date, CheapAir has served more than 3 million people, and Klee told Portfolio.com he believes the niche offering of his company, which specializes in just selling tickets, will prove to be a model that works.

"People told us, 'You can’t make money in airline tickets.' Then they told us, 'You can’t make money in just airline tickets.'" And all the while he and his company have persevered.

His advice to entrepreneurs looking to get a vision of their own off the ground?

“Don’t believe the naysayers. There have been naysayers for everything we’ve done. Persevere, work your ass off, and be prepared to commit every ounce of energy you have and more, and eventually something will work out.”

Exactly what will work out is a whole different story. And, like Klee said, he had no idea he’d end up in the travel business.

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Michael del Castillo is a freelance reporter for Portfolio.com.