Kayak's Steve Hafner on strategies for weighing opportunity and risk

How do you handle diving into opportunities when you have a company to protect?

Well, you might be a little more risk averse with a company on your hands than you might be in general, according to Kayak co-founder and CEO Steve Hafner, who has stayed with the company since co-founding it two decades ago.

“I gamble [in] my personal life, but I don't do that [in] my professional life,” Hafner said during a Center Stage session at The Phocuswright Conference last month.

While he wouldn’t get into the biggest gamble he’s taken in his personal life, he did touch on what lost business opportunities have haunted him, such as Google’s purchase of ITA flight software.

Years ago, the search giant outbid Kayak for the technology.

“I don't know if anyone remembers ITA software, but it's basically the tech engine that powers Google Flights results. And, you know, we came very close to buying. And if we had, as I said, pulled that caper off … perhaps Google would be writing us checks, not us writing them checks, right? So we'd be able to power them,” Hafner said. “It was a big miss.”

Mergers and acquisitions have been at the core of what Kayak does, the metasearch CEO said. And while it has pulled off “a lot of very successful acquisitions” he said it would have been nice to have that, too.

Looking at weighing opportunity with the risk that comes with it though, is something that Hafner believes his company has done well.

Kayak’s “tolerance for risk” may have held the company back from taking big leaps, he said. But that’s actually been positive for its development on the whole.

“You always think about the opportunities you missed. But you know, we got into Kayak Hotels, for example, [and] lost $20 million,” he said. “Could we have gone bigger? Yeah, but we would have lost a billion like Sonder did, right? So … I think we're very pragmatic at the areas that we choose to explore, and that's overall, served us very, very well.”

He also touched on artificial intelligence, agents, customer service, expansion into Asia, corporate travel, the incumbent companies and whether they will retain power in the industry, regulations and more.

Watch his full discussion with Siew Hoon Yeoh, founder and managing director of Web In Travel, below.