Brian Sharples

STORY BY SARAH TALAAT & PHOTO BY JENN LEWIS

Brian Sharples, CEO of HomeAway, Inc., is not your typical 20-something tech guru. But he said that is exactly why HomeAway, an online vacation home rental service, is successful. Both Sharples and his co-founder, Carl Shepherd, were well over 40 when they started the company.

“[We] both had held very senior positions in publicly traded tech companies. We weren’t your typical 20 year olds. It was good timing; good relationships with venture capitalists from past businesses. And it was a little bit of luck,” Sharples says.

Sharples believes that his past experiences running publicly traded IntelliQuest Information Group, Inc. and his many business ventures contributed to his understanding of large-scale entrepreneurship before HomeAway even launched.

“We spent months talking to homeowners, businesses, travelers, big companies like Expedia who had tried things similar [to HomeAway] previously. We got to know existing companies,” Sharples says. “Listening to customers gave us ability to craft a business plan to launch HomeAway. And we raised hundreds of millions of dollars through venture capitalists.”

Sharples’ past ventures also taught him what not to do: mainly that he should avoid taking oversized risks—risks that he might have taken when he was younger.

“Some people strike it big when they’re young, but generally entrepreneurship is like any other vocation—you get better as you go,” Sharples says. “Carl and I really understood how to manage risk and rather than start HomeAway from scratch, we decided to acquire the largest companies in big-market countries.”

“We did a lot of scenario planning because nothing remains static for very long. Entrepreneurship is a fluid world—you adapt constantly and anticipate what’s coming next,” he continues. Under his mentor Peter Zandan at IntelliQuest, Sharples learned that businesses operate successfully when run like sports teams.

“Entrepreneurship—the name implies an individual sport, but it’s a team sport. Look for a team who supports you and challenges you because there’s no substitute for putting together a team to get started.” Sharples also cites empathy as a key to dealing with adversity, such as HomeAway’s recent discussions with Austin’s City Council over concerns related to the growth of home rentals in Austin.

“It’s always important to understand the other side…. Understand and then try to help mitigate the things they’re upset about. And the most important thing is to make sure you’re always doing the right thing,” Sharples says. Sharples added that choosing Shepherd as his business partner was a strategic move to balance his own strengths and weaknesses with Shepherd’s. “There’s a yin and yang to business,” he says.

On the recent acquisition of HomeAway by Expedia in December of 2015, Sharples said that the change made sense for HomeAway. “Platforms like Expedia are really in the business of being one-stop shops for travel, so it’s pretty sensible for us to be in their marketplace,” Sharples says. When asked where he enjoys vacationing, Sharples hesitated.

“Well, I probably spend the most time in Colorado, and I eventually bought a place there in Aspen,” Sharples says with a little smile. “But in terms of renting houses I really love Europe: Tuscany and Provence have been really fantastic experiences.”

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