When HomeAway founder and CEO Brian Sharples ’82 visited Colby in January he shared with students his insights from years of entrepreneurial experience.


Brian Sharples ’82

1. Plan Your Attack

“A good idea is really not enough. Ideas, in a way, are a dime a dozen. … Being able to execute is probably the most important thing.”

2. Don’t Fear Failure

“I’ve had some spectacular failures at the beginning of my career and yet, with some things, like entrepreneurship, that’s the way you really learn the craft.”

3. Take Risks

“By the tenth year, only thirty percent of the companies in the U.S. that had been started are still around. … It’s a competitive world and it isn’t easy. … You have to have a bit of an affinity for risk. But if you plug at it enough, if you add a dose of experience to it, you can reduce that risk dramatically.”

4. Have a Contingency Plan

“I see an entrepreneur every week, in Austin or in California. They have a business plan and they have an idea they’re very passionate about, but very few of them think about the things that could go wrong.”

5. Be Curious

“The best skill in entrepreneurship is to be very, very curious. Curiosity leads you to look outside your own ideas and your own sense of what you think is right and allows you to explore both sides of an issue or a problem.”

6. Talk to Real People

“There’s no substitute … for getting out there in the real world and talking to people. I’m amazed at the number of people who come to me with a business plan. ‘Have you ever talked to anybody about this?’ ‘No.’”

7. Stay a Step Ahead

“The Internet has really changed [entrepreneurship]. It’s very easy for people to start businesses now. These days you can spin out businesses a lot quicker, but competition also comes very fast.”

8. Know Your Limitations

“Everybody has limitations. There are things that I’m good at, and there are things I’m bad at. Some of the things that I’m bad at I’ve learned to pinpoint to the kind of partners I need to put things together. When I launched HomeAway I did that with a team of people who complemented my skills.”

9. Learn from Your Mistakes

“My number-one interview technique at HomeAway is to ask people to tell me something they failed at. … You’d be amazed at the number of people who say, ‘Nothing.’ The second question is, ‘Tell me what you learned from that.’ What you can see in people if you ask that question is if they’ve ever really thought about it, what failures they’ve had, and how that helped them to become a stronger person.”

10. Follow Your Heart

“If you allow your passion to become your purpose, maybe someday it will become your professional life. That’s really what most successful entrepreneurs will tell you.”

Related Article: Go Big