Ashton Kutcher: What Matters Is Entrepreneurial 'Grit'

While entrepreneurship and higher education are sometimes thought to run counterintuitive, Colgate University invited five of Silicon Valley's biggest rock stars to speak to its students this month -- as well as to host a Shark Tank of sorts, in which three young founders walked away with $5,000 in funding.

Panelists included Ashton Kutcher, Airbnb co-founder Brian Chesky, eBay CEO John Donahoe, former Yahoo COO Daniel Rosensweig and former Microsoft business development head Tony Bates.

As founder of venture capital fund A-Grade, Kutcher said that each of the 50-some investments his company has made have hinged upon a person rather than an idea.

Typically, if it’s a good idea, he said, there are at least five other people trying to do the same thing. What sets a leader apart, he said, is “grit.”

While hard to come by, this trait typically develops from people who experienced hardship, humiliation and failure early on -- “It’s usually not the guy who was No. 1 in high school,” said the male model-turned-tech investor.

Airbnb CEO Brian Chesky added curiosity to the must-have list. “The most important thing you can learn how to do is to learn...There are two types of people: people that learn, and people that know.” But like a grandparent who can’t operate a computer or smartphone, he said, many people tend to stop learning as they grow older.

Former Skype CEO Tony Bates also advocated a willingness to share. One of the most exceptional facts about Silicon Valley, said the UK transplant, is that competitors frequently come together to solve problems and seek moral support.

While this doesn’t necessarily mean that people should divulge intellectual property, Bates said that entrepreneurs should never be afraid to ask questions of their colleagues. Besides, he joked, the tech scene is moving at such rapid speeds that nobody really knows what they’re talking about anyway.

Donahoe, for his part, takes issue with the term “entrepreneur,” which he says tends to put too much focus on an individual. The most successful businesses always involve a team, he said -- often with complementary skill sets.

While acknowledging that he would be a terrible entrepreneur, Donahoe says he happened to excel as a team builder. “Know who you are, and discover your own strengths,” he advised to the audience.

For Daniel Rosensweig, this discovery came a little later in life. After four years at Yahoo, he went on to become CEO of Guitar Hero, and subsequently took the helm at online textbook rental company Chegg, where he currently serves as president and CEO. As a longtime and high-ranking executive, however, Rosensweig said he didn’t become an entrepreneur until much later in the game.

“At 40, I finally said ‘I would rather bet on myself than bet on somebody else to bring me the life that I want.’”

Geoff Weiss is a staff writer at Entrepreneur.com.