Reid Hoffman knows a thing or two about combining entrepreneurial audacity with savvy risk-assessment. He co-founded LinkedIn in 2003, and his venture and angel investments with Greylock Partners include Airbnb, Facebook, Flickr, Mozilla, and Zynga. "One of the key things is maintaining a sense of youthful optimism in terms of the fact that you can make a difference," Hoffman counsels. But he adds that young entrepreneurs also have to "think crisply about how you navigate risk." So what odds did Hoffman give himself when he started LinkedIn? "I actually gave myself about a 30 percent chance that I would get where I am today," he says. Fortunately, he looked carefully at factors like timing and his network and gave himself the green light.
