“At the Northside Festival this year, Dennis Crowley admitted in his session with Jerry Colonna that one of the toughest challenges that he has faced as an entrepreneur was having everyone looking to you, counting on you, investors betting on you—and feeling like you’re supposed to know everything. Sometimes—a lot of times—he said, you have to admit that you don’t know what to do, but that you’re going to find someone smart who knows the answer.”