Footwear runs in the family. Kenneth Cole’s father had a shoe manufacturing company in Brooklyn. When Cole went into business for himself, he managed to control every aspect of the products he made including sketching designs for the shoes. Cole’s brand is also known for the social issues he embraces, from combating HIV/AIDS to calling attention to the stigma of mental illness. The new documentary A Man with Sole looks at how Kenneth Cole’s company took off after he rented a trailer, parked it in front of the Hilton Hotel, installed a red carpet and sold 40,000 pairs of shoes in three days. He also made it through some hard times, figuring out how to revive his company when the going got tough. I spoke to Kenneth Cole in his Manhattan headquarters about the downside and the rewards of being a risk taker.