In 1989, Bert and John Jacobs designed their first shirts. They knew nothing about the business. For five years, the brothers hawked tee shirts in the streets of Boston and traveled the East Coast, selling door-to-door in college dormitories. They collected some good stories, but were not very prosperous. They lived on peanut butter and jelly, slept in their van, and showered when they could. By the Fall of 1994, heading home from a long, less-than-fruitful roadtrip, Bert and John were desperately searching for answers to keep the dream alive. Little did they know, the only answer they needed was back in Boston, hanging up on their apartment wall. Jake's contagious grin, simple as it was, seemed to express everything the Jacobs brothers believed in. First day ever selling Womens Life is good Clothing, Cambridge Street Fair, September 1997 One fateful September day, they printed up 48 Jake shirts for a local street fair in Cambridge, Massachusetts. They laid Womens Life is Good Clothing out on their rickety card table. By noontime, all 48 of those tees were gone.