Bert Jacobs is the co-founder and Chief Executive Optimist of Life is Good. A $100 million privately held business based in Boston, MA, Life is Good spreads positive vibes with its colorful collection of apparel and accessories.

In 1989 brothers Bert and John Jacobs designed their first T-shirts. They began selling their designs in the streets of Boston and out of an old van at colleges and street fairs along the East Coast of the United States. In 1994, following a not-so-successful road trip, they returned to Boston, unsure of the future of their business. It was their common practice to gather friends at their apartment following such trips to share stories and to ask their friends to comment on drawings and sayings posted on their living room walls. On this occasion, one drawing received considerable favorable attention from their friends — the head of a beret-wearing, smiling stick figure and the phrase "Life is good." The brothers named the character Jake and printed up 48 shirts bearing a smiling Jake and the words "Life is good." At a street fair in Cambridge, Massachusetts, the shirts sold out in less than an hour. The brothers began to sell T-shirts and hats featuring Jake in local stores. Demand for the merchandise grew quickly,[quantify] as did national recognition of the brand.

Early on, Bert and John were inspired by stories of people, mainly children, facing great adversity. To them, these stories illustrated that optimism is most powerful in the darkest of times and inspired the creation of a fully integrated business model dedicated to helping kids in need. Life is Good donates at least 10% of its annual net profits to the Life is Good Kids Foundation to positively impact over 120,000 kids daily facing poverty, violence, and illness.