For Two Brothers, Optimism is a Way of Life and Making a Living

Life is good is a Boston-based lifestyle brand that spreads optimism via its T-shirts, home accessories, stationery, and other products. The company was founded in 1994 by brothers Bert and John Jacobs, who – surprise! – are optimists.

“Whatever the challenges are, you’ve got to find ways to laugh, smile, and celebrate every day,” says Bert.

That doesn’t mean he and his brother aren’t competitive hard workers, though. The duo’s entrepreneurial journey began in 1989 when they designed their first T-shirt. They vended their creations on the streets of Boston and door-to-door in college dorms across the East Coast. After sleeping in a van for five years, the brothers returned to their Boston apartment and saw their old drawing of a stick figure character named Jake hanging on the wall. That September, they printed 48 Jake T-shirts for a local street fair. All garments were sold by noontime. Not long after, the Jacobs’ products hit the shelves of local retailers. Today, Life is good is available at over 4,500 stores nationwide.

According to Bert, he and John learned to have a positive attitude early on in life. “While they were plenty of challenges growing up, my mom focused on what was right in the world and the family.” He shares that every dinner, their mother would ask them to tell her something good that happened that day – a practice that they have incorporated into their business meetings.

Life is good isn’t just focused on bringing optimism to its customers, but to children in need as well. So far, the company has raised more than $8 million for the cause – its fundraising efforts include the Life is good Festival, an annual music and arts event launched in 2003. This year, Sara Bareilles, Soulive, and Dave Matthews, among many other artists, will be playing.

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