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Bert Jacob, Life Is Good founder

After five years of hawking their self-designed T-shirts at weekend street fairs and college dorms along the Eastern seaboard, brothers Bert and John Jacobs were broke — and wondering how much longer they’d be sleeping in their van. They didn’t want to give up their dreams, but they did want to eat.

So they each took jobs as substitute teachers and agreed to give T-shirts just one last shot. If that flopped, they would toss in the towel on their business for good. “We were right down to the wire,” recalls Bert Jacobs. “It was pretty much if that weekend didn’t work, we were out.”

They printed 48 shirts with a new design: a simple smiling face and the slogan, “Life is good.” At a street fair in Cambridge, Mass., in 1994, they sold out in 45 minutes. “We’d never seen anything like it,” says Jacobs. “They were selling faster than one a minute. You can hardly exchange money that fast.”

And everyone seemed to be struck by the message: old and young, male and female, married and single.

The brothers were stunned. “We were like, ‘Oh my god, this is it.’ We had $78 left between us and then — boom! — that pile of T-shirts became cash in our pockets.”

Sixteen years later, life has been more than good for the brothers. Their company, Life is good (yep, they lowercase the “i” and “g”), is a $100 million business with plans to expand both its offerings (in home goods, wall art and book publishing) and its reach as a global brand. Currently, Life is good specializes in casual clothing, hats and other accessories; dog toys; and a limited selection of home goods. The company has a flagship store in Boston and other company-owned stores across the East Coast and in Canada. Customers can also shop online and find retailers throughout North America at

Jacobs believes the T-shirts resonate with consumers because of the optimistic message — a too-rare sentiment these days. “Our culture is inundated with negative messages,” he says. “It’s fun to celebrate what’s right with the world rather than what’s wrong with it. More than that, it’s healthy and it’s really powerful.”

The two youngest of six children, Bert and John learned about the power of positive thinking from their relentlessly optimistic mother, a woman who saw the brightside even when money was tight. The brothers’ ultimate dream was to share that hopeful message with the world through art.

They chose T-shirts as their message-delivery system because it seemed like the easiest route. “T-shirts were simple,” says Jacobs, who’s a Boston native. “You draw something, put it on a shirt, get in the street, and immediately you get a reaction from people.”

They never expected, however, to achieve the kind of success they’ve experienced. Neither brother knew anything about starting a business or growing one, so they simply learned on the job. “Figuring out the business is kind of mechanical,” says Jacobs. “If we could do it, anybody can do it.”

For Jacobs, 45, life is different than it was when he peddled T-shirts on the street. He traded in his old van years ago and now travels all over the world as an executive and motivational speaker. What hasn’t changed is his commitment to being “authentically engaged” in the business — and to staying in great physical shape.

“Both John and I grew up as team sports guys,” says Jacobs, who once jumped into the Boston marathon on a whim and finished in under four hours. “We played basketball, baseball, football and soccer. When we were older, we played ultimate Frisbee.” These days, his favorite physical activity is surfing. “I was awful a few years ago. I’m still bad now, but I can get up and actually surf — and I love thinking about how much better I’m going to be next year,” says the self-described Chief Executive Optimist.

He’s also hired a personal trainer for the first time in his life. “I did it because I’m on the road so much now,” says Jacobs, who spends a good deal of his exercise time outdoors hiking or mountain climbing or running. It’s made a huge difference in building his core strength and preventing lower-back issues, which can flare up when the 6-foot-5-inch Jacobs is  spending a lot of time on planes. “Since I started with the personal trainer,” he says, “I haven’t had a single back issue.”

Staying healthy helps Jacobs — and his company — give back, a core part of the company’s mission. The Life is good Kids Foundation helps children overcome life-threatening challenges, such as violence, illness and extreme poverty. The company also sponsors a variety of feel-good community events that benefit good causes.

For Jacobs, it all comes back to spreading optimism — whether through T-shirts or financial support. “When we printed the first Life is good shirt, we were so hoping that it worked, not just because we needed the money — we needed that, too — but because, above all, we loved the message. We felt like it was really us. What a gift, to be able to make a living by spreading good vibes. That’s something we’ll never take for granted.”

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