Bert Jacobs keeps a letter in his pocket that he often takes out when giving motivational talks to groups of people. The founder and chief executive optimist of Life is good got it from 10-year-old twin brothers Scotty and Charlie. Scotty’s leg was amputated at birth, and Charlie is blind. The letter is short. ­Scotty brushes over their challenges, then lauds the way they make each other laugh every day and forget their hardships. Scotty finishes by saying, “I hope you guys feel as lucky as we do to have one another.” Enclosed with the letter is a photo of the twin boys smiling big, toothless smiles with their arms around each  other. This is Bert’s poster child example of the kind of optimism he wants to inspire in anyone who comes across the Life is good brand. That life really is good, that the little things are the big things and that it’s all about your disposition.
For 19 years, Bert and his brother John have sold hundreds of thousands of T-shirts, but it’s never been about the shirts. “I don’t really care about T-shirts,” says Bert. “They’re just a vehicle for the message that life is good and that there’s tremendous power in optimism—seeing opportunities instead of obstacles.” With this in mind, the Hudson, New Hampshire-based company has built a versatile brand of clothing and lifestyle products that offer a positive message, with cartoon-y illustrations of simple pleasures and feel-good phrases like “Enjoy the ride” and “I like it here.” The goal is to get people to appreciate what they have, be it a barbecue with friends, a bicycle or even just a sunny day.
Aside from graphic designs, Life is good’s message, manifests in the philanthropic pursuits of the company and in everyday ­business decisions. The Jacobs have had several opportunities to cash in on big deals with mass retailers, but they’ve always made it their mission to put their positive message before the bottom line. Optimism has proven to be a successful element of their business model, but that has necessitated some risky decisions along the way. It’s not always easy to convince for-profit business partners to give good feelings and charity the same ­priority as dollar signs.
The brothers found themselves in a tough spot in 2004 when the company to which they’d licensed their brand, The Shirt Factory, wanted to keep selling T-shirts rather than expanding into other markets. Roy Heffernan, the Jacobs’ older cousin who handles the company’s financial dealings, recalls, “It was so clear that our agenda and the licensee’s agenda were not entirely compatible. We needed to go our own independent way to reach the goals we were most focused on.” Such goals included the Positive Purpose program, through which Life is good donates 10 percent of profits to the Life is good Kids Foundation, which in turn has donated $9.5 million to causes helping children in need.
The only problem—which the brothers, of course, saw as an opportunity, not an problem—was the $16.5 million they would have to pay to get out of the eight years left in their licensing agreement. The Shirt ­Factory had helped them grow from a $6 million company in 2001 to a $40 million company in 2005, but Life is good still didn’t have the money to meet this obligation. So after being turned down by the banks, they went to New York for a “dog and pony show” with several boutique finance companies to support their investment.
Bert hated the vibes and didn’t want to do business with any of the companies there. Then they met Jason Dratell, founder of Praesidian Capital and spent most of the meeting talking about basketball and the Boston Celtics. The chemistry was natural.
“I was impressed with their focus and passion for delivering a quality product to their consumer as well as their positive message. They’re very straightforward guys, which is pretty unusual in my line of work,” says Dratell, “and frankly, they’re very prudent businessmen. They wanted to grow but were careful not to give up too much control by selling through mass retailers.”
The biggest reason they wanted to maintain control over how their “baby” was sold? Simplicity. They just wanted to sell quality stuff and spread a positive message while making people feel good that their purchases would go to a good cause—that was it. Only two months after these stars aligned, sales jumped. The brothers originally planned to pay down their debt in five years, but they did so in two. “The growth certainly outperformed our initial projections,” says Dratell. The Jacobs and their four other partners were delighted but not shocked. They had been optimistic all along and once, they took the reigns back, everything seemed to work out naturally.

Bert and John Jacobs were the youngest members of a lower-middle-class family from Needham, Massachusetts. Their father, Al, worked in a factory making electronics and ship parts while their mother, Joan, had her hands full at home with six kids. They always knew payday was coming when there wasn’t as much food on the table. But at every dinner, no matter how hard times were, Joan would go around the table and ask each of the Jacobs to share something good that had happened to them that day. “Mom would change the feeling in the room and create a different energy,” says Bert.
The Jacobs carried Joan’s half-full glass with them a decade later when they lived in a 1990 Plymouth Voyager minivan, visiting college campuses and trying to sell T-shirts. Living on a steady diet of peanut butter and jelly sandwiches, they were trying to hang onto their dream of making their idea a success. But the Jacobs believe that even at those times, life was good. They had no money, no business experience or professional skills, and they were given a chance to start a company in a country that embraces free enterprise.
“Capitalism has a bad name right now, and it deserves everything it gets,” says Bert, referring to Wall Street corruption, the recession and CEO salaries. “But that’s because capitalism is being misused. We stand by the idea that capitalism can be the most powerful tool for social change in the world. There’s nothing like the power of free enterprise. All of society’s good inventions came about from people having an opportunity to run a business.”
This is where Bert’s tone really perks up. “In our capitalist society, consumers have shown an ability to take control over the ­sellers. If people believe in your organization, they will build your brand up—and tear it down just as quickly if they don’t. Our community has always believed in us and trusted us.”
Indeed, Life is good is a $100 million company with its own family-friendly music festival. It has expanded into outdoor lifestyle markets with frisbees and footballs, dog accessories, greeting cards (Hallmark) and even coffee (Smuckers). The more ways the Jacobs are able to spread their message of optimism, the better, they believe. They have gotten so many inspiring letters like Scotty and Charlie’s over the years—from people who are living with diseases or parents who have lost a child and still manage to appreciate what they have—that they started compiling them into coffee table books they call “fuel” for positive vibes.
Given their mission to spread the power of optimism, a spirited commitment to philanthropy just makes sense. One initiative the Life is good Kids Foundation finances is Playmakers, which provides training and support to frontline child-care professionals working with children who face “unfair challenges” like poverty, illnesses and violence. Although it’s hard to keep up with the demand for these services, Life is good’s 260 employees—and the consumers buying their products—feel good knowing they’re helping kids in need. From there, the bug continues to spread.
Bert believes this is the key to keeping the optimism engine full of steam. “Some people look at philanthropy as a zero sum thing. That’s not the way we see it at all. We think that by doing this, it helps to build the business and changes the way people look at us. So many companies feel like they have to make a choice—to make the world a better place or go make money. We’re saying you can do both! You can grow the business and grow the community in one fell swoop.”
A lot of companies could stand to take a page out of Life is good’s book, and some already have. Tom’s of Maine donates shoes to a barefoot child somewhere in the world every time it sells a pair—a simple concept that makes it easy for people to feel good about doing business with them. Patagonia is a frontrunner in corporate responsibility for protecting the environment. Whole Foods has begun to focus on selling products from local, organic farmers while continuing to grow a profitable business.
The key to fostering this movement is to reward and focus on positive deviants—people or companies doing good things in a productive way—rather than taxing and punishing everyone else. “Being an ­optimist isn’t just more fun,” says Bert. “It’s ­empowering and it enables solution-oriented action.”