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Life is good for Bert Jacobs

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Bert Jacobs may be one of the happiest entrepreneurs in business today. As Chief Executive Optimist of Life is good, he certainly holds the title as the most positive company head in America.

Bert Jacobs, in conjunction with his brother John, the company's Chief Creative Optimist, has turned his upbeat outlook on life into a thriving enterprise that exceeded sales of $100 million in 2014. As a featured speaker at Credit Suisse's sixth annual Entrepreneurs Summit on Feb 5 and 6, which featured the theme "Beyond Innovation," Bert Jacobs shared how Life is good, like corporate giant Nike, turned three simple words into financial success.

The Path of Optimism

In 1989, the brothers named their first business The Jacobs Gallery, which merely entailed the sale of T-shirts on a street corner in Boston. They later expanded their sidewalk venture to selling T-shirts from a van, a mobile business they dubbed The Enterprise, which had them traveling across Massachusetts and down the East Coast, peddling various T-shirts at fairs and universities.

Throughout their travels, the brothers noticed the inundation of overwhelmingly negative images in the media. To counteract this, they sought to create a product that focused on "what was right with the world." The brothers often invited friends to their shared apartment to get feedback on their merchandise. One evening, the informal focus group of friends appreciated a stick figure donning a beret that John had drawn and named him Jake. The character and the simple message "Life is good" resonated with many and was chosen to be printed on 48 T-shirts for an upcoming fair.

On the Right Track

In September, at a street fair in Cambridge, all 48 of the "Jake" T-shirts exhibited were sold in 45 minutes. The brothers knew their likeable mascot and heartfelt message "Life is good" had struck a chord with customers. But the question "What next?" loomed.

"We made one T-shirt that sold like mad, but we didn't know where to go from there," Jacobs explains. However, he and his brother possess the tool of optimism, which Jacobs says allows them to be receptive to suggestions. He states, "We were open when we started selling to retailers. They started telling us that we should sell T-shirts with graphics like ice cream, because it's a simple pleasure people enjoy, and mountain biking, because it's healthy and a way that people celebrate life. We listened to those suggestions and were open-minded. It was the defining moment for us."

Pushing Forward With Their Hearts

The Jacobs brothers hold degrees in Communications and Art, not Business or Finance. Thus, they have tuned into the advice of professionals and close friends over the years, even before opening their flagship store in Boston in 1994. However, the brothers admit that they only listen to advice insofar as it jibes with their own sensibilities. Though some viewed the brothers' investment in a pumpkin festival as money wasted, Jacobs considers promoting the festival for children, in lieu of commercial or print media advertising, when he knew they were on the right track.

"That event helped kids who really needed it and began to build our business. It started moving the business forward based on the authentic idea that as capitalists we can build a business profitably, move it forward, make the world a better place, and help people that really need it. We used compassion and believed that the right thing would happen for the business if we did the right thing." Since that first festival, the brothers have raised over $9 million through their organization Life is good Playmakers, various festivals, and fundraising channels on the company website.

A Positive Strategy

Life is good has exponentially grown since its inception. From the launch of the flagship store on Newbury Street just blocks from where they had set up their first table selling T-shirts, they now have 130 direct stores and 4,500 retailers in 30 countries that sell a diverse array of goods. Additionally, the company has a social following of 2.5 million optimists and growing

Although Jacobs credits the growth of their business to a strategy focused on optimism, he warns entrepreneurs that there are two kinds of optimism – blind optimism and proactive optimism – and that one hinders while the other propels. "Optimism is a pragmatic strategy for approaching anything. The higher your position is, whether that be in business or anything else in the world, the more powerful optimism is, and the more important it is to be an optimist. It's not just business, it's your life. From the moment you wake up you start thinking,'What's right in my life? What's right in my business? How do I grow those things?'" Jacobs explains.

Blind Optimism Is Dangerous

Jacobs stresses that "optimism that is not steeped in realism is dangerous." If you always believe that everything's going to work out, as a leader, you'll be in trouble. You'll sink the ship. The reality is that if you are a proactive optimist who is trying to make things, you're not only seeing the glass as half full, you're looking at the half empty glass and saying to your team, "How do we make it full?"

Life is good's metaphorical glass grows increasingly full. The company has diversified their interests and in 2012 partnered with J.M. Smucker Co. to introduce a new line of coffee to be sold in Life is good's retail stores, national grocery chains, and on the Life is good website. Jacobs has stated that in addition to distributing delicious coffee throughout North America, the partnership will help children in need. Life is good also joined forces with Hallmark, the iconic greeting card franchise, to launch a greeting card collection and co-branded products that will be available in North America. On the company's website, Life is good has reported that 10 percent of the net profits will be donated to The Life is good Kids Foundation.

Exemplary Leadership

Looking at the achievements of the company thus far, their ambition to catapult Life is good from a multimillion dollar company to a billion dollar company in the next ten years, despite their small staff of 250 employees, seems feasible. To be a successful entrepreneur, Jacobs says that one must have vision and optimism. To detractors who focus on what could go wrong or why things may not turn out as they wish, Jacobs says, "It's the optimist that enables things to move forward."

"Let's look at history, let's look at humanity," he explains. "Throughout history, you can't give me a list of the famous pessimists that you love because they've done so much. If you want to be a pioneer in your industry, if you want to be a leader in your industry, it is optimists that become the leaders, that change industries. They are the ones who are seeing something before it exists."