Meet Bert Jacobs: Chief Executive Optimist

​Bert Jacobs owes his success to the enduring power of optimism. 

As co-founder and CEO—chief executive optimist—of the apparel and accessories brand Life is Good, Jacobs has devoted his adult life to creating clothing that focuses on the positive, and he uses the company’s proceeds to help children in need. 

Jacobs and his brother John launched their business in the late 1980s, selling T-shirts in the streets of Boston and at colleges up and down the East Coast from the back of a used van dubbed “the Enterprise.” They vowed to go where no T-shirt guys had gone before. And in 1994, with less than $100 in their pockets, they formally established the company Life is Good.

In the nearly three decades since, Life is Good has grown into a business with $150 million in annual sales. The company’s T-shirts and other products are sold at thousands of retail outlets across the U.S. and Canada. Remarkably, the company has accomplished this despite spending no money on advertising. Instead, the business relies on consumer word-of-mouth to drive growth. 

Today, Jacobs remains focused on guiding the overall vision and creating the art and messages for the Life is Good brand. 

The Needham, Mass., native and his brother are also using Life is Good to give back to communities across the country. The company donates at least 10 percent of its annual net profits to the Life is Good Kids Foundation, helping more than 1 million children every year mitigate the effects of poverty, violence and illness. To

inspire others to focus on the good in their lives, the two brothers wrote Life is Good: The Book (National Geographic, 2015).

Jacobs is also an in-demand speaker, as well as the co-host with John of the popular Life is Good Ping Podcast. The pair has spoken with famous personalities such as Katie Couric, “Blue Bloods” actress Bridget Moynahan and former Beatle Ringo Starr about the power of optimism.

Jacobs will be a keynote speaker at the SHRM Annual Conference & Expo 2021, scheduled to take place Sept. 9-12 in Las Vegas. He recently spoke with HR Magazine about his life, career and optimistic outlook.

Naming the Company

When we started out, we didn’t have any money and we knew from a marketing standpoint that if nobody knew our company’s name, we would need money for advertising and marketing. Life is Good is a phrase that existed, but we just trademarked it before anyone else. We wanted the name to be uplifting because in your name you can say a lot. Oddly, a lot of people don’t think that through. People can interpret Life is Good a lot of different ways, but it sounds positive and it’s kind of a big statement. 

Life is Good is also something that we believe, and so it was something authentic that we could really get behind and work hard to build. 

Source of Personal Optimism 

My optimism came primarily from our mother. When John and I were kids, both our parents struggled with depression, believe it or not. But their coping methods were different. Our dad yelled and screamed. He wasn’t a bad guy, but he had six kids and no money and he just lost it. 

My mom, on the other hand, had her own struggles, but she coped with them by singing and dancing. She also had this ritual at the dinner table where she asked us, “Tell me something good that happened today.”

That had a huge impact because it taught us that there are always things to celebrate and while there are always bad things, it’s smarter to put your limited resources into the good things.

Optimism as a Business Philosophy 

There are a lot of misconceptions when it comes to optimism, so I like to use the analogy of shooting basketball foul shots. If you see [professional basketball player] Seth Curry step up and drain 30 in a row, people think he’s a great foul shooter. But he wasn’t born making free throws. He practiced and practiced. Optimism is like that. An organization’s leaders need to understand that optimism is important, and they have to enable people to practice it.

The best way as an organization to overcome obstacles is to put most of the focus on the opportunity. Optimism doesn’t mean being blind to the challenges; instead, it’s about focusing on solutions and working to get through problems. We consider ourselves practicing optimists.

The Pandemic—a True Test for Optimists

There’s no doubt the pandemic presented a challenge to the company. Early on, our discussions were about bankruptcy because most of the retailers in America shut their doors and canceled their orders. We were faced with trying to figure out how to cut half of our staff—and that meant 200 people losing their jobs.

In the end, we did something that was a little risky: We started a brand-new product development model—ultra-speed to market—that cut our development from 12 to 18 months to as little as two days. 

We also decided to design T-shirts about what’s happening in the pandemic, but we did it through the Life is Good lens and we promoted healthy behavior, like “Stay calm, stay cool, stay home” and that type of thing.

After we did all this, 2020 became the best year we ever had from the standpoint of business performance, and we saved every single job at the company. 

Post-Pandemic Work Life

I think the majority of changes to work as a result of the pandemic are here to stay. There were a lot of downsides and difficulties for individuals and organizations, but there were silver linings and lessons learned. 

As a country, we were forced to rethink working space. Pre-pandemic, if you asked people if it is necessary to be in the office five days a week, most would have said yes. Now you get a completely different answer. 

We conduct employee surveys in our organization, and I was really proud of our staff because they expressed a lot of personal things and not just what they thought we wanted to hear. I ended up reading all their responses. Among the things they told us is they had time to walk every day while working from home during the pandemic or they had time to fix a personal relationship because they no longer had to commute more than one hour to work each way daily. 

Our employees also were incredibly productive across all departments throughout the pandemic, and they told us, “Please don’t let it go back to the way it was, because this has been incredible for us.”