Bert Jacobs | Life is Good (Episode 502)

Bert Jacobs (@Lifeisgood) is co-founder and CEO (Chief Executive Optimist) of The Life is Good Company, which spreads the power of optimism through inspiring art, a passionate community, and groundbreaking nonprofit work. He’s also the co-author of the recently published Life is Good: The Book.

The Cheat Sheet:

  • Why is optimism so important?
  • How did Bert Jacobs and his brother John turn a t-shirt company that operated from a van into a multi-million dollar business celebrating optimism?
  • Gratitude is just one “superpower” unlocked by practicing optimism — we talk about nine more.
  • Learn how these superpowers allow you to overcome obstacles and embrace opportunities.
  • Less is more: why do simple things often resonate more than the complex?
  • And so much more…


According to Bert Jacobs, today’s guest and co-author of the book Life is Good: The Book, optimism is a powerful and pragmatic strategy for accomplishing goals and living a fulfilling life — it allows you to access the 10 key “superpowers” accessible to us all (openness, courage, simplicity, humor, gratitude, fun, compassion, creativity, authenticity, and love).

On episode 502 of The Art of Charm, Bert demonstrates how these superpowers can allow you to overcome obstacles and embrace opportunities — whether it’s growing stronger from rejection, letting your imagination loose, or simplifying your life to focus on what matters most.

(Direct Download Episode Here)

More About This Show

Bert Jacobs and his brother John launched their business with $78 in their pockets, selling t-shirts in the streets of Boston. Today, Life is Good is a $100 million positive lifestyle brand sold by over 4,000 retailers across the US and Canada. To inspire others to choose optimism and grow the good in their lives, Bert and John wrote Life is Good: The Book/ How to Live with Purpose and Enjoy the Ride, published by National Geographic in September 2015.

“We didn’t really set out to build a business around optimism,” says Bert, “but I think [optimism] was important to us when we started because pessimists see obstacles, and optimists see opportunities. So entrepreneurship, almost by definition, is optimistic. You have to try to see things, especially when they’re not totally clear or not totally obvious — otherwise you’re not going to develop anything that has a point or difference.”

Selling t-shirts and starting their own business seemed like a better option to the Jacobs brothers than signing over their lives to someone else for a regular job when they were done with school. “We liked school. We liked life. But now we were supposed to take the next stage and it looked like we might get caught behind a desk somewhere and I think that was kind of scary to us,” Bert says.

As artists who enjoyed creating but were intimidated by the world of fine art, t-shirts seemed like a financially accessible way to work their craft and make money doing what they loved. During five years of traveling around in a van and making t-shirts that covered “any and all art styles and any messages that we thought…some of them would be very Life is Good, some of them not so much,” according to Bert, they learned the ropes of the business if not overwhelming commercial success. In discussing ideas that might sell, they made the observation — as many before them — that the media always focuses on what’s wrong in the world.

“It was a bummer of a conversation,” says Bert. “Every time we had it…it really just brought things down. As optimists, we were upset about it. [We saw it as] systematic pessimism. We’re told as members of the human race that we’re failing as a team. That’s what the 6 o’clock news is.”

So in the gloomy darkness of the conversation, they did what optimists do: they saw an opportunity to create a brand to instead celebrate what’s right with the world. From an initial printing of 48 t-shirts that declared the Life is Good sentiment, they found the idea instantly contagious. “Sometimes selling 48 t-shirts would take you a week if you didn’t have a good design. This took 45 minutes! That was a first.”

And while they were lucky enough to land this idea that resonated with the masses in such a way, Bert doesn’t discount those first five years of struggling and the six years of trial and error that followed as their brand found its footing. “People always say life is good now that the business is successful, and that life was miserable in those days — it wasn’t miserable at all! We had a chance to give it a shot, and we were enjoying it, and we got to visit all the college campuses on the East Coast that we didn’t get into!”

In short, Bert advises that you shouldn’t be discouraged from starting a business just because you don’t have every last detail figured out. Inevitably, you will make mistakes, and no matter how carefully you lay your plans, a lot of them will be undone. But as long as you operate within your means, you’ll learn the lessons it takes to grow sustainably, generating ideas that fill in the gaps along the way.

One lesson Bert and John learned was their company could grow from making three million to 40 million dollars by licensing their brand to proven, experienced marketers who could handle the business end of operations while they focused entirely on the creative side of the business and refined what clicked with an expanding customer base based on their optimistic outlook.

So the optimism was there from the start; it was just a matter of time for that optimism to gain the traction that would propel the Jacobs brothers and their Life is Good brand to take off and start making a difference for others. Listen to this episode of The Art of Charm to learn how optimism unlocks the 10 “superpowers” of openness, courage, simplicity, humor, gratitude, fun, compassion, creativity, authenticity, and love, and how these superpowers can allow you to overcome obstacles and embrace opportunities — whether it’s growing stronger from rejection, letting your imagination loose, or simplifying your life to focus on what matters most.

Follow the Life is Good: The Book tour here to participate in daily #GROWtheGood challenges, earn points to win prizes, and spread optimism across your communities!


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AJ Harbinger - author of 1139 posts on The Art of Charm

AJ Harbinger is one of the world’s top relationship development experts. His company, The Art of Charm, is a leading training facility for top performers that want to overcome social anxiety, develop social capital and build relationships of the highest quality. Raised by a single father, AJ felt a strong desire to learn about relationships and the elements that make them successful. However, this interest went largely untapped for many years. Following the path set out for him by his family, AJ studied biology in college and went on to pursue a Ph.D. in Cancer Biology at the University of Michigan. It was at this time that he began to feel immense pressure from the cancer lab he worked in and began to explore other outlets for expression. It was at this point that The Art of Charm Podcast was born.

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