For a decade, I've filmed an exclusive gathering of top CEOs in the Texas Hill Country for a 3-day summit. One year, a guy in shorts and a t-shirt jumped on stage, threw frisbees into the audience, and started telling us about a superpower called “optimism” he discovered while living in his van. In today’s issue you will hear is stick-figure smile face story. Plus, you will:

• Learn 3 Lessons on storytelling from his experience

• Understand a little science behind why great stories drive sales

• Watch Bert embody this optimism as he hucks frisbees at CEOs

 Enjoy this ‘living in a van down by the river’ story.
LG

Founder Story: Bert Jacobs, Life is Good

Bert Jacobs and his five siblings grew up in a lower-middle-class family in Massachusetts. Their father was a craftsman and the breadwinner for the entire family. One day, Bert’s father was in a car accident that almost killed him. While he survived, the injuries from the accident ruined the use of his right arm, which effectively destroyed his career and led him to sink into a deep depression with volatile mood swings.

Bert’s mother, determined not to let the accident affect the family, worked hard to make sure the kids always looked for the positive in life. Every night at dinner, if things turned bad with her husband, she used a simple trick to change their mood. She would look around the table and say, “Tell me something good that happened today,” and the kids would each share their experiences. Bert observed how the energy around the table would instantly change. 

This small act of infusing optimism was a lesson that would serve him well for years to come.

When the boys graduated college, they wanted to travel, so they took odd jobs in different parts of the country. On one of their road trips to visit each other, they decided to start a business together. They looked at their combined skillset—one was good with graphic design and the other was good with words—and started a T-shirt company.

They went back to Massachusetts and bought a van so they could sell the shirts out of it while traveling from town to town. They spent their entire savings, which at the time was around $160, and bought their first set of T-shirts. For the next 5 years, they traveled up and down the East Coast, selling T-shirts at festivals and universities often sleeping in the van or at the dormitories at the universities to avoid having to spend money on hotels. 

On the return from one of their long road trips, they started talking about how pessimistic the news was—constantly telling people what was wrong with the world and preying on people’s fears. Bert and his brother began reminiscing on how their mom used to always ask about the good things in their lives. 

They started thinking that maybe they should do something with their business to add more optimism to life.

When they returned to their apartment in Boston, they invited all their friends over to work on new ideas. They had this tradition where they would get a keg, start drinking, and everyone would contribute by drawing their ideas on the apartment walls (how cool is that?).

They told everyone their idea about adding optimism to life and told them to have at it. That night, many great characters and sayings ended up on the walls, but one stood out: a beret-wearing smiley face with sunglasses on. Next to it were the words “This guy’s got it figured out.”

They loved how he looked, and after the party, they worked on that sketch and came up with a simple three-word saying: “Life is good.” They decided to take the last bit of money they had, $78, and make 48 T-shirts. They went to downtown Boston and sold all 48 shirts in 45 minutes. 

They made more in that 45 minutes than they typically made in a week.

In that moment, they knew they not only had a great idea for a shirt, but they also had the beginnings of something far more than a slogan and a drawing. They had a story—a story that captured the spirit of optimism that their mother had implanted in them as children. Now they weren’t just two guys living in a van selling t-shirts, they had a mission to spread to the world. 

The magic of their story is that they took the optimism they grew up with and turned it into a slogan and a company that represented everything positive they believed in. Their story literally changed everything for them that day. Bert and his brother went on to turn that story and that vision into what is now a $100M company, available in 4,500 retailers in all 50 states, and 30 countries. Now, everywhere you go, you can find “Life is good” and that smiley-faced spirit on everything they create.

Storytelling Lessons:  Feelings  >  Facts

Your most powerful asset might not be your product, your strategy, or even your funding. It's your story. Here are 3 lessons you can take from the Jacob brother’s journey:

1. A Good Story Changes Everything: A story gives audiences something to connect with, something to care about. It provides your customers with something to remember you by and share with others. It helps bring out the humanity of what you are trying to do, the cause you are pursuing, or the vision you are trying to make a reality.

2. Keep it Simple: Simplify your message to as few words as possible. Bert believes there is a direct relationship between the length of your message and the size of the audience you can reach. If you have a complex idea, it might reach hundreds or maybe even thousands. But if you simplify it to the point where an average person can understand then your reach is limitless.

3. Emotional Connection Sells: You have to find ways to connect with audiences emotionally. Things they care about or the people they love care about. For Bert and his brother, it had never really been a business about apparel. It has been a business about an emotional connection. The phrase and the smiley face connected with things customers love, such as optimism and joy
   

Remember, in a world of complexity, sometimes the most powerful stories are the simplest. A short motto you live by or phrase you love saying could be the key to unlocking your business's potential.

Fun Fact: Connection = Purchases

A study by Headstream reveals the measurable impact of brand narratives: when consumers connect with a brand's story, 55% are more likely to make future purchases, 44% will share the tale with others, and 15% will buy immediately. These findings underscore why Life is Good's optimistic message has resonated so deeply with customers, turning a simple t-shirt company into a lifestyle brand that spreads the power of optimism.

Video to Watch: Freedom, Fun, & Frisbees

If you want to see someone who truly embodies optimism with fun, levity, and even a few frisbees, don’t miss "Embracing Optimism with Bert Jacobs and Life is Good" I filmed at the Conscious Capitalism CEO Summit. Bert’s energy and passion for spreading positivity will leave you inspired to embrace optimism in your own life and work. It still cracks me up that, in a room full of top founders and CEOs, he’s on stage in a T-shirt, flip-flops, and shorts, slinging frisbees—and they were loving it.

Optimism is infectious—

SOFE Issue #008 - SUBJECT: The $100M Brand Born from a Smiley Face in Shades and 3 Words

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