The Story of ‘Life is Good’ & Why Entrepreneurs Need a Story

Bert Jacobs, Founder of Life is Good, speaking at @TexasWomen Event


Bert and John Jacobs were the youngest of six kids raised outside of Boston, MA. Their family had a small house, and though they were always short on money, the kids had a fairly good childhood. Their dad kept food on the table and their mom made sure there was always laughter in the home. One night, everything changed. Bert’s father, a craftsman, got into a car accident that almost killed him. 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 it affect the family, worked hard to make sure the kids always looked for the positive in life. Every night at dinner, if things got bad, 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 then had the kids would share their experiences. Bert observed how the energy would instantly change around the table and everyone would end up laughing together. It was a lesson that would serve him well for years to come.

After college, Bert and John looked for ways to keep having fun and avoid getting ‘typical’ jobs. At first, Bert taught skiing at a resort in Colorado and John got a job at a college in California. During a cross-country road trip back to Boston, they kept thinking of ways they could do something creative and fun, such as art and design, and still support themselves financially. This led to the idea of selling t-shirts to college students, a demographic they knew well.

When they got to Boston, they borrowed $200 from their brother Allan to start a t-shirt “company.” This involved a folding table they could set-up and breakdown to hop around town. The t-shirt duo started to do well by selling on the streets and decided to take the show on the road. They bought an old mini-van at an auction, tore out the back seats to make room for sleeping and inventory, and sold the seats for $160. With this $160, they purchased their first shirts and took to college campuses and festivals along the East Coast.

The Jacobs First Store - A Mini-Van bought at a car auction with their help of their other brother

Bert and his brother planned the 4-6 week long trips along the East Coast, targeting schools with similar student bodies, traveling with a single t-shirt design, and stopping at street fairs to sell the shirts for $10. Then they’d return to Boston, come up with new concepts for shirts, and get back to the road. To get new ideas, the brothers would host keg parties at their apartment and draw artwork on the walls. They’d let their friends write comments about each piece and select the best ones to go sell on the next trip.

After 5+ years of selling shirts out of their van, with only $78 to their name, the Jacobs brothers felt the pressure of giving up road life to get “real jobs.” They even had taken jobs as substitute teachers so they could make ends meet. Around this time, Bert and John were on another long road trip back to Boston when they got into a discussion about how the news spread so much negativity, always telling people what’s wrong with the world and preying on people's fears. The media rarely told the viewers what was right with the world, so the brothers thought of how they could create a message, or hero, to combat that negativity. They wanted to ‘change the story’ with something that would promote positivity, optimism, and open-mindedness much like their mom infused in them.

1st Drawing of Jake

In the morning, they modified that comment to 3 short words: “Life is Good.” And they gave the figure the name Jake. Motivated to try their new story out, they took their last $78, made 48 T-shirts with the beret-wearing stick figure, and printed the words “Life is Good” on it. They took the shirts to a craft festival in Cambridge in 1994 and sold out of all 48 shirts in 45 minutes. In all those years of hawking t-shirts they had never seen anything like this. They were lucky if they sold that many shirts in a week, much less in an hour. They knew in that moment that they created something different and that the world was ripe for their message of optimism and the story of two guys who wanted to put a smile on people’s faces.

Today you can find ‘Life is Good’ products in 4,500 retailers in all 50 states and in 30 countries with small retailers making up 98 percent of Life Is Good's accounts and 60 percent of its business. A global brand that came from the desire to spread a message they learned from their mom at the dinner table in childhood, that “Life is Good."


For five-and-a-half years, Bert and his brother lived out of van, barely scraping by, living the broke bootstrapper lifestyle. But then something magical happened.

They came up with a story that changed everything.

After they printed the new Life is Good t-shirts, in just a 45-minute window, they sold out of their shirts faster than ever before. Even selling out to a huge variety of new customers. A guy riding a Harley Davison bought one. A schoolteacher bought one. A skateboarder bought one.

Their new story and message connected with people in a way far different from anything else they had ever done. People were starving for a message of optimism and they used their shirt to feed that hunger.

But it didn’t stop there.

Customers wanted to re-order shirts. That had never happened before.

Small retailers wanted to carry their shirts regularly. That was a first for them.

Newspapers and magazines began writing about them, their stick figure, and their story.

All of these things were brand new territory for the brothers.

Since that day, Bert and John have used that story and derivations of it, thousands of times in every aspect of the business.

Bert used their story to recruit employees.

He’s used it to inspire word of mouth marketing instead of spend money on advertising.

The story has helped them create a charitable foundation.

Their story became their vehicle to deliver their message of optimism.

And the spirit of that story has carried them since that day. It helped them get through the hard times, and helped them overcome mistakes they made by creating a magnetic connection with their customers and fierce loyalty from their fans to support them and continue to buy their products. My guess is that story will continued to be the primary wind at their back for years to come.

Bert Jacobs spreading good vibes to 8,000 attendees at the Texas Women's Conference


A truly great story can change the course of your business forever.

Life is Good is just one example, but there are thousands of other entrepreneurs who have discovered the same thing – that a good story can be a game changer.

And almost every great entrepreneur you can think of started his or her company with a story. Howard Schultz (Starbucks), Scott Harrison (Charity Water), Sara Blakely (Spanx) and Hamdi Ulukaya (Chobani Yogurt) are just a few examples of amazingly successful entrepreneurs that built their brands on the basis of a story.

One of the most important reasons is that a story gives the audience something to connect with, something to care about. A story gives your customers something to remember you by and share with others. They 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.

Stories work on an intellectual level as well as on an emotional level. They are persuasive, motivating, and inspiring.

A good story can have a dramatic impact on every facet of your business:

  • Sales - Close sales that you weren’t able to before
  • Communications – Help explain what you do vs. struggling to get your message across
  • Differentiation – Make your product stand out from the crowd vs. getting lost in the noise
  • Funding – Secure funding instead of investors say they’ll get back to you
  • Press - Convince the media to write about you instead of never hearing back from them
  • Deals - Secure partnership deals
  • Recruiting - Recruit co-founders & employees to help build your crazy idea
  • Advisors - Attract experts to come on board as mentors & advisors
  • Marketing – Move people to talk about and share your story with others – for free

And the best part - stories are free.

Whether you are a first time entrepreneur with no money and no resources, or you are on your fourth company with a mountain of assets at your disposal, a story is available to everyone. It’s up to you to capitalize on this powerful resource.


A story is one of the few things that you can use every day, in every facet of the business and for as long as you own your business.

My recommendation to you is to find a story or create a story for your idea, offering or business and even for yourself.

There are limitless ways to do this so here are a couple ways to get the ball going:


A solid way to learn about entrepreneurial stories is to consume them – online or in print.

ONLINE – Media Sites, Blog Posts, Newsletters
OFFLINE – Magazines, Books, Newspapers

Journalists, bloggers and industry experts spend countless hours curating and creating inspiring, powerful and valuable stories for their audiences about a wide range of entrepreneurs.

And they are skilled at writing stories – it’s what they do day in and day out so chances are that if you go to proven sources of great content, you will find solid stories on a regular basis.

You can find great entrepreneurial stories just about everywhere you look, but I’d focus on publications that focus on this audience such as Entrepreneur Magazine, INC, Fast Company and Fortune Magazine.

If you prefer physical mediums, seek out books by or about successful entrepreneurs that you are interested in that capture their story such as Start Something that Matters (by TOM’s founder Blake Mycoskie), Pour Your Heart Into it (by Howard Schultz, Starbucks), Shark Tales (by Shark Tank’s Barbara Corcoran) and or even Bert & John Jacobs recent release, Life is Good: The Book.


ONLINE – YouTube,, Foundation,
OFFLINE – Conferences, Trade Shows, Local Events & Organizations

Another way to absorb great entrepreneurial stories and one of the best ways to learn about entrepreneurial storytelling is to watch great entrepreneurial storytellers.

Whether it be online or in person, there is nothing quite like experiencing the compelling power of a great entrepreneurial storyteller do their thing.


I met Bert last year at the Texas Conference for Women (@TexasWomen) event in Austin, TX and was blown away by how he not only told a great story, but how he tailored it to the 8,000 women in the room and had them crying one moment, laughing another and then cheering madly along the way. Here is the speech he gave at the event as well as the TEDx talk. His style may not be a good fit for you, but you can still learn quite a bit from watching as well as enjoy it.

Life is Good Co-Founder Bert Jacobs Speaks at TX Conference for Women

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  • Know that a good story can be a game changer & can impact every aspect of your business
    Consume written or verbal entrepreneurial stories on a regular basis
    Watch online or offline great entrepreneurial storytellers looking for ways that you can borrow things from their story, style and/or format and weave into your story
    Most important – find or create your story. This is an asset and skill that will pay for itself over and over in an exponential manner if you do it right


A BIG thank you for reading the first Storytelling for Entrepreneurs post. It’s just one blog for now, but an all important step on a journey that is going to continue for many years to come and a ride that I hope you will join us for along the way.

In appreciation for the Jacobs brothers, their mom, a sunglass wearing smiling guy named Jake and you the reader.


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