The Unexpected Reason 2 Brothers (and $78) Invented "Life is Good"

People become entrepreneurs for all sorts of reasons: They hated their boss (guilty !), they had a great idea, and yes, to even remember that life is good.

Bert and John Jacobs did not come from money.

The youngest of six kids, they grew up in a small house outside of Boston, where their father worked as a craftsman and their mother kept the family’s spirits high despite financial struggles.

Then, one night, everything changed.

The Night that Changed Everything

Their father was in a horrific car accident. He survived, but the injuries left his right arm useless, shattering his career and sending him into a deep depression. The man who had once provided for them became volatile and angry.

Their mother, however, refused to let darkness take over their home.

Every night at dinner, she would look around the table and ask, “Tell me something good that happened today.” 

The mood at the table would shift.

Laughter would bubble up.

And in that simple act, she taught her children a lesson that would stay with them forever: Positivity is a choice.

A Crazy Idea and a $200 Bet

After college, Bert and John had zero interest in settling for traditional jobs.

They wanted to create something fun, something meaningful—if they could just figure out what that was. It was during a cross-country road trip that an idea struck: Selling T-shirts.

They borrowed $200 from their brother, bought a folding table, and started selling T-shirts to college students.

It worked good enough that they took their show on the road; they purchased a beaten-up minivan at an auction, headed west, and hit university campuses across the country.

For five long years, they scraped by. Entrepreneurs at heart that they were, they kept going, believing in their vision.

They traveled up and down the East Coast, slept in their van, and sold shirts at colleges and street fairs.

By the time they were nearing their thirties, they had exactly $78 to their name.

The Moment That Changed Everything

On one of those long road trips back to Boston, the brothers started talking about something that had always bothered them: The news was obsessed with negativity. Fear and division dominated the headlines.

Their mom had taught them better.

What if, they thought, they could create a message that reminded people of the good in life?

That night, they sketched a simple stick figure with a goofy grin and a beret. Beneath it, they wrote three words: Life is Good.

They spent their last $78 printing 48 shirts with the design and took them to a street fair in Cambridge.

They sold out in 45 minutes.

They had never seen anything like it. Five years of hustling, scraping, and barely surviving—and suddenly, they had a hit on their hands, a message, that resonated, and a story people wanted to wear.

From a Minivan to a Global Movement

Today, Life is Good is a global brand, sold in 4,500 stores across 50 states and in 30 countries.

And all of it traces back to a lesson learned at their family dinner table from mom: No matter how hard life gets, there is always something good.

The Takeaway

The Jacob brothers are the personification of this great, and lesser-known Steve Jobs quote: “I'm convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance.”

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Steal This Strategy

📖 Book - Start with Why
Simon Sinek explains how great leaders inspire action by focusing on the deeper 'why' behind their business.

🎥 Video - The Life is Good Story
A quick hit of Bert and John Jacobs on how optimism shaped their journey and business success.

🌐 Website - Life is Good
Check out the company’s official site and how they continue spreading optimism through their brand.

Overnight Challenge

Tonight, take five minutes to identify an obstacle in your business or personal journey. Instead of seeing it as a roadblock, think of one creative way to turn it into an opportunity. Tomorrow, take one small action to move forward and change the narrative.

Let’s see what happens!

About Steve

Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!