U.S. Markets closed

How to turn $200 into $100 million

Nicole Goodkind
Nicole Goodkind

For Bert Jacobs, Life is Good. That’s because he’s the co-founder and CEO of the aforementioned company—most famous for t-shirts that picture a stick figure named “Jake,” wearing a beret with an affirming phrase scribbled below him. Life is Good began as two brothers with just $200 in borrowed funds. In 1989 Bert and John Jacobs began screen-printing T-Shirts and illegally selling them on street corners in Boston. 25 years later, the company has come of age and in 2014 made over $100 million in revenue.

So how did these brothers manage to increase their initial investment by more than 500,000 times?

The key to Jacobs’ success was finding a message that resonated with his customer and to enjoy what he was doing. At many points “it seemed like we were down and out and we didn’t have money or commercial success” he says, “but we were actually enjoying the adventure of the whole thing. Before we even had the brand we were living the brand.”

Jacobs says that he and his brother made every mistake in the book along the way, but still remained loyal to their core message. They kept it simple and listened to their customers.

Eventually the brothers bought a van for $2,200 and set out from college campus to college campus. By 1994, they were down to their last $78. They decided to focus on the positive instead of the negatives of their situation and that’s when they came up with the Life is Good mascot and motto.

“We see companies that have focus groups and develop something for years,” says Jacobs. He believes a better way to foster success is by going ahead and making something. “Get in the street and get somewhere and sell it. You’ll learn a ton—that’s one of the things we did right,” he says. They knew that they had hit on something great with their new message when they sold 48 shirts in 45 minutes. The company continued to grow and eventually they were able to sell wholesale.

Jacobs also recommends against growing too fast, a major mistake that Life is Good made. “We found this sample of a shirt that we loved and production was in Pakistan. We were a $2 million company and we single sourced everything from one factory. That factory didn’t deliver,” he says. They learned from their mistakes and recommend against rushing into decisions without doing proper research.

Overall, Jacobs says, listening to and connecting with the core customer is what makes a company thrive. It’s how he learned that his customers wanted to focus on the good, simple pleasures in life and what made him a success.

Bert Jacobs is on the cover of this month's issue of Inc. Magazine and will be releasing a book that chronicles his story and gives advice to fellow entrepreneurs later this year.

Get the Latest Market Data and News with the Yahoo Finance App

More from Yahoo Finance

Apple shines; Boeing takes off; Yahoo jumps on spinoff

Shake Shack is cooking on Wall Street

Recap: Yahoo's Alibaba spinoff plans, Q4 results