He Turned His Last $78 Into a $250 Million T-Shirt Empire — Here’s How.

Life Is Good co-founder Bert Jacobs says that true success is found at the intersection of charity and capitalism.

By Dan Bova | edited by Brittany Robins | Jan 28, 2026

There’s no shortage of bad behavior out there — but there are still plenty of people doing good. This week’s guest, Life is Good co-founder Bert Jacobs, is one of them. Starting with just $78, the apparel brand has grown to a $250 million business that donates $1 out of every $10 in profit to help over 1 million kids facing psychological trauma in foster care homes, homeless shelters and oncology departments.

The co-founder was on the How Success Happens podcast to share insight on how to build a brand around a message that resonates with buyers while doing tangible good in the world. But make no mistake — Jacobs is a capitalist to his core and believes that business offers humanity’s best shot at saving the planet.

You can listen to the episode here or watch it above and read on for takeaways from our conversation that will help inspire your own success in three, two, one

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Three Key Insights

1. Don’t Ignore Customer Feedback 

Before Life is Good became a $250 million brand, Jacobs and his brother John spent five and a half years selling T-shirts on the streets and on college campuses. They only had $78 left in the bank but kept going anyway — sleeping in their van, substitute teaching between six-week selling trips and throwing keg parties where friends critiqued their designs. One night, a friend circled an early version of their now-iconic stick-figure character, Jake, and wrote, “This guy’s got life figured out.” It inspired them to add the words “Life Is Good.” When they printed 48 of those shirts, they sold out in 45 minutes to every kind of person — a preppy teacher, a Harley guy and more — which indicated that optimism was the universal story their customers wanted to help write.​

Takeaway: Treat every stage of your business as a live laboratory with real customers — the feedback you get can reveal the one idea powerful enough to transform your business.


2. Communicate Consistently

Jacobs shared that Life is Good began giving away 10% of profits in their second year, but they didn’t think to advertise what they were doing until year 15. And that’s when things shifted. “Consumers have to see something at least three times before it even registers,” he explained. And once they started hammering home the message consistently — on hangtags, websites and at checkout — something remarkable happened: “People started donating money even though we didn’t have a vehicle for them to donate. And today, consumers are donating almost as much as we are.” Purpose matters, but communication about that purpose is what actually drives results.

Takeaway: Communicate your mission consistently and repeatedly — make it easy for people to support what you believe in and they absolutely will.


3. Capitalism Isn’t the Enemy

Jacobs challenges conventional thinking about “evil corporate business,” pointing out that “free enterprise capitalism has created upward mobility, cured diseases and created sanitation systems.” He noted that while we hear about CEO greed and corruption, we rarely acknowledge the incredible good that business creates. “I would challenge anyone who thinks we’re going to solve the world’s problems without business to show me how,” he says. He pointed out that “power shifted from kings and queens to the church, to governments and now businesses control more dollars and touch points than any entity on the planet. If you think we’re going to save the planet without the help of businesses, you’re out to lunch.”

Takeaway: Build your business with purpose and profit as complementary forces.

Subscribe to the How Success Happens newsletter for more insights and inspiration.


Two Great Ways to Learn More

  1. Visit lifeisgood.com to shop their iconic optimistic apparel and support kids in crisis.
  2. Dive into this article to learn how purpose-driven entrepreneurs are working to change the world.

One Question to Ponder

If you were to donate a percentage of your future business profits to a cause you care about, what would it be and why?

Send your answer to howsuccesshappens@entrepreneur.com. We read every response, and the best ones make it onto future episodes of the show.


ABOUT HOW SUCCESS HAPPENS

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.

There’s no shortage of bad behavior out there — but there are still plenty of people doing good. This week’s guest, Life is Good co-founder Bert Jacobs, is one of them. Starting with just $78, the apparel brand has grown to a $250 million business that donates $1 out of every $10 in profit to help over 1 million kids facing psychological trauma in foster care homes, homeless shelters and oncology departments.

The co-founder was on the How Success Happens podcast to share insight on how to build a brand around a message that resonates with buyers while doing tangible good in the world. But make no mistake — Jacobs is a capitalist to his core and believes that business offers humanity’s best shot at saving the planet.

You can listen to the episode here or watch it above and read on for takeaways from our conversation that will help inspire your own success in three, two, one

Dan Bova

VP of Special Projects
Entrepreneur Staff
Dan Bova is the VP of Special Projects at Entrepreneur.com and host of the How Success Happens podcast. He previously worked at Jimmy Kimmel Live, Maxim, and Spy magazine. His latest books for kids include This Day in History, Car and Driver's Trivia Zone, Road & Track Crew's Big & Fast Cars, The Big Little...

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