Life is Good : Selling T-shirts from an old used van → $100M clothing Empire

Read time: 4 minutes

Hello Rebels

Fun one-liner 🏖️  :

Why do entrepreneurs always write with pencils? Because they know it’s important to always 'erase' their mistakes.

Onto Today’s story….

Picture this: Two brothers, a beat-up van, and a dream.

No, this isn't the start of a bad joke—it's the beginning of a $100 million empire.

Buckle up, my entrepreneur friend, because you're about to dive into a story that's part comedy, part thriller, and 100% real-life business madness.

Meet Bert and John Jacobs, two guys who thought selling T-shirts out of a van was a better career move than getting a "real" job.

Their secret weapon? An unwavering belief that life is good, even when you're sleeping on top of unsold merchandise and living on peanut butter sandwiches.

The Seeds of Optimism 🌱

Let's rewind to the Jacobs' childhood.

Picture a chaotic Boston suburb household with six kids running amok.

In the midst of this beautiful mess, their mother Joan drops a game-changer.

No, not a new Xbox—something way more valuable: the power of optimism.

Every night at dinner, she'd ask, "Tell me something good that happened today."

It wasn't just small talk; it was a deliberate choice to focus on the positive, even when life threw curveballs their way.

Little did young Bert and John know that this simple question would one day become the foundation of their empire.

Fast forward to 1989.

Bert and John are fresh out of college, armed with degrees but clueless about life.

Sound familiar?

Instead of joining the corporate rat race, they decide to do something crazy: turn their love for art into a business.

Their brilliant plan? Selling T-shirts.

Oh, and not just any T-shirts.

We're talking about T-shirts with their own artwork plastered all over them.

Genius, right?

The sad part

But the Jacobs household wasn't all sunshine and rainbows.

When Bert and John were in elementary school, their parents were in a near-fatal car accident.

Their mother escaped with a few broken bones, but their father lost the use of his right hand.

The stress and frustration from his physical therapy led to a harsh temper, filling the house with tension.

Yet, even in these difficult times, their mother Joan remained a beacon of optimism.

She'd sing, tell stories, and act out children's books, showing her kids that happiness isn't dependent on circumstances.

It was a lesson that would shape the brothers' future in ways they couldn't yet imagine.

The $2,100 Gamble 💰

Most people might start small, maybe set up a stall at a local fair.

But Bert and John? They went all in.

They scraped together $2,100—a fortune for two broke college grads—and bought a van.

Not a cool Volkswagen, mind you, but a used soccer mom Plymouth Voyager.

They christened it "The Enterprise," because it literally contained their entire enterprise: them and a bunch of T-shirts.

Picture this dynamic duo, cruising up and down the East Coast, knocking on dorm room doors at 1 a.m., trying to sell T-shirts to sleepy college students.

It's not exactly the glamorous start-up story you read about in business magazines, is it?

But here's where it gets interesting.

Instead of getting discouraged by the constant rejections (and there were many), Bert and John turned it into a game.

They competed to see who could spend less money each day.

They slept in the van, on top of their unsold T-shirts.

Showers? Those were a luxury they couldn't afford.

But beer? Well, if someone offered, who were they to refuse?

The $78 Dilemma 💸

Fast forward five years.

Our intrepid entrepreneurs have been at this T-shirt game for half a decade.

They've tried and failed "a thousand times," as John puts it.

They're pushing 30, still living with their parents, and their bank account is looking sadder than a wet T-shirt in a thunderstorm.

One day, they check their balance: $78.

That's it.

Seventy-eight dollars to show for five years of blood, sweat, and T-shirts.

Most people would throw in the towel at this point.

Maybe it's time to listen to those well-meaning friends who keep saying, "You've got a college degree. Get a real job!"

But remember that optimism their mother taught them? It's about to pay off in a big way.

Despite their dwindling funds, Bert and John decide to throw a party.

Yes, you read that right.

With just $78 to their name, they're hosting a keg party.

But this isn't just any party.

It's a tradition they've kept alive through all their struggles.

At these gatherings, they pin up their latest T-shirt designs and let their friends scribble comments on them.

The Birth of Jake 👨‍🎨

During one of their road trips, Bert and John got into a deep discussion about the media's tendency to focus on negative news.

They wondered: What if there was room for a symbol of optimism in this sea of negativity?

Inspired by this idea, John grabbed a pen and started sketching.

The result was a bohemian guy with a beret, sunglasses, and the biggest, goofiest grin you've ever seen.

They called him Jake, and added the phrase "Life is Good" beneath it.

At their next keg party, something unexpected happened.

The sketch of Jake was getting more attention than any other design.

People were clustering around it, pointing and smiling.

Someone scribbled a comment next to the drawing: "This guy's got life figured out."

Armed with this new design and a renewed sense of purpose, Bert and John were ready to give their T-shirt business one last shot.

They scraped together enough money to print 48 shirts featuring Jake and his "Life is Good" mantra, hoping against hope that this would be the breakthrough they'd been waiting for.

The $48 Test 🧪

With their last few dollars, Bert and John print 48 shirts featuring Jake and his "Life is Good" mantra.

They head to a street fair in Cambridge, expecting another day of lukewarm sales and polite rejections.

But something magical happens.

By noon, all 48 shirts are gone.

Sold out.

Kaput.

They even sell the shirts off their own backs.

And it's not just college kids buying them.

It's grandparents, punks, preppies—everyone seems to "get it."

For the first time in five years, Bert and John feel like they're onto something big.

But hold your horses, because this rollercoaster ride is far from over.

The Great T-Shirt Tour 🚐

Excited by their success, the brothers load up their trusty van and hit the road, ready to conquer the Boston retail scene.

They're going to be millionaires by Christmas, right?

Wrong.

Store after store turns them down.

Nobody wants to stock their "Life is Good" shirts.

It's like the universe is testing their optimism, daring them to give up.

Just when they're about to throw in the towel, they stumble upon a small flip-flop shop on Cape Cod.

The owner, Nancy, takes a chance on them and orders 24 shirts.

Two weeks later, those shirts are sold out.

And just like that, the tide begins to turn.

From Container to Empire 📦

As demand picks up, Bert and John make their first hire.

But this isn't your typical job interview.

They ask Kerrie Gross, their 23-year-old neighbor, what's the least amount of money she needs to pay her bills.

"$17,000," she says.

"You're hired!" they reply.

Their first office? A 40-foot shipping container on a dirt lot.

Glamorous? Hardly.

But it's a start.

By the end of 1994, Life is Good manages to pull in $87,000 in revenue.

It's not much, but it's a far cry from their $78 bank balance just a year ago.

1995 sees their sales double to $250,000.

Things are looking up, but they're still far from living the high life.

Peanut butter sandwiches remain a staple in the Jacobs brothers' diet.

Then comes 1997, and Life is Good breaks the $1 million mark in sales.

They celebrate by hiring three more employees and moving into a real office.

But don't think for a second that success has gone to their heads.

They still send out invoices with a photo of themselves in the shipping container, pleading with customers to pay on time so they can "keep these lights on and pay our hungry warehouse staff."

The 9/11 Test 🇺🇸

Just when everything seems to be going well, tragedy strikes.

The 9/11 attacks shake the nation, and suddenly, the idea that "Life is Good" seems out of touch, even insensitive.

But instead of backing down, Bert and John double down on their message.

They create an American flag T-shirt with their signature phrase and use it to raise over $200,000 for families affected by the attacks.

This moment becomes a turning point.

Life is Good isn't just about selling T-shirts anymore.

It's about spreading optimism, even in the darkest times.

By 2003, just two years after 9/11, the company's revenue has skyrocketed to $30 million.

Their message of optimism resonates even more strongly in challenging times.

The $100 Million Smile 💯

Fast forward to 2007, and Life is Good hits a major milestone: $80 million in annual revenue.

What started as two guys in a van selling T-shirts has transformed into a full-fledged lifestyle brand.

They're selling in 4,500 retail stores across the U.S. and have expanded to 30 countries.

But here's the kicker: They've done it all without traditional advertising.

No flashy commercials, no celebrity endorsements.

Just a simple message that resonates with people: Life is Good.

Today, Life is Good is no longer just two brothers in a van.

They're pulling in $100 million annually.

It's a thriving company with 160 employees, a product line that goes way beyond T-shirts, and a charitable foundation that's raised millions for kids in need.

Both the brothers are multi-millionaires.

Lessons from the Road 🛣️

So, what can we learn from Bert and John's wild ride? Let's break it down:

1. Embrace the hustle: Bert and John spent years sleeping in a van and eating peanut butter sandwiches and they enjoyed it.

2. Make it fun: The brothers turned their financial struggles into a game of who could spend less. How can you make working on your business fun.

3. Turn obstacles into opportunities: When 9/11 threatened their message, they used it as a chance to give back to spread optimism.. What's your business's equivalent of making lemonade when life hands you lemons.

Your Turn 🚀

Now, as you sit there reading this, maybe you're thinking, "That's all well and good for Bert and John, but I could never do something like that."

Hold on.

Remember, these guys started with nothing but a beat-up van and a whole lot of unsold T-shirts.

They faced rejection, slept on cold floors, and came within inches of giving up more times than they can count.

But they didn't.

And that's the secret.

It's not about being smarter, or luckier, or having more money.

It's about waking up every day, putting one foot in front of the other, and choosing to see the good in life—even when life seems determined to knock you down.

So, what's your "Life is Good" moment waiting to happen?

What crazy idea have you been sitting on, too afraid to try?

Remember, every empire starts with a single step.

For Bert and John, it was a goofy drawing and a simple phrase.

What will it be for you?

The road may not be easy, but you can make it fun.

You'll face doubts, setbacks, and more than a few nights wondering if you've lost your mind.

But if you can hold onto that spark of optimism, if you can find joy in the journey itself, you might just end up changing the world.

Or at the very least, you'll have one hell of a story to tell.

So, what are you waiting for?

Life is good.

Now go make it great.

Let the good times roll for you!. 🍨

Yours “Rooting for your success” Vijay Peduru