Blake Mycoskie didn’t just sell shoes, he sold a story that people couldn’t stop sharing.

What started as 250 pairs in a duffel bag became a global movement built on one simple line: 

Buy a pair, give a pair.

In this week’s issue, I share how Blake turned that idea into TOMS, along with:

Enjoy walking in Blake’s shoes on this journey… LG

In 2002, Blake Mycoskie and his sister Paige competed on the reality TV show "The Amazing Race," finishing third and missing the million-dollar prize by just four minutes.

Following his reality television experience, Mycoskie attempted to launch an all-reality cable TV network called Reality Central. 

Despite raising capital and securing big partners, the venture failed after several years, a very public failure in front of the entire TV entertainment industry. 

Within months, Blake bounced back, co-founding Drivers Ed Direct, an online drivers education service that quickly gained traction.

With the company building momentum, Blake kept a promise he'd made to himself: take time off to refresh and feed his soul. In January 2006, he headed to Argentina for 30 days to relax, take tango lessons, visit wineries, and learn polo.

Towards the end of his trip, he had a chance meeting with an American woman in a Buenos Aires café who was volunteering with a shoe drive. They collected slightly used shoes from wealthy families and delivered them to poor children in villages outside the city.

Intrigued, Blake joined them. He quickly learned that many children in Argentina went through their lives completely barefoot. The lack of shoes prevented them from attending school, complicated trivial tasks, and exposed them to infections and diseases.

He couldn't believe kids needed shoes to go to school and didn't have them, it seemed like such an easy thing to provide.

But the organization was completely dependent on donations, limited by funds and donated shoes that were often the wrong size.

Blake desperately wanted to help these children. At first he thought about starting a charity, but believed it wouldn't be sustainable. Eventually, his list of family and friends to ask for donations would run out, and he hated asking for money anyway.

One night while writing ideas down in his journal, he started thinking about a solution that guaranteed a constant flow of shoes rather than depending on donations. Maybe the solution was in entrepreneurship, not charity.

Why not build a for-profit company based on giving?

For every pair sold, a pair would be given away.

No formulas, no tracking, just a simple one-for-one model.

He didn't know it yet, but that line,

…would spark a business model that transformed an industry.

The shoe itself came from an idea he'd already fallen in love with: Argentina's national shoe, the alpargata. A soft, casual canvas slip-on worn by everyone, rich or poor. Blake thought he could bring the same simple style to the U.S.

He teamed up with his Argentinian polo coach, stayed an extra month, and worked with local artisans to design a sturdier, more stylish version for American consumers. In dusty workshops surrounded by roosters and old sewing machines, they produced 250 pairs.

Blake packed them into three duffel bags, flew home to Los Angeles, and set out to sell them, one story and one pair at a time.

Back in LA with 250 shoes, Blake had to figure out how to sell them. He knew nothing about fashion, retail, or the footwear business. Instead of reaching out to experts, he invited a group of female friends over for dinner.

Blake shared his story about Argentina, the shoe drive, and his big idea for TOMS. Then he showed them the shoes. The women unanimously loved the story, the concept, and especially the shoes, insisting on buying pairs that night. They also gave him a list of stores that might be interested. Now he had his first paying customers and a list of retailers.

Blake started calling stores but didn't get far, so he grabbed the duffel bag and visited American Rag in person.

The shoe buyer listened to the TOMS story and ordered 80 pairs on the spot, becoming TOMS' first retail customer.

A week later, a fashion writer from the Los Angeles Times called, wanting to do an interview. A week after that, Blake woke up on Saturday morning to his BlackBerry buzzing non-stop. He'd set the TOMS website to email him with each order, previously once or twice a day. Now it was vibrating so much the battery died. When he met friends for brunch, he saw why: his story was on the front page of the Los Angeles Times' Calendar Section.

Blake was soon back in Argentina figuring out how to make 4,000 more pairs. Major magazines like Vogue, Time, People, O Magazine, and Elle heard about TOMS and started writing about Blake's story. Celebrities like Scarlett Johansson and Tobey Maguire were spotted wearing TOMS. Big retailers like Nordstrom, Whole Foods, and Urban Outfitters started placing orders.

They sold 10,000 pairs that first summer, all out of Blake's Venice apartment with 3 interns, a polo instructor from Argentina, and a shoe entrepreneur who knew nothing about shoes—all while Blake still worked at his other company.

They met up with Alejo, the shoemakers, and artisans, and rented a large sleeper bus with storage for 10,000 shoes. They started in Buenos Aires and drove 18 hours to the northeastern part of the country, going village to village.

They spent 10 days traveling through Argentina, driving from clinics to schools to soup kitchens to community centers, hand-placing 10,000 pairs of shoes on children's feet.

As they were leaving one village, a woman approached Blake crying, speaking in Spanish. Through a translator, he learned she had three boys with her, all wearing brand new shoes from the drop.

She told him her three sons had been sharing a single pair of shoes for the past year. Her oldest son would go to school on Monday, come home and give his shoes to his brother, then wait until Thursday to go to school again.

Blake thought. They all got emotional. In that moment, Blake knew this is what he wanted to do with his life.

TOMS wasn't going to be just another business. 

The one-for-one idea had created a business model that impacted all aspects of his life and provided him with a sense of fulfillment unlike anything he'd ever felt.

When Blake returned, he approached his partners in the driver-education business about pursuing TOMS full-time. They agreed and bought him out. He used the money to hire industry veterans, scale operations, and keep up with demand.

By 2013, TOMS was working with over 100 giving partners in 56 countries, reportedly generating $250 million in annual sales and had donated 10 million pairs of shoes.

The next year, Blake sold 50% of the company to Bain Capital in a deal that valued TOMS at approximately $625 million, providing resources to accelerate its growth and impact.

Blake's vision for TOMS pioneered the "One for One" business model and revolutionized the giving industry. TOMS has donated over 100 million shoes in 76 countries, generating over $400 million in revenue.

Blake Mycoskie’s story is one of simplicity, soul, and storytelling at scale. He built a global movement not from technology or capital, but from a story so clear and emotionally charged that anyone could repeat it.

The Buy a pair, give a pair  line captured everything TOMS stood for. Simple enough to explain in seconds. Emotional enough to inspire action. Contagious enough to spread worldwide. Here are 3 lessons you can learn from Blake:

A Harvard study of over 38,000 startups found that scaling too early (in the first year) increases the risk of failure by up to 40%. Most sustainable, successful companies spend years serving a small group of passionate customers, testing, refining, and building trust, before rapidly expanding.

Just like Blake Mycoskie with TOMS, starting small creates space to perfect your idea and build organic momentum that travels far.

The TOMS story was unlike anything the business world had seen before.

And in this profile piece on by CNBC,  ‘Blake Mycoskie, Founder of TOMS | The Brave Ones from CNBC, you’ll see how Blakey transformed a simple act of giving into a global movement. Through personal interviews and behind-the-scenes moments, the film traces Blake’s journey from his early ventures and Survivor obsession to the trip to Argentina that sparked it all.

It’s a powerful look at how his curiosity, creativity, and storytelling turned TOMS into one of the most memorable brands of our time.