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Blake Mycoskie won by losing. He lost the $1 million prize on the second season of the Amazing Race by four minutes, and yet if had won, he may not have founded his hugely successful and philanthropic TOMS Shoe company. He and his sister had entered the CBS reality race program and high-tailed it through 13 countries in thirty-one days, but another team beat them to the final treasure on the global scavenger hunt. “The experience opened my eyes to looking at the world in a new way,” explains Mycoskie, who is now best-known as the Chief Shoe Giver who appears on the popular AT&T television commercial.

In fact, while I was meeting with Mycoskie in New York to hear about how his shoe company is bringing loyal customers to South America and Africa on community shoe drops, the ad appeared on a TV over the bar. Waiters and waitresses looked from the screen to our table and back. “Is that you?” one of them mouthed at him across the room. He nodded. Big grins broke out all around. After all, as the ad emphasizes, this is a guy whose business is built on doing good. For every pair of shoes TOMS sells, they give a pair away to a child in need. “I believe that you can do good by doing well,” he says on the ad, as smiling children try out their new shoes, “and this year we will give away over 300,000 pairs of shoes.” With the company’s growth, Mycoskie is investing more of his time in research and development, but true to his beliefs, part of that research involves community outreach and promoting philanthropic travel by bringing his customers along with him on company missions.

What inspired you to start TOMS?

After the Amazing Race finished, I decided I wanted to take time to travel differently. I was an entrepreneur and had been doing a tech company which allowed me to have a flexible schedule. I decided to go to Argentina. One: because I had been there on the Amazing Race and two, because I had always wanted to learn how to play polo. I am from Texas. I went to a polo camp, a cheap one that I found on the internet. I spent three weeks learning polo, drinking great red wine and met some girls from the U.S. who were doing a shoe drive. They were collecting discarded shoes and then taking them to villages to kids who didn’t have any. They asked me to go with them. I had never done anything like that, but it was a transformative experience. I thought, “There has to be a better way. What if we create a business, with the idea of one for one: Every time someone buys a pair, we give a pair away.”

What was the response when you launched the company?

We started in 2006 and our goal was to sell 100 pairs at $40 a pair. We made them in a garage in Argentina; shoes that were comfortable, fun and colorful. Then the L.A. Times ran a story, and we sold 2,200 pairs online. Then we met Sally Singer, the fashion director at Vogue and she featured us, and we got orders from Nordstroms and Bloomingdale’s and sold 10,000 pairs in four months. To give away the first 10,000 shoes, I went with 16 friends for a “shoe drop,” and we filmed it with a hand-held camera and the documentary premiered at the Tribeca Film Festival. Last year, we sold 150,000 pairs and this year, 300,000.

So now you are inviting customers to join you on the shoe drops, not just friends, family and employees?

A year ago we started offering for people to apply to go on the shoe drops. We have done 20 trips, and we have 300 people on the waitlist. Most of the trips go to Argentina, and they include wine tastings, polo, shopping and the shoe drop. The idea is that you should have fun and that a vacation that gives back does not mean you don’t get pleasure but that doing good can go hand-in-hand with fun. Like the shoes you get something you desire and you give back. We did two trips to South Africa for seven days, and have done them in New Orleans.

What are some of your upcoming trips?

We are planning one to Ethiopia for ten days. I’m going to Ethiopia in the fall. We have a factory there, which is creating jobs, but there is so much need in that country that I am really committed to focusing efforts there. In addition to the shoe giving, we will visit some ruins, go canoeing, sample Ethiopian foods and meet women who make incredible tapestries and scarves. The best part is always the shoe giving, because by taking people to clinics and schools, where they hand out the shoes (each pair is individually given and fitted on the feet), we are showing what we need to do but also inspiring people to do what they can on their own. The letters and videos that we get from people who have traveled with us is amazing; it really changes their lives.

If your work has you on the road much of the year, what do you do for vacation?

This year, I have decided to have a staycation. I had planned to visit friends who rent a house in the South of France and instead, I decided to just be in L.A. I am going to spend what I would on a vacation on exploring my own hometown. I want to go sailing, go to museums, visit galleries in L.A. I realized that I’m more excited about staying home than going anywhere.

To sign up to apply for a TOMS Shoe Drop trip, go to www.tomsshoes.com. As TOMS travel program expands, we will have updates and itineraries so sign up to receive our free email news blasts

Read about other entrepreneurs whose companies give back, like Katharine L’Heureux from Kahina Giving Beauty

Read about a special philanthropic travel program in Cambodia

Read postcards from contributor Tiffany Schauer about her philanthropic trips to Jamaica, Burma and Thailand

Read a Q&A with the founder of Thailand’s Lotus Flower Foundation