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Keeping it real

The bright, midafternoon sun is beating down on Satori, a Jeanneau 53, as she floats placidly in her slip in Marina del Rey, California. I’m waiting for Blake Mycoskie, the founder and “chief shoe giver” of the TOMS One for One empire, and he is running late.

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When he finally walks down the dock, he doesn’t look like a man whose net worth is estimated to be more than $300 million. He looks like a surfer bro, in a faded V-neck T-shirt, shorts, an ancient pair of madras TOMS shoes and multiple necklaces and bracelets.

Mycoskie has come from a hell of a busy day — TOMS had just announced its new CEO this morning. But that’s not why he’s late — he has been waiting for me at another slip, where he keeps his Hunter 45, the boat he lived aboard for five years as the business was just taking off. (Publicists had crossed wires.) I’m disappointed because, truth be told, I’d much rather have seen the Hunter.

We climb aboard, and Mycoskie ducks below to grab a beer. Is the new CEO a good thing, I ask? Is he worried about the company’s culture changing? He pops the cap off the bottle, stretches out in the cockpit and shakes his head. “I think the culture will be better — it will be more cohesive with one day-in-and-day-out leader,” he responds.

“About a year and a half ago, I realized we had so many growth opportunities, but all the big decisions were being made by me. And I was more interested in the giving side of the business.” It was bad for the company, Mycoskie thought, to have so much riding on one person’s decisions, especially when his role also demanded a lot of travel and time away from the office.

“So I decided we needed a CEO, but we were going to need a different growth structure to attract the right one.” Enter Bain Capital, which acquired a 50 percent stake in the business last August. At the time, Forbes estimated the value of TOMS at $625 million.

Not bad for a business that the former Amazing Race contestant began a mere nine years ago while working out of his apartment. On a trip to Argentina in 2006, Mycoskie admired the local alpargatas, a durable and inexpensive espadrille-like shoe. Why not start a for-profit business that also does good? For each pair of TOMS shoes purchased, a free pair would be given to a shoeless child. And that’s how the “one for one” philosophy was born.

In less than a decade, TOMS has provided more than 35 million pairs of shoes to children. An eyeglasses product launch in 2011 has helped 275,000 children see clearly by providing glasses and cataract operations. And last year’s launch of TOMS coffee roasting business has provided more than 67,000 weeks of safe drinking water. The TOMS Bag Collection is the latest one-for-one product — each purse, tote or shoulder bag that’s purchased provides a bag with a birth kit to help a pregnant woman in a developing country safely deliver her baby.

Blake Mycoskie and wife Heather have done a lot of sailing together.

As the shoe business started taking off in 2007, Mycoskie’s apartment was feeling impossibly cramped — he needed more room for TOMS. So he bought the Hunter 45, got rid of most of his stuff, moved aboard and learned to sail. The sense of freedom is what he loves most about sailing, and he found that life aboard such a small place, with little room for possessions and clutter, was also very freeing.

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“I loved living on a boat. There was just no room for excess.” Some of his most creative moments happened aboard the Hunter, he says.

When he met his girlfriend Heather (now his wife), she took to sailing, too, and also moved aboard. There were a lot of trips to Catalina, and they have chartered in Greece a few times with friends. Heather, like her husband, has become a passionate fly fisherman.

“Yeah, I think when I realized how much Heather liked to sail, and then she took up fly-fishing and was really good at it, I thought, Where else am I going to find a woman like this who I also like having sex with?” he jokes about getting married.

Now the couple has a young son and a sprawling new house in Topanga Canyon. But on Wednesdays, Mycoskie gets together with friends and races Satori. He treasures that time because it keeps him connected to the water until he can get back to cruising when his kid is older. Someday he’d like to take a year or two and circumnavigate.

And his dream boat for this big expedition? Mycoskie still wants nothing fancier than a Jeanneau 64. That’s big enough to see the world in, to bring the family and have a couple of crew aboard. He loves his 53.

The philanthropic side of the business is what excites Mycoskie, seen here in his travels as TOMS’ “chief shoe giver.”

For now, though, there’s still a lot of work to be done at TOMS. New CEO Jim Alling, who was president of Starbucks U.S. and COO of T-Mobile, will take over the business side of the company, freeing Mycoskie to be more creative and focused on the philanthropic mission of TOMS. And the company’s goals aren’t modest.

Last year’s launch of the coffee roasting product invited skeptics to wonder whether TOMS was finally biting off more than it could … um, brew. With artisanal coffee brands spreading like overcaffeinated ideas, was there room for another brand among Starbucks, Blue Bottle and Stumptown?

Mycoskie enjoys a cup of TOMS coffee at the flagship store in Venice Beach, California. The cafe feels like a laid-back place to hang out and is decorated with souvenirs and talismans from Mycoskie’s travels.

TOMS launched with sales at Whole Foods Markets nationwide, through its webshop and with a series of cafes the company has created that retail other TOMs products in an atmosphere that feels more like a groovy, laid-back clubhouse for former Peace Corps volunteers than a coffee shop. But is it working? A year after the coffee launch, there are now five TOMS Cafes in the United States, one in Amsterdam and one opening soon in London. Water projects are supported in the seven countries that source the free-trade coffee beans.

TOMS has promised a new product rollout every year, an incredibly ambitious goal. But with Bain’s capital influx and the inevitable demands for returns on that investment, the opportunities seem endless. Tea and chocolate may be next, but there have been murmurings of partnerships on everything from hotels to ticket sales.

I ask Mycoskie what he’s going to do with the Hunter 45 he used to live aboard. “Oh, I’ll never sell that,” he says with a smile. “Now that I’m a dad, and we have this big house, I look forward to my kids knowing that I lived on that boat for five years. I want them to know I was as happy in 250 square feet as I ever was. I think that’s something great that I could teach them.”

This article originally appeared in the August 2015 issue.