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RACHEL IDZERDA/The Globe and Mail

Blake Mycoskie became a fashion star in the mid-aughts with TOMS footwear – casually chic shoes that allowed consumers to feel as good as they looked, since TOMS donates one pair of shoes for every pair purchased. Expanding the one-for-one business model to serve other global needs, Mycoskie launched TOMS eyewear in 2011 – for every pair of frames or sunglasses sold, the company helps to restore sight to a person in need. In advance of World Sight Day (Oct. 9), Mycoskie shares some of the secrets to his success, and explains why plaid pants are perfectly appropriate business attire.

The wisdom of plaid

My grandmother had an eccentric sense of style – all kinds of very bright colours and patterns. It was great. Her clothing would always attract strangers, which led to adventures and excursions. That's something that I picked up from her. It started as a strategy to get attention from girls when I was single, and later I realized that having a look could also be useful in business. Part of it is just having something that makes you unique – think of Steve Jobs's black turtleneck – but it's even more than that. When you wear something kind of crazy and fun, immediately people know that you don't take yourself too seriously. That will make them more relaxed, and when people are relaxed around you, that is good for business. I wore bright plaid pants and a corduroy blazer to the White House. It's fun, plus it's my way of signalling to people that, even though I've had success, I am an approachable person, and maybe a bit different. Every other man there was in a navy or black suit and a tie.

Clear house, clear head

When I was 29 I moved onto a boat and lived there for the next six years. I was living in California and this was the early days of TOMs. One of the great things was that, because of the limited space, I had to get rid of a lot of my stuff and just totally declutter. I only realized this later, but not having a lot of stuff helped me to focus and to just have complete tunnel vision in terms of this business that I was creating. I highly recommend it, in the right situation. I moved off the boat when I got married. Now we live in an old repurposed barn house. It's a different stage of life and now I feel like having a certain amount of stuff, knick-knacks and whatnot, is great because all of these things help to keep my travels and all of my inspiration top of mind. I still try to keep the clutter under control, though. It can really creep up on you.

Know the playing field before you get in the game

I started a television network in 2002 that ultimately went bust, but it definitely taught me a lot in terms of my evolution as an entrepreneur. I learned that the television industry, at least in the States, is fully controlled by five or six media companies, and if you're not partnered with one of those companies, then your chances of success are close to zero. I didn't know that going in. The larger lesson is that its much better to enter an industry where you can start small and build momentum and not have to make that megadeal right out of the gate just to stay alive. That's what's great about fashion and shoes. We started by selling TOMs in a few mom-and-pop boutiques. That got us some press and it grew from there. We were never in a situation where it was like, if we don't get into Nordstroms in the first six months then we're out of business. In fashion there are many paths to success. If you look at almost every major company today, almost every one of them had a gestation period where they had organic growth. Even if it was crazy growth like some of these dot-com companies, we are still looking at companies that were able to grow without that one big deal.

Sometimes strategy comes after the fact

Today, people talk about our one-for-one sales strategy as a business model, but when we were starting out, we weren't thinking in those terms. It was more like, okay, we want to help kids get shoes and we knew that giving away one pair of shoes for every pair sold would keep things easy. It's not a percentage or a formula. It's really transparent. Who could mess that up? We have gone on to use the model with other projects – our eyeglasses and now coffee. The plan is that we will be able to introduce a new one-for-one product every year. It has really become a signature for us, and of course I am happy to see other companies use it. I wish I could say we were smart enough to recognize what we were creating at the time, but I guess the result is what's important.

Success is staying in the game

The thing I learned from being on the Amazing Race is that whenever you think things are over, you're about to get kicked out, something amazing will happen and you're back in the game. Like Winston Churchill said, never, never, never give up. It's a cliché, but it's so true. You never want to take yourself out of the game before it's over. The people who did the best on the Amazing Race were the people who kept a pretty level head in both the good times and the bad, and that's something that definitely applies in business. In the early days of TOMS, we would get shipments from a factory that would be totally messed up and we would think we were going to go out of business, but we just kept going and it always seemed to work itself out. Success is putting one foot in front of the other, even when the bad things happen or a crisis hits.

This interview has been condensed and edited