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Alex Tilley was in his early 40s when he set out to design a classy, durable hat for weekend sailors like himself. The iconic Tilley hat became a Canadian success story, and spawned the Tilley Endurables line of outdoor garments and accessories. Thirty-five years later, the hats and clothing are still made in Canada, using a painstaking production process, but the business has struggled recently. This spring, at age 77 and no longer involved in day-to-day operations, Tilley sold his beloved company to Re:Capital, a financial firm that specializes in restructurings and turnarounds.

Your early career wasn't very promising, was it?
I was struck by a car when I was 11 or 12, and I landed on my head. That may have given me my exceptionally poor memory, which might have led to my achieving an educational record: six years at university, passed just three of them. Later, I was fired by Bell Canada after one month and by the Bank of Nova Scotia after about nine months. My dad said I was too full of piss and vinegar to survive in banking.

Did you have any formal training in business?
At one point, I entered an MBA program, not knowing what the term "business administration" meant. I don't like to administer businesses. I like to set them up. I don't want to do the nitty-gritty. I flunked out after a year.

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Yet you ran other businesses before you made the hat. How did you make a career switch?
I could do it because I worked only in the mornings in the art-rental firm I owned then. The hat was so costly to make, and I never thought it could be a business. But after selling it at boat shows for four years—at higher and higher prices—I learned that people will pay for long-lasting quality.

What is your advice to young people starting out?
Test a business idea for $500 or less, to see if the product or service is truly desired. Then get a mentor. I had several mentors. The last one was a veteran executive, Jack Parker, who was in his mid-80s when I was in my 60s. Twice a week he would dress up and drive to our company in his Cadillac. He listened to us—and he was so wise. He enjoyed it so much that he had some of his ashes scattered on the front lawn of our store in Don Mills.

What is your advice to Tilley's new owners?
One of my favourite quotes is: "A stranger's eyes see clearest." I wasn't able to stand back and see what changes were necessary. It was time to pass the mantle.

Will you have any association with the company?
My wife, Hilary, and I recently met the new owners for the first time and we all got along famously. They have asked me to be involved in social media, and I'm waiting to hear back from them. But I have never Twittered in my life.

So they value your role as the embodiment of Tilley Endurables?
I have created the feeling of the company and the way we do things. I have come up with most of the good ideas on the clothing, although other people have taken them and made them elegant.

Looking 10 or 20 years down the road, will people still pay $80 for a hat when cheap knockoffs are available?
I haven't the faintest idea. I never think that far ahead. And the knockoffs generally don't bother me. I'm pleased they think well enough of us to knock it off. But they never put in the quality that we do.

Is selling a business like watching a child leave home?
In a way, but you have to let children go and find themselves. It was time to leave it in good hands. But the business will always be mine. I'm its father; I gave birth to it, and I will always stand back and care for it.

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What is your legacy?
On my tombstone, I'd like to have: A good man who built a better hat.

This interview has been condensed and edited.

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