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That famous hat

Picture of Alex Tilley

Alex Tilley and the boat that begat the wonderous Tilley hat

Picture of Alex Tilley

Issue 39 : Nov/Dec 2004

Her name was Karmananda. Keith Storey, now commodore of the Alexandra Yacht Club in Toronto, remembers her vividly. His voice in a telephone message betrays a slight tremble when he recalls his days as yard master when he watched year after year as she sat neglected in her cradle, her varnish peeling, her wood rotting. “Such a beautiful boat. It was enough to break your heart.” Finally, after almost a decade exposed to the rain and wind of summer, and the snow and sleet of winter, the owner just walked away, and the club had no choice but to sell her for one dollar to a boat restorer they hoped would do right by her.

It was not the first time that Karmananda had seen hard times. Years before, with the name Rangatira fading on her weather-beaten transom, she had sat in the same state on a cradle down at the National Yacht Club. That’s when she was discovered by the man in the hat . . . but at the time it was not the Tilley hat because the Tilley hat had not yet been created.

From his days as a young lad in Kitchener, Ontario, when he had learned you could buy pumpkins in the poor section of town, put them in a wagon and take them to the rich part of town and sell them for a lot more, Alex Tilley had been an entrepreneur. As such, his life had been a roller coaster ride of euphoric success and desperate failure. He graduated from the University of British Columbia with majors in psychology and economics and came back to Toronto, ready to make his mark in the business world. His first job at Bell Canada had him shaking the corporate ladder with enthusiasm. He was going to find new ways to energize an old company. He was fired after one month.

A shy and reserved young man, he struggled as a salesman for Office Overload before moving on to sell the services of a tutoring school. Before long, he was convinced that he had a better way to run the business and clashed with management. To prove his point he started his own tutoring school, enjoyed some initial success, but eventually found himself broke and living with relatives in Montréal. Now he was a husband and father, and the pressure to put away these foolish ideas and take a steady job became overwhelming. He sold printing presses with little success until he decided that the road to fame and fortune ran straight through an MBA from York University. The problem? How does one provide for a growing family while holding a full-time class load? The answer came from the entrepreneurial mind that once sold pumpkins in Kitchener, Ontario.

Karmananda awaits her salvation.
Karmananda awaits her salvation.

Simple proposition

Sitting comfortably in a large leather chair beside a portrait of Winston Churchill in his well-appointed office at the Tilley Endurables head office in Don Mills, a slight smile crosses Alex’s face as he remembers. “Sunoco was running a contest at the time. If you drove into a Sunoco station and your license number was listed, you could win a cash prize anywhere from $10 to $1,000. That was a considerable sum of money at the time.” What Alex realized immediately was that he could secure the name, address, and telephone number of every winner simply by calling the motor vehicle licensing bureau of Ontario.

He would then contact the winners with a simple proposition. “When I show you a way that you’ll receive $100, would you pay me $20?” In a time before telemarketers, when people actually trusted each other, the answer was invariably “Yes!” And so, Alex would tell them to drive into a Sunoco station to fill up and become a cash prizewinner. “Aside from providing the money to put me through York, that experience taught me how to write very persuasive letters. Sometimes the winners had memory lapses about our agreement, and my letter using phrases such as ‘promised by you’ and ‘doing what is fair,’ brought in almost all of the agreed-upon commissions. Very few people went back on their word.”

In many ways, York University became a microcosm of Alex Tilley’s world . . . tremendous elation when he was chosen class president after a rousing, humorous speech to his classmates and then bitter disappointment when he “flunked out” and failed to get his MBA after taking the financial risk of going back to school. His attempt at higher education did yield him a job at the Bank of Nova Scotia. Once again, he just didn’t seem to fit in and was fired. Now his was a life very much in limbo.

Redemption began when he read a Financial Post article about a firm that leased artwork to major corporations. Alex had always enjoyed art as a form of expression, and the idea of providing paintings to adorn the walls of corporate offices in downtown Toronto captured his imagination. Before long he had a very successful business, operating with offices in Toronto, Montreal, and Calgary. It provided him not only with a substantial income, but also time to pursue his latest passion — sailing.

“During the summer I was able to complete my work in the morning and then spend my afternoons down at the National Yacht Club, sailing and working on my Silhouette, an open-design boat used for sailing the English Channel. I became known as ‘Tilley the Circumnavigator’ for the number of times I’d sailed around Centre Island.”

It was during these voyages of discovery around Toronto harbor that the idea first occurred to Alex that the world really did need a better sailing hat. Baseball hats would blow away in a strong wind and allow the sun to burn the tops of your ears. More elaborate hats seemed to last less than a season, unable to withstand the rigors of wind, rain, and sun. Alex searched without success for a strong, durable sailing hat that would stay on his head and protect him from the elements, but with a young family to raise, an art business to run, and a boat to sail, it was not something that kept him awake nights.

Something unique

“When I decided to move up to a larger boat, I wanted to find something very special. I wasn’t too sure exactly what I wanted, but I was looking for something unique . . . a ship with a very elusive quality. I call it ‘character,’” Alex says.

Alex searched aggressively far and wide. Ironically, he found exactly what he was looking for in the yard of his very own National Yacht Club. Her name was Rangatira. She was sitting derelict, almost beyond repair, in her cradle. She was a 30-foot homebuilt based on a Brandlmayr design (see Good Old Boat, September 2004, “How Spencer Yachts began”). Her wooden hull had been layered with fiberglass, but her once beautiful teak and mahogany cabin and brightwork was now stripped, peeling, and weathered gray. She’d not felt the water beneath her in some time, and only a man with time, money, and a business life that had become far too predictable and boring of late, could save her. At the time, that would describe Alex Tilley.

“I spent an average of $100 per week for over five years, and I did a lot of the work myself. In the winter I’d bring the wood home and refinish it in my basement. But when she was finished, she was something to behold.”

Her hull was painted a dark green, with cream accents at the rail and waterline. All her rigging, tackle, and hardware looked like new and gleamed bronze and silver in the summer sun. Her teak and mahogany, both above decks and in the cabin below were sanded and varnished to brilliant perfection. Her Sitka spruce mast stood tall and proud, raked back distinctively for better performance to windward. Circling the bottom of the mast was a wooden ring holding six belaying pins for a quick release of the halyards. At her bow shone a polished chrome plow anchor with white, plastic-covered rode, and on her transom bold letters announced her new name, Karmananda.

“It’s an East Indian expression meaning, ‘Bliss through good Karma,’ and that describes exactly the way I felt when I sailed her,” Alex says.

A younger Alex Tilley contemplates his project boat.
A younger Alex Tilley contemplates his project boat.

Better hat

As Alex sailed her, he became more and more obsessed with the idea of creating a better sailing hat. He had spoken to designers and developed one prototype after another. Each was an improvement over its predecessor. When the people at Genco suggested 10-ounce cotton duck for the material and brass grommets to facilitate the tie-down cord, things began to come together. One day while sailing out the Eastern Gap in heavy weather with several inexperienced guests aboard, his favorite jacket slipped overboard in the whitecaps. Rather than put boat and crew in jeopardy with a rescue attempt in the narrow channel, he watched helplessly as the jacket sank out of sight. It was then he resolved that one of the most endearing features of the new Tilley hat must be that it floats.

The first test of a Tilley hat did not take place on the beautiful Karmananda on Lake Ontario. Instead, it was on a boat chartered in Belize for a family winter vacation. The hat was worn in all weather conditions, even while swimming. It emerged battered, but not beaten, and Alex was ready to present it to the world. At first he filled the requests of friends and fellow sailors who admired his hat and wanted one of their own. Then he left the art business in the hands of employees while he traveled to boat shows to demonstrate the hat. His problem was one of profitability. His hat cost more than $12 to manufacture. He felt that he could not ask more than $16 for a cotton sailing hat at the time. What with travel, marketing and administrative costs, he was actually losing money every time he sold a hat.

As time went on and word of the world’s finest sailing hat spread across North America, he kept hearing from customers that the Tilley hat was the best purchase they had ever made. Instead of buying five or more $3 hats every year, they bought the Tilley hat, which seemed like it would do them for a lifetime. Taking a huge chance, Alex increased the price and offered a “lifetime guarantee.”

Increased price

“I remember one of the first boating shows I went to after increasing the price. I was nervous that it just wouldn’t sell. I kept the cash in a Tupperware bowl below the counter at the booth. At the end of the day, I took the bowl back to my hotel room and spread the money across the bed,” Alex remembers. “I sat there counting it, and I was thrilled. It wasn’t the amount of money because I was already quite secure financially. It was the fact that after all this time and trial, my belief in the Tilley hat had been justified. It was a wonderful feeling.”

Rejuvenated by the success of the Tilley hat, Alex threw himself enthusiastically into the task of reinventing sailing shorts. He watched as his crew lost cigarettes and wallets overboard while wrestling with a jib on the foredeck, and he thought of Velcro pockets. He designed a loop to hold winch handles at a time when you had to go forward to hoist a mainsail. He incorporated a stainless-steel D-ring to secure a Swiss Army knife. He thought of the double bottom so he could offer another lifetime guarantee for his product. And again he found
himself with a cost of manufacturing that was higher than most of his competitors were charging retail for their shorts. People knew the Tilley hat and loved it, but the price of a pair of Tilley shorts just seemed too high.

Two years later, he was ready to give up his “hobby” of designing sailing clothing when he donated a full set of Tilley sailing shorts to the crew of the Canadian boat sailing in the America’s Cup races. The resulting publicity and enthusiasm of the crew for the product breathed new life into the idea that Tilley durability was worth it in the long run.

“With the demise of the art business and the formation of Tilley Endurables, the next step was just common sense,” Alex says. “Tilley sailing shorts led to Tilley trousers, and Tilley trousers led us to the fact that travelers need the same kind of sensible, durable clothing that sailors need. And so the full line of Tilley Endurables travel clothing was born.”

Blissful Alex

And what of Karmananda, the beautiful 30-foot wooden sloop that danced across the waters of Lake Ontario with a blissful Alex Tilley at the helm?

“Success in business does not come without a price,” ponders a reflective Alex Tilley. “It hasn’t always been easy. I’ve made horrendous mistakes in business, and I’ve been incredibly lucky. But just like being in a gale with Karmananda, you stay your course, keep a firm hand on the tiller, and you get through it.”

For Alex, the demands of being president of Tilley Endurables, a multi-million-dollar international business, left little time for sailing in Toronto harbor. Combine that with a new wife who didn’t enjoy sailing, and Karmananda found herself once more on a cradle in a shipyard, at the mercy of the elements for 10 years. Bliss through good Karma.

Alex leans back in his leather chair, steel-gray hair and neatly trimmed beard accentuating a firm jaw and unyielding dignity. He embodies the quality that he so coveted in his beloved sloop, Karmananda — character. While other clothing companies have fled to the cheap labor of Southeast Asia, he has insisted on keeping Tilley products Canadian-made. He has backed all his products with a no hassle money-back guarantee. And he has traveled the world to test all his products and create new ones through his own personal experiences.

“I love my life,” he says. “I turned my hobby into my life. I travel and discover new people, new places, and enjoy new adventures every year . . . and I get paid to do it. I feel I’m the luckiest man alive.”

It seems like a happy ending, except for Karmananda. What happened to Karmananda, and equally as intriguing, why has Alex Tilley not sought after her? The wisdom garnered from a lifetime of success and failure in both his business and personal life smiles wistfully at the question and answers in a whisper.

“Never look back.”

Thank you to Sailrite Enterprises, Inc., for providing free access to back issues of Good Old Boat through intellectual property rights. Sailrite.com

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