As I moved through 1976 and finished my second year in business school, the faculty politely suggested that, perhaps, business school was not for me. I couldn’t pass accounting.
By then, I was so tired of school I took the easiest courses I could just to finish quickly. Despite my struggles with accounting, I majored in economics and got near perfect marks without very much effort. I was a creative business student, and economics is an art. It is a subject in which there is never a right answer, so I succeeded. Economics seemed a relatively easy way to bullshit my way through. I concluded that everyone should take the easiest courses they could because what comes easiest will ultimately be the most fulfilling in life.
Having transferred to the University of Calgary, I played football (a sport in which I was mediocre), wrestled (quite poorly), and swam (only on relay teams). In 1979, after a two-week stint with the local pro football team, I quit to learn how to distance run and to get my 250 pounds down to 210.
I graduated in 1979, seven years after I’d started university, with a degree in Economics. I hadn’t blown all my Alaska money just yet. There was one more thing I would spend a lot of money on.
Chip Wilson, Global Person
I still had five free airline tickets anywhere in the world each year. I took full advantage of the opportunity. Although the tickets were free, I spent a lot of money on the trips outside of airfare.
I was very fortunate to have travelled the world by my early 20s. On one trip, I had a four-hour layover in Rio while on my way to Cape Town, South Africa. I got off the plane, walked around, and within an hour I had decided Cape Town could wait, maybe indefinitely. At that moment, Rio seemed like the most fantastic place in the world.
It helped, I suppose, that it was New Year’s Eve. I knew nothing about places with names like Copacabana or Ipanema, but everywhere I looked the Brazilians were dressed up in their best. I loved the Latin flair of the culture and how everybody was so expressive, especially when I contrasted Rio against the conservatism of North America.
On another trip, I went to Barbados. I finished my last exam and got on a plane the next day. I told no one I was going. In all these travels, I learned how small the world was. Imagine getting on a plane and going anywhere.
It was 3:00 a.m. on my fourth day in Barbados, and I was at a disco called Alexandria’s. After a few drinks, I turned around and saw someone that looked like my dad. I went up to the man, thinking that perhaps every person really did have a doppelgänger, and asked, “Are you my dad?”
He replied, rather matter-of-factly, “Yes,” then asked me if I wanted to go surfing the next day.
I laughed and politely declined. The last place that I had ever wanted to meet my dad was in a disco in the Caribbean, so we went our separate ways. That moment was surreal.
Towards the end of 1979, my university days were finished, and my free travel perks had come to an end. I had about $85,000 left in the bank and was thinking about what was next.
California Wrap Shorts
As with many other things in my life, the answer turned out to be in California.
In the fall of 1979, on a trip to visit my grandmother in San Diego, I noticed Ocean Pacific (OP) making men’s street style corduroy surf shorts and hoodies for men to wear when not surfing. At the same time, I saw girls wearing wrap shorts that were tied on one side, then brought up underneath and tied again in the back. They came in bright, bold colors and patterns, often safari or Hawaiian-printed fabrics.
From what I knew about sewing and tailoring – from watching my mother over the years – I noticed how simple, comfortable, and functional these shorts were.
Since I visited California annually, I knew this was a new style. I knew the critical mass of people and trends in California had a way of eventually influencing what people would wear everywhere else. I brought a pair of the shorts back to Calgary as a present to my then-girlfriend, Cindy Wilson (no relation).
I showed her the wrap shorts from California, and she loved them. So did her friends. This was the first positive sign of the demand for the shorts.
My initial thought was for us to make them ourselves. The pattern seemed simple enough, and Cindy and I had learned a thing or two about sewing from our mothers, such as making the first pattern from newsprint. It turned out I’d overestimated my abilities somewhat, and even though I sewed a few pairs after I’d cut the pattern, I don’t think anyone would have wanted to wear them.
I reflected on my mom’s skill. I believed there had to be other great seamstresses like her that would love to make extra money. I put an ad in the newspaper and quickly got replies from perhaps a dozen women. This was an encouraging response, but I wanted to narrow the field further, so I could ensure high-quality work.
To do this, we cut bolts of fabric – all of it 100 percent cotton and brightly-flowered or otherwise boldly-patterned – and delivered the fabric to each seamstress who’d answered the ads. I asked them to make 10 of the wrap shorts. From there, I narrowed it down to the five who did good work.
Of those five, one woman produced significantly more than the other four. Her name was Josephine Terratiano. Josephine, a wonderful Italian woman, was sharing the work with her relatives, who, like her, were all highly-skilled couture tailors. They became my own Italian connection.
By this time, my mother, her husband, and my sister and brother had moved back to the States, and my dad was spending more and more time at the Esalen Institute in Big Sur. The Terratianos became like a second family to me.
“My mom was a seamstress, and my sisters were seamstresses,” Josephine recalls, “but my only profession is sewing. I did all my sewing with all my heart. And Chip, he was lucky to find me!”
Josephine and her sisters made about 300 pairs of the shorts, and I branded them Fine as Wine as a nod to Billy O’Callaghan, my old mentor on the pipeline. After Cindy and I sold the shorts to her friends, I took them to the major department stores in Calgary to see if they might be interested in selling them.
Nobody seemed to believe these shorts were viable or sellable on any level.
This was my first inventory problem – lots of product and nowhere to sell. But I was confident if I could get past the store buyers, people would want the product. The idea was to get people living at least a kilometre above sea level and under a 12-hour drive from the West Coast who were excited about Southern California-inspired surf wear. I couldn’t do it by selling wholesale to big department stores. That meant I would have to figure out how to get out of this inventory mess myself.
The more I considered the problem, the more I came back to one of the most basic sales concepts I could imagine – a lemonade stand!
The plan was simple – a nice-looking wooden booth and a three-month summertime lease in down- town Calgary. That was my plan to sell my stock of shorts and the genesis of a sophisticated vertical retail business. Cindy would work the booth all week. We would both work on weekends.
Assessing Career Options
A few months after making 300 pairs of shorts and graduating from University, I’d received a letter from London Life Insurance, one of the biggest insurance companies in Canada. It was a wonderful letter, full of compliments. Apparently, these people knew who I was from my varsity sports.
“We have been following you and your esteemed athletic career at University, and we feel you’d be a great employee at London Life,” they told me. Here was one option.
I called London Life, and they invited me for an interview. When I arrived, I noticed how everyone was very prim and proper, wearing the Calgary formal look: a Prada suit with alligator cowboy boots. But anyone who knew me back then knew all I ever wore were shorts and sandals, even through the winter. That was how I dressed for the interview. I’d been so enamored by their letter, I thought they knew me on some personal, intimate level – enough to know how I liked to dress.
In reality, London Life’s initial correspondence with me was more of a form letter, made to sound intimate and personal. They didn’t know me at all. I did not get the job at London Life.
I then applied for a job at Dome Petroleum, a Calgary-based oil and gas company. I wore a suit. With my economics degree in hand, Dome hired me on as a landman. I remember getting dressed in a suit in front of the mirror and saying to myself, “Halloween, every day.”
Working as a landman meant negotiating mineral rights, exploration rights, and various business agreements. I worked on the 30th floor of the Dome Tower in downtown Calgary, and my salary was about $30,000 a year – good money for a young man of 25. I was terrible at my job, and I apologize to anyone with whom I had to work.
My manager was one of the first female managers in the oil business. She was great, but I wasn’t the right putty out of which to make a decent employee. I was sent to many courses, but I couldn’t pay attention because my own mind was too busy. My mind was muddled with fundamental questions of life. Would I ever get married? Could I get a date for Friday night? Would I have enough money to retire? Would I ever have children? Could I pay for a family? What would happen if I got sick? Etc.
There were no courses that would develop my maturity. I couldn’t pile on work development courses until I had myself figured out.
Shortly after I started at Dome, I met a guy named Scott Sibley, who had just come to Dome through a merger. We’d both been at the University of Alberta at the same time. Some of Scott’s closest friends had been on the football team with me. We figured we must have been at dozens of house parties together (as I recall, Scott would have a cocktail in his hand and a girl on his arm, while I would have a litre of milk in mine and no girl), but we’d never formally met.
As much as I knew my job at Dome was a good one, I knew I was looking at the same trap I’d experienced on the pipeline in Alaska – trading my life for money. The goal of working for myself by age 30 gave me a tangible sense of something to work toward, particularly with Fine as Wine (now renamed Westbeach) just getting off the ground.
The name, Westbeach, was derived from my subconscious need to get back to the West Coast. My childhood on Ocean Beach in San Diego had imprinted a feeling in me that I was trying to recreate in the prairie city of Calgary.
Throughout the same period, in the spring and summer of 1980, I had become interested in triathlons. There were a few ways I’d come across the idea of doing a triathlon. As a competitive swimmer,
the 2.4-mile swim was easy, since that was the distance swimmers swam to warm up for a workout. I’d also recently taken up cycling, as I found the act of pulling up with foot cages on the pedals had fixed the back injuries I’d sustained from playing football. So, I was already regularly doing two of the three main exercises that compose a triathlon.
I was also looking for a new physical challenge. Through swimming I’d come to believe my mind had ultimate power over my body – but what about something I hadn’t tried? Something like the Ironman? The first Ironman was held in Hawaii in 1978. Since so few people had done it, there was really no context, no collective understanding of what it demanded. I may as well have said I wanted to run across the Gobi Desert.
However, I believed if I could do an Ironman 50 pounds heavier than average, I could train my brain that anything was possible. Knowing you can achieve what seems impossible is one of the most significant things someone can derive from athletic activity.
No one had figured out how to make clothing for triathletes. The average time to complete a short triathlon was a couple of hours. For the Ironman, it was about 9 to 10 hours, or 13 in my case. Either way, it was a lot of time. Transitioning out of saltwater, if the seams inside an athlete’s apparel were off a little bit, or if there was any rubbing or chafing, it would be a pain more painful than the race itself.
I spent a little time and money designing a Lycra garment with the seams moved away from the inner thighs and from under the arms. The result was a pair of cycling shorts with a look, feel, and function that had never existed before. I was excited by the technical achievement of these shorts. This design appealed to me in a far more creative way than the wrap shorts we’d made for Westbeach, since those wrap shorts weren’t solving a functional problem of any kind.
Unfortunately, I was eight years ahead of the mainstream popularity of the triathlon movement. There just weren’t enough people participating in the sport to make the demand worthwhile – not yet, anyway. I sold the shorts wholesale to a few cycling shops, but the experiment went no further.
Still, I couldn’t ignore that deep-seated, creative satisfaction I’d felt from designing and producing a high-quality technical garment. This was a passion that would stay with me during the Westbeach years when we moved away from surfing to skateboarding and then to snowboarding gear, and this same passion would move to the forefront of my thinking with lululemon, still two decades away.
The First Season in Business
At last, Cindy and I opened our booth when spring arrived. It didn’t take long to see how high the demand was. The incredible thing about the first season at the booth was seeing how many people actually wanted to buy our product. It excited them.
Fortunately, the Dome Oil Tower was across the street from our booth. At the end of the day, I would collect the cash, go buy fabric, and take it to the other end of the city to the seamstresses and tailors. I would then go for a 90-minute swim, eat all I could, and go to bed. In the morning, I would wake up early and go for a two-hour bike ride, then go to the other side of the city to pick up finished goods from Josephine and deliver them to the store. I would then skateboard into work in my suit and run a 10k at lunch.
Those days of starting a business and training for a triathlon were wonderful and energizing. I loved it all.