Chip Wilson’s Biggest Business Mistakes

Mike Berner
5 min readNov 19, 2020
artwork by author

In 2005, lululemon founder and CEO Chip Wilson seemed unstoppable.

His Vancouver-based yoga apparel company had already expanded across Canada and was entering the United States. Management estimated lululemon’s value at $225 million. Big investors and large retailers, including Victoria’s Secret, had written to Wilson expressing their interest in the company.

Just eight years later, Wilson would be fired from lululemon.

In his book Little Black Stretchy Pants, the Canadian entrepreneur recounts his career and the founding of the company that arguably sparked the athleisure trend. Like many people crazy enough to start companies, Wilson is certainly a bit of a character. At times, the book is a bizarre read.

But while many similar autobiographies only focus on the successes, Wilson’s book is unique in that he spends a lot of time on his failures as well.

Don’t Doubt Your Own Abilities

Many people told Wilson that he didn’t have the expertise to take lululemon from $100 million in sales to $1 billion in sales.

Even though skeptics had said the same thing when the company was only doing $15 million in revenue, Wilson decided that he needed outside help. He had a young family, and he doubted his ability to…

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Mike Berner

Publisher of TheTycoonist.com. Sign up for my free daily business and money news bulletin.