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Canadian businessman and billionaire investor Andrew Wilkinson has made a successful career out of channeling his entrepreneurial spirit, but he knows that sometimes that energy can be a double-edged sword. On this episode, Wilkinson goes in-depth on the lessons learned from a career that’s seen him build a business empire of more than 40 companies, but also why he’s had to re-calibrate his personal goals after struggling to find happiness in the summer of 2021. He also discusses mimetic desire, building a business in a small Canadian market, competing with venture-backed companies, strategies for hiring CEOs, the mistakes that have cost him millions of dollars, and so much more.

 

Wilkinson is the co-founder of Tiny Capital, which boasts an enterprise value of more than $1 billion and owns 35 different companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses. He is based in Victoria, British Columbia.

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