Sean Silcoff had a thoughtful article in Saturday’s Globe & Mail on my path from entrepreneur to investor. It is a well-written piece with many great quotes and anecdotes and included the most important lesson about early-stage investing that I learned over the past 8 years:

“If the fail rate of our companies is not high enough, it’s not because we are exceptional investors, it’s probably because we’re not taking enough risks. You need to invest in things that nobody has seen, where nobody recognizes the opportunity, and where nobody else would invest – and be right.”

Taking huge risks can be scary for entrepreneurs and investors alike, but risk lays the foundation for what can ultimately be special companies and outsized returns. Every day I remind myself that there is no such thing as a stupid idea, as a market that is too early, or a company that has too many missing pieces. Many of our bets might fail. But when they succeed, it’s pure magic to get to be a part of something special from the beginning.