How Great Investors Show Up

I was extremely lucky to get my start in venture under the late Derek Smyth at OMERS Ventures in 2013.

He was one of the rare VC’s who had a deep respect for entrepreneurs and the sacrifices required to build great companies. He took a sincere interest in getting to know founders as people before working together, and understood that trust takes years to build and seconds to lose.

Where he truly excelled was in his pursuit of a deal.

If he wanted to invest, he went all-in and took risks where others wouldn't.

He backed Frederic Lalonde at Hopper at what many felt was an aggressive valuation for a pre-launch company. He simply believed in the founder. Turns out he was right. When all is said and done, that investment will likely be a multiple fund returner.

The pursuit I remember most clearly though was Shopify. I shared this story with someone recently and he thought I should share it more widely, so here it is.

After OMERS missed an opportunity to invest in the Series B, Derek and the team were determined to make it right.

He took a deep interest in getting to know Tobias Lütke and Harley Finkelstein as people.

To better understand the opportunity, he shopped exclusively from Shopify merchants for many months. The company was under $1B GMV at the time (today they are $370B), which made this genuinely difficult to do. I have fond memories of him walking into the office with the most obscure, hilarious purchases 😂.

When Shopify hit $1B GMV, he bought an old cash register, filled it with $1B in fake “SHOP” money, and drove his Tundra 5 hours to Ottawa to deliver it in person.

In 2015, in what I still see as an act of Canadian patriotism, Tobi and Harley chose OMERS — a young Canadian fund — over many global tier 1 VCs to lead the pre-IPO round.

Winning that right was an all in team effort, but Derek's hustle and persistence in the lead up is something I think a lot about now as a VC with more grey hair.

Derek lost his battle with brain cancer in 2017. I’m grateful for every day I got to learn under him.