Canadians endlessly chase our tails worried about how we’re doing relative to each other. It drags us all down. I'm over it. And you should be too.

I can’t help but hear Mandy Patinkin’s voice in my head when some founders pitch me their startups. Not because of mistakes in language or grammar, but because many founders misunderstand how certain words and phrases are interpreted by investors.

Here are 5 of the of the most common phrases that founders and investors interpret differently.

If you’re a founder in Canada — or are involved in the Canadian tech scene in any way — then you’re familiar with the letters CDL. The Creative Destruction Lab helped create more than $19 Billion in equity value. And it's completely changed the Canadian tech landscape.

Americans are born confident. So much so that the rest of the world often mistakes it for arrogance. But in many aspects of life, American confidence — born of a deeply held belief that success is manifest destiny — is an unfair advantage.

In fundraising, it’s a game-changer.

Long before I was a VC, I cofounded DataHero, the world’s first cloud BI company. I recently came across one of our old fundraising decks and boy, did it suck! Let’s look at all the mistakes we made in that deck.

As a Canadian investor, I get to meet incredible founders from Victoria to St. John’s every single week. But as much as I enjoy crisscrossing this magnificent country, for me to be an effective investor, it's essential that I get out of Canada.

Since moving from San Francisco to Vancouver in late 2020, I’ve been asked one question over and over: “Why did you come back to Canada?