Let’s Celebrate Risk-Taking!

It seems like we can’t go a week without someone in Canada complaining about this country’s lack of ambition.

Look, I get it. Right now, everyone in Canada is looking to point fingers at someone or something to explain this country’s lackluster growth. It’s the taxes! It’s the politics! It’s the 600 lb beavers (wtf?).

Who, me?

I’ve already posted about my belief that Canada’s problem isn’t ambition. At least, not directly. But there is an aspect of Canadian culture that I think holds many founders and would-be founders back: Canadian society does not value or celebrate risk-taking.

Kevin Carmichael recently wrote about the difference in Canadian and American growth following the War of 1812 and the long-term impacts on each country’s business culture. He noted that, following the war, risk-taking entrepreneurs were actively discouraged from settling in Canada:

“British overseers actively discouraged the risk-takers from settling in Upper Canada because they preferred docile farmers who had little interest in challenging the order of things.”

The University of Waterloo’s Horatio M. Morgan highlighted stark differences in the two countries’ historical treatment of bankruptcy as a key element in the long-term divergence between how Canadians and Americans view risk:

“Having had a more protracted colonial history and post-colonial experience under English law than the United States, some parts of Canada…maintained more punitive debt or bankruptcy laws than the United States. Notably, jail time for unpaid debt was still possible in Canada even in the early 1860s. Moreover, it would take Canada until 1919 to establish a federal bankruptcy act. This could also mean that indebted or failed business leaders were more protected and less stigmatized decades earlier in the United States than in Canada.”

In other words, failed entrepreneurs in Canada risked jail time and stigmatization for decades after America had widely embraced business risk and its long-term economic benefits. And it wasn’t just Canada. Commonwealth countries around the world have similar endemic risk-aversion due to their common historical experiences (thanks Britain 🤦‍♂️).

Today, risk-taking founders in the United States are broadly encouraged and supported by their communities as they pursue the American Dream. In contrast, most Commonwealth cultures have some form of “tall poppy syndrome,” where successful, ambitious individuals are frequently cut down by their community instead of celebrated.

This clip about entrepreneurship from British comedian Simon Brodkin perfectly encapsulates what I’m talking about:

I can’t help but wonder how much of the flow of entrepreneurs from Commonwealth countries to America isn’t so much because of taxes, infrastructure or other strictly logistical reasons as it is that the most ambitious founders simply want be in an environment that is supportive of the risks they’re taking. If you’re a founder trying to change the world, would you rather be around people who think you can do it and cheer you on or in a community that encourages you to lower your ambitions and “be more realistic”?

But the times, they are a-changin. Post-Covid, we’re seeing new grassroots communities pop up in startup ecosystems around the world that are explicitly focused on fostering ambition and risk-taking — something that wasn’t always the case in the past. Jesse Rodgers recently wrote about the need to intentionally foster ambition and risk-taking within founder networks and startup communities,

“Ambition is the foundation for growth and achievement, and when combined with the power of a supportive network, it can propel you to incredible heights. Surrounding yourself with others who share your drive makes every challenge feel more achievable, every victory more meaningful, and every goal closer.”

Speaking of risk-taking, this past Friday, I shared the news that after 3+ years at Panache Ventures, I’m taking (another) big risk and embarking on my next adventure.

The folks at BetaKit were kind enough to write about it, and I shared with them this observation on my upcoming endeavor,

“The changes that are happening right now across tech and the venture industry are opening up some new adjacent opportunities that are in areas that I’m interested personally in looking into,”

I’m not ready to share any further details yet, but I hope that you’ll celebrate the risk-taking with me.

I might succeed. I might fail. But either way, it’s going to be awesome!

P.S. If you want to be the first to know what’s next, sign up for my weekly newsletter.