Rethinking Entrepreneurship
Unpopular opinion ahead... On Monday I attended an event hosted by TechTO, part of Open House Montreal this week. The guests — Harley Finkelstein(Shopify) and David Segal (David’s Tea) — shared their entrepreneurial journeys, their connection to Montreal, and answered audience questions.
It was an inspiring event, I really loved it, but... I also had some mixed feelings about the overall message left behind.
It was my first time hearing Harley speak. He’s incredibly high-energy, charismatic, and genuinely inspiring — it’s easy to get swept up in that passion. But much of his message stems from a hustle culture I no longer subscribe to. I felt that strange push-pull between feeling energized and also realizing how misaligned some of it was with my values.
At one point, Harley and David talked about their new podcast, Big Shot, where they interview self-made billionaires now in their 80s and 90s, after decades of building their empires (Tim Ferris deja-vu feelings). When asked when they realized “made it,” every single one said they haven’t yet. They’re still hustling — still chasing the next thing. Themes around working on vacation, being “always on,” and the idea that if you want it badly enough, you can make it happen (disregarding systemic challenges) came up again and again.
Part of me gets it, because I have felt that drive before - and that entrepreneurial fire is hard to be stopped (and honestly, feels amazing to be that passionate about something). As David said, “Entrepreneurship is a personal pursuit disguised as a business endeavor.” I couldn’t agree more. And it's an exciting place to be.
But I’ve also worked closely with CEOs and Presidents who were brilliant and visionary — and still, I don't envy their day-to-day lives for a moment. There was never true time off, little family presence, and man - don't even get me started on the amount of stress they carry. It is exciting, but at what cost?
Yet I still love building businesses and helping others do the same. So it makes me wonder: Am I too naïve to believe there’s another way to do entrepreneurship? When I am in rooms like this - it feels like it, however, I've been to other stages where the conversation is much different.
TechTO Made In Montreal: From Bagels to Billion-Dollar Ideas with Harley Finkelstein and David Segal
Of course there will always be hustlers — and their drive is inspiring in its own right. But that model has dominated the spotlight for too long. It’s time to amplify stories of those who have built successful, fulfilling businesses without burning themselves out in the process (yes - they exist!).
We need more diversity on stages and in the stories we tell. Not just in identity — but in definitions of success. Voices that speak to sustainability, authenticity, and joy in the process. There are so many brilliant people doing things differently and achieving incredible results.
I’d love to hear more of those stories — the ones that remind us that building something meaningful doesn’t have to mean losing ourselves in the hustle.
If I had to pick one role model in this regard, it would be Sara Blakely, the self-made founder of Spanx, who famously turned about $5,000 into a billion-dollar company and later sold a majority stake for around $1.2 billion. What inspires me most about her isn’t just the scale of her success, but the way she built it — with humour, intuition, and heart. She speaks openly about failures, prioritises joy and balance, and shows that you can build something extraordinary without sacrificing your humanity in the process. (Just follow her on Instagram and you will see what I mean!).
On the other end of the spectrum, there are so many local small-business owners on the same path to success. I listened to Tara Bosch, founder of SmartSweets, at the Startup Canada Tour in Vancouver a couple of years ago — and her story about how only 4 years after its launch, she sold a majority stake of her company to a private equity firm for $360 million. Just as impressive (we are talking about a gummy bear company generating $100M in sales/ year in just 4 years).
Curious to hear: who are the role models that inspire your version of inspiring entrepreneurship? I'd love to follow more people who are challenging the system and doing things differently! (Or if you are into the old models - who inspires you and why?).
