Tyler Chisholm is the creator of Curious as Hell, a growing leadership platform built on one core belief: better questions make better leaders. After more than 550 conversations on his long-running podcast Collisions YYC, he realized curiosity, not certainty, is what truly drives meaningful growth. Now, through his newsletter, YouTube channel, and upcoming projects, Tyler helps leaders ditch the facade of having all the answers and embrace curiosity as their superpower.
What is your channel called and what is it about?
I run Curious as Hell, a newsletter, YouTube channel, and leadership platform built around a simple idea: that better questions make for better leaders. It’s purpose-built for people who are tired of pretending they have it all figured out and are ready to lead with clarity, humility, and curiosity.
When did you start it? What motivated you at the beginning?
The seed was planted during my work on my podcast, Collisions YYC, which I’ve hosted since mid-2019. Over 550 conversations later, I realized that the throughline wasn’t just innovation or entrepreneurship, it was curiosity. I launched Curious as Hell to go deeper into that lens and offer tools, not just talk.
Who were you inspired by? Any influences?
I’ve always been inspired by people who lead with openness, like Brene Brown, Adam Grant and Simon Sinek. Anyone who’s more interested in asking the next question than having the final say. But some of the biggest influences have been closer to home. Kevin Crowe was the one who nudged me to start Collisions YYC. That single push opened the door to hundreds of conversations and changed how I show up as a leader. And Emily Ptak, who challenged me to not just talk about curiosity but to start writing about it. That challenge became a blog, which became a book, and now a full platform.
How would you describe your audience?
Leaders in transition & evolution. People building companies, leading teams, or growing their own potential who realize they don’t want to do it the old way. My audience craves insights, not noise. They want tools that work in real life, not just leadership theory that they have no idea how to implement or where to start.
What is your creative process? Do you have people who work with you?
Curiosity drives everything. I listen, I reflect, and I write. I’m lucky to collaborate with a creative team that helps shape the voice of Curious as Hell into newsletters, digital tools, and speaking content that meets people where they’re at. One of my regular newsletter contributors is Jennie Gilbert, a facilitator at SAIT, who specializes in people, culture and leadership. Collaborating with individuals like her helps me go beyond my own ideas and provide even more depth and value.
How do you monetize your content? Do you also have another job?
I am the co-founder and CEO of Clearmotive Marketing, an advertising agency. Curious as Hell has quickly become a core part of my daily focus. The newsletter will introduce a paid tier in 2026, and I speak regularly on curiosity as a leadership superpower.
What is your favourite piece of content you have created?
My book, Curious as Hell, hands down. It’s the most distilled, honest version of what I believe about leadership. It’s practical without being preachy or prescriptive. It’s full of real stories, hard-won lessons, and questions that challenge readers to lead with more intention and less ego. It’s the book I wish I had when I started leading more than 20 years ago. You can get a copy here.
What is the best part about what you do? What is the worst part?
The best part? Seeing curiosity change someone’s leadership in real time. When my community tells me, “That one question changed how I approached a tough conversation,” or “I finally realized I didn’t need all the answers,” that’s the win. The hardest part is choosing depth over dopamine. There’s always pressure to go for quick wins and viral soundbites. But I’m in this to build something that lasts, which means staying focused even when an algorithm wants a shortcut.
What are your future plans for your channel?
In January 2026, I’ll be winding down my podcast Collisions YYC after five incredible years. All of my focus will be going to Curious as Hell: growing the newsletter, expanding the YouTube channel, launching a Curious as Hell podcast, creating more valuable content, and speaking to leaders across North America through keynotes and personalized curiosity-based training sessions.
Where can we follow you?
Newsletter | YouTube | LinkedIn | Instagram | Website
PAY IT FORWARD: What is another Canadian content creator that you love?
Jeff Humpheys from the Calgary Sessions. His work is fantastic.
