What if the trail you fear most is the one that sets you free? We talk with illustrator and writer Cy Whitling about his journey from a strict Christian upbringing in northern Idaho to the welcoming trails of Bellingham, where bikes, art, and community changed his life. Cy tells us how a simple hardtail bike, a supportive shop mentor, and a well-worn Kona catalogue helped him see the world differently. In college, he found skiing, search and rescue, and people whose kindness mattered more than rules, which led him to make the tough decision to leave his old life and build a new, chosen family.
Cy shares why he came out when he released a Pride poster, the backlash he faced, and the stronger connections that made it worthwhile. We discuss queerness in mountain biking, how pronouns and representation help people feel safe, why bisexuality is often misunderstood, and how the industry is quietly making progress thanks to real people.
Cy’s art is intentional: he uses animal characters so more people can relate, keeps a notes app to capture honest moments on the trail, and creates weekly comics to help riders feel seen. We also cover his creative process, meeting deadlines, and how he tries to keep his art true to himself without turning it into just another product.
Finally, we head west. Cy takes a solo road trip to Seattle and Bellingham, where he discovers steep trails, rock features, and even a birthday party which most of the attendees arrived at by rather than by car. His riding improved quickly, thanks to friends who push their limits and a community that makes speed feel safe.
Cy talks about how mountain biking feels more stable than skiing, remembers avalanche accidents that changed how he thinks about risk, and explains why he still wants to create work that gives back. Listen in for a story about letting go, choosing kindness, and finding a sense of home on two wheels.