The Trailhead

Oladimeji Ajegbile, known online as Hello Dim, went viral for filming bike rides through Edinburgh with his two-year-old son perched on the handlebars, narrating every tree and bus he sees. He's also a former architect, UX designer, startup founder, stay-at-home dad, and, as of last year, a runner who clocked a sub-50 10K on roughly two training runs and just finished his first half marathon with a 50K trail ultra on the calendar.

Zoë and Brendan talk with Dim about why the toddler videos connected when a decade of content didn't, the 90-day rule he uses to test every new pursuit, what the Piston Cup in Cars taught him about chasing medals, learning to ride a bike at 21, running the Union Canal in the pitch-black Scottish dark, getting dizzy at 30K of a track ultra, and his Substack essay on why achievement won't fix your emptiness. It's a conversation about being a beginner on purpose, making things for the process instead of the result, and what happens when the internet decides which part of your life it wants to see.