The Trailhead

The Freedom of Being a Beginner with Oladimeji "Dim" Ajegbile

September 15, 2026·53 min
Episode Description from the Publisher

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.

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