Ep. 246: Dermot Kennedy How an Irish Busker Became a Worldwide Phenomenon

Today's guest is the Irish troubadour who sold out arenas across the world and built one of the most durable careers in modern music, entirely on his own terms. From Dublin street corners and busking for strangers to headlining Madison Square Garden, this conversation is about what that actually costs to build the slow, deliberate construction of a career that answers to no one, yet resonates with millions around the world. He carries three things simultaneously that most artists never figure out how to hold at once: the ambition of someone who was never going to settle for Ireland only, the sensitivity of a songwriter who writes for his whole community, and the creative instincts of a kid who grew up on hip hop and folk and refused to let either one fully win. This is one of the more honest conversations about what a creative life actually looks like from the inside — not the version that gets posted, the version that gets lived. And The Writer Is... Dermot Kennedy! In this episode of And The Writer Is... We go deep on: • His whole journey • The moment he realized the audience could feel how hard he was trying — and why that was the problem • How to carry ambition, sensitivity, and creative instinct in the same body without one of them destroying the other • Building an international career without a viral hit — and what that reveals about how the industry actually works • The busking years, and the secrets for how he survived • Why he deliberately toured smaller venues on his last run — and what that decision says about success • Imposter syndrome, insecurity, and the reality of growing a career from 0-100. And much more... Hit

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Ep. 246: Dermot Kennedy How an Irish Busker Became a Worldwide Phenomenon is an episode from And The Writer Is...with Ross Golan by And The Writer Is.

This episode is 1:20:46 long.

This episode was published on Apr 7, 2026.

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