Sondra, Long-Term Career Thinking

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...

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Every week, we go deep with the most interesting creatives in music.

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Chapter timestamps:

0:00 Intro

3:30 The 3 Sides Every Creative Has to Balance

4:30 You Shouldn't Rinse Your Shows. It's a Sacred Thing.

5:00 What Dermot Beats Himself Up About On Stage

5:30 Anxiety After the Show Starts, Not Before

6:00 The Struggle of Being Lucky Enough to Have a Career

8:00 Childhood

9:00 "I Know I'm Good. But I Feel Very Insecure in Other Ways."

14:00 How Dermot Built a Career With No Algorithm and No Social Pressure

18:00 Why He Doesn't Play Music for People

19:19 How He Started Busking

20:15 Why Most People Couldn't Busk — and the Genius Who Changed Everything

21:00 The Importance of Branding When Selling Anything

22:00 How to Make Real Money Busking

26:00 How Dermot Built His Name and Started Playing Shows

29:00 Into the Music Business — and the Most Successful He's Ever Felt

31:00 Being Sought After and Avoiding Bad Record Deals

32:40 How to Build Out Your Team

36:00 A Note About Touring: Enjoy Where You're At

38:23 His Advice to His 15-Year-Old Self: Find Your Contentment

39:23 How Dermot Kennedy Built a Worldwide Fanbase

Credits:

Hosted by Ross Golan

Produced by Joe London & Jad Saad

Edited by Jad Saad

Post-Production VFX by Pratik Karki

Watercolor Art by Michael White

Hosted on Acast. See acast.com/privacy for more information.