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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.

Follow us on socials: @andthewriteris

A special thank you to our sponsors...

Our lead sponsor, NMPA — the National Music Publishing Association. Your support means the world to us.

And @splice — the best sample library on the market. Period.

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.

Today’s guest is one of the most quietly enduring artists in modern pop — a songwriter and performer who’s spent over a decade growing up in public, learning how to separate perception from identity.

She was discovered online as a teenager and quickly thrust into an industry that had already decided who she was.

But behind the headlines, she was doing the real work — writing, refining her sound, and slowly building a career on her own terms.

This is a conversation about perception vs reality, creative control, and what it actually takes to become yourself in an industry that benefits from misunderstanding you.

And The Writer Is… Madison Beer!

What you'll learn:

• What it actually feels like to grow up in the public eye

• The gap between how artists are perceived vs who they really are

• Why longevity in music requires emotional resilience

• How Madison developed her sound and creative identity over time

• The pressure of early success — and rebuilding from it

• Why being misunderstood can either break you or sharpen you

This episode is brought to you by the NMPA — supporting songwriters and protecting the value of music.

And by Splice — the world’s largest library of sounds and samples, built for creators.

Chapters:

0:00 Intro

1:42 Madison’s favorite songs of hers

3:00 Lyrics or melody first?

4:30 Ross meeting Madison at 13

6:00 Madison’s childhood, early memories

7:00 Going through parent’s divorce in early childhood

9:45 Why singing the national anthem is hard

10:00 Her family’s early encouragement

11:00 Madison’s first song

13:00 Starting her career at 10

18:40 Getting discovered overnight from a Justin Bieber tweet.

19:11 Contracts in music industry

19:58 Meeting Justin Bieber

21:46 Why getting dropped is a blessing

24:00 Struggling with early music identity

26:00 Why she felt she couldn’t fight back on creative control early on

28:00 finding her power through social media

31:55 Reclaiming creative control

33:50 writing reckless

35:28 Home with you

36:25 the importance of your collaborators

39:12 the original demo to Reckless

41:13 being easier to write dark songs than happy songs

41:40 the challenge of writing her new album

41:54 NMPA

42:36 Splice

43:26 Going back into the label system

45:00 her first tour in lockdown

46:50 Madison’s touring non negotiables

52:00 the story of Home to another one

53:41 Writing darker songs while in a happy relationship

55:55 Setting boundaries for mental health

56:55 “Showed Me” as an interpolation

58:37 Her mental health struggles and path to healing

1:01:54 How her album locket Freed her

1:03:25 the unlikely story of bittersweet

1:05:30 what writing a song with strangers is like

1:09:00 loneliness and missing out on a normal childhood

1:12:00 Dealing with constant criticism and how she manages it

1:12:47 Surviving the lowest point of her life

1:16:30 how she currently manages her mental health

Hosted by Ross Golan

Produced by Joe London and Jad Saad

Edited by Jad Saad

Post Production VFX by Pratik Karki

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