How Andy Grammer Kept Singing on The Streets... Even When No One Listened

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In this episode of Behind The Wall, I sit down with the incredibly talented Andy Grammer - an artist known for massive hits like “Honey, I’m Good” and “Keep Your Head Up,” but whose story goes so much deeper than the charts.
Before selling out arenas and racking up billions of streams, Andy spent four years singing on the streets, performing for anyone who would listen. No label. No fame. Just a dream and a guitar. In this conversation, Andy opens up about that journey - what it took to keep going when nobody was cared, and how he stayed rooted in optimism even when success felt impossible.

🎵 In this episode, we dive into:
* His early days as a street performer and how it shaped him
* The story behind his first breakout hit
* How he defines success today vs. when he started
* His perspective on creativity, perseverance, and staying grounded
* What it really takes to build a career in music from the ground up

Andy’s story is a reminder that greatness doesn’t come from luck - it comes from heart, hustle, and staying true to your purpose. Whether you’re an aspiring artist or someone chasing a dream of your own, this conversation is for you.

Thank you, Andy, for going Behind The Wall with us and sharing your truth. This is one of the most important interviews I’ve ever released for artists. It’s a powerful reminder that every journey looks different—and sometimes the road to where you’re meant to be starts on a sidewalk with no one watching.

Huge thank you to everyone who helped bring this episode to life. Even though it was recorded a while ago, the insight, honesty, and inspiration Andy shares will stick with creatives everywhere. 🙏

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00:00 Andy Grammer Has Arrived
00:40 How Andy Knows Daniel & Why Daniel Does This
02:00 Why Andy Loves Songwriters
02:42 Why Daniel Loves Andy’s Story
03:17 Rejected from Acapella in College
04:18 Purpose with Work Ethic
05:14 Good Taste vs Your Work
05:52 Andy Was a Street Performer for 4 Years
07:18 What is Good Art and Why Street Performing Taught Andy His Music
08:18 The First Years of Street Performing
10:00 How Singing on The Street Taught Andy Confidence
10:53 Early Stages of Performing and Giving a Service
12:25 Was Andy Proud to be a Street Performer?
13:33 Andy was one of the first celebs on TikTok
15:05 What’s Crazy about Street Performing
16:02 What Kept Andy Grammer Going for 4 Years
16:45 How Andy’s First Hit Song Was Made - Keep Your Head Up
18:12 How Many Songs Andy Wrote until Keep Your Head Up
19:43 Andy wrote 100 songs to get Honey I’m Good
20:28 Andy’s Advice to Every Artist - Write 100 Songs
21:23 How Andy Starts Every Song
21:52 How To Not Be Afraid of Failure
23:10 Daniel Shows Andy The Video
26:40 Andy’s Advice for Daniel to Sing with Coldplay
27:44 Daniel Asks Andy The Question
29:09 Thank You Andy for Going Behind The Wall With Us!