Ep. 215: Jessie Reyez | The Story of Betting On Herself (For Anyone Starting Over)

Today’s guest is a fearless storyteller whose voice is as raw as her lyrics—bold, emotional, and unapologetically real. A first-generation Colombian-Canadian, she turned hustle into art, weaving her experiences into songs that hit like truth bombs. Whether she’s penning heart-wrenching ballads or delivering razor-sharp verses alongside icons like Eminem and Beyoncé, her work is grounded in authenticity and fire. She’s busked, she’s bartended, she’s broken through. And now, with her third studio album, she continues to push boundaries—proving that vulnerability, grit, and honesty never go out of style. From Toronto to the world… And the writer is… Jessie Reyez!

Produced by Joe London, Ross Golan, and Jad Saad

Special thank you to our season sponsor NMPA!

Chapters:

00:01:36 – Start Here: Why This Episode Will Change You

00:02:37 – How Jessie Met Eminem and Earned His Respect

00:09:50 – What Jessie Learned Giving Back to Songwriters

00:16:52 – Jessie’s First Song Ever (It’s Cringey… and Brilliant)

00:18:28 – Jessie’s Crazy Lyric Memory & Why It Matters

00:18:51 – From Choir Rooms to Stadiums: Where It All Began

00:27:57 – The Moment She Gave Herself One Year 

00:31:12 – How Her Mom’s Brutal English Drills Made Jessie a Genius

00:35:35 – What Happens After the Hit? Jessie Tells All

00:37:11 – The Exact Moment She Knew Her Life Was Changing

00:42:36 – The Video That Changed Everything (She Almost Didn't Post)

00:45:14 – How a $50 Bus Ride Got Her Into the Remix Project

00:48:18 – Why She Stayed Up 14 Hours Editing Her First Video

00:50:12 – The Brave Story Jessie Told That Changed Everything

00:51:17 – Writing 'Figures' — The Raw, Drunken, Real Truth

00:56:44 – The Writing Camp That Sparked Her Breakthrough Hit

00:57:11 – How 'Figures' Was Really Written (And Why It Still Hurts)

01:00:00 – Gatekeeper: Calling Out Sexism in the Music Industry

01:01:42 – What MeToo Missed — And What Jessie Risked to Say

01:02:58 – The Heavy Cost of Telling the Truth

01:05:43 – Why Being Vulnerable is Jessie’s Greatest Superpower

01:06:20 – Jessie on Drake, Bieber, The Weeknd & Canadian Greatness

01:07:14 – Why So Many GOATs Come Out of Canada

01:08:11 – From Open Mics to Eminem: The Legacy She’s Building

01:18:14 – The Insane Calvin Harris Story (You Won’t Believe This One)

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