Meet Me in Napa Podcast

Meet Me In Napa | Skylar Grey “From a Cabin in the Woods to 3.5 Billion Views”

jeremy Jackson Season 1

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In this episode, host Jeremy Jackson sits down with Grammy-nominated singer-songwriter Skylar Grey, best known for co-writing the massive hit “Love The Way You Lie” featuring Eminem and Rihanna — one of the most-streamed songs in history with over 3.5 billion YouTube views. Now calling Napa Valley home, Skylar opens up about her extraordinary journey: from performing as a child duo with her Celtic harpist mother in Wisconsin, to signing with Linkin Park’s label as a teenager, to hitting rock bottom in LA — and ultimately writing one of the biggest songs of the 2000s alone in a rustic Oregon cabin with no running water.

She also gives us a first look at her upcoming album “Wasted Potential” (out May 22nd) and what turning 40 means for her artistry and self-reflection.


🎙️ About Skylar Grey

Skylar Grey (formerly known as Holly Brook) is a Grammy-nominated singer, songwriter, and producer based in Napa Valley. Her credits include:

  • “Love The Way You Lie” — Eminem ft. Rihanna
  • “Where’d You Go?” — Fort Minor (Mike Shinoda of Linkin Park)
  • “Coming Home” — Diddy-Dirty Money
  • “I Need a Doctor” — Dr. Dre ft. Eminem
  • “Glorious” — Macklemore ft. Skylar Grey


    ⏰ Topics Covered

    [0:00]  Welcome & Intro — Jeremy introduces Skylar and why Meet Me In Napa is more than a wine podcast
    [1:00]  “I came for the wine, but I stayed for love” — how Napa found Skylar
    [2:00]  Meeting her partner Elliott at Bottle Rock 2016 at Oxbow Market — he asked to carry her melon 🍉
    [3:00]  Her first glass of wine that changed everything: Inglenook in Japan, and connecting with Carlo Mondavi in Park City, Utah
    [5:00]  Why Napa reminds her of growing up in Wisconsin — open landscapes, peace, and wide open space
    [7:00]  Growing up musical: dad in a barbershop quartet, great-grandma an opera singer, mom a Celtic harpist and folk musician
    [8:00]  Performing with her mom starting at age 6 — three albums and a Midwest tour later, she went solo at 12
    [10:00]  Using her college savings to move to LA at 17 — and calling her dad after her first Grammy nomination
    [11:00]  Getting signed to Linkin Park’s Machine Shop Records (Warner Brothers) — and what happened after it fell apart
    [13:00]  Manifesting a collab like Eminem’s “Stan” since age 13 — and “Where’d You Go?” with Mike Shinoda as her first billboard hit
    [15:00]  Hitting rock bottom in LA at 23 — broke, lost, and no longer in love with music
    [17:00]  Moving alone to a rustic Oregon cabin (no running water, hiking up a sand dune with a flashlight) — trading art gallery work for rent
    [20:00]  Writing “Love The Way You Lie” six months into her cabin retreat — sent off a quick demo and a month later it was #1 in the world
    [23:00]  “I just wrote what I felt” — on NOT knowing it would be a hit
    [24:00]  Imposter syndrome, flukes, and the songs she slaved over that went nowhere
    [28:00]  The pressure of songwriting rooms — and why her best work always came when she was alone
    [33:00]  The remote collab: Skylar in Oregon, producer in New York, Eminem in Detroit, Rihanna in Dublin — first time all in the same room was the Grammys
    [37:00]  Her new album “Wasted Potential” — what it means and where the title comes from
    [44:00]  From Holly Brook to Skylar Grey — evolving as an artist and co-producing her own music now
    [46:00]  Turning 40, looking back, and why the 40s are actually a golden decade
    [51:00]  Napa’s creative renaissance — Bottle Rock, Blue Note Festival,

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