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Modern WisdomModern Wisdom

“We Won 3 Grammys and Still Felt Like Failures” - Dan + Shay (Live Performance)

Dan Smyers and Shay Mooney are American country music singers, songwriters, and Grammy Award-winning artists.

Chris WilliamsonhostShay MooneyguestDan Smyersguest
Nov 14, 20261h 34mWatch on YouTube

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At a glance

WHAT IT’S REALLY ABOUT

Dan + Shay on success, pressure, reinvention, and writing “Say So”

  1. Dan Smyers and Shay Mooney recount meeting in Nashville while broke, then reflect on how success changes motivation, identity, and what they can write about.
  2. They describe how wins and losses—like losing every award at a major ceremony or winning Grammys without savoring them—can warp expectations and happiness.
  3. They explain the high-stakes pressure of performing the national anthem at the World Cup opening ceremony and why they insisted on a traditional, singable arrangement.
  4. They detail reinventing their writing process by discarding a completed album and rebuilding a new project around songs that felt urgent and personally honest for their current season of life.
  5. They share the origin of “Say So,” written in grief after losing their friend Ben Vaughn to suicide, and how listener reactions reinforced their purpose beyond charts and awards.

IDEAS WORTH REMEMBERING

5 ideas

Comfort can shrink your creative fuel, so you need new sources of meaning.

Shay Mooney describes how early scarcity (sleeping on couches, scraping by) gave them lots of life experiences to draw from, but as life becomes more “settled,” they have to dig deeper to find compelling material.

Uncertainty and a strong partner can preserve drive even after big success.

Dan Smyers says the music business can flip overnight (he cites COVID as an example), and that volatility keeps them hungry; both also frame their duo as mutual accountability that keeps them moving.

Following success can be psychologically harder than earning it in the first place.

Shay Mooney says once they had massive songs like “Tequila” and “Speechless,” they felt a new internal bar that made follow-ups feel harder, and they had to focus on the process rather than chasing a repeat outcome.

Awards and charts can distort priorities and steal moments you should celebrate.

They describe losing every award they were nominated for at one ceremony, and also winning major awards (including Grammys) but not fully celebrating because they were chasing the next milestone.

Some “high honor” gigs are high-risk, so clarity on approach matters more than flash.

Shay Mooney explains the pressure of singing the national anthem: minimal upside, huge downside; for the World Cup opening ceremony they insisted on a traditional, sing-along-friendly approach rather than embellishments.

WORDS WORTH SAVING

5 quotes

Reframing from, "We have to go do this," to, "I get to go do this," and even if it's just, like, a, a motto that we keep hammering, it's like we try to say that out loud as much as possible 'cause I think if you say that and you lead with gratitude, I feel like you'll start to believe it.

— Dan Smyers

I think when people start off, they have this assumption that success is going to fill some sort of internal void. Sure. Mm-hmm. Then they get it. That hasn't fixed it.

— Shay Mooney

"Nobody panic, but I'm gonna die."

— Shay Mooney

Even if this song doesn't go crazy, if it dies at 70 on the radio charts, if it just doesn't take off- if it helps one person, if it saves one life, it was a win. That's as good as a Grammy for us.

— Dan Smyers

If you don't go out of your way to foster a relationship, what we do is like a marriage, 50/50 split. It's, uh, it's probably even more difficult than a marriage. I mean, there's like money on the line. There's notoriety. We have this brand. We have this business we're trying to uphold.

— Dan Smyers

Read the available transcript
Early Nashville struggle and meeting storyDrive after success and reframing gratitudePressure of follow-up hits and shifting goalpostsAwards, validation, and habituationWorld Cup national anthem anxiety and approachRebuilding an album-writing process around honesty“Say So,” grief, suicide, and music’s real-world impact

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SPEAKERS

  • Chris Williamson

    host

    Podcaster and host of Modern Wisdom.

  • Shay Mooney

    guest

    Singer-songwriter and one half of the country duo Dan + Shay.

  • Dan Smyers

    guest

    Singer-songwriter, producer, and one half of the country duo Dan + Shay.

High quality AI-generated summary created from speaker-labeled transcript.

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