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“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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CHAPTERS

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Chapter summaries

Merch plug, freestyle intro, and the “Dominoes” inside joke
Chris kicks off with a quick merch mention before Dan and Shay jump in with a playful musical intro. The conversation immediately turns into a long-running inside joke about calling Domino’s pizza “Dominoes,” and how the misunderstanding lasted for years.
- •Chris mentions a limited-time Modern Wisdom merch drop
- •Shay opens with a comedic sung intro and banter about Chris’s outfit
- •They explain the “Dominoes”/Domino’s joke and how it started
- •Shay describes how the joke spread and became part of their group language
Broke Nashville days: odd jobs, cheap rent, and the first meeting at a house party
Dan describes taking strange paid research gigs for rent money, including taste tests. Shay tells the story of meeting Dan for the first time at a run-down Nashville house where Shay had to basically break in because the door wouldn’t work.
- •Dan recalls doing research groups and taste tests to get paid
- •Dan describes their early Nashville living situation: cheap rent and a falling-apart house
- •Shay narrates arriving at the party and getting in through a broken door
- •They joke about an early headline referencing meeting “under the sheets”
Does success kill drive? Staying hungry by reframing “have to” into “get to”
Chris asks whether success makes it harder to stay motivated, and Shay reflects on how fewer life struggles can mean fewer experiences to write from. Dan argues the music business is volatile, which forces constant hunger, and both emphasize gratitude and loving the work itself.
- •Shay says early-life experiences are rich songwriting fuel that can diminish as life stabilizes
- •Dan says volatility in music (including sudden downturns) keeps them hungry
- •They compare having a duo partner to having a “lifting partner” for accountability
- •Dan explains the mindset shift from “I have to” to “I get to” as a sustainability tool
Chris’s “Tequila made me move to America” story — then a live performance
Chris tells the story of hearing “Tequila” on Broadway in Nashville and deciding that moment to move to America. The story leads straight into an in-studio performance of “Tequila,” followed by reactions, nerves, and celebration.
- •Chris recounts a 2019 U.S. road trip and experiencing Broadway on July 4th
- •He describes the crowd anticipating the key moment in “Tequila” for shots and singalong energy
- •They perform “Tequila” live in the room
- •They debrief the performance, joking about nerves, silence, and the moment’s intensity
Was “Tequila” really about tequila? Credit, culture, and the brand that never called
After the performance, Chris asks whether “Tequila” was truly about the drink or something else. Shay jokes about how the song coincided with tequila’s surge in popularity, and how no tequila company capitalized on it with a partnership.
- •Shay says tequila felt like it exploded in popularity around the song’s release
- •They joke that a tequila brand should have reached out since they did “marketing 101” unintentionally
- •Shay shares his drink preference: tequila soda with no lime (“no bad fruit”)
- •They riff on bar limes, prep habits, and why he avoids garnish
Following a hit: moving goalposts, competitiveness, and not savoring wins (even Grammys)
Chris asks whether writing the first hit or the follow-up is harder, and Shay says the follow-up can become mentally crushing once a bar is set. They talk about chasing results, the emotional whiplash of awards culture, and how even major wins can feel empty if you never stop to celebrate them.
- •Shay says following a breakout song can create pressure to match or exceed the “bar”
- •He emphasizes controlling the process because outcomes can’t be controlled
- •They describe the pain of losing awards on camera and the odd incentives of award shows
- •Shay says they won three Grammys but still felt like failures because they kept chasing the next thing
Looking back on “eating shit”: radio tour grind and the UK tour that became a favorite memory
Dan and Shay reflect on brutal early-career stretches that felt miserable in the moment but became treasured memories later. They describe the exhausting reality of radio tours and Shay shares how a winter UK run felt dark at the time yet became legendary in hindsight.
- •Dan describes radio tour as a sales job with early mornings, travel, and little sleep
- •They contrast in-the-moment exhaustion with the gratitude that comes later
- •Shay recalls a first UK tour where he barely saw sunlight and binged what was on the bus hard drive
- •They conclude that memories aren’t wasted, even when the moment feels rough
High-stakes performance: singing the national anthem at the World Cup opening ceremony
They explain why the national anthem is a uniquely high-pressure gig with little upside and huge downside. Dan and Shay recount being asked to perform at the World Cup opening ceremony, rejecting an initial “marching band” arrangement, choosing a traditional approach, and feeling the weight of the moment.
- •Shay describes intense nerves and the feeling of the moment’s magnitude hitting on stage
- •Dan explains why they often said no to anthem performances due to risk and scrutiny
- •They describe pushing for a simple, traditional version so people could sing along
- •They recall surreal details, including almost losing focus when the screen cut to famous audience members
Reinventing the album process: scrapping finished songs and writing for the present moment
Shay explains that they had nearly a full album completed but sensed something missing in its DNA for the season they were in. Conversations about AI and meaning pushed them to write songs that felt personal and inevitable, resulting in a burst of focused writing over a short period.
- •Shay says they had an album’s worth of songs but decided it didn’t fit what they needed now
- •He describes career changes happening around that time, including management changes
- •They felt pressure from modern release expectations and fan demand for constant new songs
- •They adopted a standard of inevitability: why a song has to exist and has to come out now
The story behind “Say So”: grief, vulnerability, and messages from listeners
Shay tells the story of losing their friend Ben Vaughn to suicide and how that led to writing “Say So” in a deeply honest session. Dan describes realizing the song needed to exist, deciding its purpose mattered even if it wasn’t a massive radio hit, and receiving intense listener messages about its impact.
- •Shay shares that Ben Vaughn’s death by suicide deeply affected them and their Nashville community
- •He explains how the song began organically from conversation rather than a typical title-driven session
- •Shay admits initial hesitation about releasing such heavy, exposing material as Dan + Shay
- •Dan says the song’s value would be proven if it helped even one person, and they received long, emotional DMs and in-person stories
Why humans keep making art: AI, real connection, pain vs happiness, and authenticity
The conversation widens into what makes art meaningful in an AI-heavy future and why pain-based songs often connect more deeply than happy ones. They discuss sincerity, the difficulty of being emotionally open, and why long-form conversations can reveal authenticity in ways short interviews can’t.
- •Shay argues that as long as humans consume art, there will be demand for human-made art
- •They explore why sad songs can heal and create a feeling of not being alone
- •Chris and Shay discuss empathy and why pain can connect people more strongly than happiness
- •They talk about authenticity being highly valued now, while sincerity can still trigger backlash
Live acoustic debut of “Young,” and a candid talk about aging and changing inspiration
They perform “Young” acoustically for the first time in this setting, then reflect on why the song hits so hard. Shay describes how aging becomes real in the mid-30s, how parenting shifts perspective, and how the themes they write about evolve as life settles.
- •They attempt an on-the-spot acoustic performance of “Young” without lyrics available online
- •Shay says the song made him cry when he first played it for his dad
- •They discuss when aging stops being a number and starts being felt in recovery, energy, and resilience
- •Shay describes writing more literal snapshots of adult life and believing listeners can sense what’s real
Criticism, social media distortion, and staying grounded in real-world feedback
Dan and Shay describe how online negativity can warp perception and make artists doubt themselves, even after success. They contrast comment-section reality with the clarity that comes from meeting fans face-to-face and focusing on excitement for the craft rather than chasing approval.
- •Dan says existing only in digital space can make negative comments feel more real than they are
- •Shay argues social media is toxic, especially for kids, and describes why he’d delay his children using it
- •They discuss polarity online: super fans and super haters, with little in the middle
- •Chris explains his own validation loop: how excited he feels before an episode and after it’s done
How they nearly drifted apart — and the conversation that rebuilt Dan + Shay
Dan explains that their hardest period wasn’t one blow-up but slow separation: less time together, less communication, and not actively nurturing the partnership. Both describe a late-night porch conversation that included apologies, perspective shifts, and a renewed commitment to staying on the same team.
- •Dan says time and distance eroded connection as families grew and schedules changed
- •He describes realizing their relationship needed intentional maintenance like a marriage (or harder)
- •Dan recounts initiating an emotional sit-down conversation before a major tour opportunity
- •Shay highlights empathy, respect, grace to grow, and remembering they share the same goal
What makes a great creative/business partner, then closing updates on album and tour
They answer what traits matter most in a partner: someone who challenges you, complements you, and makes you better—while you do the same for them. They also revisit how no amount of success eliminates criticism, and finish with where to find them, plus upcoming album and tour timing.
- •Dan says a great partner challenges you and pushes you past “perfect” into better
- •Shay emphasizes reciprocation: bringing out the best in each other and grounding each other in what’s real
- •They discuss how criticism still stings regardless of achievements and how negativity dominates online feedback
- •They close by sharing upcoming album and tour details and wrap the conversation

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