#386 - Hailey Whitters On The Country Stars Who Have Slept On Her Couch + Once Being So Broke She Had To Sleep In The Airport + Funding Her Own Album That Led To Her Breakthrough
Bobby Bones Presents: The BobbyCast
Nashville Podcast Network
4.8 • 4.6K Ratings
🗓️ 28 February 2023
⏱️ 63 minutes
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Summary
Hailey Whitters (@HaileyWhitters) first single at country radio "Everything She Ain't" is climbing the charts and she stopped by Bobby's house before going on her new headlining Raised Tour. Hailey moved from a small town in Iowa to Nashville 15 years ago to pursue a career in country music but kept facing struggles. She talks about all the difficulties she had and ways she tried to make it, the jobs she had to take to survive, and the moment she got her publishing deal and first big song recorded by another artist but was still so broke she had to sleep in the airport one night. Hailey shares how she self-funded her 2020 album 'The Dream' that lead to her first breakthrough before getting her record deal. She also talks about the country artists who have slept on her couch and watching them all become successful before she did, and how it feels to finally have a song on radio. Plus cool moments like getting to perform on Jimmy Kimmel and Kelly Clarkson covering her song.
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Transcript
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| 0:00.0 | Just a few miles off the Thailand coast, the island of Kothau looks like a postcard. |
| 0:07.0 | I'd underneath the surface lies something sinister. |
| 0:11.0 | In the last 20 years dozens of tourists have died mysteriously on the island. |
| 0:16.0 | A dark cloud who's come over the island, death, mystery and danger. |
| 0:23.0 | Listen to Death Island every Wednesday on the I Heart Radio app, Apple Podcasts or wherever you get your podcasts. |
| 0:34.0 | You get great news like that and I was like so broke and busted. |
| 0:39.0 | My flight got canceled and I literally couldn't afford a hotel in Boston, so I slept in the airport then. |
| 0:48.0 | You know, Haley Witters, I mean she absolutely could have made it just based on talent in her first year in town. |
| 0:54.0 | But what I like about her story is, just the timing, it wasn't right, but she just kept on. |
| 1:02.0 | Like, timing is a big part of it because she's had the talent. |
| 1:05.0 | But what's cool is she didn't really change who she was and now she gets to be who she really is and now she gets to root. |
| 1:12.0 | She's having a real moment here. |
| 1:14.0 | And so I really like Haley. |
| 1:16.0 | We've had her on the radio show to play and I don't know, her spirit is awesome. |
| 1:21.0 | And she's very open about the fact that she's been here 10, 11, 12 years and took her that long. |
| 1:26.0 | And she talks about how to go back to waiting tables. |
| 1:29.0 | And if anything, I want people to take away from this, not even the music part of it that like as long as you're still going to day and over. |
| 1:36.0 | And it's super cool. |
| 1:37.0 | Big fan of her episode 386. |
| 1:39.0 | Her current single is everything she ain't. |
| 1:42.0 | The whiskey and your soda will line me up on the shot. |
| 1:47.0 | Turn it down briefly so we don't get sued. |
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