#566 - Sean Ryan on Being Mistaken by Us for a Different Shawn Ryan + Overcoming Homelessness + Busking Early on In Order to Make a Living
Bobby Bones Presents: The BobbyCast
Nashville Podcast Network
4.8 • 4.6K Ratings
🗓️ 26 December 2025
⏱️ 45 minutes
🧾️ Download transcript
Summary
Sean Ryan stops by after the guys realize they accidentally booked him while trying to track down a different Shawn Ryan leading to a hilarious “wait… who are you?” moment that turns into one of the most memorable conversations we’ve had in a while. Sean talks about what his life looked like when he was homeless, how he kept his head up when things felt stuck, and the small breaks that helped him start climbing out of it. He also breaks down the reality of busking: where he plays, how he draws a crowd, what a “good day” actually pays, and the way street performing teaches you to win people over in seconds. Along the way, we get into the hustle of making just enough money to keep moving, the pride that comes with earning it the hard way, and why being the “wrong” booking ended up being exactly the right conversation.
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Transcript
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| 0:00.0 | This is an IHeart podcast. |
| 0:02.5 | Guaranteed human. |
| 0:07.0 | New Year's resolution. |
| 0:08.8 | Own how you show up online. |
| 0:10.7 | It's easy with a domain and matching email from GoDaddy. |
| 0:13.7 | Now just 99 cents per month for new customers their first year. |
| 0:18.2 | Ring in 2026 with a domain and matching email at goaddy.com slash new year. That's |
| 0:24.2 | go daddy.com slash new year to own how you show up online. I did go to school until we were homeless and then I was homeschooled for a little bit. |
| 0:43.4 | I taught myself and then I took my GED even. |
| 0:45.6 | I was 16 because we were already doing music by then. |
| 0:50.4 | Welcome to episode 566 with Sean Ryan. |
| 0:53.6 | S-E-A-N-R-Yan. |
| 0:55.4 | We talked about how this was an accidental booking. |
| 0:59.0 | You're going to hear the whole story, but it turned out, I would say, delightful. |
| 1:03.9 | New single, How Country Goes, was released a few months ago. |
| 1:08.0 | We have him describe his music, but it's kind of a traditional country sound |
| 1:11.1 | in a newish country era, I'd say. He's all over. Give this one a chance. Check out his website, |
| 1:18.9 | Sean Ryan Live, also his socials, Sean Ryan Live. This interview was never supposed to happen, |
| 1:24.2 | but here he is, the musician, Sean Ryan. All right, Sean, good to see you, buddy. |
| 1:28.5 | Nice to see you. |
| 1:29.5 | We have ended in this place very interestingly. |
| 1:34.0 | Yes. |
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