44 minutes | Friday, December 26, 2025
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. Check Sean's Music and Tour Dates HERE Follow on Instagram: @TheBobbyCast Follow on TikTok: @TheBobbyCast Watch this Episode on Youtube See omnystudio.com/listener for privacy information.