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With his 16th album Permanent Change – Part 1 now on the horizon, Matt Pond PA proves he’s nowhere near slowing down. After delivering the sun‑soaked anthem “Endless Summer,” he’s back with “Learn How to Lose,” paired with a video w/a cameo by Kate Walsh (Grey’s Anatomy, 13 Reasons Why, Emaily in Paris) as she tries out to be a drummer in Matt Pond’s band . Out now, “Learn How to Lose” turns the whole thing into a wager: If you’re going to spend your life touring and trying to reach people through music, “You gotta learn how to lose, you gotta try and be better at digging your own grave.” Matt further explains:

“Learn How To Lose came from a steady diet of Elliott Smith and Steely Dan. I wrote it as an offhand basement demo and texted it to Anya upstairs. She fell in love with it, sent it back downstairs with revisions, and somehow helped me find the celebration inside all my regrets. The older I get, the less I think this life is about being richer or more famous than anyone else. It's about making your stupid songs, giving them everything you've got, letting go of the rest, and being grateful if someone decides to sing along.

We made the video with our friend Kate Walsh and my friend Mike's kids. Mike played guitar in my first band, so having his family be part of it felt quietly full circle. The idea was to capture something universal: no matter where you are in life, you're always auditioning for something—whether it's a role, a relationship, a job, or simply the person you're hoping to become. We filmed it at Utopia Studios in Bearsville, where we recorded most of the album, which made it feel even more connected to the song. Chase Pierson shot the video, Scott Coffey directed, and Robin Gonsalves brought it all together in the edit.”

Kate Walsh adds: ‘First of all I’m a massive fan of Matt’s (& Anya’s!) music. This is our 2nd music video collaboration together…No More Tragedies was an inter-hemisphere collaboration as I was living in Australia & my part was shot in Perth. It was so fun to shoot Learn How To Loose & Straight Into The Night in-person, with Matt & Anya, Scotty & the rest of the crew at the iconic Utopia studios in Bearsville.’