Breaking the Mold: Sabrina Carpenter, Coachella Strategy, and Collectible Culture

On this episode of Group Chat, Bentley welcomes Chelsea O’Donnell, founder of Angry Girl Music and singer-songwriter of Stress Dolls; Josh Holtzman, CEO and co-founder of Twenty6 Productions and owner of Buffalo Iron Works; and Chloe Kowalyk, marketing director at both Buffalo Iron Works and Twenty6 Productions. The panel kicks things off with the newly announced Coachella lineup, unpacking everything from the early drop to the strategy behind the headliners. From there, the conversation turns to Sabrina Carpenter’s headlining moment and what it signals for the future of pop. The group also dives into the challenges and allure of physical media in the streaming era before wrapping up with personal stories of live music, from chaotic festival memories to the magic of first concerts.