Simon Oslender: From Piano Prodigy to Playing With Legends

What does it take to have Steve Gadd and Will Lee playing your music before you even hit your peak years? 🎹🔥 In this episode, Rob Cass sits down with Simon Oslender, one of the most exciting rising stars in jazz, to uncover the mindset, passion, and moments that shaped his incredible journey.Simon shares how a deep curiosity for sound started almost from childhood — from being fascinated by anything that made noise to discovering the piano as a true turning point. One of the most powerful parts of the conversation is how he earned the respect of legends like Steve Gadd and Will Lee, leading to collaborations that most musicians only dream of. We dive into his first album About Time, working with world-class rhythm sections, and why he refuses to slow down or compromise his love for playing live. His perspective is refreshing: if someone plays a wrong note — who cares? It’s all about the feeling 🎶Beyond the achievements, Simon opens up about his musical philosophy — his love for Brazilian music, how harmony shapes his arranging, and the importance of staying authentic in a world that often pushes perfection. From touring globally to recording Grammy-nominated projects and building a sound rooted in groove and soul, his story is both inspiring and deeply human. Stick around for a special moment where Simon plays his most influential piano motifs — a glimpse into the mind of an artist who’s only just getting started ✨