Pianist, songwriter, and performer Jacob Jeffries the morning after he played Madison Square Garden with Vulfpeck, reflecting on the surreal thrill of performing in the legendary arena with his close friends, while also grounding the experience in the everyday reality of being a working musician.

The conversation traces his journey from South Florida (where his childhood was shaped by Beatles records, summer theater programs like Lovewell, and the absence of a bar mitzvah he later regretted) to his early career with the Jacob Jeffries Band and formative studio experiences with Grammy-winning producer Sebastian Krys and guitarist-producer Dan Warner. He describes being taken under their wing, signed to Warner Chappell at 18, and even meeting Rick Rubin as a teenager—moments that felt like he was “six inches from Madison Square Garden,” only to discover it would take another 20 years of steady work to get there.

Along the way, Jeffries talks about grief (losing both parents by his mid-20s), his bond with fellow Vulfpeck member Theo Katzman, the power of collaborative creativity, and the balance between sincerity and playfulness in his own music. He reflects on the intimacy of his new record You Got the Right Idea, the surreal humor of songs like This Is Not the Song I Wrote, and how he embodies a kind of singer, storyteller, and surrealist performer all at once.

Jacob is on tour this month opening for the band Lawrence.

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