Chris Schembra: The Strange Mercy of a Good Middle

Headstone with Pete Wright · May 23, 2026 · 1h 3m

This is the last conversation of my first season, and I almost didn’t finish it.

Chris Schembra came to me the way the best guests do, as a name pressed into my hand by someone I trust. Aliza Kline told me I needed to talk to him, and Aliza is rarely wrong about people. What I didn’t expect was how quickly the conversation would stop being about him.

On paper, Chris is the gratitude guy: the 7:47 dinners, the pasta, the rooms full of leaders he teaches to thank the people they have forgotten to thank. I’m fascinated by the keynote version. And I wanted to talk to the kid underneath it, the…