#141

Josh sits down with Maddy Shannon, Head of Product Strategy at SpotOn, who has spent her career making independent restaurants more profitable. From a start at Bain, to the business team at The Alinea Group under Nick Kokonas, to the finances at SingleThread Farms in Healdsburg, to a Stanford MBA and now leading SpotOn's reporting, Profit AI, and analytics teams, Maddy sits at the rare intersection of hospitality and product. The conversation keeps circling one idea: great hospitality and great product design solve the same problem. Both anticipate what someone needs before they ask, and both disappear when they work. She calls it the invisibility problem, and it reframes everything from how a point of sale should feel to why diners undervalue what a restaurant gives them.

The two dig into what a restaurant meal is really worth, and why pricing a plate off the cost of the prawns misses the wine glass that gets refilled and the person clearing your crumbs. Maddy floats David Nayfeld's idea of billing a meal the way a plumber does, materials, labor, total, so guests see what they are paying for. From there it turns to leadership, where she sets Nick Kokonas's clarity of vision against Kyle Connaughton's prove me right approach at SingleThread, and Josh on unlearning twenty years of knowing every station when he moved into tech. On AI, they land on the line that anchors the back half: data is plentiful, attention is scarce. Both agree the real unlock is not another dashboard but software that tells an operator what to do, the way a doctor diagnoses rather than asking where it hurts. It closes on mastery, the donabe rice pot Maddy treasures, and the tension that restaurant economics rarely leave a chef room to master one thing. Her parting advice: next time you sit down to eat, take a beat, look around, and do not look at the prices so closely.