There was a specific moment I knew I was done with big tech.
I was in a meeting with a multi-unit restaurant operator. 54 locations to be exact. Complex business. Tough margins as anyone in the food business knows.
He was trying to figure out how much he actually made on DoorDash last month.
Basic visibility. What's our real margin after platform fees? Which location is bleeding?
He couldn't get to it. The data existed. He just couldn't reach it without pulling reports from Toast, cross-referencing with DoorDash, reconciling with Uber Eats, and stitching it together in a spreadsheet at midnight.
I'd just spent 10+ years at Uber, Instacart and other startups in the space, building real-time products for the platforms. Meanwhile, the operators on the other side of those platforms, the ones ACTUALLY doing the work, were running on spreadsheets and prayer.
Which meant.... the only person who knew what was actually happening in the business was the owner. Every time. For everything.
WTAF? How did that make sense? Why couldn't they make this easier for the hard working folks running the businesses that make our communities worth living in?
So I left to try and change that.
Every local service business is living some version of this.
The contractor who can't tell you which jobs are profitable.
The gym owner whose revenue went up but profit didn't.
The agency founder running five tools that don't talk to each other.
So I made a private podcast about how I think about it and what I've learned over the years. Five episodes. About an hour. The thinking I use with every operator I work with, built for the drive home.
