⏱ Episode Breakdown
00:00 – Andrew questions the real value of being on a board
02:00 – Jesse’s framework: people, impact, learning, and comp
04:00 – The unique story of Schnucks: family values and $4B scale
06:00 – What makes a board seat “worth it” for Jesse
08:00 – How he ended up on the Schnucks board
09:00 – The role of impact in Jesse’s decisions
11:00 – Mistaking board work for operational work
12:00 – A pivotal moment: “You think in a way none of us do”
13:00 – Desired Future State (DFS) and shifting legacy companies
14:00 – What Jesse learned from the Festival Foods acquisition
16:00 – The Boomerang Principle & culture as a daily habit
18:00 – Why having kids at home is the most finite resource
19:00 – Business never stops—even at 70+
21:00 – Why grocery hasn’t been fully rolled up (yet)
22:30 – What's happening at Gateway X behind the scenes
23:30 – Jesse’s goal: build an AI-focused startup studio in St. Louis
25:00 – The talent challenge: how to attract builders to the Midwest
26:30 – Borrowing ideas from South Park Commons and Brickyard
28:00 – “My only dogma is no dogma”: bootstrapping vs. seed-strapping
29:30 – Why Jesse doesn't feel like a fraud when changing direction
30:30 – The deep commitment to St. Louis and building there
32:00 – Closing: unapologetically building the thing that only you can
In this episode, Jesse and Andrew go deep on something unexpected: what it’s really like to sit on the board of a $4B+ grocery company—and why Jesse said yes.
It turns into a powerful conversation about board dynamics, generational leadership, family legacy, the nature of impact, and Jesse’s renewed mission to attract startup talent back to cities like St. Louis. They also touch on ego, post-exit motivation, and why some founders never stop building.
Whether you're a founder thinking about joining a board, building something meaningful in a smaller city, or wondering what “impact” actually means, this one hits home.