Most operators try to scale their restaurants by tightening systems or adding tech and somewhere along the way, they lose the soul that made guests fall in love in the first place.
Chef Jackson Kalb never made that trade.
From being fired at 26 and sleeping in his childhood bedroom to now running seven successful restaurants across Southern California, Jackson has built a hospitality group that scales without sacrificing humanity.
In this episode of Restaurant Reset, host Andy Grindstaff sits down with Jackson to unpack the lessons, systems, and failures behind his rise from rejection to resilience.
You’ll learn how to operationalize gut instinct, design systems that listen to guests, and build culture that embraces iteration instead of fearing it.
Episode Timestamps
00:00 — Introduction and why breakfast burritos still matter
01:30 — How a free burrito giveaway turned into a line around the block
04:30 — The secret to the perfect breakfast burrito (and why details matter more than hype)
06:00 — Balancing gut instinct and data when making big decisions
09:00 — The power of learning through mistakes: “Mistakes aren’t optional. They’re required.”
11:40 — Pivoting Jemma di Mare into Ospi Brentwood: how to evolve a concept without losing culture
15:50 — Getting fired at 26, hitting rock bottom, and the vow that started it all
20:30 — Raising $90K after 450 rejections and opening a 22-seat restaurant on $3K rent
28:40 — Why ignorance can be an advantage when starting out
34:30 — What competing on Top Chef without taste or smell taught Jackson about resilience
40:00 — The invisible systems that make or break profitability
44:20 — Scaling across cities: balancing standardization with local adaptability
47:30 — How to use guest feedback as your most valuable data source
48:00 — Why stoic philosophy powers Memento Mori Hospitality (“Remember you’ll die” really means “Remember you’re alive”)
50:00 — Closing thoughts and what’s next for Jackson and Memento Mori Hospitality
Listen to this episode on: Spotify | Apple Podcasts | YouTube
And make sure you subscribe so you never miss an episode.