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006 : His Name Is Earl

October 8, 2026 · 1 hr 29 min

Josh has hired an assistant. His name is Earl. Robb has one question: who the hell is Earl?In episode 006, Josh introduces his AI assistant, a tireless organizer with the attitude of Orioles legend Earl Weaver. Earl sorts founder messages, untangles a…

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Show notes

Josh has hired an assistant. His name is Earl. Robb has one question: who the hell is Earl?


In episode 006, Josh introduces his AI assistant, a tireless organizer with the attitude of Orioles legend Earl Weaver. Earl sorts founder messages, untangles a stack of toll notices, checks in with Josh’s wife, and offers thrift-store advice with a grumpy baseball-manager streak. Robb wonders when a computer became the third guy on the show—and whether his own assistant, Hector, needs a personality upgrade.


Then the guys tackle baseball’s unwritten rules: stop blocking home plate for your selfie, and if you catch a playoff foul ball, do you really have to give it to a kid? Josh’s World Series longing leads to a Super Bowl memory involving Paul McCartney, which Robb takes very personally.


Josh shares an encouraging update on Bella after a rough stretch of emergency-vet visits. Robb’s love of The Sting opens the door to an impressive playing-card collection, a shopping cart he wisely abandoned, and ideas for the final TMOS cruise. Plus: Disney pin collecting, memories of Robert’s Make-A-Wish trip, and a lightsaber adventure at the happiest—and hottest—place on earth.


Meet Earl. He handles the paperwork. Josh and Robb handle the tangents.


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