Two operators who shipped AI at opposite ends of the scale, asked for the unfiltered version. Chuck Yates left energy private equity to co-found Collide, the first generative AI platform built for oil and gas, now 6,000 users in 122 countries and backed by Mercury Fund. Charles Jessup rolled AI out to roughly 100,000 people at Raytheon. What broke, what they would redo, and what the vendors do not tell you.

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