Ben Reitzes spent years warning that AI would destroy legacy software companies. He made a career out of this take. Then Microsoft started bolting ChatGPT onto everything they own and suddenly Ben loves them. This is called analysis.
Wall Street rewarded Microsoft for their AI pivot. The stock went up. Reitzes, who used to think AI was the enemy, now thinks Microsoft is positioned perfectly for the AI race. He flipped. Nobody cares that he flipped. They care that the stock went up after he flipped.
Retail traders are studying this headline right now. They're highlighting the part where a longtime skeptic changed his mind. They think this means something. They're opening positions based on the emotional arc of Ben Reitzes. A man changed his opinion about enterprise software and now Kevin from Ohio is buying calls.
Microsoft added AI features to products people already hate using. Teams still freezes during meetings. Outlook still takes six clicks to do what Gmail does in one. But now there's a chatbot in the sidebar that can summarize your emails poorly. Revolutionary stuff. Ben Reitzes looked at this and decided he was wrong about everything.
The headline says it's just the beginning. That's the part that should scare you. Not because AI will fail. Because Ben Reitzes will change his mind four more times before this is over and retail traders will follow him into every single trade like ducklings walking into a wood chipper.
Wall Street rewards whatever moved last. Ben Reitzes rewards whatever he feels like rewarding on a given Tuesday. The only constant is Kevin from Ohio losing money while reading analyst notes he doesn't understand about products he's never used.
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