Tech titans are riding high on the AI wave right now—and none more visibly than Larry Ellison. His massive $300 billion position in AI and cloud infrastructure has repositioned Oracle at the heart of Silicon Valley's latest boom. But here's the uncomfortable question nobody wants to ask loudly: what happens when sentiment shifts? Every bubble has two sides. The money flows in, valuations skyrocket, everyone builds for scale. Then reality checks in. If the AI cycle cools or investors start taking profits hard, does Ellison's enormous bet hold up, or does it become a cautionary tale about timing the market wrong? The playbook isn't new—we've seen it play out before. Worth watching where the big money actually moves next.