In the first episode of Morgan Stanley’s new Hard Lessons series featuring iconic investors, Blackstone President and Chief Operating Officer Jon Gray sits down with Morgan Stanley Co‑President Dan Simkowitz to unpack two out‑of‑consensus calls that shaped his perspective. Gray takes viewers behind the scenes on Blackstone’s decision to buy Hilton Hotels, sharing how his conviction in the strength of the business and its leadership turned a challenging situation into one of the most successful private equity deals in history. He also recalls a hard-won lesson about navigating hype cycles, and explains how the dotcom bubble can teach us about investing in AI.

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