Advertise on podcast: Hard Lessons

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. Disclosures: The proceeding/preceding content is/was informational only and based on information available when created. Opinions expressed by the guest speaker are solely their own, and do not necessarily reflect those of Morgan Stanley. All opinions are subject to change without notice. Neither the information provided nor any opinion expressed constitutes an offer or a solicitation nor is it tax or legal advice. ©2026 Morgan Stanley CRC 5159913 

Iconic investors sit down with Morgan Stanley leaders to go behind the scenes on the critical moments – both successes and setbacks – that shaped who they are today.