Host Raphael Sidelsky sits down with David O'Reilly, CEO of Howard Hughes Holdings, to discuss his path from engineering and investment banking to leading one of the country’s most innovative real estate platforms. The conversation explores the company’s master-planned community model, its long-term “flywheel” approach to development, and how projects like Summerlin and Ward Village create value over decades. David also shares insights on current market conditions, disciplined capital allocation, and the firm’s evolution toward a Berkshire Hathaway-style structure, including the potential role of insurance in scaling long-term growth. 

00:00: Intro – Raphael Sidelsky welcomes David O’Reilly 

02:00: Career Path – From engineering to investment banking to CEO 

06:00: Lessons Learned – Finance and capital markets insights 

12:00: Howard Hughes & MPC Model – Master-planned communities and flywheel approach 

20:00: Balancing Short- & Long-Term – Profits, land, and growth strategy 

30:00: Signature Communities – The Woodlands, Summerlin, Ward Village 

38:00: Market & Capital Allocation – Current conditions and disciplined investing 

45:00: Holding Company Strategy – Berkshire Hathaway-style growth and insurance 

50:00: Closing Thoughts – Long-term value and strategic insights