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Posted Aug 18, 2026

The Discipline of Betting Against the Crowd

Brandon Sedloff and Bill McMorrow trace the evolution of Kennedy Wilson from a $57,000 real estate auction company in 1988 to a global investment firm managing nearly $38 billion in assets. McMorrow shares how a series of pivotal relationships, from early banking mentors to partnerships with George Graziadio and Fairfax Financial's Prem Watsa, shaped the firm's trajectory across four decades of real estate cycles. The conversation on The Distribution reveals how McMorrow identified opportunities in Japan during the 1990s, Ireland and the UK following the Great Recession, and multifamily housing markets when regional banks retreated in 2023.

They discuss:

  • Why McMorrow focuses exclusively on housing across the US, Ireland, and the UK after owning every asset type
  • How a half-hour conversation at a Berkshire Hathaway meeting led to $20 billion in joint ventures over sixteen years
  • The discipline of saying yes to start the journey, even when the path forward isn't clear
  • Why narrowing focus and tuning out noise matters more than ever in today's information-saturated environment
  • What McMorrow learned from working on commercial fishing boats, in a slaughterhouse, and growing up in a family of nine kids

This episode offers insight for investors navigating uncertainty, building long-term institutional relationships, and recognizing contrarian opportunities when markets feel murky.

Listen to the full interview