Jay Sugarman on contrarian investing
From Thinking Differently with Philadelphia Union's Jay Sugarman (Ep. 16) · · Bryn Mawr Trust
“Real estate, this is the moment. It's, you know, it's finally hated enough that a contrarian play is available. And so we went and found two really young, smart guys who, you know, were willing to, you know, go against the grain and started a company called Starwood at the time that's gone on to great things. But, you know, at that moment, people kind of looked at us and the families we had investing with us both looked at us like, 'Are you sure?' You know, every day the Wall Street Journal says this is a terrible asset class, but those are when the opportunities come when everybody's looking this way and you look the other way. Uh, sometimes those are the best opportunities.”
On , Jay Sugarman, Chief Executive Officer & Chairman at SAFEHOLD INC, spoke about contrarian investing during Thinking Differently with Philadelphia Union's Jay Sugarman (Ep. 16) on Bryn Mawr Trust.
About Jay Sugarman
Jay Sugarman, chairman and CEO of Safehold and principal owner of the Philadelphia Union, discussed his career and approach to decision-making on the "Planning Perspectives" podcast in April 2026. He described founding the real estate company Starwood in the late 1980s as a contrarian move, saying he and his partner saw opportunity when real estate was "finally hated enough." He said he aimed to modernize real estate finance by applying corporate-world methods, similar to his current work with ground leases. Sugarman also explained his investment in the Philadelphia Union, stating that during the 2000s internet boom he believed soccer would grow in the U.S. as the world's sport. He said the club chose to focus on youth development, style of play, and innovation rather than trying to outspend larger ownership groups in the Eastern Conference.