Jay Sugarman on real estate finance
From Thinking Differently with Philadelphia Union's Jay Sugarman (Ep. 16) · · Bryn Mawr Trust
“For me, I didn't know much about real estate. I just knew if everybody's, you know, throwing throwing the baby out with the bath water. Let's go see if we can find some of the babies. And uh for me, it was really on the finance side of the business. It seemed really archaic. the way real estate thought about uh capitalizing itself was way behind where the corporate world had gotten to. And I knew more about the corporate world. I'm like, well, they think about risk and reward in in little packets of uh risk and packets of reward. And real estate was like, well, we have a mortgage. And so, we developed a new idea that was very much about taking things we had seen work in the corporate world and bringing it to real estate. And back then, real estate was kind of down the hall and around the corner. And we brought it almost in the same way we're trying to do with ground leases. We tried to modernize. We said it should be next to the trading floor. It should be next to the corporate finance folks. It's part of an integrated uh you know capital market. It's not this separate thing.”
On , Jay Sugarman, Chief Executive Officer & Chairman at SAFEHOLD INC, spoke about real estate finance 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.