In this episode of Caddyshack to Corner Office, Kai sits down with David Dorros, Managing Director at Eastdil Secured, to discuss how his early days as a young caddie shaped the foundation for a career in real estate investment banking. Dave reflects on growing up outside Washington, D.C., riding his bike to Burning Tree Club for early morning loops, and learning discipline, preparation, and resilience in the caddie yard. Along the way, he shares stories about the culture of the caddie shack, lessons learned from members and fellow caddies, and how those early experiences helped him develop confidence, relationships, and a strong work ethic. The conversation explores how the lessons from carrying a golf bag - service, anticipation, and accountability - translate directly into leadership and success in business.
Prior to Eastdil Secured, David spent seven years as Vice Chairman of Cushman & Wakefield’s Capital Markets Group, overseeing its loan sales business. Prior to his time at Cushman & Wakefield, he founded and led CBRE’s National Loan & Portfolio Sales Group. Mr. Dorros also served as an advisor to the Federal Deposit Insurance Corporation during the global financial crisis, where he led over 110 assignments on its behalf.
In this episode of Caddyshack to Corner Office, host Kai Sato welcomes Jon Orszag, Founding Partner of Econic Partners, an economic consulting firm with a global footprint. He was previously a co-founder of Compass Lexecon, LLC, an economic consulting firm. Prior to entering the private sector, Jon served as the Assistant to the U.S. Secretary of Commerce and Director of the Office of Policy and Strategic Planning. Jon shares his unique journey from caddying at Brooklawn Country Club to advising major corporations on mergers, antitrust matters, and economic strategy. The discussion examines Jon’s remarkable career trajectory — including working with President Clinton at the White House right after graduating from Princeton — and explores his lifelong passion for golf. He reflects on the invaluable lessons golf has taught him, his extensive involvement as a board member of both the TGR Foundation (formerly the Tiger Woods Foundation) and The First Tee, and why he continues to give back to the game he loves. Jon has accomplished the rare feat of playing Golf's Top 100 Courses, where he has also served as a course rater.
Jon currently serves on the Board of Directors of the Friends of the Global Fight Against AIDS, Tuberculosis, and Malaria, as well as the Board of the First Tee (both nationally and in Los Angeles) and the TGR Foundation. Orszag also serves on the Academic and Regulatory Advisory Council for Coinbase One River Asset Management. Orszag received a M.Sc. from Oxford University, which he attended as a Marshall Scholar. He graduated summa cum laude in Economics from Princeton University, was elected to Phi Beta Kappa, and was named a USA Today All-USA College Academic Team. He is also a graduate of Phillips Exeter Academy.
In this episode of Caddyshack to Corner Office, Kai sits down with David Simas, an American lawyer and former government official currently serving as Managing Director of Research and Impact at Emerson Collective and a Fall 2025 Fellow at the USC Dornsife Center for the Political Future. He is best known for his senior roles in the Obama administration and his tenure leading the Obama Foundation, first as CEO and later as President, where he spearheaded efforts to establish the Obama Presidential Center in Chicago and develop global leadership programs.
Before that, Simas held several high-level positions in the White House under President Barack Obama, including Director of the Office of Political Strategy and Outreach, Director of Opinion Research for the 2012 re-election campaign, and Deputy Assistant to the President, where he worked closely with senior advisors David Axelrod and David Plouffe. Prior to his time in Washington, he served as Deputy Chief of Staff to Massachusetts Governor Deval Patrick. Simas began his career in his hometown of Taunton, Massachusetts, where he served on both the Taunton School Committee and the Taunton City Council.