Caddyshack to Corner Office
Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path.
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Billionaires who grew up caddying.
Ray Dalio learned about the stock market on the bag. Steve Ballmer caddied in Michigan before running Microsoft and buying the Clippers. These stories aren't accidents — they're patterns. The caddy yard is the world's most underrated business school, and we're building the proof.
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Official Caddying Story: David Dorros
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.
Fourteen, twenty-four, thirty-four — it doesn't matter. The math is the same.
A single $5,000 investment, growing at a historical 10% annual return, crosses $1 million in about 56 years. Caddies have a huge advantage by earning early in life. Learn how others have built wealth.
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