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. [00:00:00] Kai introduces the podcast and welcomes David Dorros to discuss how caddying shaped his life and career. [00:00:50] Dave explains his role at Eastdil Secured and the work he does advising clients on large real estate transactions. [00:04:20] Shares how he started caddying at Bethesda Country Club as a 13-year-old, riding his bike to the course and waiting hours for a loop. [00:06:30] Describes the early realities of the job—heavy leather golf bags, long days, and learning quickly how demanding the work could be. [00:10:40] Kai asks about the culture of the caddie yard and how Dave adjusted to a completely new environment. [00:11:11] Dave recalls the caddie shack culture, arriving early, playing cards to pass the time, and learning to be prepared for long days without guarantees of work. [00:18:58] Reflects on how caddying exposed him to a different world and helped him observe how successful professionals carried themselves. [00:24:43] Discusses how skills learned as a caddie—anticipation, service, and awareness—later translated into business and client relationships. [00:29:06] Shares how interacting with accomplished people at a young age helped him develop confidence and professional presence. [00:32:09] Talks about the discipline and work ethic required both in the caddie yard and later in investment banking. [00:36:51] Explores the importance of mentorship and the responsibility successful professionals have to support the next generation. [00:40:49] Reflects on the lasting impact of caddying and why the experience continues to influence how he approaches work and leadership. [00:47:24] Offers advice to young caddies and early-career professionals about humility, preparation, and building strong relationships. [00:50:19] Final reflections on how the lessons from the caddie yard continue to shape his perspective today. Links: Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato David Dorris on LinkedIn: https://www.linkedin.com/in/david-dorros-b07330350
