Caddyshack to Corner Office

Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path

Caddyshack to Corner Office is a sports podcast hosted by The Lama, with 14 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

The Lama hosts Caddyshack to Corner Office, a sports show with 14 episodes published.

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  Caddyshack to Corner Office

  Official Caddying Story of David Simas

  Apr 7, 20261h 2mS0

  <p>David Simas is 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.<br>Before that, Simas held several high-level positions in the White House under President Barack Obama, including Director of the Office...

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  Caddyshack to Corner Office

  Official Caddying Story of David Dorros

  Mar 20, 202650 minS0

  <p>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...

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  Caddyshack to Corner Office

  Official Caddying Story of Jon Orszag

  Jul 23, 202548 minS0

  <p>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 work...

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  Caddyshack to Corner Office

  Official Caddying Story of Rick Reilly

  Jul 18, 202530 minS0

  <p>In this episode of Caddyshack to Corner Office, host Kai Sato chats with acclaimed sportswriter Rick Reilly, formerly of Sports Illustrated and ESPN as well as an 11-time winner of the NSMA's National Sportswriter of the Year Award. Rick shares captivating tales from his first caddying experience at The Masters for Tommy Aaron to humorous encounters on the bag with Donald Trump, John Daly, Tom Lehman, and Bob Newhart. From his early days in journalism to his celebrated book, Who's Your Caddy?, Rick reveals how caddying offers unique insights into golf and life. He also previews his upcoming sequel, S...

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  Caddyshack to Corner Office

  Official Caddying Story of Bob Ford PGA

  May 22, 202542 minS0

  <p>In this episode of Caddyshack to Corner Office, Kai speaks with Bob Ford, a storied golf professional and former head pro at both Oakmont Country Club and Seminole Golf Club, the former where he got his start thanks to US Open champion Lew Wersham. Bob shares stories from his early caddying days at Aronimink Golf Club, his experiences playing professionally around the world, and what it was like to loop for pros like Ed Sabo and Jay Siegel. He reflects on key moments from his playing career, his deep rooted connections to legends like Arnold Palmer, and Palmer's pivotal r...

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