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PODCAST

Caddyshack to Corner Office

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

sports golf

All Episodes

00:50:49

Official Caddying Story of Michael Bapis

Caddyshack to Corner Office ·

2025/08/19

In this episode of Caddyshack to Corner Office, Kai sits down with Michael Bapis, Managing Director with Vios Advisors at Rockefeller Capital Management, to trace his journey from youthful caddie to thought leader in the financial services industry, regularly appearing on CNBC, Bloomberg TV and Yahoo Finance. Michael reflects on his early days looping at Salt Lake Country Club, learning life lessons from local legends and PGA pros. He shares colorful memories from working with Jim Flick at Desert

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00:47:41

Official Caddying Story of Jon Orszag

Caddyshack to Corner Office ·

2025/07/23

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

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00:30:26

Official Caddying Story of Rick Reilly

Caddyshack to Corner Office ·

2025/07/19

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

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00:42:13

Official Caddying Story of Bob Ford PGA

Caddyshack to Corner Office ·

2025/05/22

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

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00:01:23

Caddyshack to Corner Office (TRAILER)

Caddyshack to Corner Office ·

2025/05/19

Welcome to the Caddyshack to Corner Office podcast. Subscribe and follow anywhere you get podcasts.Learn more:https://www.caddyshacktocorneroffice.com/Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato

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00:49:02

Official Caddying Story of Josh Isner

Caddyshack to Corner Office ·

2025/05/08

In this episode of Caddyshack to Corner Office, Kai sits down with Josh Isner, President of Axon and former caddy at New Seabury Country Club. Josh reflects on his early days lugging bags in Cape Cod, his competitive golfing years, and the leadership values he’s carried into the tech world. Drawing inspiration from Bill Belichick and Dave Portnoy, he unpacks lessons on mentorship, culture-building, and staying relentlessly driven. The conversation touches on his Harvard years, the Patriots playbook,

en

00:58:58

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2025/04/17

In this episode of Caddyshack to Corner Office, Kai sits down with longtime friend Brian “Sully” Sullivan, founder of Five Oceans Capital. From MC-ing at the D.C. Improv to slinging golf bags in Pasadena, Sully walks us through the winding road from a stand-up comedy career to a $2.5 billion lending fintech that they later exited. He shares his eye-opening intro to entrepreneurship—thanks to an unexpected caddying gig—and reflects on what golf, grit, and gambling taught him about character, class,

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00:33:26

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2024/06/18

Newmark Executive Managing Director, Tom Adelson shares his experience growing up in Fargo, North Dakota, and starting his caddying career at a young age. He caddied for his dad and eventually became a regular caddy at the Fargo Country Club. Adelson describes the tight-knit caddy group and the fun and camaraderie they had. He also talks about the importance of tipping and how it made a big impact on him. Adelson later went on to play college golf at the University of Arizona and reflects on his

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00:55:07

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2024/06/11

Casey Cowell, co-founder of US Robotics, shares his journey from growing up in Detroit to building a successful business, which was later acquired by 3Com in a transaction valued at nearly $6.6 Billion, making it the largest merger ever in the history of the data communications industry. He emphasizes the importance of being on a mission and constantly achieving things that align with that mission. Casey also reflects on his experience as a caddy and the valuable lessons he learned from being around

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00:28:51

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2024/01/28

Kai Sato sits down with entrepreneur and High Pointe Golf Club owner, Rod Trump, who helped launch his career as a caddy in Maryland.

en

00:28:45

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2023/03/21

Kai Sato sits down with 8AM Golf President, Hoyt McGarity, who got his start working as a caddy in the Hamptons long before he could even drive a car.Hoyt was a stand-out collegiate golfer at Lynn University and played competitively on various professional tours. He co-founded Modern Golf in 2011, a Canadian club fitting company, then became CEO of True Spec Golf in 2014, a brand agnostic club fitting company. In 2017, Hoyt assumed the role of President and CEO of Miura Golf. Soon after, Howard

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00:40:14

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2022/09/06

Once a caddy at The Beverly Country Club, Sheila is the Managing Director of Edelman's corporate brand and reputation practice in Chicago. She leads a team of over 50 specialists across Chicago, Atlanta, Dallas, Houston and Austin. She oversees a dynamic portfolio of clients centered on delivering solutions that promote, protect and evolve their corporate brand; while earning trust and engagement across a multistakeholder universe. Her over 20 years of communications background encompasses corporate

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00:35:05

Caddyshack to Corner Office: Official Caddying Story...

Caddyshack to Corner Office ·

2021/06/30

Corey Pavin needs no introduction. The winner of the 1995 US Open at Shinnecock Hills, he won 15 tournaments on the PGA Tour and also topped its money list in 1991, garnering Player of the Year honors from the PGA of America. He also won over a dozen tournaments as a professional on other tours around the world. He was the captain of the Ryder Cup in 2010, having previously been a 3-time participant on the US team. He also competed on two Presidents Cup teams. In college, he was the NCAA Player of

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13 results

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