Caddyshack to Corner Office: Official Caddying Story of Brian "Sully" Sullivan

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Caddyshack to Corner Office

The Lama

12 episodes

1 week ago

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

Golf

Sports

RSS

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

Golf

Sports

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Caddyshack to Corner Office: Official Caddying Story of Brian "Sully" Sullivan

Caddyshack to Corner Office

58 minutes 58 seconds

6 months ago

Caddyshack to Corner Office: Official Caddying Story of Brian "Sully" Sullivan

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, and second chances. This one’s equal parts humor and hustle.

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[00:00:00] Brian “Sully” Sullivan joins the show during Masters Week

[00:01:12] Origin of the first online small business loan

[00:03:22] Early partnership with Groupon

[00:04:24] Sully’s pivot from unpaid intern to stand-up comic

[00:05:29] Touring with Gilbert Gottfried and deciding to attend business school

[00:06:25] His first loop at Annandale Golf Club and what not to wear as a caddy

[00:08:17] How getting stiffed at a tennis camp led him to the caddy yard

[00:11:14] Learning the ropes and carrying mismatched bags

[00:12:34] The pivotal FBO conversation that sparked his entrepreneurial thinking

[00:14:55] Making $125 in three hours and the draw of cash tips

[00:17:38] Navigating racial dynamics and building trust with other caddies

[00:22:24] Sneezing disasters and a handkerchief that stood the test of time

[00:25:00] Culture of early morning cocktails, high-stakes games, and family rounds

[00:28:08] Gambling lessons and adapting tennis skills to golf

[00:30:38] Getting banned from Annandale after being discovered as a member’s kid

[00:32:17] Contrasts between caddying at elite and rougher clubs

[00:35:02] Reflections on privilege and member-caddy dynamics

[00:38:20] Helping Eduardo get a second chance at Annandale

[00:41:31] Golf’s reputation and the philanthropy behind elite clubs

[00:45:12] Cheating, character, and what you never forget in golf

[00:49:18] How judges and lawyers supported caddies facing legal trouble

[00:50:28] Recapping his earnings and additional caddying in Chicago

[00:52:33] Comparing SoCal’s pro-level loopers to Evans Scholars culture in Chicago

[00:54:06] Navigating player preferences and building caddy intuition

[00:55:00] Secret caddy bets and controlling reactions mid-round

[00:56:08] The “Warbird” story and other caddy legends

[00:57:12] Identifying fellow former caddies by their behavior on the course

Links:

Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato

Brian Sullivan on LinkedIn: https://www.linkedin.com/in/brian-sullivan-730306172

Five Oceans Capital: https://www.fiveoceanscap.com/