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/

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 time as a college golfer. He offers advice to young caddies and emphasizes the importance of enjoying the journey and surrounding oneself with positive people.

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 successful people. He highlights the significance of treating others with respect and the impact of golf on character development. Casey discusses the role models that influenced him and the importance of thinking ahead and setting ambitious goals. Casey Cowell shares his experiences and insights on building a successful company, overcoming challenges, and giving back to the community. He emphasizes the importance of planning backwards and celebrating victories as a team. Casey also discusses the tough times and low points he faced, highlighting the constant struggle and the need to stay focused and determined. He shares the story of how his company almost went bankrupt three times but managed to survive and thrive. Casey emphasizes the value of building a cohesive and inspired team, focusing on self-confidence and teamwork. He also talks about his philanthropic initiatives and venture capital investments in the Traverse City area, aiming to create year-round jobs and economic growth. Casey's passion for golf and his involvement in the High Pointe Golf Club project are also highlighted.

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 successful people. He highlights the significance of treating others with respect and the impact of golf on character development. Casey discusses the role models that influenced him and the importance of thinking ahead and setting ambitious goals. Casey Cowell shares his experiences and insights on building a successful company, overcoming challenges, and giving back to the community. He emphasizes the importance of planning backwards and celebrating victories as a team. Casey also discusses the tough times and low points he faced, highlighting the constant struggle and the need to stay focused and determined. He shares the story of how his company almost went bankrupt three times but managed to survive and thrive. Casey emphasizes the value of building a cohesive and inspired team, focusing on self-confidence and teamwork. He also talks about his philanthropic initiatives and venture capital investments in the Traverse City area, aiming to create year-round jobs and economic growth. Casey's passion for golf and his involvement in the High Pointe Golf Club project are also highlighted.

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

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 Milstein acquired True Spec and GOLF and consolidated his golf investments into a holding company, 8AM Golf, where Hoyt became President. His role includes creating, communicating, and implementing 8AM’s vision, mission and direction. Hoyt has created synergies and efficiencies throughout 8AM and pursues the highest quality everywhere.

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 reputation management, transformation advisory, media relations, executive positioning, and corporate storytelling. She has diverse industry experience representing clients in both the public and private sectors including industrials, financial services, retail and food and beverage. She has led C-level advisory, thought leadership and corporate brand programs for clients across diverse industries and the Fortune 500. She sits on the Board of Trustees for the Peggy Notebaert Nature Museum. Before joining Edelman, she worked for Chicago-based public affairs firm Jasculca/Terman & Associates (JT). Her political- event work with JT, includes the Clinton Presidential Library Opening, the American Democracy Institute Chicago and Philadelphia Summits and Illinois Attorney General Lisa Madigan’s campaign launch.

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 the Year and a member of the Walker Cup. Now a member of the PGA Tour Champions, he’s been named to various halls of fame, in recognition of his many accomplishments in golf. What few people know, however, is that Corey helped put himself through college by working as a caddie.