by The Lama
Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path
Language
🇺🇲
Publishing Since
6/30/2021
Email Addresses
1 available
Phone Numbers
0 available
April 17, 2025
<p>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.</p><p>____________________________________________________________</p><p>[00:00:00] Brian “Sully” Sullivan joins the show during Masters Week</p><p>[00:01:12] Origin of the first online small business loan</p><p>[00:03:22] Early partnership with Groupon</p><p>[00:04:24] Sully’s pivot from unpaid intern to stand-up comic</p><p>[00:05:29] Touring with Gilbert Gottfried and deciding to attend business school</p><p>[00:06:25] His first loop at Annandale Golf Club and what not to wear as a caddy</p><p>[00:08:17] How getting stiffed at a tennis camp led him to the caddy yard</p><p>[00:11:14] Learning the ropes and carrying mismatched bags</p><p>[00:12:34] The pivotal FBO conversation that sparked his entrepreneurial thinking</p><p>[00:14:55] Making $125 in three hours and the draw of cash tips</p><p>[00:17:38] Navigating racial dynamics and building trust with other caddies</p><p>[00:22:24] Sneezing disasters and a handkerchief that stood the test of time</p><p>[00:25:00] Culture of early morning cocktails, high-stakes games, and family rounds</p><p>[00:28:08] Gambling lessons and adapting tennis skills to golf</p><p>[00:30:38] Getting banned from Annandale after being discovered as a member’s kid</p><p>[00:32:17] Contrasts between caddying at elite and rougher clubs</p><p>[00:35:02] Reflections on privilege and member-caddy dynamics</p><p>[00:38:20] Helping Eduardo get a second chance at Annandale</p><p>[00:41:31] Golf’s reputation and the philanthropy behind elite clubs</p><p>[00:45:12] Cheating, character, and what you never forget in golf</p><p>[00:49:18] How judges and lawyers supported caddies facing legal trouble</p><p>[00:50:28] Recapping his earnings and additional caddying in Chicago</p><p>[00:52:33] Comparing SoCal’s pro-level loopers to Evans Scholars culture in Chicago</p><p>[00:54:06] Navigating player preferences and building caddy intuition</p><p>[00:55:00] Secret caddy bets and controlling reactions mid-round</p><p>[00:56:08] The “Warbird” story and other caddy legends</p><p>[00:57:12] Identifying fellow former caddies by their behavior on the course</p><p><br></p><p><strong>Links:</strong></p><p>Kai Sato on LinkedIn: <a href="https://www.linkedin.com/in/kaisato" target="_blank" rel="ugc noopener noreferrer">https://www.linkedin.com/in/kaisato</a></p><p>Brian Sullivan on LinkedIn: <a href="https://www.linkedin.com/in/brian-sullivan-730306172" target="_blank" rel="ugc noopener noreferrer">https://www.linkedin.com/in/brian-sullivan-730306172</a></p><p>Five Oceans Capital: <a href="https://www.fiveoceanscap.com/" target="_blank" rel="ugc noopener noreferrer">https://www.fiveoceanscap.com/</a></p>
June 18, 2024
<p>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.</p>
June 11, 2024
<p>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.</p>
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