Caddyshack to Corner Office
Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path.
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Billionaires who grew up caddying.
Ray Dalio learned about the stock market on the bag. Steve Ballmer caddied in Michigan before running Microsoft and buying the Clippers. These stories aren't accidents — they're patterns. The caddy yard is the world's most underrated business school, and we're building the proof.
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Official Caddying Story: David Simas
In this episode of Caddyshack to Corner Office, Kai sits down with David Simas, 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.
Before that, Simas held several high-level positions in the White House under President Barack Obama, including Director of the Office of Political Strategy and Outreach, Director of Opinion Research for the 2012 re-election campaign, and Deputy Assistant to the President, where he worked closely with senior advisors David Axelrod and David Plouffe. Prior to his time in Washington, he served as Deputy Chief of Staff to Massachusetts Governor Deval Patrick. Simas began his career in his hometown of Taunton, Massachusetts, where he served on both the Taunton School Committee and the Taunton City Council.
Fourteen, twenty-four, thirty-four — it doesn't matter. The math is the same.
A single $5,000 investment, growing at a historical 10% annual return, crosses $1 million in about 56 years. Caddies have a huge advantage by earning early in life. Learn how others have built wealth.
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