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Caddyshack to Corner OfficeAuthor: The Lama
Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path Language: en Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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Official Caddying Story of David Simas
Tuesday, 7 April, 2026
David Simas is 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.[00:00:00] David opens by describing himself as “the luckiest person I know” and introduces his current role at Emerson Collective. [00:01:07] Kai asks about David’s career journey, including his time in politics, the Obama White House, and leading the Obama Foundation. [00:03:43] David shares how his parents’ immigration story and their deep sense of civic duty inspired his interest in politics. [00:06:30] Reflects on early political involvement, volunteering as a child and running for school board at age 22. [00:09:21] Discusses how his parents’ emphasis on education and citizenship shaped his worldview and career aspirations. [00:13:56] David describes arriving at Sankaty Head at 16 with no golf experience and being thrown into a highly structured caddie camp. [00:15:30] Details the intense camp routines—inspections, discipline, and team-based accountability among caddies. [00:21:21] Explains how he learned to caddie despite poor eyesight, relying on observation, hustle, and adaptation. [00:25:58] Shares the excitement of earning meaningful money for the first time and learning financial responsibility. [00:27:20] Recalls interactions with business leaders like Jack Welch and exposure to high-level conversations. [00:30:09] Discusses learning how to read people and adapt to different personalities on the course. [00:35:42] Highlights mentorship from member Michael O’Reilly and the importance of relationships. [00:40:41] Reflects on the discipline and structure instilled by camp leadership and its long-term impact. [00:43:06] Describes leadership lessons from camp director Doug Ellsworth, particularly around truth and accountability. [00:47:16] Shares early leadership challenges and learning how to delegate and find his own style. [00:53:25] Talks about how relationships from caddying, including Jack Welch, influenced his career path. [00:55:06] Connects caddying lessons to his role advising President Obama, including delivering honest feedback. [00:58:31] Discusses excitement about current societal and technological change and the opportunity to make impact. Links: Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato David Simas on LinkedIn: https://www.linkedin.com/in/david-simas Emerson Collective: https://www.emersoncollective.com/
