Where can I listen to this podcast?

This podcast is available on 6 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

No, this podcast does not typically feature guests.

Caddyshack to Corner Office

Claim This Podcast

by The Lama

15 episodes

Updated Weekly

Accepts GuestsHas SponsorsLocation 🇺🇸

Podcast Overview

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

Language

🇺🇲

Publishing Since

6/30/2021

Visit Website View on Apple Podcasts RSS Feed

1 verified contact email on file for Caddyshack to Corner Office

Pitch yourself as a guest, propose sponsorships, or reach out directly to the host.

See contact details

Recent Episodes

April 7, 2026

Official Caddying Story of David Simas

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: <a href="https://www.linkedin.com/in/kaisato" target="_blank" rel="noreferrer noopener">https://www.linkedin.com/in/kaisato</a> David Simas on LinkedIn: <a href="https://www.linkedin.com/in/david-simas" target="_blank" rel="noreferrer noopener">https://www.linkedin.com/in/david-simas</a> Emerson Collective: <a href="https://www.emersoncollective.com/" target="_blank" rel="noreferrer noopener">https://www.emersoncollective.com/</a>

March 20, 2026

Official Caddying Story of David Dorros

In this episode of Caddyshack to Corner Office, Kai sits down with David Dorros, Vice Chairman at Eastdil Secured, to discuss how his early days as a young caddie shaped the foundation for a career in real estate investment banking. Dave reflects on growing up outside Washington, D.C., riding his bike to Burning Tree Club for early morning loops, and learning discipline, preparation, and resilience in the caddie yard. Along the way, he shares stories about the culture of the caddie shack, lessons learned from members and fellow caddies, and how those early experiences helped him develop confidence, relationships, and a strong work ethic. The conversation explores how the lessons from carrying a golf bag - service, anticipation, and accountability - translate directly into leadership and success in business. [00:00:00] Kai introduces the podcast and welcomes David Dorros to discuss how caddying shaped his life and career. [00:00:50] Dave explains his role at Eastdil Secured and the work he does advising clients on large real estate transactions. [00:04:20] Shares how he started caddying at Bethesda Country Club as a 13-year-old, riding his bike to the course and waiting hours for a loop. [00:06:30] Describes the early realities of the job—heavy leather golf bags, long days, and learning quickly how demanding the work could be. [00:10:40] Kai asks about the culture of the caddie yard and how Dave adjusted to a completely new environment. [00:11:11] Dave recalls the caddie shack culture, arriving early, playing cards to pass the time, and learning to be prepared for long days without guarantees of work. [00:18:58] Reflects on how caddying exposed him to a different world and helped him observe how successful professionals carried themselves. [00:24:43] Discusses how skills learned as a caddie—anticipation, service, and awareness—later translated into business and client relationships. [00:29:06] Shares how interacting with accomplished people at a young age helped him develop confidence and professional presence. [00:32:09] Talks about the discipline and work ethic required both in the caddie yard and later in investment banking. [00:36:51] Explores the importance of mentorship and the responsibility successful professionals have to support the next generation. [00:40:49] Reflects on the lasting impact of caddying and why the experience continues to influence how he approaches work and leadership. [00:47:24] Offers advice to young caddies and early-career professionals about humility, preparation, and building strong relationships. [00:50:19] Final reflections on how the lessons from the caddie yard continue to shape his perspective today. Links: Kai Sato on LinkedIn: <a href="https://www.linkedin.com/in/kaisato" target="_blank" rel="noreferrer noopener">https://www.linkedin.com/in/kaisato</a> David Dorris on LinkedIn: <a href="https://www.linkedin.com/in/david-dorros-b07330350" target="_blank" rel="noreferrer noopener">https://www.linkedin.com/in/david-dorros-b07330350</a>

August 19, 2025

Official Caddying Story of Michael Bapis

In this episode of Caddyshack to Corner Office, Kai sits down with Michael Bapis, Managing Director with Vios Advisors at Rockefeller Capital Management, to trace his journey from youthful caddie to thought leader in the financial services industry, regularly appearing on CNBC, Bloomberg TV and Yahoo Finance. Michael reflects on his early days looping at Salt Lake Country Club, learning life lessons from local legends and PGA pros. He shares colorful memories from working with Jim Flick at Desert Mountain, golfing at the University of Utah, how sports shaped his leadership style, and the mentors who guided him on and off the course, like former Morgan Stanley CEO Philip Purcell. Their conversation spans grit, gratitude, and how caddying helped him build a people first approach to business and life. ____________________________________________________________ [00:00:00] Michael shares his path from college golf to Morgan Stanley and eventually to Rockefeller Capital Management.[00:03:55] Reflects on early caddying experiences at Glendale and Salt Lake Country Club and what he learned from older members.[00:05:35] Tells a memorable story about caddying for a U.S. Open qualifier and falling into a bunker.[00:07:21] Recalls important etiquette lessons from early mentors that still influence his expectations today.[00:12:33] Describes the powerful mentorship he received from legendary golf instructor Jim Flick.[00:14:04] Shares a formative experience observing Flick coach Phil Mickelson and Tom Lehman in the rain.[00:22:14] Talks about working at Desert Mountain and life lessons learned from the variety of people he encountered there.[00:23:13] Recounts a humorous caddie revenge prank involving lotion and golf grips.[00:28:26] Reflects on why he loved caddying and how it shaped his appreciation for people and hard work.[00:36:06] Discusses how his past as a caddie shapes the way he treats caddies today.[00:40:00] Talks about building teams and why he values hiring athletes for their discipline and grit.[00:44:40] Explores the importance of mental toughness and how self-talk impacts performance.[00:46:30] Pays tribute to his mentor Phil Purcell and the lessons he passed on about leadership and humility.[00:48:55] Emphasizes the value of mentoring young professionals and giving back. Links: 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>Michael Bapis on LinkedIn: <a href="https://www.linkedin.com/in/michael-bapis-23a93127" target="_blank" rel="ugc noopener noreferrer">https://www.linkedin.com/in/michael-bapis-23a93127</a>

15 total episodes available

Deep-dive analytics for Caddyshack to Corner Office

Frequently asked questions

Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.

What is Caddyshack to Corner Office?: Recognizing the most accomplished people who once caddied and growing the game by assisting those following their path
How often does this podcast release new episodes?: This podcast updates weekly.
Where can I listen to this podcast?: This podcast is available on 6 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

Legal Disclaimer

Pod Engine is not affiliated with, endorsed by, or officially connected with any of the podcasts displayed on this platform. We operate independently as a podcast discovery and analytics service.

All podcast artwork, thumbnails, and content displayed on this page are the property of their respective owners and are protected by applicable copyright laws. This includes, but is not limited to, podcast cover art, episode artwork, show descriptions, episode titles, transcripts, audio snippets, and any other content originating from the podcast creators or their licensors.

We display this content under fair use principles and/or implied license for the purpose of podcast discovery, information, and commentary. We make no claim of ownership over any podcast content, artwork, or related materials shown on this platform. All trademarks, service marks, and trade names are the property of their respective owners.

While we strive to ensure all content usage is properly authorized, if you are a rights holder and believe your content is being used inappropriately or without proper authorization, please contact us immediately at hey@podengine.ai for prompt review and appropriate action, which may include content removal or proper attribution.

By accessing and using this platform, you acknowledge and agree to respect all applicable copyright laws and intellectual property rights of content owners. Any unauthorized reproduction, distribution, or commercial use of the content displayed on this platform is strictly prohibited.