Caddyshack to Corner Office

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/ 

In this episode of Caddyshack to Corner Office, Kai sits down with David Dorros, Managing Director 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: https://www.linkedin.com/in/kaisato David Dorris on LinkedIn: https://www.linkedin.com/in/david-dorros-b07330350 

In this episode of Caddyshack to Corner Office, host Kai Sato welcomes Jon Orszag, Founding Partner of Econic Partners, an economic consulting firm with a global footprint. He was previously a co-founder of Compass Lexecon, LLC, an economic consulting firm. Prior to entering the private sector, Jon served as the Assistant to the U.S. Secretary of Commerce and Director of the Office of Policy and Strategic Planning. Jon shares his unique journey from caddying at Brooklawn Country Club to advising major corporations on mergers, antitrust matters, and economic strategy. The discussion examines Jon’s remarkable career trajectory — including working with President Clinton at the White House right after graduating from Princeton — and explores his lifelong passion for golf. He reflects on the invaluable lessons golf has taught him, his extensive involvement as a board member of both the TGR Foundation (formerly the Tiger Woods Foundation) and The First Tee, and why he continues to give back to the game he loves. Jon has accomplished the rare feat of playing Golf's Top 100 Courses, where he has also served as a course rater.

In this episode of Caddyshack to Corner Office, host Kai Sato chats with acclaimed sportswriter Rick Reilly, formerly of Sports Illustrated and ESPN as well as an 11-time winner of the NSMA's National Sportswriter of the Year Award. Rick shares captivating tales from his first caddying experience at The Masters for Tommy Aaron to humorous encounters on the bag with Donald Trump, John Daly, Tom Lehman, and Bob Newhart. From his early days in journalism to his celebrated book, Who's Your Caddy?, Rick reveals how caddying offers unique insights into golf and life. He also previews his upcoming sequel, Still Your Caddy, which covers a whole new spectrum of caddying, from looping in the nude to a transformational program using caddying to help soldiers with PTSD.____________________________________________________________[00:00:00] Rick Reilly’s humorous introduction to caddying at the Masters with Tommy Aaron.[00:02:09] Rick's initial challenges and lessons learned as a caddy at Augusta National.[00:03:48] Rick's passion for writing, early career, and working at Sports Illustrated.[00:06:01] Upcoming book Still Your Caddy, spotlighting caddy school for soldiers with PTSD at St. Andrews.[00:08:52] Rick’s experience at the world’s only nude golf course.[00:10:11] Inspiration behind his popular book Who's Your Caddy?.[00:12:48] Caddying for Donald Trump and humorous anecdotes leading to the book Commander in Cheat.[00:16:28] Insights from looping for Tom Lehman and the importance of positivity in caddying.[00:22:56] How Rick built trust and gathered behind-the-scenes caddy stories from the PGA Tour.[00:25:33] Rick’s reflections on caddying as a partnership and a key takeaway from his experiences.[00:28:12] The transformative role of caddying in the lives of soldiers with PTSD.Links:Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisatoRick Reilly on X: https://x.com/reillyrick?lang=en

In this episode of Caddyshack to Corner Office, Kai speaks with Bob Ford, a storied golf professional and former head pro at both Oakmont Country Club and Seminole Golf Club, the former where he got his start thanks to US Open champion Lew Wersham. Bob shares stories from his early caddying days at Aronimink Golf Club, his experiences playing professionally around the world, and what it was like to loop for pros like Ed Sabo and Jay Siegel. He reflects on key moments from his playing career, his deep rooted connections to legends like Arnold Palmer, and Palmer's pivotal role in shaping golf culture, a lot of which he now sees in Rory McIlroy. The conversation touches on the evolution of the game, mentoring junior golfers, and his current contributions through roles with the Pennsylvania Golf Association, the USGA, PGA of America and beyond. Bob’s wisdom and humor offer a compelling look at a life dedicated to golf, which has commanded admiration from all who meet him.____________________________________________________________[00:00:00] Introduction to the episode and guest Bob Ford[00:00:19] Bob Ford's background and early influences[00:01:02] College years and beginning of professional golf journey[00:02:09] Working at Oakmont and Seminole[00:03:26] Early caddying experience and inspiration to pursue golf[00:05:22] Volunteering at major tournaments and early competitive play[00:07:08] Joining Oakmont as an assistant and becoming head pro[00:07:38] Breaking into the caddy yard and first loops[00:08:51] Recollections of members and community at Aronimink[00:11:50] Continued involvement with Evans Scholars and reflections on caddying[00:15:27] Tour caddying experience and influence on playing career[00:18:57] Traveling the world as a young professional[00:23:01] Lessons from caddying and traits of great caddies[00:26:50] Influences and relationship with Arnold Palmer[00:30:06] Growth and changes in golf post-COVID[00:33:38] Raising kids around golf and teaching philosophy[00:38:30] Expectations for upcoming U.S. Open at Oakmont[00:40:59] Involvement in golf organizations and notable stories[00:42:59] Golf's philanthropy and final thoughtsLinks:Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisatoUSGA: https://www.usga.org/articles/2017/02/bob-ford-selected-as-2017-bob-jones-award-winner.htmlThe Legend of Bob Ford: https://www.taylormadegolf.com/clubhouse/570940-the-legend-of-bob-ford.html?lang=en_US

In this episode of Caddyshack to Corner Office, Kai sits down with Josh Isner, President of Axon and former caddy at New Seabury Country Club. Josh reflects on his early days lugging bags in Cape Cod, his competitive golfing years, and the leadership values he’s carried into the tech world. Drawing inspiration from Bill Belichick and Dave Portnoy, he unpacks lessons on mentorship, culture-building, and staying relentlessly driven. The conversation touches on his Harvard years, the Patriots playbook, and the role of authenticity in leadership and mentorship.____________________________________________________________[00:01:03] Josh’s start at Axon and the company’s evolution from TASER to a tech-driven public safety platform.[00:02:56] His first caddying job at New Seabury and why he sought it out.[00:04:43] How he first got into golf and escaped summer camp.[00:06:06] His early playing experience and how golf shaped his character.[00:07:00] First day caddying, what he wore, and who he looped for.[00:08:25] Remaining connected with early caddying contacts and returning to the club as a member.[00:09:08] Learning curves and blunders from caddying as a teen.[00:10:04] Club culture and how being a member’s kid shaped the experience.[00:11:22] Pay, humidity, and how he spent his earnings.[00:13:04] Golfing updates and stories from Whisper Rock.[00:14:52] Early exposure to leadership and life direction from caddying.[00:16:43] Balancing golf and managing Harvard basketball; lessons in leadership.[00:19:25] Recruiting former athletes and veterans at Axon for their resilience and adaptability.[00:20:20] Axon’s “Patriots dynasty” leadership and culture model.[00:24:14] Advice for young people on finding purpose and work experience during college.[00:26:33] Prioritizing work experience over GPA and learning outside the classroom.[00:30:04] Compounding success through marginal daily improvement.[00:31:08] Personal drive rooted in being underestimated and rejected early.[00:34:05] Treating people well and the impact of leading with respect.[00:35:05] Mentors from sports and identifying with authentic leadership.[00:39:29] Developing real mentorships through organic, personal relationships.[00:44:33] Perspective as a member having been a caddy—mutual respect on and off the course.[00:47:16] Suggestion to feature Kevin Streelman, former caddy turned PGA Tour player.Links:Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisatoJosh Isner on LinkedIn: https://www.linkedin.com/in/joshisnerAxon on LinkedIn: https://www.axon.com/

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.____________________________________________________________[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 courseLinks:Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisatoBrian Sullivan on LinkedIn: https://www.linkedin.com/in/brian-sullivan-730306172Five Oceans Capital: https://www.fiveoceanscap.com/

Welcome to the Caddyshack to Corner Office podcast. Subscribe and follow anywhere you get podcasts.Learn more:https://www.caddyshacktocorneroffice.com/Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato

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.