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.

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[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/kaisato

Josh Isner on LinkedIn: https://www.linkedin.com/in/joshisner

Axon on LinkedIn: https://www.axon.com/