From West Point to Startups: Leadership Lessons from Colonel (Ret.) Jim Orbock cover art

From West Point to Startups: Leadership Lessons from Colonel (Ret.) Jim Orbock

From West Point to Startups: Leadership Lessons from Colonel (Ret.) Jim Orbock

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In this special fireside chat edition of Startup Anthology, host Jeremy Willis sits down with Colonel (Ret.) Jim Orbock—a West Point grad, combat-tested US Army leader, and now, startup founder of Spartan Financial (https://spartanfinancial.pro/) in Austin, TX.

What You’ll Learn in This Episode:

  • The leadership mindset that took Jim from leading troops in Afghanistan to launching his own business.
  • How to transition from the military to entrepreneurship with purpose and confidence.
  • Why “servant leadership” isn’t just a buzzword—it’s a culture-defining principle.
  • The toughest part of startup leadership: letting go without losing control.
  • Tactical advice for early-stage founders on team-building, narrowing vision, and staying aligned with your purpose.


Whether you’re a veteran exploring the startup path, a founder trying to build a resilient team, or someone fascinated by leadership under pressure, this episode is packed with wisdom, war stories, and real talk.

“If you aim at nothing, you’ll hit it every time.” —Jim Orbock

Recorded live at the Military-Connected Mentorship Meetup with support from Command Post Cohort, Texas Veteran Chambers Coalition, and sponsors including IVMF Bunker Labs, Combined Arms, Texas Veteran Commission, Capital Factory, and JPMorganChase.

Don’t forget to like, comment, and subscribe for more deep dives into startup leadership and culture.

Chapters

00:00 Introduction to Startup Anthology

01:01 Meet the Guest: Retired Colonel Jim Orbock

03:24 Jim's Journey to West Point

05:26 Transitioning from Military to Entrepreneurship

08:21 Lessons Learned and Advice for Entrepreneurs

11:19 Narrowing Your Vision in Business

13:12 Exploring Team Building and Mentorship

13:48 The Power of Vision and Goal Setting

15:13 Maintaining Focus and Intent in Business

15:51 Investing in People and Building Trust

18:07 Challenges of Leadership in Different Contexts

20:45 Servant Leadership and Organizational Spirit

21:45 Balancing Leadership and Delegation

26:05 Encouraging Psychological Safety and Freedom to Fail

28:08 Conclusion and Final Thoughts

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