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