CS #66: Bill Ostlund and The Burden of Commanding the Most Decorated Unit Post-9/11

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Today we hear a special Combat Story of one of the military’s most revered leaders who many have never heard of (but should). This is the experience of retired Colonel Bill Ostlund, a beloved mentor and leader developer who served 35 years in the Army working his way up from a private and growing into combat command in some of the bloodiest fighting of any unit in the post-9/11 era.

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Bill’s command in Kunar Province, recounted countless times in dozens of books including Sebastian Junger’s War and the documentary Restrepo, resulted in over 400 awards for valor and three Medals of Honor (all living honorees).

This episode is an embarrassment of riches for those who want to know what real leadership looks like; what the Burden of Command actually means; how you show up after losing a soldier six hours into a 15 month deployment; or leading joint SpecOps task forces with Delta, DEVGRU, 160th, and other Tier 1 elements over thousands of operations.

Bill Ostlund will remind so many listeners of Todd Opalski in how he cared for and treated his soldiers and explains why, so many years later, his soldiers and officers still seek his advice as they step into greater roles of responsibility in the military and their personal lives.

I’m honored to have had a chance to spend this time with what so many think of as the pinnacle of battlefield leadership and hope you enjoy this Combat Story on leadership as much as I did.

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Intro Song: Sport Rock from Audio Jungle

Show Notes:

0:00 - Intro
0:40 - Guest introduction (Bill Ostlund)
1:31 - Interview begins
3:44 - The jump into Iraq in March 2003 with almost 1000 paratroopers
12:09 - Bill’s perspective on the current conflict in Ukraine
17:32 - Childhood and getting into the military
42:19 - Combat Story #1 - Lightning in the Storm Air Assault and leadership lessons learned
1:06:49 - Instilling expectations in his soldiers and his love of soldiers
1:26:57 - Combat Story #2 – Troops in Contact 6 hours into a 15 month mission after just taking command
1:37:08 - Awards process and how combat provides a unique opportunity for leaning and growth
1:49:30 - Combat Story #3 - Battle of Wanat
2:08:48 – Feelings about now having a son in the military
2:10:09 - What did you carry into combat?
2:11:41 - Would you do it all again?
2:15:23 - Listener comments and shout outs