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EO 360°, a podcast by Entrepreneurs’ Organization, explores entrepreneurship with a wide perspective, moving beyond business to those insights not often shared by high-profile thought leaders.

Host and serial entrepreneur, Dave Will, leads in-depth interviews, whose featured guests include: Gazelles founder and CEO, Verne Harnish; popular podcast host and founder of Genius Network, Joe Polish; award-winning entrepreneur, Zahra Al-Harazi; and more. Tune into this top podcast made by entrepreneurs, for entrepreneurs.

Learn more about Entrepreneurs’ Organization, the leading peer-to-peer network exclusively for entrepreneurs.

Feb 20, 2016


In this episode, Dave interviews Tim Jennings, a U.S. Army Veteran and long-time resident of Fort Bragg, one of the largest military installations in the world. Together, they talk about what military personnel go through during training and active duty, what life is like following discharge, and how the U.S. Military creates natural entrepreneurs through its emphasis on leadership and initiative.

Time Stamped Show Notes:

  • 00:30 – Dave welcomes Tim Jennings
  • 01:26 – Talking Fort Bragg
  • 01:31 – American Dream U and the military transition
  • 03:40 – Dave recounts his experience at Fort Bragg
  • 04:55 – Dave looks tiny next to Tim J
  • 05:16 – Tim’s role in the army
  • 08:00 – Tim shares why he joined the service
  • 09:41 – Went to West Point with the help of football
  • 10:25 – “No one else is going to do it. It’s got to be me.”
  • 11:41 – Start with Why by Simon Sinek
  • 12:20 – The Why that is baked into the military
  • 13:34 – Life in Afghanistan
  • 14:04 – Soldiers and junior officers don’t want to talk about the Why on a political level
  • 14:48 – Typical mission in Afghanistan – talk to local leaders
  • 16:12 – Action versus Attacks
  • 17:55 – Prep Work and debrief of the mission
  • 20:01 – Blue Angels Show
  • 21:38 – Recruiting/Hiring/Training in the military
  • 22:12 – Quality control is essential for hiring
  • 25:00 – Passion is the key to being a good soldier
  • 25:15 – Sometimes you don’t need the Why –just say yes and let the chips fall where they may
  • 25:48 – If you want to be good at giving direction, don’t be afraid to dive into the trenches with your subordinates
  • 27:01 – Time shares the leadership lessons learned in the military
  • 29:00 – Recall and cherish the relationships you’ve built
  • 29:37 – Allow subordinates to make decisions but guide them as they do so…give them intelligent autonomy
  • 31:00 - Admiral William McRaven’s Graduation Speech – “Make Your Bed”
  • 33:19 – Tim’s 3 different mentors
  • 35:43 – Tim’s keys to life—community, family, profession and personal
  • 40:02 – More on Fort Bragg
  • 41:44 – Dave thanks Tim and everyone in the military for their service

 3 Key Points:

  1. “No one else is going to do it. It’s got to be me.”
  2. If you want to be good at giving direction, don’t be afraid to dive into the trenches with your subordinates.
  3. Don’t just blindly give your subordinates (employees) autonomy—consciously guide them along the way.

Resources Mentioned:

  • Entrepreneur's Organization – The EO Network
  • Fort Bragg – One of the largest army bases on the planet
  • American Dream U – An organization that helps military members transition to life outside the military
  • Start with Why by Simon Sinek – Book mentioned by Tim
  • Blue Angels Show – U.S. airshow where debriefing is of great importance