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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What if real leadership isn’t about holding power tighter but knowing when to give it back? In this episode Eddie Wilson unpacks the story of Cincinnatus, the Roman farmer who was pulled from his field, given absolute power as dictator, saved Rome in just 15 days and then walked away to go back to his plow. Eddie uses this ancient story to challenge modern leaders, founders, and parents who never “asked” to lead but now have people watching them, along with breaking three core leadership truths. From business owners stuck at the $5M ceiling because they won’t relinquish control, to parents learning when to let their kids fail and grow, to politicians who “die in the spotlight” because they hold power too long, this episode will force you to ask: Am I building something that shines without me, or something that only works as long as I’m in the room?
TIME STAMPS:
- 00:00 – Leadership isn’t ego, it’s letting go
- 00:37 – Who is Cincinnatus? The farmer turned Roman dictator
- 01:32 – When leadership finds you
- 02:44 – For leaders who never asked to lead but answered the call
- 04:21 – Accepting the role: abandoning what was, embracing what is
- 05:37 – In one day: from farmer’s clothes to dictator’s robe
- 07:41 – Overnight march, citizen soldiers, and outmaneuvering the enemy
- 09:39 – Victory in 15 days and Cincinnatus walks away from power
- 11:34 – Lesson #1: Power is a tool, not a throne
- 14:00 – Lesson #2: True leaders know when to step up and step away
- 15:42 – Why most small businesses never get past $5M
- 16:16 – Letting go as a parent: leading sons at different stages
- 17:51 – Lesson #3: Discipline over dominance restraint is greatness
- 19:56 – Give your followers the credit, not yourself
- 21:09 – Are you building a business that can thrive without you?
- 22:03 – Don’t just build for power; build for peace
- 22:47 – When leaders hold power too long: politics, ego, and dying in the spotlight
- 25:09 – Final challenge: use power as a tool, then let it go
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