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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Most founders aren’t failing, they’re just sitting in the wrong seat. In this episode, Eddie breaks down the three seats in every business Owner, Operator, CEO, and shows you how blurred lines create bottlenecks, burnout, and stalled growth. You’ll learn what each seat actually owns, how to transition from Operator to CEO without the business collapsing, why systems are better than sweat, and the exact one week challenge to audit your calendar, color code your tasks, and offload what keeps you stuck. If you want scale, rest, and real freedom, this is your roadmap.
TIMESTAMPS:
- 00:00 – Why most founders are stuck: wrong seat, blurred lines.
- 02:36 – Clarity brings freedom: define Owner, Operator, CEO.
- 03:47 – The Owner seat: equity, decision rights, profit participation.
- 07:03 – The Operator seat: in the weeds, approvals, bottlenecks.
- 11:17 – The CEO seat: strategy, culture, leading leaders systems, not sweat.
- 13:11 – Think in quarters and years, not hours and days.
- 14:21 – Review data over drama; build rhythm and plan the exit.
- 16:26 – Step 1: identify all seats you’re sitting in now.
- 17:05 – Phase 1 Operator season: necessary, but temporary.
- 18:49 – Transition to CEO: delegate, lead by metrics, replace yourself.
- 22:14 – Why visionaries must reach CEO: scale, sell, rest.
- 24:33 – The one week challenge: audit calendar, color code, offload.
- 27:13 – Decide to shift now; empires aren’t built by do it alls.
- 27:58 – Final line: “Design everything to get done without you.”
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43 episodes