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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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SUMMARY:
In this episode, Aaron and Terryn break down the art and strategy behind annual planning—why it matters, how to do it well, and how to keep your team aligned for success. They share personal stories from early days planning with sticky notes in an attic to running structured multi-business offsites in Montana. Learn how to start small, scale your planning process, and create a rhythm that eliminates chaos and builds long-term clarity. Whether you're a solo entrepreneur or leading a full team, you'll discover actionable insights, templates, and mindset shifts to make your next annual planning session your most productive ever.
Minute by Minute:
01:07 – Welcome to Ops Experts Club 01:30 – Why Annual Planning Matters 02:40 – The Power of Offsite Planning 04:25 – Starting Small: Two People and Sticky Notes 06:27 – Building Scalable Habits for Growth 07:18 – Free Resources for Planning 2026 08:51 – Wins, Lessons, and Preparing Your Team 13:19 – Vision Time: Casting the Future 15:33 – Setting Quarterly Rocks That Actually Work 21:30 – Make It Fun: The Secret Ingredient to Great Culture
90 episodes
