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Bet On The People Who Show Up - Tim Flanagan

Your E.P.I.C Pursuit

Release Date: 03/05/2026

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More Episodes

From Bold Decisions to People-First Leadership: Tim Flanagan on Scaling, Strategy & Courage | Your Epic Pursuit Podcast

What does it really take to lead through a strategic inflection point? In this episode, Mike Mooney sits down with Tim Flanagan - third-generation leader, General Agent at the Pelora Group (MassMutual), Charlotte's 40 Under 40 honoree, and Most Admired CEO - for a raw, honest conversation on leadership, courage, and building high-performance teams.

Tim shares the moment he looked across a conference table and realized his team had split into two camps - and what he did about it. He unpacks why hope is not a plan, how to think 10X when the pressure is on, and the "slow down to speed up" strategy he and his business partner use to cut through the chaos without stopping the business.

In this episode, you'll learn:
✅ How to apply 10X thinking to compress your vision timeline
✅ Why strategic inflection points demand bold people decisions
✅ The "slow down to speed up" practice for leaders under pressure
✅ What "honoring someone's choice" means in real leadership
✅ How micro moments and experience wakes build (or break) culture
✅ The people-first principle that's driven decades of Charlotte business success

Whether you're a founder, executive, team leader, or aspiring entrepreneur, this episode delivers the kind of practical leadership wisdom you can put to work immediately.

🎙️ Guest: Tim Flanagan | General Agent, Pelora Group | MassMutual | Charlotte, NC
🏆 Charlotte's 40 Under 40 | Most Admired CEO | Best Places to Work

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📌 Chapters:
0:00 – Welcome & Tim's Introduction
2:16 – The Science of Scaling & 10X Thinking
10:37 – The Bold Decision That Changed Everything
24:02 – Slow Down to Speed Up
31:40 – The People-First Leadership Principle
37:33 – Micro Moments & Experience Wakes
39:21 – Closing Thoughts