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Phoebe Pincus: Discipline, Confidence, and the Running Cult

Phoebe Pincus: Discipline, Confidence, and the Running Cult

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Phoebe Pincus — COO of Startmate, co-founder of Cheeky Run Club, and marathon runner — joins Execs Who Run to share how running has transformed her approach to life and leadership. From ocean swims in Bronte to the cultural boom of run clubs post-COVID, Phoebe shows how running can be more than exercise — it can reshape identity, community, and confidence.


In this episode, we explore:

  • Why her Always Swim mantra is about more than just the ocean

  • The leap from Startmate Women Fellowship to COO

  • The founding story of Cheeky Run Club and the rise of running culture

  • Discipline, systems, and the myth of willpower

  • How running builds resilience and self-confidence in work and life

  • The lessons she’s learned from burnout, overtraining, and recovery

  • Her advice on balance, leadership, and doing hard things with joy


Quote from Phoebe:


“Discipline isn’t forcing yourself to do hard things — it’s building systems so the good things feel easy.” — Phoebe Pincus


Follow Phoebe Pincus:

Instagram: @cheekyrunclub

LinkedIn: Phoebe Pincus

Stay Connected with Jason & Execs Who Run:

Jason Hunt: LinkedIn | Instagram

Execs Who Run: LinkedIn | Instagram

Website: execswhorun.com

Join the community: Execs Who Run Strava Group

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