In this episode of Execs Who Run, Phoebe Pincus brings both momentum and honesty to the mic. As COO of leading startup accelerator Startmate and co-founder of Cheeky Run Club, she’s someone who knows how to build systems — whether in companies, communities, or her own running life. Our conversation begins with her simple but powerful mantra: Always Swim. On the surface, it’s about diving into the ocean after a run in Bronte. But for Phoebe, it’s a metaphor for living with intention — recognising what matters most and making sure you actually do it. Discipline, in her eyes, isn’t about willpower or punishment. It’s about designing habits and systems that make the important things easy, and that perspective has shaped how she approaches running, leadership, and life. From there we dive into her journey: the casual college loops that gave her space and freedom, the early marathons run on limited knowledge and pure grit, and the transformation that came when she joined a structured run club and trained with a coach. The result was a breakthrough that reframed her sense of possibility — taking more than an hour off her marathon time and proving that the limits we set are often the ones we imagine. We also explore the rise of running as culture. As co-founder of Cheeky Run Club, Phoebe has tapped into the social and identity-building side of the sport. What started as a frustration with the “serious” image of running has become a rebrand: running as joyful, welcoming, and deeply communal. And yes, we tackle the question head-on — is running a cult? Phoebe laughs, but doesn’t deny it. Underneath the stories of marathons, podcasts, and startups, this episode is really about confidence. It’s about proving to yourself that you can do hard things, and learning to balance that drive with the honesty to know when you’ve gone too far. For Phoebe, that balance has come from hard lessons — burnout, overtraining, and the need to “earn the right” to do more. This is an episode for anyone who’s curious about how the discipline of running translates into resilience at work, how self-confidence is built mile by mile, and how a community can change the way we see ourselves. It’s a conversation about identity, systems, and the joy of finding momentum in movement.