Laura Nicol dials into Phoebe Pincus, Chief Operating Officer at Startmate and Co-Founder at Cheeky Run Club.

The Women’s Fellowship reunions keep on reunioning. This time with Phoebs.

We cover a lot. Learning to lead when you've never had female leadership role models. Being the opposite of a perfectionist. Her career journey from psychology student to general manager to chief of staff to COO.

We also get into Cheeky Run Club: Phoebe's podcast and amateur running community. Why it started, balancing passion projects with big jobs, and finding your “bumper rails.” If Cheeky Run Club brought you here. Hello cheeky friends! 

Inside this conversation:

• The Good Weekend Quiz: A pandemic-born family ritual that still lives on today.
• Becoming a leader others want to follow: Phoebe’s aha moment? A halftime pep talk at social touch rugby. “I’ve seen you give half-time pep talks at social touch… you just need to find a way to do it that feels authentic to you.”
• Gratitude compounding: a nighttime ritual she's taken to adulthood
• Designing COO-CEO partnerships and her role managing internal operations and external fundraising
• Transitioning from Chief of Staff to COO:
  • Differences: Different team dynamics, moving from supporting to driving, directing strategy, and shifting from internal to external focus.
  • Common ground: Solve problems, push the business forward.
  • Practical to-dos: Interview COOs, map your remit against the CEO’s, create your own model of great leadership, start doing the role before you get the title.
• “How do you set goals?” One of the most-asked questions in Chief of Staff circles. 
• Life rules and systems: “Always Swim,” prioritising what you know you should be doing, and the shadow theory of values.
• Representing running the Cheeky way: joyful, social, best thing for your mental health:
  • “You’ve changed our relationship with running”
  • The outlet: “this is my thing, it feels like an extension of us”
  • Being content in the “work a lot” phase
  • "A lot of our listeners don’t even like running". Why even non-runners turn up for the health content for women

Want to connect with Phoebe? Find her on LinkedIn.

Also mentioned:

• Maisy Bennett
• Michael Batko
• Jason Fang
• Cheeky Run Club: Spotify, Apple, Instagram, Cheeky’s Substack
• Anna Coldham
• How to fall in love with running with Phoebe & Anna from Cheeky Run Club (KICPOD)
• How to fall in love with running (Cheeky Run Club)

Pre-interview chats:

• Bronte McHenry (Listen to Bronte's Calling Operator episode)
• Kelly Spoerk

Guest ideas?

Do you have an operator on speed dial who could be perfect for the show? Please share your suggestions with me via LinkedIn.

A note from your host, Laura:

My goal for Calling Operator is to open-source stories from startup operators across various functional areas and learn how they excel at building and scaling companies. As a Chief of Staff, I often find myself in (virtual) rooms with people facing similar challenges and reinventing the wheel. I want this podcast to open a line for operators across Australia and New Zealand to learn from fellow operators. Each episode shares personal stories, the execution behind big ideas, career-defining moments, successes, failures, and lessons.

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