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The Founder’s Dilemma: What to Let Go Of—and What to Hold Tight
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In this powerful and refreshingly candid conversation, Ben Morton welcomes back Tessa Clarke, co-founder of Olio, to reflect on the scale-up phase of building one of the UK’s leading sharing economy apps.
From their $43 million Series B raise to restructuring through a turbulent 2023, Tessa takes us inside the mindset shifts, leadership lessons, and cultural priorities that have defined Olio 3.0.
For leaders navigating the messy middle between startup energy and operational maturity, this episode is a masterclass in clarity, courage, and culture-first decision-making.
Why this episode matters:
Scaling a business often comes with the risk of losing what made it special in the first place. Tessa shares how Olio kept its startup spirit alive, even while hiring a C-suite and overhauling internal systems, without letting bureaucracy creep in or values drift.
What You’ll Learn:
- How to evolve from "scrappy startup" to a mature organisation without killing agility.
- The importance of ‘mission obsession’ in hiring, onboarding, and performance.
- The surprising downside of hiring too many “brilliant” people too quickly.
- Why founders shouldn’t always let go of product ownership, and how to decide.
- How gender bias affects female founders during fundraising, and how Tessa navigated it.
Ben’s Standout Moments:
- Tessa’s “Uniquely Me” document—a weekly discipline to focus on what only she could do as CEO.
- Her approach to maintaining trust and culture in a growing team.
- The candid admission of being “too idealistic for too long”—and what changed her thinking.
Want to Assess Your Own Leadership Readiness?
Discover how your organisation scores across nine core capabilities with Ben’s Leadership Capability Scorecard. https://ben-darwj4ma.scoreapp.com
It’s a practical, free tool designed to help you lead with confidence through growth and change.
Resources & Mentions:
- Dana Kanze TED Talk – The Real Reason Female Entrepreneurs Get Less Funding
- The Lean Startup by Eric Ries
- Olio App
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