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Posted: Fri 31st Oct 2025
Welcome to the Small Business Sessions: Founder Fails podcast, brought to you by Enterprise Nation, in collaboration with Hiscox.
In this series, we're sitting down with bold business voices to talk candidly about their biggest fails, unexpected lessons and the power of getting back up.
Expect honest conversations, tales of resilience and real talk from founders who turned mistakes into movement.
In episode two, we're joined by Deepak Ravindran, co-founder of Oddbox, the UK’s first sustainable fruit and veg box delivery service.
Deepak is now an executive coach for start-up founders and leaders, helping others navigate the personal and professional challenges that come with building mission-led businesses.
In this conversation, Deepak shares the personal and leadership lessons behind building a food-waste-fighting business – from early doubts and bold career moves to burnout, identity shifts and the surprising ways failure shaped the journey.
The leap from a stable career in finance to founding Oddbox
How to separate your self-worth from your business identity
Burnout, therapy and rebuilding purpose after growth and pressure
Why founders should reframe "failure" as an experiment, not an identity
The importance of reconnecting with your "why" and values
You can also listen on other platforms and Enterprise Nation.
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