"At each stage of the business, your identity has to evolve. From individual contributor, to manager, to leader. Most founders miss the moment when that shift needs to happen."
Deepak Ravindran co-founded Oddbox, the UK's leading ugly produce subscription service, and scaled it from a church hall side project to a nine-figure valuation in under a decade. But the real story isn't the growth. It's what happened to him inside it.
In this episode, Deepak talks honestly about what hypergrowth actually feels like from the inside: going from 25 to 100 people in a year, becoming the bottleneck in your own business, and the moment he realised his leadership style hadn't kept pace with the company he'd built.
He also gets into the stuff that rarely gets talked about- the identity crisis that comes when your business becomes you, the Sunday dread that crept in at Series B, and how a 360 review and a coach helped him surface the blind spots that were quietly holding the business back.
Now working as a founder coach, Deepak helps consumer brand founders scale themselves - not just their businesses. In this conversation he shares what he sees again and again in the founders who most need help but are least likely to ask for it.
In this episode:
- What breaks (operationally and personally) when you scale fast
- The shift from startup operator to organisational leader - and why it's so hard to spot in real time
- Why exit interviews and investor feedback were the making of him as a leader
- The difference between coaching and mentoring - and why it matters
- What "contentment through values alignment" actually looks like in practice