In this reflective and wide-ranging conversation, I sit down with agency founder Simon Bollon, founder of Boutique and long-time leader in the UK agency world, to explore ambition, belief, resilience, leadership, and the deeper questions that sit behind success.
Simon founded the agency Boutique in 2012 and has spent more than a decade navigating the rollercoaster of building and leading a business. But what makes this conversation fascinating isn’t just the agency journey – it’s the mindset behind it.
From the almost irrational confidence it takes to start a business, to the self-development habits that shape leaders over time, Simon shares the philosophies that have guided both his career and his life.
We talk about the beliefs we inherit about success, the experiences that build resilience, and why many high achievers eventually realise they’ve been climbing the wrong mountain.
Together we explore:
✨ The mindset that allows entrepreneurs to start businesses in uncertain times
✨ “You can if you think you can” – why belief shapes outcomes
✨ Simon’s obsession with self-development and learning from others
✨ Why realising your potential doesn’t mean chasing external success
✨ Internal vs external measures of achievement
✨ The importance of resilience – and why losing is part of winning
✨ Leadership, feedback, and building cultures where people feel recognised
✨ The balance between confidence, introversion, and leading a business
✨ The idea of The Second Mountain – and what happens when success forces you to rethink your path
This episode is a conversation about ambition, identity, and the stories we tell ourselves about what success should look like.
Because sometimes the biggest realisation isn’t whether you can reach the top. It’s whether the mountain you’re climbing is the right one.