The myth of the self-made leader: Matthew Westerman CBE on winning, leadership and resilience

Matthew Westerman CBE has spent his career operating at the highest levels of global finance, but his story is about much more than banking. In this episode of Winning, Ian Rosenblatt OBE sits down with Matthew to explore the experiences, setbacks and lessons that shaped his remarkable career. From losing his father at a young age to being rejected by firms he desperately wanted to join, Matthew reflects on the resilience, ambition and self-belief required to succeed. Together, they discuss leadership under pressure, the importance of culture, and why the most successful people never stop learning. Matthew also shares why he believes business leaders should embrace mentorship in the same way elite athletes embrace coaches, drawing on his work with Global Mentors GroupThe conversation also explores his time at Goldman Sachs and HSBC, his experiences living and working in China, and his commitment to preserving history through his work with the Imperial War Museum and the UK Holocaust Memorial Foundation. This episode explores:▪️ Learning through loss: Why setbacks, rejection and failure often provide the foundations for long-term success. ▪️ The power of mentorship: Why business leaders need coaches and mentors just as much as elite athletes do. ▪️ Leading under pressure: How to make decisions, build culture and inspire teams in high-stakes environments. ▪️ Thinking long-term: Why history, memory and responsibility are essential ingredients of effective leadership.Above all, Matthew shares his philosophy on winning that you can only truly understand success if you've learned how to deal with the consequences of failure.Music: "Piano Concerto No. 23 in A major, K. 488. I. Allegro | by Mozart, performed by [Mira Ma, Eric Jacobsen, Odyssey Orchestra], sourced via [Epidemic Sound]. Licensed under Epidemic Sound