Inside the Mind of One of London’s Most Iconic Lawyers - Simon Olswang Lessons

In this episode of The Free Lunch Podcast, Eddie Ross sits down with Simon Olswang - legendary founder of the UK law firm Olswang, board adviser, entertainment lawyer, and a pioneer in the world of media & communications.We dive into leadership, culture, high-pressure decisions, talent, integrity, and how to build organisations that last. Simon shares extraordinary stories from his career:• Founding Olswang in 1980 and scaling it into one of the UK’s most influential media & entertainment law firms• Working with major film productions (including Gandhi), Monty Python, and global icons like Diana Ross• Leadership lessons from decades working at the intersection of law, media, private equity and technology• How values, integrity and culture shape teams — and what happens when they disappear• The real challenges of succession, growth, reinvention and personal resilience• AI, change, and what he believes is coming next for societyThis conversation is packed with wisdom, unforgettable stories, and practical leadership insights from someone who has operated at the highest levels for decades.If you're interested in leadership, entrepreneurship, law, media, or personal growth — you will love this episode.Subscribe for more conversations on leadership, culture, and the hidden realities of building organisations.