In this insightful episode of "Challenger City TO," Iain Montgomery sits down with Hilton Barber, a seasoned marketer and thought leader, to explore the transformative power of culture in shaping Toronto’s future. Hilton discusses the critical role that bold, courageous decisions play in driving cultural change, emphasising the need for Toronto to shift from a mindset of playing it safe to one of striving for greatness. He shares his thoughts on what it means to have a winning strategy, how culture impacts execution, and why defining Toronto’s unique version of “gold” is essential for the city's success.

Key Topics Discussed:

• The importance of culture in organisational and urban success
• Hilton’s career journey and insights on cultural impact
• Why curiosity alone isn’t enough—execution is key
• The need for safety and bravery in decision-making
• Examples of strong corporate culture, including Izzy Sharpe and Four Seasons
• Toronto’s current cultural landscape and the call for greater ambition
• The concept of playing to win versus playing to not lose
• The role of leadership in setting and executing grand ambitions
• Personal responsibility and collective effort in driving Toronto’s transformation
• The importance of storytelling in creating a shared vision for the city

Quotes to Remember:

• "Strategy is one thing. Execution is the game."
• "What is the size of our ambition? If we have a grand ambition, do we have the courage, the fortitude, the comfort with failing along that journey?"
• "If we don’t create a compelling story that brings people along, that engages them and says, 'Imagine this better future for Toronto,' we’re dead in the water."

Actionable Takeaways:

• Toronto must define its unique version of success and aim for it with boldness.
• Leaders need to create a culture that supports ambitious, transformative decisions.
• Personal and collective responsibility is crucial for Toronto’s progress.