In this episode of Challenger City TO, host Iain Montgomery sits down with Alex Tribe to discuss Toronto's transformation from a vibrant entertainment hub to a growing global city. They explore the city's evolving challenges, including housing affordability, risk aversion, and cultural mediocrity. Alex shares his unique insights from his journey as a DJ turned entrepreneur and small business consultant, highlighting the need for clear vision and ambitious leadership to navigate Toronto's growing pains and unlock its full potential.

Key Topics Discussed:

• Alex's Background:
  • Transition from DJ to entrepreneur.
  • The value of experimentation and taking risks in career and business.
• Evolution of Toronto’s Entertainment District:
  • Changes from a nightlife hotspot to a more residential area.
  • Impact of these changes on the city's cultural landscape.
• Toronto’s Growing Pains:
  • The city’s transition into a global city and the associated discomfort.
  • Challenges of applying old solutions to new problems.
• Cultural Mindset:
  • Tendency to choose mediocrity and avoid bold decisions.
  • Impact on the city's development and problem-solving.
• Affordability and Risk-Taking:
  • Economic realities forcing creative and entrepreneurial talent out of the city.
  • The alarming trend of people leaving Toronto for more affordable areas.
• Perception and Real Change:
  • The overwhelming focus on housing affordability overshadowing other critical issues.
  • Importance of perception and culture in driving real change.
• Clear Vision and Leadership:
  • The need for ambitious leadership with a clear vision for the city's future.
  • How solving housing and transit issues could unlock Toronto's potential.

Notable Quotes:

• "I'm a firm believer that just doing stuff for the sake of it and seeing where that takes you is one of the biggest launching pads for the best opportunities."
• "Toronto is kind of becoming a grown-up city... with a bunch of people who I think are reluctant to the idea or fail to recognize that we're becoming a global city."
• "We seem to just choose the middle of the road... it creates a culture of kind of, I guess, good enough or tolerate mediocrity."
• "Places that are less expensive are where experiments can be made because the risk of failure is lower."
• "Nine and a half out of ten conversations I have with people my age somehow get brought back to housing. I'm sick of talking about housing. I want to talk about way more interesting things than housing."
• "If we solve housing affordability and transit, it allows us to change the conversation to something higher leverage."