Challenger Cities

In this conversation, Iain Montgomery speaks with Mary Rowe, the head of the Canadian Urban Institute, about the importance of local engagement in urbanism, the challenges faced by cities, and the role of community in fostering resilience and innovation. They discuss the need for a ground-up approach to urban development, the significance of local economies, and the mission of the Canadian Urban I...

In this episode of Challenger Cities , host Iain Montgomery sits down with Chris Eby, Executive Vice President of Northcrest, to explore one of Toronto’s most ambitious urban redevelopment projects: the transformation of the Downsview lands (YZD). Chris shares the vision for this 520-acre project, which promises to shift Toronto’s center of gravity north, creating a network of vibrant, walkable ne...

Iain Montgomery sits down with Chris Bruntlett of the Dutch Cycling Embassy to explore how cycling infrastructure can transform urban life. Chris shares insights from the Netherlands, where bikes are seamlessly integrated into daily life, and discusses how other cities can adapt these principles to their unique contexts. From leadership lessons to e-bike revolutions, this conversation uncovers wha...

In this conversation, Iain and Hayden discuss the complexities of urban transit systems, the historical context of public transportation in North America, and the political dynamics that affect transit development. They explore case studies like La Sombrita, the need for reform in institutions, and the importance of public trust in transit systems. The discussion also touches on international comp...

What some cities get so right about transportation, why others get it so wrong, and how we can make the whole thing much better. In this episode of Challenger Cities , Thomas Ableman, a leading voice in transportation innovation, takes us on a journey through the world of urban mobility. From the seamless efficiency of Swiss trains to Oslo’s ambitious integration of electrification and autonomy, T...

Iain Montgomery of Now or Never Ventures speaks with Paul Kalbfleisch, author of The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society . Paul shares his unique journey from marketing executive to accidental urbanist and his mission to reimagine cities as spaces for connection, joy, and belonging. Drawing from his experiences in Ontario’s Waterloo Region and beyond, Paul off...

In this episode of Challenger City TO , host Iain sits down with Chris Spoke, a partner at Toronto Standard and a vocal advocate for smarter urban development. Chris shares his journey from the world of software to real estate, diving deep into the challenges and opportunities facing Toronto's housing market. The discussion covers a range of critical topics, including the impact of restrictive zon...

In this episode of Challenger City TO , we sit down with Antoine, a seasoned transit professional with global experience, to dive deep into the complexities of Toronto's transit system. Antoine shares his unique insights into the city's current challenges and opportunities, drawing on examples from his work across Europe and North America. Key Topics Discussed: Toronto's Identity Crisis: Antoine d...

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...

In this enlightening episode of Challenger City TO, host Iain Montgomery sits down with Aileen Nandy, an expert in digital marketing, community building, and former journalist. Recorded amid the tranquil sounds of a camping trip, the conversation delves deep into what makes a city truly family-friendly and how Toronto can rise to the challenge. Aileen shares her unique perspective on urban develop...

In this episode of Challenger City TO, Iain welcomes Jordan Ostapchuk, a pioneering capital designer, to explore the transformative role of capital design in urban investment. Jordan, who often finds himself as the "token capitalist in a room full of designers" and the "token designer in a room full of capitalists," shares his unique perspective on integrating creative thinking with traditional fi...

Episode Summary: In this episode of Challenger City TO, we sit down with Hans Bathija, a seasoned consultant with a rich history in Toronto. Hans shares his insights on the city's evolving identity, the impact of amalgamation, the importance of public safety, and the need for a renewed focus on arts and culture. Join us as we explore what it means for Toronto to be a Challenger City and how it can...

In this episode, futurist Nik Badminton shares his insights on the future of cities, emphasizing the need for human-centric, community-focused urban planning. Drawing from his global experiences, Nik discusses the challenges of balancing legacy systems with innovative solutions and highlights the importance of creating resilient, vibrant cities like Toronto. Key Topics Discussed: Introduction to N...

In this episode of Challenger City TO, we sit down with Chris Burchett, a telecommunications expert turned transit visionary, to explore the transformative potential of train stations. Chris shares his journey from Wi-Fi to transit hubs, highlighting the often-overlooked importance of stations in shaping the overall passenger experience. He discusses the challenges of the engineering-centric appro...

In this episode of "Challenger Cities," host Iain Montgomery sits down with two influential figures in Toronto's creative landscape: Tabassum Siddiqui, a freelance journalist and communications specialist, and Faisal Siddiqui, founder of the Creative Business Company. Together, they delve into the strengths, challenges, and future prospects of Toronto's vibrant arts and culture scene. Key Topics:...

In this enlightening episode, we sit down with Ramy Nassar, a leading expert in foresight and urban innovation, to discuss his vision for Toronto as a Challenger City. Drawing inspiration from his favourite movie Back to the Future , Ramy shares his thoughts on why foresight is essential for shaping the future we want rather than having it imposed on us. From tackling AI fatigue to addressing the...

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 consu...

Episode Description In this episode, we sit down with Laura Manes, a strategic change agent with over 20 years of experience in retail and consumer brand innovation. Laura shares her insights on how Toronto can reclaim its status as a Challenger City. We discuss the importance of human-centric design, the need to focus on often overlooked stakeholders, and how vibrant local neighborhoods can foste...

Summary In this conversation, Iain interviews Jasmine about the concept of Challenger City and how cities can embrace this mindset to drive innovation and growth. They discuss the unique challenges and opportunities for cities in Canada, particularly smaller and mid-sized cities. They also explore the current state of Toronto and the need for the city to redefine itself and create a more vibrant a...