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 neighborhoods centered around sustainability, public spaces, and transit integration.

From reimagining a 2.1-kilometer runway into Toronto’s answer to New York’s Highline to tackling stormwater management with a groundbreaking “sponge city” approach, Chris explains how YZD is redefining what a city can be. Along the way, they discuss the challenges of urban planning in Toronto, the lessons learned from Sidewalk Labs, and the cultural factors that have held Canadian cities back from creating world-class public spaces.

What You’ll Learn in This Episode:

• Why Toronto needs multiple hubs, not just one downtown, to thrive in the future.
• How the Downsview project is balancing bold vision with community engagement.
• The role of sustainability in creating a fully electric, future-proof urban center.
• What Toronto can learn from global cities like Copenhagen, New York, and Montreal.
• Why Canadian modesty has limited urban innovation—and how YZD is changing that.

Memorable Quotes:

• “This is going to shift the center of gravity north. Downtown is great, but we need a variety of hubs.”
• “The success or failure of this project hinges on getting public spaces right.”
• “We will not be building any new fossil fuel infrastructure on the site.”
• “A lot of older Canadians have cottages, places up north or in the country. When they have free time, they leave the city. There’s never been a push on governments to build great public spaces in the city.”
• “We’ve got to stop being so unambitious about transit. You look at the map in London, New York, or Tokyo—ours just pales in comparison.”

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 what it takes to build cities that are healthier, happier, and more livable.

What We Cover in This Episode:

• Chris’s journey from advocating for bike lanes in Vancouver to working with the Dutch Cycling Embassy in Delft.
• Why cycling isn’t just about bikes—it’s about livability, inclusivity, and prosperity.
• The importance of cohesive cycling networks versus piecemeal infrastructure.
• How bold leadership, particularly female leaders like Anne Hidalgo in Paris, drives transformative change.
• The game-changing potential of e-bikes and intermodal transportation.
• Challenges like weather and cultural perceptions—and how to overcome them.
• Why even car-centric companies like Walmart are embracing cycling.

Notable Quotes:

• “It’s not just about bikes. It’s about livability, inclusivity, prosperity—all the things that getting more people cycling can do for your city.”
• “The bicycle has a range problem, and public transport has a convenience problem. Combine the two, and you’ve got a real alternative to the car.”
• “Bold decisions aren’t always popular at first, but when streets become safer and cities more livable, the results speak for themselves.”

Resources and Links:

• Learn more about the Dutch Cycling Embassy.
• Follow Chris Bruntlett on LinkedIn.
• Stay tuned for Chris and Melissa Bruntlett’s upcoming book on female leadership and urban transformation, releasing in 2025.

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 comparisons, the role of the private sector, and the vision for future transit systems that are interconnected and efficient. Ultimately, they emphasize the need for a new democratic urban agenda that prioritizes building and delivering effective transit solutions.

https://thetransitguy.substack.com/p/10-principles-for-a-new-democratic

takeaways

• Transformative transit is essential for urban development.
• Historical governance issues have led to poor transit systems in North America.
• Public trust is crucial for the success of transit projects.
• Reforming institutions can lead to better transit outcomes.
• International examples show the benefits of interconnected transit systems.
• The private sector has a significant role in urban development.
• Political dynamics often hinder effective transit solutions.
• Case studies can provide valuable lessons for future projects.
• A new democratic urban agenda is needed to prioritize building.
• We must shift from studying to implementing transit solutions.

titles

• Reimagining Urban Transit: A Conversation with Hayden Clarkin
• The Future of Public Transportation: Challenges and Solutions

Sound Bites

• "We need to rebuild these institutions."
• "Stop studying. Just do."
• "We need a housing industrial complex."

Chapters

00:00Introduction to The Transit Guy

04:53The Evolution of Public Transit in America

07:45The Impact of World War II on Urban Development

10:24The Challenges of Rebuilding Transit Systems

13:30La Sambrita: A Case Study in Transit Failures

16:09Political Trust and Institutional Failures

18:59The Need for Institutional Reform

21:37Comparative Analysis of Global Transit Systems

24:33The Importance of Incremental Development

27:23Public Perception and the Future of Transit

32:51The Experience Beyond the Stadium

36:41Zoning and Urban Design Challenges

40:50Homeowner vs. Renter Dynamics

46:29The Inefficiency of Government Processes

51:44Political Vision and Local Governance

53:41A National Vision for Transportation

55:51Introduction to Urban Challenges

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, Thomas shares lessons from cities that are getting transportation right—and the pitfalls of those that aren’t.

We dive into:

🚉 Why public transport isn’t just about moving people, but creating places where they want to be.

🏙️ London’s success stories, like Golders Green and Walthamstow, and how strategic planning shaped their growth.

🇨🇭 What makes Swiss Federal Railways a gold standard, from punctuality driven by pride to intelligent funding mechanisms.

🌍 Oslo’s pioneering work in electrification and autonomous vehicles as part of public transit—not just private luxury.

🛤️ Why trains feel more trustworthy than buses and how simple design changes can dramatically improve the rider experience.

🗳️ The political fear that stalls bold ideas—and why leaders who embrace change often win bigger than expected.

🛑 Hidden car subsidies like free parking that distort the true cost of driving.

✨ Thomas’s vision for making public transport so good that driving feels irrational.

Key Takeaway: Bold leadership and smart design can transform transportation systems into something that not only moves people but inspires them. "If the Swiss can do it, so can we. We just need to believe it’s possible," says Thomas.

You can find more from Thomas here:

https://www.freewheeling.info/

https://www.linkedin.com/in/thomasableman/

https://www.youtube.com/watch?v=-b8grwoUqvo&pp=ygUOVGhvbWFzIGFibGVtYW4%3D

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 offers fresh perspectives on the transformative power of public spaces and why cities that prioritize play are the key to building stronger, more resilient communities.

What You'll Learn in This Episode

• How Paul’s background in branding led to his work in urbanism.
• Why mid-sized cities are uniquely positioned to become "challenger cities" and lead innovation.
• The power of “play, live, work” as a new framework for designing cities.
• Real-world examples of public art and play fostering community, like Meander in Cambridge, Ontario.
• Why joy is not just an emotion but a practical tool for city building and social resilience.
• How everyday people can influence their cities and advocate for joyful, engaging spaces.

Key Quotes from Paul

• “Cities that know how to play, that's where we start this healing. We will change the world by how we change cities.”
• “Play is the most complex social activity humans do. It’s where we learn to collaborate, see differences as assets, and celebrate together.”
• “We will not solve the problems of the world by using grim determination to tackle grim problems. If we double down on grim, people will feel society is failing.”
• “A city should make you happy. It should make you feel like you belong to something.”

Links and Resources

• Paul’s Book: The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society
• Connect with Paul: [LinkedIn/Profile Link]
• Mentioned Projects:
  • Meander installation in Cambridge, Ontario
  • The Bentway in Toronto

Actionable Takeaways

1. Engage with your city: Attend events, visit public spaces, and participate in community-driven activities.
2. Advocate for joy: Let your city officials know you value joyful, engaging public spaces—and celebrate them when they’re created.
3. Think differently about public spaces: Consider how parks, benches, and plazas can foster connection and play, not just quiet retreat.

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 zoning laws, the need for bold leadership in city planning, and the importance of simplifying Toronto’s official plan and zoning bylaw to foster more inclusive growth.

Chris also offers his vision for the future of Toronto, touching on how the city can learn from global examples, particularly in how regulations impact housing accessibility and design. From the concept of Toronto as a "Potemkin city" to the challenges of building viable infill projects, this episode is packed with insights for anyone interested in the future of urban living.

Key Topics Discussed:

• Chris Spoke's unconventional path into real estate development.
• The paradox of Toronto’s development: dense downtown, stagnant neighborhoods.
• The need to simplify Toronto’s official plan and zoning bylaw.
• The impact of North American vs. European building regulations on housing.
• Why bold, early-term leadership is essential for meaningful change.
• Recent policy changes in Toronto and their potential impact on housing.
• Chris’s vision for a more inclusive, accessible, and vibrant Toronto.

Top Quotes:

• "Toronto is like a seven-foot basketball player who can't dunk. It's got all the potential in the world and just needs to learn how to dunk."
• "We've halted natural growth through zoning. We skipped all the steps of development in between."
• "Our elevators are generally much larger, but what happens in practice is we just have fewer elevators, more walk-up apartments, which is bad for accessibility."

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 discusses why Toronto needs to embrace its unique character rather than constantly comparing itself to other global cities.
• Governance and Accountability: The conversation explores the fragmented nature of Toronto's transit governance and the urgent need for a unified leader or entity to take charge of transportation outcomes.
• The Role of Cars and the Future of Transit: Antoine explains why cars will continue to play a role in Toronto but stresses the importance of planning for a future where transit, cycling, and walking are prioritized.
• Optimizing Streetcars: Antoine suggests "LRT-izing" Toronto's streetcars, drawing inspiration from European cities like Prague, where streetcars are seamlessly integrated into both new and historic urban areas.
• Importance of User Experience: The episode delves into the need for transit systems to respect and attract passengers, highlighting improvements in bus services and the potential of cycling infrastructure.
• Progress in Infrastructure: Antoine points out successes like the Finch and Hazel McCallion Lines, as well as new GO train infrastructure, showing that Toronto can learn from past challenges like the Eglinton Line.

Memorable Quotes:

• "Toronto is just Toronto. It’s not New York or Switzerland—it’s unique, and that’s why we need to love it."
• "Everybody's in charge of something, but nobody's in charge of the whole."
• "A streetcar is a subway that stops for cars."
• "The bus is magical; we need to make it clean, efficient, and a respected part of the transit system."

Final Thoughts: Antoine leaves us with a call for Toronto to stop looking outward and start focusing on its own potential. With the right leadership and a commitment to long-term planning, Toronto can transform its transit system into one that is reliable, user-friendly, and fully integrated.

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.

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 development, the importance of affordable housing, and the concept of "extroverted spaces" that foster community interaction. Tune in to explore the complexities and possibilities of designing a city that supports families, and gain valuable insights on urban planning and community building.

Key Topics Discussed:

• Aileen Nandy's journey from journalism to community building
• Defining a Challenger City and its relevance to Toronto
• Balancing the core of the city with its suburbs
• The housing dilemma: affordability and availability for families
• Creating extroverted spaces that encourage community interaction
• Criticisms of Toronto's Vision Zero initiative and street safety
• The critical role of community programming and services
• A call for inclusive urban planning and redesigning housing
• Addressing Toronto's car-centric culture and its impact on walkability

Notable Quotes:

• "A Challenger City is one that thinks about what kind of communities or society they want to build and is not shackled by just building block upon block."
• "We end up with a profoundly family-unfriendly city that a lot of people can't afford to live in."
• "Cities should be designed to be extroverted. They should be designed to be easy to read and easy to understand and easy for lots of different people to engage with."
• "You need enough affordable housing that you have teachers who can work in the schools and not have totally ridiculous commutes because they can't afford to live in the city."
• "Only in the face of abject tragedy does it seem like we get any meaningful progress on Toronto's Vision Zero."

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 finance to address the complexities of modern urban challenges.

Key Discussion Points:

• Introduction to Capital Design:
  • Jordan explains the concept of capital design, blending the rigor of investment with the creative logic of design.
  • The importance of framing problems correctly to develop effective solutions.
• Role of Institutional Capital:
  • How institutional capital, encompassing over a hundred trillion dollars globally, influences urban development.
  • The need for design to help risk-averse and conservative investors adapt to new challenges with modern tools.
• Challenges and Innovations:
  • The mismatch between traditional asset classes and the modern world.
  • Jordan's experiences in driving innovation at a major real estate developer in Toronto during the rise of WeWork.
  • The example of APG changing their definition of infrastructure to include equality and quality of life.
• Toronto as a Challenger City:
  • The potential for Toronto to become a Challenger City by articulating clear aspirations and leveraging its strengths.
  • The role of institutional capital in contributing to the city's long-term viability and vibrancy.
  • Jordan's vision of a future where Toronto's decision-making processes are inclusive and future-oriented, with an Office for the Future dedicated to strategic planning.
• Designing Better Decision-Making Systems:
  • The need to improve the consultation process in urban planning.
  • The potential of innovative decision-making processes like quadratic voting.
  • Balancing top-down and bottom-up approaches in urban planning, drawing inspiration from natural systems.
• Toronto's Unique Position:
  • Toronto as a leading hub for pension investors, known for the Maple model.
  • The opportunity for Toronto to leverage its strengths and innovate, despite a tendency towards complacency.
• Future Outlook:
  • Jordan's speculation on where we might be in 10 years, potentially discussing urban investment in the headquarters of the Toronto Civic Strategic Sensing Centre.
  • His hope for a city that looks more like a thriving forest than a rigid Lego set.

Quotes:

• "If we can frame the problem correctly, I think we're 80% of the way there to solving it."
• "Institutional capital will be the most transformative force of the 21st century."
• "A Challenger City has a distinct aspiration for what it wants to be and a strategy to achieve it."
• "We're sitting in the headquarters of the Toronto Civic Strategic Sensing Centre, where we have a robust process for thinking about the future and incorporating multiple voices and perspectives and constantly adapting."
• "I hope that we can say the city looks a lot more like a forest than it does a Lego."