Challenger Cities

What if cycling policy wasn’t about bike lanes but about joy, dignity, and connection? In this episode of Challenger Cities , we sit down with Michela Grasso — Italian researcher, urbanist, and co-author of the Urban Cycling Manifesto — to explore how cities can rethink mobility through culture, inclusion, and imagination. We talk about: Why benches might matter more than bike lanes. How e-bikes a...

We talk a lot about fixing cities—but less about why we’ve let them decline in the first place. This conversation with civic pride expert Jeff Siegler is a deep, uncomfortable, and often inspiring look at how we got here and what it takes to turn it around. Jeff doesn’t believe in sugar-coating. He’s spent his life fighting against civic apathy and calling out the ways we’ve outsourced care, maint...

Russell King didn’t start out in transport. But somewhere between regenerating Battersea and reforming Sydney’s transit system, he became—by his own admission—“a transport tragic.” In this wide-ranging conversation, Russell shares what it actually takes to build infrastructure that shapes cities, why most governments lose the capability they’ve just built, and how our obsession with roads and cost...

Episode Description: Dave Cairns used to sell downtown towers. Then he left the city—and the real estate orthodoxy behind. In this episode, the former poker pro turned office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance . We talk about: – Why...

Architect and urban planner Naama Blonder didn’t set out to be a suburban revolutionary. She’s raised her kids in a condo, doesn’t own a car, and rides her bike everywhere. But now she’s challenging the idea that suburbia has to be bad—and that density has to be boring. In this episode, we dig into her award-winning Sub-Divillage project, why charm is a strategic tool (not a luxury), and how even...

If you’ve ever tumbled down a YouTube rabbit hole about public transportation, chances are you’ve come across Reece Martin — the sharp, relentless mind behind RMTransit. With over 1,000 videos filmed across dozens of cities, Reece has quietly become one of the most insightful, entertaining, and occasionally exasperated voices in the transit world. In this episode, we talk about: Why North America...

In this conversation, Iain Montgomery interviews Mike Schreiner, the leader of the Ontario Greens, focusing on the pressing issue of housing in Ontario. They discuss the challenges of housing affordability, the Ontario Greens' comprehensive housing policy, and the importance of community engagement in addressing these issues. Mike emphasizes the need for a multi-faceted approach that includes both...

This was never meant to be a podcast with a “Series 3.” Challenger Cities started as a bit of a rant, with a hint structure. I was living in Toronto, feeling stuck. Not just physically, but mentally. Stuck in a city full of potential but seemingly allergic to risk, creativity, or even a dash of novelty. A city that calls itself “world-class” while making it nearly impossible to build homes, run tr...

Policy may not be sexy. But it is what shapes your city — or keeps it stuck. In this episode, I talk with Tom Goldsmith, one of the sharpest minds on innovation and public policy in Canada, and the writer behind Orbit Policy’s must-read Deep Dives. Together, we explore why cities can’t just wait for permission — they need to start shaping policy on their own terms. Tom cuts through the usual fog,...

When we think about building better cities, nature rarely gets top billing. Jan Sumner wants to fix that. As Executive Director of the Wildlands League, Jan makes a powerful case that urban nature isn’t just nice to have — it’s critical infrastructure. From wetlands that reduce flood risk to green corridors that support biodiversity and mental health, she’s helping cities across Canada reconnect w...

What if your city’s most underused asset wasn’t a park or a waterfront—but an office tower? In this episode, I talk with Steven Paynter, Global Lead for Building Transformation and Adaptive Reuse at Gensler, who’s made it his mission to turn tired, half-vacant office blocks into vibrant places to live. Before "Is Downtown Dead?" became a post-pandemic cliché, Steven and his team were building the...

Rik Adamski doesn’t believe in big, dusty plans. He believes in action. In this episode, we sit down with the unorthodox but deeply practical urban planner and designer Rik Adamski, who’s made a career out of helping cities do rather than just plan . His approach? Start small. Start now. Test it. Prove it. Then go big. Rik shares stories from his journey—from growing up in walkable Midwest neighbo...

The Newcomer Perspective: What Works and What Could Be Better in Toronto with Arthur Smith In this episode, we flip the perspective and hear from a newcomer to Toronto—Arthur Smith. With a background in micro-mobility and a fresh set of eyes on the city, Arthur shares what drew him here, what he loves about Toronto, and where he sees untapped potential. What We Discussed: 🔹 Why Toronto? Arthur’s...

In a world where healthcare systems strain under ageing populations, chronic diseases, and practitioner shortages, innovation has never been more critical. In this episode, we explore how cities can rethink health through the lessons of Sault Ste. Marie. Healthcare: The Urban Blindspot Healthcare often sits on the periphery of urban planning—a blindspot that Anna Foat, with her wealth of experienc...

Urban design often focuses on hardcore infrastructure—but what about the people who use it? In this episode, we explore how psychology, neuroscience, and philosophy can make urban spaces work better for everyone. From Oboist to Urban Innovator “Musicians handle time—we take a note from the future, play it in the present, and it instantly becomes the past.” Nick Tyler’s journey into urban design be...

Summary In this conversation, Iain and Nick Tyler explore the intricate relationship between urban design, human behavior, and well-being. They discuss how cities can be designed not just for efficiency but for human flourishing, emphasizing the importance of empathy and social connectivity in urban planning. Nick shares insights from his background in music and engineering, illustrating how these...

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...