Challenger Cities

Takeaways Michael Wexler's journey into urbanism began unexpectedly. He transitioned from cycling-focused projects to broader transit planning. Cargo bikes represent a gap in North American urban mobility. Infrastructure is crucial for increasing cycling and cargo bike usage. Copenhagen's cycling culture serves as an inspiration for Montreal. Mulo aims to fill the cargo bike market gap in Montreal...

Exploring Urban Evolution with Diana Lind Join host Iain Montgomery in a captivating conversation with Diana Lind, renowned urbanist and author, as they delve into the complexities of modern cities. From the challenges of zoning reform to the potential of urban public education, this episode offers a thoughtful exploration of how cities can transform and thrive. Key Topics: The evolution of cities...

What if commuting from Niagara to Toronto didn’t mean hours in traffic or waiting on a slow, infrequent train? Erika Potrz thinks there’s a better way, and it involves a military‑grade hovercraft gliding across Lake Ontario in just 30 minutes. In this episode, we talk about why Hoverlink could change more than just the QEW commute: from making travel joyful again (yes, DJs on board), to giving peo...

Northern has long been the UK’s biggest rail operator by stations—and one of its most under-loved. But under Alex Hornby, it’s getting a dose of something different: warmth, character, and a clear sense of purpose. In this episode, we talk to Alex about his journey from making buses in Burnley genuinely desirable to leading a railway that serves some of the North’s most complex and underserved pla...

Every city tells itself a story. In Kansas City, it’s one of manageability: there’s parking when you want it, space to drive, and just enough shine in a few key places to make it feel like things are ticking along. But scratch the surface—or take a walk down the streets that aren’t newly polished—and another story emerges. One of unrealised potential, oversized roads, empty sidewalks, and neighbou...

The City’s Recipe Book: Borrow the Technique, Use Your Own Ingredients with Guillermo Bernal Cities don’t work because of glossy plans or polished renderings. They work because people use them, reshape them, and often subvert them in ways no planner predicted. That’s the world Guillermo Bernal inhabits. A political scientist turned place-maker, Guillermo has spent the past decade helping communiti...

What happens when you take someone fluent in corporate innovation and drop them into the world of council-led adult social care? A surprising amount of clarity on what actually counts as value. In this crossover episode, Iain Montgomery is joined by his usual SIDEBAR co‑conspirator, Charlie Rowat, to explore how innovation changes when you swap corporate executives for councillors, consumers for c...

What does it take to make a city work after dark? In this episode, we're speaking with Mathieu Grondin , Ottawa’s first-ever Nightlife Commissioner, about why nightlife isn’t just parties and late bars, it’s infrastructure. The conversation explores why Ottawa created this role, what mid-sized cities can teach their bigger siblings about cultural development, and how better policy can make cities...

The Magnetic, Messy Cities People Don’t Leave — with Sofia Song What actually keeps people in cities? It isn’t just housing supply, transit plans, or economic growth. It’s something far less tangible, emotional connection. In this episode, we speak with Sofia Song, Head of Global Cities Research at Gensler, about the City Pulse study, one of the most ambitious looks at urban life anywhere in the w...

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...