Challenger Cities

One of the best people I met last year was Samantha Peart. We were in Copenhagen for a few days and of our fellows group, I have to say she asked the best questions. She’s also exceptionally good at getting you to question your assumptions or reflect on why you might think what you’re thinking. And that really comes through in this conversation, with real examples that have had a massive impact on...

If you liked our episode with Ilana Altman about The Bentway, then you'll like this one with Ken Greenberg, because he's part of that origin story. Ken is a legend in Toronto urbanism circles, as someone who did pioneering work in his early career in the city and then took it to the likes of St. Paul and Boston in the US. We set up this episode to discuss work he's doing around the newly free'd up...

This is a bit of a different episode because we're talking about what cities are made of, rather than how we make our cities. I had the pleasure of meeting Saurabh Mangla on a day where I was hot, tired and just wanted a beer. But getting the story of his materials lab and how he's working to explore how cities use their materials more effectively, efficiently and in many ways, delightfully is a g...

Gerald Babel-Sutter is the founder of Urban Future, a 14-year-old event that has grown from a workshop for ten city officials in Graz to a gathering of 2,000 people from 290 cities in 48 countries. The premise hasn't changed: get the actual project managers in a room, not the communications directors, and ask them to talk honestly about what went wrong. In this conversation we cover how a frustrat...

Jen Angel thinks Canada is closer to a moment of triumph in how it builds than it has been in her lifetime. The conditions are there. What's missing is enough people in positions of authority with the permission to say yes. Jen leads Evergreen, the national organisation behind the Brick Works in Toronto and a portfolio of public space projects across the country — from school grounds transformatio...

Alex Bozikovic is the architecture critic for the Globe and Mail, which in practice means he writes about everything from housing politics to the public realm to the quiet cultural erosion that happens when a city stops expecting much of itself. In this episode, Iain and Alex dig into why Toronto ... a city with extraordinary people, genuine sophistication and real financial muscle ... keeps faili...

Exploring Urban Troubleshooting In this episode, Heath Gledhill and Tom Shield, founders of GledHill Shield, share their extensive experience navigating complex urban infrastructure projects. They discuss how early decision-making, constraints and collaborative design principles can transform city development. Whether you're an urbanist, engineer, architect, designer or planner, their insights cha...

When the cod fishery collapsed in the nineties, Fogo Island lost its economy almost overnight. What came next — slowly, imperfectly and without a guarantee of success — became one of the most compelling stories in Canadian community development. Shorefast, the charity behind the Fogo Island Inn, wasn't built on the logic of charity. It was built on the logic of place. Every business decision, from...

Bronwyn Williams is a South African futurist and economist, a combination she'll tell you should not be the oxymoron most people assume it is. She's been doing sharp thinking about cities lately, and this conversation is a good example of why. We get into South African cities as a lens for the future with Johannesburg and Cape Town as two very different experiments in what happens when you try to...

Phil Tabah is the co-founder of The Main, Montreal's city magazine, and one of the most thoughtful people working on the question of how cities see themselves and tell their own story. In this conversation we get into why Phil started The Main at 21 as a Twitter account and what it's become, the publications that used to do this job well and what happened to them, why Montreal is a city that has c...

Most cities debate their troubled infrastructure to a standstill. Toronto has been arguing about the Gardiner Expressway for decades. Ilana Altman didn't wait for that debate to resolve. As CEO of The Bentway — a public space and cultural platform built underneath Toronto's elevated waterfront highway — she's been proving that you don't have to tear something down, or wait for it to die, to embed...

We have spent a lot of time on the podcast talking about physical cities as streets, buildings and the spaces between them. What we perhaps don't talk about enough is the digital layer underneath all of it, and how badly most cities are fumbling it. This week's guest has spent the last decade thinking about almost nothing else. Alistair Croll runs FWD50, perhaps the biggest gathering of digital fi...

Anson Kwok has spent fourteen years building Canada's tallest tower at the foot of Yonge Street. As VP of Sales and Marketing at Pinnacle International, he's had a front row seat to how Toronto has transformed from a city of downtown parking lots to one of the most dense urban skylines in North America. We talk about what it actually takes to build a vertical city inside a city that wasn't designe...

At first glance, SPNKD might look like a BDSM venue. But Paul Meyers real focus is something deeper ... finding connection and creating intimacy. We explore how intimacy is designed, why many people use kink to avoid connection rather than deepen it, and what the concept of creating an arena in BDSM can teach us about relationships, work and even how cities function. Along the way we discuss: • Wh...

What if the problem with buses isn’t frequency, funding or technology ... but attitude? In this episode, we're in person with Ray Stenning, founder of Best Impressions and arguably the most prolific bus livery designer in the world. For more than 40 years, Ray has been quietly reshaping how buses look, feel and function across the UK — from iconic interurban routes like the X43 and the 36 to count...

Füsun Aydın has spent twelve years reading people from a window in Amsterdam. Cities would be better places if the people planning them had half her instinct. Füsun is Turkish-born, a trans woman, a former sex worker, and now the madam of a bordello in Amsterdam's red light district. She came to the Netherlands as an asylum seeker at nineteen, having grown up in Istanbul where trans women have no...

In this episode of Challenger Cities , Iain Montgomery is joined by urban designer, filmmaker, and author Mikael Colville-Andersen for a wide-ranging conversation about why cities so often know what works, yet struggle to act on it. We start with train stations and the importance of arrival, before moving through cycling, design, experimentation, Nordic urbanism, and finally Mikael’s recent work i...

Cities are usually explained through buildings, infrastructure, policy and planning. Food rarely gets a look-in. Which is strange, because for most of human history, cities existed in the first place because we learned how to feed ourselves at scale. Farming allowed settlement. Settlement allowed specialisation. Specialisation gave us civilisation. Long before zoning codes or masterplans, food dec...

Tourism is big business. Cities spend vast sums attracting visitors, promoting landmarks and polishing their image. What they’re far less good at is thinking through the experience of actually being there. How a place works once you arrive. How you move around it. What makes sense, what doesn’t, and what quietly undermines the affection people might otherwise develop for a city. In this episode, I...

In this episode of Challenger Cities , we've got Pete Brown, one of the UK’s most thoughtful writers on beer, pubs, and drinking culture. Pete has spent decades writing about pubs not as lifestyle accessories or nostalgic backdrops, but as places where history, behaviour, economics and everyday social life collide. We talk about why pubs weren’t designed, branded or planned into existence, but evo...

Most cities are designed around a surprisingly narrow idea of who gets to feel comfortable in public. In this episode of Challenger Cities , Iain Montgomery chats with Patti Baston , who runs a feminisation makeover service in Manchester. On the surface, her work might sound niche. In practice, it turns out to be a sharp and unexpected lens on how cities really work, who they quietly exclude, and...

Iain Montgomery talks with Glenn Auerbach about why sauna, bathing and cold-water culture has suddenly gone mainstream in cities around the world, and why the reasons go far beyond health trends or wellness hype. From floating saunas and mobile heat rooms to dawn swims in urban rivers and harbours, we explore how shared rituals of heat, cold and recovery are reintroducing forms of social connectio...

We reconnect with Jasmine Palardy almost eighteen months after our very first conversation to reflect on what has changed in how we think and talk about cities, and what hasn’t. Exploring why real progress in cities comes not from imposing control but from embracing uncertainty, loosening the grip of over-planning and letting “accidental urbanists” and informal city builders shape change on the gr...

Ruchita Bansal discusses what happens when modern infrastructure projects are built at speed but don’t connect with the deep, informal systems that make cities work. Drawing on her experience across Indian urban planning and large-scale delivery, we explore how cities in India are being transformed rapidly with metros, highways and ambitious timelines, yet often miss the connective tissue of every...

Chris Fair, CEO of Resonance and publisher of "World's Best Cities" talks about what really separates the world’s cities. As Chris explains, obsessively measured performance isn’t enough to explain why some cities feel magnetic and others feel interchangeable. We unpack the World’s Best Cities framework and how liveability, prosperity, and a often-overlooked dimension of lovability shape both the...