Challenger Cities

Copenhagen is Jan Gehl's city. So it's a bit of a jolt to hear someone who lives and works there admit that nobody has ever really been able to say what a "human-centric city" actually is.

That's Jakob Norman-Hansen. Along with Ann-Britt Elvin Andersen, he's spent about a decade at BLOXHUB explaining Copenhagen to visiting delegations — and watching most of them decide it could never work back home. Neither of them came to urbanism the usual way. Ann-Britt arrived through media and innovation, including a spell as an editor-in-chief in Japan. Jakob thought he'd spend his career in...

This is a bumper episode where we bring you 4 guests that share the privilege of working for an awesome agency called Mosaic. And while yes, Mosaic did pay me to speak at their team offsite at a Cineplex earlier in the year, that's not why we're making this podcast.

We're doing it because I loved what they did after I spoke. Several people from the team were invited to share what they do with their passions in their 5-9 hours, i.e. outside of work.

You're going to hear from Mo, who has a much...

John V Willshire is the third corner of a loose triptych of British innovation-strategy types I can never quite give a single job title. He runs Smithery, carries a little yellow card called an obliquoscope for teaching himself to notice things, and has a gift for the metaphor that reframes everything. In this case, swapping the language of levers and control for gardening where you can't tell a plant what to do, you can only offer it a trellis and see what climbs.

We get from there to Sussex, its improbable 2006-vintage "ancient" charter, and We Wunt...

You cannot build a humane, serendipitous city with teams who are transactional, risk-averse and don't really know themselves. It's not my usual territory, and it's a tough argument to have with the logical, rational, "serious" types who populate engineering, economics and urbanism — but I've been converted. The unlikely converters are Florence Okin and Sam Cohen, who run a workshop called Know Thyself under their business The Twenty Six Collective, and who arrive at cities from completely outside the usual circles: the talent side of startups and the full entrepreneurial tour, plus an apprenticeship under two Dutch master coaches. Their pr...

Giacomo Biraghi has spent fifteen years and two thousand interviews trying to answer one question: is there really a distinctive European way of making a city? His answer, after all that fieldwork, is a cheerful and slightly heretical no — what actually runs the modern city, he reckons, is a global, real-estate-driven standard, and we should be a little more cynical about the green, healthy, peaceful renderings we keep selling ourselves. This is a man who's built his whole life around cities and stays ahead of the curve by avoiding urbanists — going out of the bubble to talk to the vent...

In this spirit of being the world's most eclectic podcast about cities and places, this episode is a bit random. Which is good, because it's with Matt Ballantine and he's written a book, called Random with Nick Drage.

Some might say 120 short stories that can be shuffled into any order isn't actually a book, but I read it as one, and it's excellent. Plus many of the stories are about cities, places and people in them.

In a world where we spend so much time filtering out opportunities for luck, serendipity or just the unplanned...

This is an episode about a big, ambitious idea. Which is why people are quick to label it as crazy. But Britain, like many developed nations has a housing crisis. The country simply doesn't build enough good homes for the people who want to live there, and incremental approaches are going to solve for it.

So along comes Shiv Malik, a journalist by trade, with an idea for a new city, not too far from Cambridge, becoming a place one million people will call home. Naturally, he's had a lot of scrutiny, but he's steadily winning people...

This episode is a zinger. Because Gil Penalosa came in ready to talk!

He doesn't hold back as he discussed the issues with Toronto municipal projects, where the city could be amazing but is often found lacking in ambition. We explore ideas from the absolute basics of providing space to walk, why we might want to reframe the idea of the NIMBY to the one of the CAVE person - Citizens Against Virtually Everything!, and how rather than debating an idea to death ... maybe we just try it and see what happens.

As Toronto comes...

Alicia Pederson went from a Renaissance literature PhD and a two-year stint as an au pair in Florence to becoming one of the best voices on a deceptively simple idea: the courtyard in the middle of apartments.

After watching family friends priced out of Chicago one by one - not because they disliked the city, but because the only family housing on offer was a million-dollar house with a private yard - she started asking why North America builds apartments as huge, hotel-like buildings when European cities solved this centuries ago. Her answer is the courtyard block...

Canada is about to spend more on transit and rail than the oil sands are worth, and it's doing it without a national rulebook, a training pipeline or much recent memory of how to build well. So is that a crisis, or the best shot a country has ever had at becoming a genuine transit Challenger? This episode is a double act with two people who think about this for a living.

Mark Salsberg is co-founder of TRACCS (the Transit Rail Association for Canadian Contractors, Maintainers, Operators and Standards), and his mission is the unglamorous connective tissue...

Good new Challenger Cities episode today, all about autonomous vehicles and the bit that our guest, Bern Grush, thinks cities need to be thinking about more now.

Like them or not, robotaxis are coming to cities. And for all the spectacular technology that helps cars drive themselves, the have some meaty challenges ahead.

One of them being what happens when they interact with the curb. We've already seen how fleets of autonomous cars can create new forms of congestion, and we've seen tragic accidents come about as people open doors into the likes of passing...

Canada is, well might be, building a high speed train. At long last after 50 odd years of talking about doing so. But concerningly, there is much negative noise around the project as it seems it might not really be learning the lessons for how successful projects have been delivered elsewhere, and where projects for building fast trains have gone wrong.

This podcast is with Michael Schabas, a Canadian, who knows all about how to make these projects successful. It's a really honest and open conversation about how to build HSR, what Canada is missing just now, and...

Two risk-management cultures looking at each other across a table, each waiting for the other to move. That's rail's relationship with venture capital. Iain talks to Richard Fisher, founder of Future Travel Studio, about why nobody would fund his Dream Suite flatbed seat for trains, even after InnovateUK had backed it and operators had tested it.

About rail's proposition gap, the incumbents who monetise complexity rather than solve it, and why every discipline in the chain can be doing its job correctly while the sector as a whole still can't move. Plus what a transatlantic venture studio...

This is a lovely episode with Thomas Ableman (a returning guest!) that is mostly about an amazing project he and a few volunteers recently secured funding to go and deliver called Mini Switzerland in the Derbyshire hills.

We often hear about how it's not possible to deliver high quality public transport because there simply aren't enough people to make it worthwhile. That makes a lot of people feel quite clever in saying no to it. But then go an explain how Switzerland works then.

If a nation that has some of the most challenging geography...

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 projects and places.

I’m such a fan of hers, that I even let her destroy the magic wand question. Becaus...

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 airport lands in Pickering, ON and his vision to turn this into a new part of the Rouge National Urban...

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 good reviver.

We talk about Singapore, India and how material resources can be an excellent way for cities to demonstrate their...

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 frustrated city official's complaint over a beer became the founding logic of one of Europe's most distinctive urbanism events, why Oslo's deputy mayor told a room full of city planners to never...

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 transformations in Halton and Winnipeg, to a Mi'kmaq Native Friendship Centre-led project in Halifax, to the Toronto ravines programme. Before Evergreen, she ran a Nova Scotia crown corporation that built the Ha...

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 failing to act on what it already knows.

We cover the Spadina Expressway and the identity it left behind, the Ontario Science Centre closure and what it reveals about the state of progressive urban...

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 challenge conventional project setups and advocate for more intentional, purposeful city shaping.

Key Topics:

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 the number of rooms in the inn to where every dollar gets spent, runs through a single question: does this strengthen the local economy?

Tasha Freidus, Shorefast's Director of Education and Entrepreneurship, joins Chal...

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 impose order on a place that has other ideas. We talk about why the cities that look like they're working are often the most troubling ones of...

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 cracked culture but not confidence, the economics of being a springboard city, and what it would actually take for Montreal to claim what it's...

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 new values in it.

In this conversation, Ilana and Iain cover the full arc: how the Bentway went from idea to open in under three years, what it actually takes to run a 24/7 publ...

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 first public servants in the world. He also wrote the book on lean analytics, literally, with Ben Yoskovitz. And last year he published Just Evil Enough with Emily Ross...

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 designed for one, why the rules written for 20-storey buildings don't survive contact with a 106-storey one, and what patience has to do with getting any of it...

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:

• Why Paul created SPNKD after finding most kink venues “tacky dungeons”

• How BDSM spaces deliberately design trust, consent, and emotional safety

• Why many coupl...

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 countless urban fleets most people ride without ever knowing who shaped them.

But this isn’t a conversation about paint schemes.

It’s a conversation about dignity.

Ray...

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 legal discrimination protections and sex work on the street is both common and dangerous. The move wasn't idealism — it was survival arithmetic. In four years...

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 in Ukraine, where urbanism takes on a very different meaning.

We cover:

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 decided where cities formed, how power worked, and why empires survived or collapsed.

In this episode, I’m joined by architect and writer Carolyn Steel, whose books Hungry City and Sitopia have quietly reshaped how many people think about fo...

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, Iain Montgomery is joined by Maryam Siddiqui, a Toronto-based travel and culture journalist who came to travel writing sideways rather than by design. Starting out in PR before moving into business jour...

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 evolved slowly through circumstance, need, and habit. Why that matters for cities obsessed with masterplans and placemaking. And why attempts to “recreate” pub culture so often feel hollow.

Pete offers a...

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 how play, permission, and experimentation get designed out of adult life.

We talk about growing up without space to express yourself, getting ready in café toilets, the freedom c...

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 connection that cities have quietly lost.

Glenn traces sauna’s roots as everyday civic infrastructure rather than luxury amenity, reflects on the risks of gatekeeping and elitism as the scene grows, an...

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 ground.

Jasmine reframes urbanism as a messy, lived practice rather than a rigid discipline, and highlights how everyday friction and irritation are often the beginning of meaningful change.

This episode refram...

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 everyday life such as first-mile/last-mile walking, informal transport, street life and safety.

We dig into whether building faster actually deepens resilience or erodes memory, how imported models can misfit local context, and what it me...

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 experience of place and its global perception.

We explore the gap between performance and perception, why most cities lack resonance on the world stage, and how the interplay between infrastructure and experience may de...

Researcher and strategist David Akermanis talks about how young people are navigating a world where traditional financial stability has eroded and cities themselves shape economic life.

We explore why the familiar narratives about youth finance, savvy versus reckless, miss the deeper tension underneath. Across stories of early career precarity, the blending of gambling and investing, the limitations of traditional banking advice, and how mobility and access matter as much as income, we dig into how young people are improvising within a system that no longer feels trustworthy.

The conversation reframes stability, money, and the urban...