Challenger Cities

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 public space underneath a working highway, and why the conservancy model it pioneered is still largely foreign to Canadian cities. They get into the practical constraints — maintenance access, lighting limits, the challenge of food and beverage on a linear site — and what those constraints have forced the team to do creatively. Including turning highway maintenance equipment into community mascots.But the deeper conversation is about civic joy as a strategy. The Bentway's Dominoes project — 2.7 kilometres of oversized dominoes run through Toronto streets by 300 volunteers — became one of the city's most shared moments in recent memory. Ilana traces what that kind of project actually does: not just entertain, but rebuild the connective tissue of a city that's been losing its volunteers, its optimism, and its willingness to celebrate what it's accomplished.With FIFA FanFest coming to the Bentway this summer and the full seven-kilometre Under Gardiner Public Realm Plan now approved by council, the window to get the rest of the corridor right is open. Ilana is clear-eyed about how short that window is.In this episode:How the Bentway went from philanthropic idea to open public space in under three yearsWhat makes it genuinely different from the High Line and other post-industrial urban renewal projectsThe conservancy model and why it's still novel in CanadaShade as a climate virtue — and how the Bentway reframed itThe Boom Buddies: turning maintenance constraints into public educationWhy volunteerism in Toronto is down 30% and what Dominoes did about itThe urgency of the eastern Gardiner corridor and the window that's closingToronto's self-confidence problem — and what it would take to fall back in love with the city

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, which is about recognising the systems you're inside and getting them to behave in ways their creators didn't intend. As it turns out, that's a pretty useful instinct when you're trying to drag government into the 21st century.We talked about why digital government is slow ... and it's not the reason most people think, about what AI is about to do to the relationship between citizens and the state and why cities need to start thinking a lot weirder than they currently do.Basically if you're into cities as one of the original forms of artificial intelligence more than you are the built environment, this is the conversation for you.

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 right.

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 couples visit not because something is broken, but because they want to invest in their relationship • The idea of the “arena” and what workplaces could learn from it • Why four hours together changes how people interact • How cities succeed or fail based on how they enable human interaction • The difference between technical performance and real connectionThis is a conversation about intimacy, but also about architecture, culture and subtle infrastructures that shape how we relate to each other.In other words: what happens when you design spaces for connection rather than efficiency.

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 argues that every rattling panel, every hard plastic bench, every grey-on-grey interior sends a message about who the passenger is assumed to be. When we design buses like cattle trucks, people behave accordingly. When we design them like shared public rooms, behaviour shifts.We explore:Why anxiety — not speed — is the real barrier to bus useThe psychology of reassurance in public transportHow small design details change passenger behaviourWhy manufacturers optimise spreadsheets instead of humansThe hidden importance of noise, seat spacing and eye-linesWhy drivers are always “on stage”The missed opportunity of electric buses that still feel like diesel punishmentAnd why a bus is closer to a café than a carRay makes a simple but uncomfortable point: buses have been treated as the lowest common denominator because the people who use them are assumed to be the lowest common denominator.If we want more people on public transport, we don’t just need better timetables. We need better environments. Better hospitality. Better ambition.Because public transport isn’t just about moving bodies. It’s about how we choose to treat one another in shared space.

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 Istanbul she knew fifteen women who were killed. In twelve years in Amsterdam, one. That is what regulation does.In this conversation we get into what it actually means to work behind a window in a residential neighbourhood — who walks past, how you read them, what the difference is between a local and a tourist, and what the red light district looks like from the inside at ten on a Monday morning versus nine on a Friday night. We talk about sex work as informal social infrastructure, the overlap between care work and sex work, and why the women Füsun has worked with who came from healthcare backgrounds didn't leave because the instinct to care disappeared — they left because the pay wasn't enough. And we get into the fight that matters most to her right now: Amsterdam's proposal to relocate the red light district, what it would actually mean for safety, and what it reveals about who gets listened to when cities make decisions about the places that matter most to the people who live in them.Füsun also writes about her life and work on Substack - https://substack.com/@fusunaydin, where she brings the same directness and warmth to the page that she brings to this conversation.

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:Why train stations are still one of the clearest signals of a city’s confidence and prioritiesWhat cities lose when arrival becomes a throughput problem rather than a civic momentWhy Copenhagen doesn’t have “cyclists,” only people on bikesHow removing friction works better than persuading or moralisingWhy design creates behaviour, and why blaming people misses the pointParis as an example of what happens when infrastructure forces constant negotiationThe limits of theory, optimisation, and data-heavy urbanismWhy pilot projects shouldn’t be scary, and how fear quietly paralyses citiesHow Copenhagen built momentum by testing ideas quickly and publiclyWhat the Nordics get right, not as a model to copy, but as a cultural operating systemDemocratic urbanism and designing cities for the five-year-old and the ninety-year-oldTrust as an overlooked form of infrastructureMikael’s work in Ukraine, where benches, trees, and shade become “urbanism as medicine”What peacetime cities should learn from urban interventions built under air-raid sirensA provocation: what would happen if one city simply did everything it already knows to be right?

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 food and place. Carolyn doesn’t approach food as lifestyle or culture. She treats it as infrastructure. A lens that connects geography, logistics, politics, economics, health and social life in ways that most urban conversations completely miss.We talk about cities as food machines, moving from Rome, Paris and London to Chicago, tracing how grain, rivers, canals, railways and refrigeration shaped very different political and economic outcomes. We explore how technology didn’t just speed food systems up, but fundamentally altered them, separating calories from nutrition and convenience from ritual.A big part of the conversation centres on Carolyn’s idea of exo-evolution: the moment when humans stopped adapting themselves to their environment and instead began redesigning the environment to suit their desires. Cities, it turns out, adapt very quickly. Human biology does not.We also dig into what was lost when markets gave way to supermarkets, how food was deliberately redesigned to remove human interaction, and why eating together remains one of our most overlooked forms of civic infrastructure.This is a conversation about food, but it’s really about cities. About how we live together, what we take for granted, and why so many urban problems make more sense once you stop looking at buildings and start following what’s on the plate.Don’t expect to walk through a supermarket in quite the same way afterwards.In this episode, we cover:• Why food is one of the fastest ways to understand how a city actually works • How Rome, Paris and London evolved very different food systems, and why that mattered politically • The role of grain, rivers and trade in shaping empires and revolutions • How Chicago became a global food hub through geography, railways and refrigeration • What exo-evolution means, and why cities adapt faster than human bodies • How ultra-processed food and constant availability changed our relationship with eating • Why markets were once the social heart of cities, and what happened when supermarkets replaced them • Eating together as low-tech civic infrastructure in an increasingly fragmented worldAbout CarolynCarolyn Steel is an architect and writer best known for Hungry City and Sitopia, two influential books exploring the relationship between food, cities and civilisation. Her work examines how food shapes the physical form of cities, the way societies organise themselves, and how modern food systems affect health, culture and everyday life.

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 journalism, then arts and culture, Maryam brings a critical, socially minded lens to how cities are marketed, experienced and lived in.Our conversation treats tourism not as leisure, but as a stress test for cities. We talk about over-tourism and the post-pandemic reckoning it forced into the open. About why cities are often better at selling themselves than explaining how they work. About transit systems that feel like puzzles, wayfinding that assumes insider knowledge, and why visitors notice problems locals have learned to tolerate.We dig into regenerative tourism, not as a buzzword but as a philosophy rooted in care, stewardship and Indigenous knowledge. If cities invite people in, what responsibility do they have for how those people move, behave and experience the place? And why are metrics like “heads in beds” still crowding out harder questions about emotion, memory and whether people actually want to come back?Toronto becomes a case study, from the confusion of its transit system to the disconnect between what’s officially promoted and what people actually love. Small theatres. Independent restaurants. Neighbourhood scenes that don’t lend themselves to brochures. As Maryam puts it, “The places that don’t need publicising are the ones with the money to do publicising.”We also talk about how people really plan trips today, bypassing official channels in favour of TikTok, Instagram, Reddit and word-of-mouth, and what that means for tourism organisations still behaving like broadcasters rather than curators.We close with Maryam’s magic wand: making it genuinely safe and easy to bike around cities, and pushing tourism organisations to show up for locals, not just visitors. Sponsoring neighbourhood festivals. Supporting cultural life. Making it obvious how tourism contributes to the everyday city.Because at its best, tourism doesn’t invent affection. It amplifies what’s already there.Topics covered:Tourism as a stress test for citiesOver-tourism and the post-pandemic shiftWhy cities sell highlights but neglect experienceTransit, wayfinding and everyday frictionRegenerative tourism and care for placeTikTok, trust and the collapse of official travel commsToronto as a case studyThe gap between what cities promote and what people loveWhy tourism organisations need to show up for locals

Pete Brown, British beer and pub writer with decades exploring drinking culture. He talks about how pubs evolved naturally, alcohol as a social technology, and the subtle design rules—bars, queues and rituals—that create accidental conversations. The conversation also covers loneliness, rising pressures on independents, corporatisation, apps, and ideas to keep local pubs alive.