Challenger Cities

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 with apartments that live like houses, with a front door onto the street and a back door onto a shared green courtyard. It's a housing idea that's genuinely lovable, demonstrably doable and cheaper to build ... and, as we get into, almost entirely illegal to build in many North American cities.In this conversation we dig into why a shared courtyard somehow feels more private than a fenced backyard, why your kids don't actually want a yard (they want friends to play with), and why the amenity-stuffed apartment building — gym, dog wash, rooftop — is starving the very neighbourhood that should be the amenity. Alicia and Iain make the case that density is a feeling before it's a number, that the cities which kept their apartments are the ones that proved resilient, and that the fix isn't masterplanning but handing cities back their oldest tool: lay the streets, cut the right parcels, and let a hundred small builders fill them in. We also push on where it's hardest — the cold-start problem, who governs the shared space, the parking question — but suspect you will come away convinced this is a concept every Challenger City should be looking at as it reimagines the home, the street and the shape of a life.

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 cyclists. A few years ago I was involved in a project for a big tech firm looking at this, but it was rather quickly mothballed as big automotive clients shooed them away from it. The hardest part though was the orchestration layer between the operators of autonomous vehicles (think the ridehailing firms minus drivers) and deliveries that are seeking to move away from having a human at the wheel too. It effectively means redesigning who can stop where, when, for how long, and normally monetising it in the same way on-street parking is done today. So if you want to stop on a busy road to pickup/dropoff ... well you're going to pay for that. And you might be incentivised to do so somewhere quieter, or even let that tempt you towards public transport instead. We have finite space in urban areas, so we're going to need to be clever to make sure autonomous driving doesn't choke the city.

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 is trying to build instead.

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. Because she makes an excellent point about it. So if you’re involved in any sort of urbanism, placemaking or infrastructure project. This really is one you need to have a listen to.

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 Challenger mindset.

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 Halifax Waterfront, Peggy's Cove and Lunenburg Waterfront, alongside rural broadband and innovation hubs. She also sits on the Canadian Infrastructure Council, the ministerial-appointed arm's-length body writing Canada's first national infrastructure assessment.In this episode we get into:— Why "it's not that much harder to build a good one than a crappy one" might be the most damning line about Canadian infrastructure this year— The permission problem: why no has become the safe answer across our institutions, and what it costs us— Multi-benefit projects, and why our funding model is almost institutionally incapable of recognising them as legible— Why this particular moment — tariffs, geopolitical pressure, a public mood that actually wants things to be tried — might be a generational opportunity— What the East Coast knows about resilience that the rest of the country keeps forgetting— The Evergreen Conference at the Brick Works, May 6–7, theme: Cities Bursting with Life

Exploring Urban TroubleshootingIn 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:The importance of framing the core problem before designing solutionsHow constraints foster innovative and effective urban designThe role of the business case in guiding project decisions and maintaining focusChallenges with briefs, approvals and stakeholder engagement in infrastructure projectsThe power of compromise and trade-offs in city developmentEmbedding aspiration and community impact through creative public programsCross-disciplinary integration as a necessity for successful urban projectsThe influence of cultural attitudes—Australia, Canada, the UK—on project deliveryThe potential of digital tools and visual artifacts to ground project visionBuilding trust and social license through transparency and stakeholder inclusionThe value of humility, purpose and intentionality in urban planning

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 all, and what Dubai, Brazil and China tell us about the limits of control as a city-building strategy.We also get into AI and the data confidence problem including why shinier models don't mean better assumptions, just more expensive mistakes at greater scale. And we end up at the one question I always ask urban planners that they never quite know how to answer.Bronwyn is a futurist-economist based in Johannesburg. She works at the intersection of foresight and economic analysis, and has done work with Metropolis and UN-Habitat among others.

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

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.

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.

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?

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