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Challenger Cities

Iain Montgomery
Challenger Cities
Latest episode

70 episodes

  • Challenger Cities

    Challenger Cities EP68: The Bus Deserves Better with Ray Stenning

    03/03/2026 | 58 mins.
    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 use
    The psychology of reassurance in public transport
    How small design details change passenger behaviour
    Why manufacturers optimise spreadsheets instead of humans
    The hidden importance of noise, seat spacing and eye-lines
    Why drivers are always “on stage”
    The missed opportunity of electric buses that still feel like diesel punishment
    And why a bus is closer to a café than a car
    Ray 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.
  • Challenger Cities

    Challenger Cities EP67: Watching a World From Behind the Window with Füsun Aydın

    25/02/2026 | 51 mins.
    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.
  • Challenger Cities

    Challenger Cities EP66: Urbanism Without the Excuses with Mikael Colville-Andersen

    19/02/2026 | 1h 3 mins.
    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 priorities
    What cities lose when arrival becomes a throughput problem rather than a civic moment
    Why Copenhagen doesn’t have “cyclists,” only people on bikes
    How removing friction works better than persuading or moralising
    Why design creates behaviour, and why blaming people misses the point
    Paris as an example of what happens when infrastructure forces constant negotiation
    The limits of theory, optimisation, and data-heavy urbanism
    Why pilot projects shouldn’t be scary, and how fear quietly paralyses cities
    How Copenhagen built momentum by testing ideas quickly and publicly
    What the Nordics get right, not as a model to copy, but as a cultural operating system
    Democratic urbanism and designing cities for the five-year-old and the ninety-year-old
    Trust as an overlooked form of infrastructure
    Mikael’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 sirens
    A provocation: what would happen if one city simply did everything it already knows to be right?
  • Challenger Cities

    Challenger Cities EP65: Sitopia with Carolyn Steel

    16/02/2026 | 1h 21 mins.
    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 world
    About Carolyn
    Carolyn 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.
  • Challenger Cities

    Challenger Cities EP64: Tourism as a Stress Test with Maryam Siddiqi

    10/02/2026 | 1h
    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 cities
    Over-tourism and the post-pandemic shift
    Why cities sell highlights but neglect experience
    Transit, wayfinding and everyday friction
    Regenerative tourism and care for place
    TikTok, trust and the collapse of official travel comms
    Toronto as a case study
    The gap between what cities promote and what people love
    Why tourism organisations need to show up for locals

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About Challenger Cities

Iain Montgomery of Now or Never Ventures interviews urbanists, creatives, transit and development types to explore how cities can punch above their weight and create distinctive new futures outside of the tired playbooks.
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