Challenger Cities

Iain Montgomery
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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.

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

    2 DAYS AGO

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

    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

    1 hr
  2. Challenger Cities EP63: The Pub Is a Public Service with Pete Brown

    6 DAYS AGO

    Challenger Cities EP63: The Pub Is a Public Service with Pete Brown

    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 compelling reframing of alcohol as a form of social technology. Dangerous if mishandled, but deeply valuable when surrounded by the right rituals, spaces, and social rules. We explore how pubs moderate behaviour, teach people how to drink, and create a crucial middle ground between sobriety and excess that many cultures understand instinctively. We also get into the overlooked design intelligence of pubs. The bar as a place for accidental conversation. The invisible queue. The unspoken rules about who you talk to, where, and for how long. How pubs create weak ties between people who would never otherwise meet, without forcing intimacy or participation. From there, the conversation widens out to loneliness, screens, and a world increasingly engineered to keep people at home. Pete makes the case that pubs sit in direct opposition to frictionless, algorithmic life, and that this discomfort is precisely what makes them socially valuable. We talk about flat-roof pubs, post-war housing estates, and why the loss of informal gathering places has left many newer neighbourhoods socially hollow. We look at how pubs are being squeezed from all sides: cheaper beer in supermarkets, rising costs, higher taxes, and policy frameworks that treat them like any other retail unit while ignoring the social work they do for free. This is a conversation about pubs, but it’s really a conversation about cities. About what we value, what we price, and what we quietly allow to disappear while wondering why public life feels thinner than it used to.

    49 min
  3. Challenger Cities EP62: Cities for People Who Want to Try Things with Patti Baston

    2 FEB

    Challenger Cities EP62: Cities for People Who Want to Try Things with Patti Baston

    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 cities can offer through anonymity and density, and why permission might be one of the most overlooked forms of urban infrastructure. Along the way, the conversation touches on femininity, masculinity, power, vulnerability, internet culture, gentrification, and what happens when cities mistake control for care. This isn’t a culture-war conversation. It’s a human one. About joy, play, and what it means to feel at ease in public. Expect some swearing.

    1h 7m
  4. Challenger Cities EP61: Sweat and the City with Glenn Auerbach

    27 JAN

    Challenger Cities EP61: Sweat and the City with Glenn Auerbach

    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, and explains why inclusive, well-held sauna culture can strengthen community, public trust and even environmental stewardship. The conversation reframes sauna not as a fad, but as a clue to how cities might better balance pressure, release, togetherness and solitude.

    51 min
  5. Challenger Cities EP60: Designing Cities in Pencil, Not Pen with Jasmine Palardy (again)

    19 JAN

    Challenger Cities EP60: Designing Cities in Pencil, Not Pen with Jasmine Palardy (again)

    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 reframes control, imagination and experimentation in the design of cities.

    50 min
  6. Challenger Cities EP59: Building Faster Than Memory with Ruchita Bansal

    19 JAN

    Challenger Cities EP59: Building Faster Than Memory with Ruchita Bansal

    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 means to design infrastructure that truly serves people rather than object-centric headlines.

    54 min
  7. Challenger Cities EP58: The World's Best Cities with Chris Fair

    19 JAN

    Challenger Cities EP58: The World's Best Cities with Chris Fair

    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 determine the future of urban success https://www.worldsbestcities.com/

    53 min
  8. Challenger Cities EP57: Young People and the New Rules of Money with David Akermanis

    19 JAN

    Challenger Cities EP57: Young People and the New Rules of Money with David Akermanis

    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 experience, and challenges cities and institutions to rethink how they build opportunity and trust for future generations. https://www.fasterhorses.ca/blog/young-people-amp-money

    56 min
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About

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.

Information

  • Creator
    Iain Montgomery
  • Years Active
    2024 - 2026
  • Episodes
    66
  • Rating
    Explicit
  • Copyright
    © Challenger Cities 2024
  • Show Website
    Challenger Cities

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