Challenger Cities

Iain Montgomery

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 EP72: The Case for Civic Joy with Ilana Altman

    7 AVR.

    Challenger Cities EP72: The Case for Civic Joy with Ilana Altman

    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

    1 h 3 min
  2. Challenger Cities EP68: The Bus Deserves Better with Ray Stenning

    3 MARS

    Challenger Cities EP68: The Bus Deserves Better with Ray Stenning

    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.

    59 min
  3. Challenger Cities EP67: Watching a World From Behind the Window with Füsun Aydın

    25 FÉVR.

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

    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.

    52 min
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À propos

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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