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 EP78: Saying Yes More with Jen Angel

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    Challenger Cities EP78: Saying Yes More with Jen Angel

    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

    44 min
  2. Challenger Cities EP72: The Case for Civic Joy with Ilana Altman

    7 ABR

    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

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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.

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