HeyJaredChallenger 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.
- Indexed episodes, last 90 days
- 11
- Latest publication
- Sep 21, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
Challenger Cities EP102: Getting to Yes with Laura Dean (opens the original)
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Challenger Cities started as an attempt to shake things up in Toronto. So when a municipal lawyer left her partnership to run for mayor, I wanted to hear why. Laura Dean isn't a politician. She spent her career working out why the city says no, and how to get it to yes. We talk about why Toronto has so many ways to block things and so few to let them happen. We also cover the plans the city still doesn't have, and her positive pitch for a city that's "better, easier and more beautiful". And she
Challenger Cities EP101: Chain Drain with Bryan Boyer & Greg Lindsay (opens the original)
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A restaurant learns something every night. They hear what people say about a dish, see what comes back on the plate and see the financial impact it has on the books. It's a pretty awesome feedback loop. But the urban realm doesn't work like that. There is a much longer and less responsive chain at play where the planners, developers, architects, engineers, construction firms, designers, financiers and clients do not have such rapid or sophisticated mechanisms of connection and communication. An
Challenger Cities EP100: How Big Things Get Done with Bent Flyvbjerg (opens the original)
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This is the 100th episode of Challenger Cities. A bit of a milestone right? This thing started as an attempt to explore and make a difference specifically in Toronto, but early on took a bit of a turn to have conversations about cities and infrastructure that didn't seem to be happening anywhere else … … the ones that fall between planners, architects, engineers, economists and what ‘regular’ people want in cities. I didn't expect to still be at it, let alone to have talked my way through 100 gu
Challenger Cities EP99: Bottom Up & Top Down Cultural Infrastructure with Jacquelyn West (opens the original)
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What does a city need in order for culture to happen? Venues are the easy answer, and the least complete one. Jacquelyn West is a cultural industries strategist based in Montréal, by way of Toronto, where she spent much of her career working with artists, festivals and creative organisations. She watched the same cycle run several times over: artists move into a cheap neighbourhood, the neighbourhood becomes desirable, and the people who made it desirable can no longer afford to be there. In thi
Challenger Cities EP98: Stations & Airports of the Future ... a Megacast (opens the original)
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Most episodes of Challenger Cities are a conversation with a guest. This one isn't. Shortly after publishing our whitepaper The Welcome Mat, a few listeners joined a live session to stress test the thinking and bring their own — which is a rather Challenger way of doing it, and only really possible when you can have Tokyo, Boston, Toronto and London in the same room. Greg Dyson joins from Thailand, late at night, to explain why most Japanese stations are visually drab and work anyway: wayfinding
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