
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.
| Publishes | Twice weekly | Episodes | 87 | Founded | 2 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | Places & TravelArtsDesignSociety & Culture | |||

Two risk-management cultures looking at each other across a table, each waiting for the other to move. That's rail's relationship with venture capital. Iain talks to Richard Fisher, founder of Future Travel Studio, about why nobody would fund his Dre... more
This is a lovely episode with Thomas Ableman (a returning guest!) that is mostly about an amazing project he and a few volunteers recently secured funding to go and deliver called Mini Switzerland in the Derbyshire hills.
We often hear about how it'... more
One of the best people I met last year was Samantha Peart. We were in Copenhagen for a few days and of our fellows group, I have to say she asked the best questions. She’s also exceptionally good at getting you to question your assumptions or reflect... more
If you liked our episode with Ilana Altman about The Bentway, then you'll like this one with Ken Greenberg, because he's part of that origin story. Ken is a legend in Toronto urbanism circles, as someone who did pioneering work in his early career in... more
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Love Iain’s breadth and interview style.
Look forward to every episode
Key themes from listener reviews, highlighting what works and what could be improved about the show.
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #240 | |
Apple Podcasts | #11 | |
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Apple Podcasts | #19 | |
Apple Podcasts | #48 | |
Apple Podcasts | #57 |
Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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A forward-thinking show that explores how cities can reinvent themselves beyond traditional planning playbooks. Conversations thread through urban design, public spaces, transportation, governance, and community engagement, often emphasizing systems thinking, sustainability, and long-term impact over quick wins. Guests include architects, planners, educators, and developers who share practical stories from real projects, from repurposing infrastructure to nurturing place-based economies. The podcast stands out for its mix of critique, ambition, and hands-on insight, offering listeners concrete ideas for shaping livable, resilient cities while highlighting the people and processes that drive transformative urban outcomes.
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These podcasts share a similar audience with Challenger Cities:
1. The Messy City Podcast
2. The Strong Towns Podcast
3. The Urbanist
4. Upzoned
5. The War on Cars
Challenger Cities launched 2 years ago and published 87 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Challenger Cities include:
1. Sam Peart
2. Ken Greenberg
3. Saurabh Mangla
4. Gerald Babel-Sutter
5. Jen Angel
6. Alex Bozikovic
7. Heath Gledhill
8. Tom Shield
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