
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 | 97 | Founded | 2 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | DesignArtsPlaces & TravelSociety & Culture | |||

This is a bumper episode where we bring you 4 guests that share the privilege of working for an awesome agency called Mosaic. And while yes, Mosaic did pay me to speak at their team offsite at a Cineplex earlier in the year, that's not why we're maki... more
John V Willshire is the third corner of a loose triptych of British innovation-strategy types I can never quite give a single job title. He runs Smithery, carries a little yellow card called an obliquoscope for teaching himself to notice things, and ... more
You cannot build a humane, serendipitous city with teams who are transactional, risk-averse and don't really know themselves. It's not my usual territory, and it's a tough argument to have with the logical, rational, "serious" types who populate engi... more
Giacomo Biraghi has spent fifteen years and two thousand interviews trying to answer one question: is there really a distinctive European way of making a city? His answer, after all that fieldwork, is a cheerful and slightly heretical no — what actua... more
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Love Iain’s breadth and interview style.
Look forward to every episode
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Apple Podcasts | #211 |
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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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Challenger Cities launched 2 years ago and published 97 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. Morad Reeder-Fifi
2. Jeff Moore
3. John Willshire
4. Florence Okin
5. Sam Cohen
6. Giacomo Biraghi
7. Matt Ballantine
8. Shiv Malik
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