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Artwork for Challenger Cities

Challenger Cities

Iain Montgomery
Toronto
Urban Planning
Public Transit
Public Transport
Urbanism
Housing
Urban Development
Transportation
London
Urban Design
Montreal
Community Engagement
Paris
Parking
Copenhagen
Urban Transportation
Healthcare
Youth Financial Awareness
Housing Crisis
Urban Living

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.

PublishesTwice weeklyEpisodes97Founded2 years ago
Number of ListenersCategories
DesignArtsPlaces & TravelSociety & Culture

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Artwork for Challenger Cities

Latest Episodes

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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Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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PivotNew York Magazine

Recent Guests

Morad Reeder-Fifi
Mo; Toronto-native who started in nightlife and moved into marketing/media/culture
Mosaic (former/Mosaic North American creative team)
Episode: Challenger Cities EP95: The 5-to-9 Episode with Mo, Laura & Nick from Mosaic
Jeff Moore
Lead of the North American Creators Team at Mosaic
Mosaic
Episode: Challenger Cities EP95: The 5-to-9 Episode with Mo, Laura & Nick from Mosaic
John Willshire
Strategic design practitioner; founder of Smithery
Smithery
Episode: Challenger Cities EP94: We Wunt Be Druv with John V Willshire
Florence Okin
Co-founder of The Twenty Six Collective; Know Thyself workshop facilitator
The Twenty Six Collective
Episode: Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen
Sam Cohen
Co-founder of The Twenty Six Collective; Know Thyself workshop facilitator
The Twenty Six Collective
Episode: Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen
Giacomo Biraghi
Founder/lead at Stratisferica and organizer of Utopian Hours
Stratisferica; Utopian Hours
Episode: Challenger Cities EP92: Cities Are Mental Weapons with Giacomo Biraghi
Matt Ballantine
Author of Random, urbanist/educator
Author; Writer of Random
Episode: Challenger Cities EP91: Expanding Your Luck Surface Area with Matt Ballantine
Shiv Malik
Founder of Forest City, journalist
Forest City / Albion City Development Corporation
Episode: Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik
Gil Penalosa
Urbanist, advocate for walkable cities
Penalosa & Associates (in episode context)
Episode: Challenger Cities EP89: To Do, Not Just Be with Gil Penalosa

Host

Iain Montgomery
Host of Challenger Cities

Reviews

5.0 out of 5 stars from 20 ratings
  • Countries come & go, cities endure

    Love Iain’s breadth and interview style.

    Apple Podcasts
    5
    Acorrn
    Canada6 months ago
  • Top Notch

    Look forward to every episode

    Apple Podcasts
    5
    Marshdogg
    Canada6 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Great insights into urbanism and public spaces from thoughtful guests.
Listeners appreciate the host's breadth and interview style.
High-quality guests and practical storytelling stand out for sponsors and guests alike.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#52
Canada/Arts/Design
Apple Podcasts
#71
Denmark/Arts/Design
Apple Podcasts
#85
Sweden/Arts/Design
Apple Podcasts
#86
Japan/Arts/Design
Apple Podcasts
#105
South Africa/Arts/Design
Apple Podcasts
#211
Poland/Arts/Design

Talking Points

Recent interactions between the hosts and their guests.

Challenger Cities EP83: A Little Piece of Switzerland in the Derbyshire Hills
Q: What does success look like for Mini Switzerland in Hope Valley?
Success is framed as delivering a set of transport outcomes—hourly services, integrated ticketing and timetabling, clear wayfinding, and a measurable improvement in end-to-end journeys—rather than chasing a single target number, so that data can guide further expansion.
Challenger Cities EP82: The Purpose is Not the Function with Sam Peart
Q: What is the key shift you're trying to drive in how projects are framed from the start?
The shift is to separate the purpose from the function of a project and to start with place analysis that considers impact beyond the boundary, which guides better decisions and collaborations.
Challenger Cities EP82: The Purpose is Not the Function with Sam Peart
Q: How did you end up in a sustainability role that spans engineering, government, and design?
Sam describes a career path from Arup through public sector roles into Hassell, emphasizing a pattern of moving between problem-solving, design, and governance to understand how different organizations influence place.
Challenger Cities EP78: Saying Yes More with Jen Angel
Q: If you had a magic wand, what would you do with it to accelerate urbanism and infrastructure?
Jen would create conditions that let decision-makers say yes to innovative ideas from a wide range of sources, allowing experimentation and rapid implementation of collaborative, multi-stakeholder solutions.
Challenger Cities EP78: Saying Yes More with Jen Angel
Q: Give me the short version of what's the Evergreen Conference? Why should people be there? What would they get from it?
Jen describes the conference as a gathering that blends grassroots and policy perspectives, emphasizes interactive experiences in the ravines and public spaces, and showcases a diverse group of practitioners to foster collaboration and practical ideas for vibrant cities.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
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Frequently Asked Questions About Challenger Cities

What is Challenger Cities about and what kind of topics does it cover?

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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How many listeners does Challenger Cities get?

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How many subscribers and views does Challenger Cities have?

To see how many followers or subscribers Challenger Cities has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Challenger Cities?

These podcasts share a similar audience with Challenger Cities:

1. The Strong Towns Podcast
2. UCLA Housing Voice
3. The Ezra Klein Show
4. The Prof G Pod with Scott Galloway
5. Pivot

How many episodes of Challenger Cities are there?

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.

How do I contact Challenger Cities?

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Where can I see ratings and reviews for Challenger Cities?

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What guests have appeared on Challenger Cities?

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

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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