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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 weeklyEpisodes83Founded2 years ago
Number of ListenersCategories
DesignSociety & CultureArtsPlaces & Travel

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Artwork for Challenger Cities

Latest Episodes

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

This is a bit of a different episode because we're talking about what cities are made of, rather than how we make our cities.

I had the pleasure of meeting Saurabh Mangla on a day where I was hot, tired and just wanted a beer. But getting the story... more

Gerald Babel-Sutter is the founder of Urban Future, a 14-year-old event that has grown from a workshop for ten city officials in Graz to a gathering of 2,000 people from 290 cities in 48 countries. The premise hasn't changed: get the actual project m... more

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 ... more

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Recent Guests

Ken Greenberg
Urbanist and former city planner involved in Toronto's urban design initiatives
Former City of Toronto Urban Design Group; various international civic projects
Episode: Challenger Cities EP81: A Chair in the City and a Stool at the Rouge with Ken Greenberg
Saurabh Mangla
Founder of Ipsum and Lumatera; materials innovator focused on moving IP from lab to market
Lumaterra / Ipsum
Episode: Challenger Cities EP80: The Materials of Cities with Saurabh Mangla
Gerald Babel-Sutter
Founder/ organizer of Urban Future, urbanist behind Challenger Cities discussion
Urban Future
Episode: Challenger Cities EP79: The Best Practice Industrial Complex with Gerald Babel-Sutter
Jen Angel
Leader, Evergreen
Evergreen
Episode: Challenger Cities EP78: Saying Yes More with Jen Angel
Alex Bozikovic
Architecture critic for the Globe and Mail
Globe and Mail
Episode: Challenger Cities EP77: The Will To Build with Alex Bozikovic
Heath Gledhill
Co-founder, GledHill Shield
GledHill Shield
Episode: Challenger Cities EP76: Urban Troubleshooting with Heath Gledhill & Tom Shield
Tom Shield
Co-founder, GledHill Shield
GledHill Shield
Episode: Challenger Cities EP76: Urban Troubleshooting with Heath Gledhill & Tom Shield
Tasha Freidus
Director of Education and Entrepreneurship, Shorefast Institute
Shorefast Institute
Episode: Challenger Cities EP75: What a Rock Off a Rock Can Teach the Rest of Us with Tasha Freidus
Bronwyn Williams
South African futurist and economist
Self-described futurist and economist
Episode: Challenger Cities EP74: Embrace the Chaos with Bronwyn Williams

Host

Iain Montgomery
Host of Challenger Cities Podcast, Now or Never Ventures

Reviews

5.0 out of 5 stars from 18 ratings
  • Countries come & go, cities endure

    Love Iain’s breadth and interview style.

    Apple Podcasts
    5
    Acorrn
    Canada3 months ago
  • Top Notch

    Look forward to every episode

    Apple Podcasts
    5
    Marshdogg
    Canada3 months ago

Listeners Say

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

High-quality guests who bring diverse perspectives on urbanism.
Great for sponsors seeking thought leadership in urban development and placemaking.
Curious, thoughtful conversations that respect lived experience in cities.
Loved the focus on practical design details and real-world impact.
Energetic hosting with clear curiosity and critical thinking.

Chart Rankings

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

Apple Podcasts
#36
Canada/Arts/Design
Apple Podcasts
#172
Spain/Arts/Design
Apple Podcasts
#186
Poland/Arts/Design
Apple Podcasts
#240
Denmark/Arts/Design

Talking Points

Recent interactions between the hosts and their guests.

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.
Challenger Cities EP72: The Case for Civic Joy with Ilana Altman
Q: What's next for The Bentway and the Gardiner corridor?
Expansion involves completing the seven-kilometer plan, extending programming and public realm improvements, and maintaining a strong partnership between government and philanthropy to realize a connected vision that keeps the space active, safe, and meaningful for residents and visitors.
Challenger Cities EP72: The Case for Civic Joy with Ilana Altman
Q: What have been the biggest learning moments or missteps, and how did you adapt?
The learning comes from running a live space with evolving needs: not every initiative works, so you test, iterate, and keep a constant dialogue with the community. Dominoes demonstrated the power of volunteer-driven projects, while food and beverage models still need iteration to anchor activities across the length of the site.
Challenger Cities EP72: The Case for Civic Joy with Ilana Altman
Q: How did The Bentway start and evolve to what it is today?
The Bentway grew from the idea of reimagining the space under Toronto's Gardiner Expressway through private philanthropy, public sector collaboration, and a design firm's vision, turning a controversial infrastructural element into a functional, flexible public realm that can host art, events, and everyday gathering.

Audience Metrics

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Frequently Asked Questions About Challenger Cities

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

A thoughtful exploration of urban life, infrastructure, and cultural expression, with recurring emphasis on how design, policy, and community action shape livable, distinctive cities. Episodes cycle through public-transport aesthetics, inclusive urbanism, food systems in cities, tourism, and the social roles of third spaces like pubs, saunas, and maker spaces, often highlighting practical, human-centered design and the social impacts of planning decisions. A notable strength is its willingness to challenge conventional planning playbooks by centering marginalized voices, grassroots initiatives, and real-world case studies from cities around the world, making it a compelling listen for practitioners, policymakers, and creatives curious about... more

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Which podcasts are similar to Challenger Cities?

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 Urbanist Agenda

How many episodes of Challenger Cities are there?

Challenger Cities launched 2 years ago and published 83 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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What guests have appeared on Challenger Cities?

Recent guests on Challenger Cities include:

1. Ken Greenberg
2. Saurabh Mangla
3. Gerald Babel-Sutter
4. Jen Angel
5. Alex Bozikovic
6. Heath Gledhill
7. Tom Shield
8. Tasha Freidus

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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