Challenger Cities artwork

Design · Iain Montgomery

Challenger Cities

by Iain Montgomery

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.

Latest episodes

Showing 20 · updated from the feed

Challenger Cities EP107: Cities Are Ritual Factories with Lev Kushner

Lev Kushner sent me an email saying public art is rarely cool, not very good at attracting visitors, and kind of a waste of money. So we made a podcast out of it. Lev ru

Oct 27
52 min

Challenger Cities EP106: The View from the Fish Counter with John Sills

An 82-year-old widow told a supermarket CEO that his new fish counter had hidden the only person she came in to talk to. John Sills, senior partner at The Foundation and

Oct 15
37 min

Challenger Cities EP105: Coming to Play with the Downtown Denver Partnership

Challenger Cities EP105: Coming to Play with the Downtown Denver Partnership Kourtny Garrett, Gretchen Hollrah and Aisha Ahmad-Post were among 71 Denver leaders who spen

Oct 5
53 min

Challenger Cities EP104: Just Doing Our Thing with @JamesinSerbia

Challenger Cities EP104: Just Doing Our Thing with @JamesinSerbia James, the Brit behind the Instagram account jamesinserbia, thinks of the UK as a cul-de-sac. "You kind

Oct 5
50 min

Challenger Cities EP103: What Airports Know That Cities Don't with Philip Galway-Witham & Chris Belisle

Airports can anxiety machines dressed up in statement architecture. So how do you design for delight in the different modes people turn up in, while building something de

Sep 24
1 h 15 min

Challenger Cities EP102: Getting to Yes with Laura Dean

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

Sep 21
1 h 01 min

Challenger Cities EP101: Chain Drain with Bryan Boyer & Greg Lindsay

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

Sep 15
1 h 02 min

Challenger Cities EP100: How Big Things Get Done with Bent Flyvbjerg

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

Sep 8
1 h 01 min

Challenger Cities EP99: Bottom Up & Top Down Cultural Infrastructure with Jacquelyn West

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

Sep 1
58 min

Challenger Cities EP98: Stations & Airports of the Future ... a Megacast

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

Aug 27
1 h 16 min

Challenger Cities EP97: Developers as Citymakers with Stratton Townley

I met Stratton Townley at the Waterworks Food Hall in Toronto, a couple of hours before it opens, with ten or twelve people sat about with coffees and nobody hovering to

Aug 27
1 h 09 min

Challenger Cities EP96: The Paradox of Proximity with Ann-Britt Elvin Andersen and Jakob Norman-Hansen

Copenhagen is Jan Gehl's city. So it's a bit of a jolt to hear someone who lives and works there admit that nobody has ever really been able to say what a "human-centric

Aug 11
1 h 02 min

Challenger Cities EP95: The 5-to-9 Episode with Mo, Laura & Nick from Mosaic

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

Aug 4
1 h 38 min

Challenger Cities EP94: We Wunt Be Druv with John V Willshire

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 littl

Jul 29
1 h 00 min

Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen

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 toug

Jul 15
1 h 04 min

Challenger Cities EP92: Cities Are Mental Weapons with Giacomo Biraghi

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

Jul 7
43 min

Challenger Cities EP91: Expanding Your Luck Surface Area with Matt Ballantine

In this spirit of being the world's most eclectic podcast about cities and places, this episode is a bit random. Which is good, because it's with Matt Ballantine and he's

Jul 2
47 min

Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik

This is an episode about a big, ambitious idea. Which is why people are quick to label it as crazy. But Britain, like many developed nations has a housing crisis. The cou

Jun 29
1 h 04 min

Challenger Cities EP89: To Do, Not Just Be with Gil Penalosa

This episode is a zinger. Because Gil Penalosa came in ready to talk! He doesn't hold back as he discussed the issues with Toronto municipal projects, where the city co

Jun 25
1 h 34 min

Challenger Cities EP88: The Neighbourhood is the Amenity with Alicia Pederson

Alicia Pederson went from a Renaissance literature PhD and a two-year stint as an au pair in Florence to becoming one of the best voices on a deceptively simple idea: the

Jun 21
58 min

Chart trend

Position in the Design chart (US), last 90 days.

#29
all-time peak
6
days in the top 50 since Dec 2024

Chart positions

Where Challenger Cities ranks today in each Apple Podcasts chart (US, Oct 28, 2026).

#147 NEW Design US

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Here you find the Apple Podcasts chart positions of Challenger Cities, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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