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PODCAST

Challenger Cities

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.

arts design

All Episodes

46:22

Challenger Cities EP75: What a Rock Off a Rock Can...

Challenger Cities ·

2026/04/21

When the cod fishery collapsed in the nineties, Fogo Island lost its economy almost overnight. What came next — slowly, imperfectly and without a guarantee of success — became one of the most compelling stories in Canadian community development. Shorefast, the charity behind the Fogo Island Inn, wasn't built on the logic of charity. It was built on the logic of place. Every business decision, from the number of rooms in the inn to where every dollar gets spent, runs through a single question: does

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44:57

Challenger Cities EP74: Embrace the Chaos with...

Challenger Cities ·

2026/04/17

Bronwyn Williams is a South African futurist and economist, a combination she'll tell you should not be the oxymoron most people assume it is. She's been doing sharp thinking about cities lately, and this conversation is a good example of why.We get into South African cities as a lens for the future with Johannesburg and Cape Town as two very different experiments in what happens when you try to impose order on a place that has other ideas. We talk about why the cities that look like they're working

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43:50

Challenger Cities EP73: Showing a City to Itself with...

Challenger Cities ·

2026/04/14

Phil Tabah is the co-founder of The Main, Montreal's city magazine, and one of the most thoughtful people working on the question of how cities see themselves and tell their own story.In this conversation we get into why Phil started The Main at 21 as a Twitter account and what it's become, the publications that used to do this job well and what happened to them, why Montreal is a city that has cracked culture but not confidence, the economics of being a springboard city, and what it would actually

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63:07

Challenger Cities EP72: The Case for Civic Joy with...

Challenger Cities ·

2026/04/07

Most cities debate their troubled infrastructure to a standstill. Toronto has been arguing about the Gardiner Expressway for decades. Ilana Altman didn't wait for that debate to resolve. As CEO of The Bentway — a public space and cultural platform built underneath Toronto's elevated waterfront highway — she's been proving that you don't have to tear something down, or wait for it to die, to embed new values in it.In this conversation, Ilana and Iain cover the full arc: how the Bentway went from idea

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53:26

Challenger Cities EP71: Welcome to Your Agentic City...

Challenger Cities ·

2026/03/30

We have spent a lot of time on the podcast talking about physical cities as streets, buildings and the spaces between them. What we perhaps don't talk about enough is the digital layer underneath all of it, and how badly most cities are fumbling it. This week's guest has spent the last decade thinking about almost nothing else.Alistair Croll runs FWD50, perhaps the biggest gathering of digital first public servants in the world. He also wrote the book on lean analytics, literally, with Ben

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54:21

Challenger Cities EP70: Building a Village in the Sky...

Challenger Cities ·

2026/03/16

Anson Kwok has spent fourteen years building Canada's tallest tower at the foot of Yonge Street. As VP of Sales and Marketing at Pinnacle International, he's had a front row seat to how Toronto has transformed from a city of downtown parking lots to one of the most dense urban skylines in North America. We talk about what it actually takes to build a vertical city inside a city that wasn't designed for one, why the rules written for 20-storey buildings don't survive contact with a 106-storey one,

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47:13

Challenger Cities EP69: Designing for Intimacy with...

Challenger Cities ·

2026/03/16

At first glance, SPNKD might look like a BDSM venue. But Paul Meyers real focus is something deeper ... finding connection and creating intimacy.We explore how intimacy is designed, why many people use kink to avoid connection rather than deepen it, and what the concept of creating an arena in BDSM can teach us about relationships, work and even how cities function.Along the way we discuss:• Why Paul created SPNKD after finding most kink venues “tacky dungeons” • How BDSM spaces deliberately design

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58:58

Challenger Cities EP68: The Bus Deserves Better with...

Challenger Cities ·

2026/03/03

What if the problem with buses isn’t frequency, funding or technology ... but attitude?In this episode, we're in person with Ray Stenning, founder of Best Impressions and arguably the most prolific bus livery designer in the world. For more than 40 years, Ray has been quietly reshaping how buses look, feel and function across the UK — from iconic interurban routes like the X43 and the 36 to countless urban fleets most people ride without ever knowing who shaped them.But this isn’t a conversation

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51:59

Challenger Cities EP67: Watching a World From Behind...

Challenger Cities ·

2026/02/25

Füsun Aydın has spent twelve years reading people from a window in Amsterdam. Cities would be better places if the people planning them had half her instinct.Füsun is Turkish-born, a trans woman, a former sex worker, and now the madam of a bordello in Amsterdam's red light district. She came to the Netherlands as an asylum seeker at nineteen, having grown up in Istanbul where trans women have no legal discrimination protections and sex work on the street is both common and dangerous. The move wasn't

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63:38

Challenger Cities EP66: Urbanism Without the Excuses...

Challenger Cities ·

2026/02/19

In this episode of Challenger Cities, Iain Montgomery is joined by urban designer, filmmaker, and author Mikael Colville-Andersen for a wide-ranging conversation about why cities so often know what works, yet struggle to act on it.We start with train stations and the importance of arrival, before moving through cycling, design, experimentation, Nordic urbanism, and finally Mikael’s recent work in Ukraine, where urbanism takes on a very different meaning.We cover:Why train stations are still one of

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81:36

Challenger Cities EP65: Sitopia with Carolyn Steel

Challenger Cities ·

2026/02/16

Cities are usually explained through buildings, infrastructure, policy and planning. Food rarely gets a look-in.Which is strange, because for most of human history, cities existed in the first place because we learned how to feed ourselves at scale. Farming allowed settlement. Settlement allowed specialisation. Specialisation gave us civilisation. Long before zoning codes or masterplans, food decided where cities formed, how power worked, and why empires survived or collapsed.In this episode, I’m

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60:08

Challenger Cities EP64: Tourism as a Stress Test with...

Challenger Cities ·

2026/02/10

Tourism is big business. Cities spend vast sums attracting visitors, promoting landmarks and polishing their image. What they’re far less good at is thinking through the experience of actually being there. How a place works once you arrive. How you move around it. What makes sense, what doesn’t, and what quietly undermines the affection people might otherwise develop for a city.In this episode, Iain Montgomery is joined by Maryam Siddiqui, a Toronto-based travel and culture journalist who came to

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49:15

Challenger Cities EP63: The Pub Is a Public Service...

Challenger Cities ·

2026/02/06

In this episode of Challenger Cities, we've got Pete Brown, one of the UK’s most thoughtful writers on beer, pubs, and drinking culture.Pete has spent decades writing about pubs not as lifestyle accessories or nostalgic backdrops, but as places where history, behaviour, economics and everyday social life collide. We talk about why pubs weren’t designed, branded or planned into existence, but evolved slowly through circumstance, need, and habit. Why that matters for cities obsessed with masterplans

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66:44

Challenger Cities EP62: Cities for People Who Want to...

Challenger Cities ·

2026/02/02

Most cities are designed around a surprisingly narrow idea of who gets to feel comfortable in public.In this episode of Challenger Cities, Iain Montgomery chats with Patti Baston, who runs a feminisation makeover service in Manchester. On the surface, her work might sound niche. In practice, it turns out to be a sharp and unexpected lens on how cities really work, who they quietly exclude, and how play, permission, and experimentation get designed out of adult life.We talk about growing up without

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50:55

Challenger Cities EP61: Sweat and the City with Glenn...

Challenger Cities ·

2026/01/27

Iain Montgomery talks with Glenn Auerbach about why sauna, bathing and cold-water culture has suddenly gone mainstream in cities around the world, and why the reasons go far beyond health trends or wellness hype. From floating saunas and mobile heat rooms to dawn swims in urban rivers and harbours, we explore how shared rituals of heat, cold and recovery are reintroducing forms of social connection that cities have quietly lost. Glenn traces sauna’s roots as everyday civic infrastructure rather than

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49:54

Challenger Cities EP60: Designing Cities in Pencil,...

Challenger Cities ·

2026/01/19

We reconnect with Jasmine Palardy almost eighteen months after our very first conversation to reflect on what has changed in how we think and talk about cities, and what hasn’t. Exploring why real progress in cities comes not from imposing control but from embracing uncertainty, loosening the grip of over-planning and letting “accidental urbanists” and informal city builders shape change on the ground. Jasmine reframes urbanism as a messy, lived practice rather than a rigid discipline, and

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53:41

Challenger Cities EP59: Building Faster Than Memory...

Challenger Cities ·

2026/01/19

Ruchita Bansal discusses what happens when modern infrastructure projects are built at speed but don’t connect with the deep, informal systems that make cities work. Drawing on her experience across Indian urban planning and large-scale delivery, we explore how cities in India are being transformed rapidly with metros, highways and ambitious timelines, yet often miss the connective tissue of everyday life such as first-mile/last-mile walking, informal transport, street life and safety. We dig into

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52:56

Challenger Cities EP58: The World's Best Cities with...

Challenger Cities ·

2026/01/19

Chris Fair, CEO of Resonance and publisher of "World's Best Cities" talks about what really separates the world’s cities. As Chris explains, obsessively measured performance isn’t enough to explain why some cities feel magnetic and others feel interchangeable. We unpack the World’s Best Cities framework and how liveability, prosperity, and a often-overlooked dimension of lovability shape both the experience of place and its global perception. We explore the gap between performance and perception,

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56:12

Challenger Cities EP57: Young People and the New...

Challenger Cities ·

2026/01/19

Researcher and strategist David Akermanis talks about how young people are navigating a world where traditional financial stability has eroded and cities themselves shape economic life. We explore why the familiar narratives about youth finance, savvy versus reckless, miss the deeper tension underneath. Across stories of early career precarity, the blending of gambling and investing, the limitations of traditional banking advice, and how mobility and access matter as much as income, we dig into how

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50:05

Challenger Cities EP56: Why Empty Space Is Never...

Challenger Cities ·

2026/01/19

Evan Snow, co-founder of Zero Empty Spaces talks about why vacancy in cities isn’t a neutral pause but an active force shaping how we feel, move and connect in urban places. We explore how empty storefronts, abandoned commercial spaces and obsolete interiors drain confidence and disrupt movement, and how creative, low-risk activation can turn them into meaningful places without waiting for the “perfect tenant” or a grant. Evan’s work reframes empty space as opportunity, showing how activation builds

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77 results

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