Iain Montgomery
Challenger Cities
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.
Author
Iain Montgomery
Category
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
Challenger Cities EP92: Cities Are Mental Weapons with Giacomo Biraghi 07.07.2026 43:53
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 actually runs the modern city, he reckons, is a global, real-estate-driven standard, and we should be a little more cynical about the green, healthy, peace...
Challenger Cities EP91: Expanding Your Luck Surface Area with Matt Ballantine 02.07.2026 47:31
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 written a book, called Random with Nick Drage. Some might say 120 short stories that can be shuffled into any order isn't actually a book, but I read it as one, and it's excellent. Plus many of the stories are about cities, place...
Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik 29.06.2026 1:04:03
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 country simply doesn't build enough good homes for the people who want to live there, and incremental approaches are going to solve for it. So along comes Shiv Malik, a journalist by trade, with an idea for a new city, not too far fr...
Challenger Cities EP89: To Do, Not Just Be with Gil Penalosa 25.06.2026 1:34:37
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 could be amazing but is often found lacking in ambition. We explore ideas from the absolute basics of providing space to walk, why we might want to reframe the idea of the NIMBY to the one of the CAVE person - Citizens Against Virtual...
Challenger Cities EP88: The Neighbourhood is the Amenity with Alicia Pederson 21.06.2026 58:36
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 courtyard in the middle of apartments. After watching family friends priced out of Chicago one by one - not because they disliked the city, but because the only family housing on offer was a million-dollar house with a private ya...
Challenger Cities EP87: Bringing Sexy Back to Transit with Mark Salsberg and Jonathan English 15.06.2026 1:00:32
Canada is about to spend more on transit and rail than the oil sands are worth, and it's doing it without a national rulebook, a training pipeline or much recent memory of how to build well. So is that a crisis, or the best shot a country has ever had at becoming a genuine transit Challenger? This episode is a double act with two people who think about this for a living. Mark Salsberg is co-founde...
Challenger Cities EP86: How the Robocars Meet the Curb with Bern Grush 11.06.2026 58:37
Good new Challenger Cities episode today, all about autonomous vehicles and the bit that our guest, Bern Grush, thinks cities need to be thinking about more now. Like them or not, robotaxis are coming to cities. And for all the spectacular technology that helps cars drive themselves, the have some meaty challenges ahead. One of them being what happens when they interact with the curb. We've alread...
Challenger Cities EP85: Canada Needs a Railway Architect with Michael Schabas 08.06.2026 1:08:41
Canada is, well might be, building a high speed train. At long last after 50 odd years of talking about doing so. But concerningly, there is much negative noise around the project as it seems it might not really be learning the lessons for how successful projects have been delivered elsewhere, and where projects for building fast trains have gone wrong. This podcast is with Michael Schabas, a Cana...
Challenger Cities EP84: The De-Risking Industrial Complex with Richard Fisher 03.06.2026 1:12:51
Two risk-management cultures looking at each other across a table, each waiting for the other to move. That's rail's relationship with venture capital. Iain talks to Richard Fisher, founder of Future Travel Studio, about why nobody would fund his Dream Suite flatbed seat for trains, even after InnovateUK had backed it and operators had tested it. About rail's proposition gap, the incumbents who mo...
Challenger Cities EP83: A Little Piece of Switzerland in the Derbyshire Hills 27.05.2026 48:39
This is a lovely episode with Thomas Ableman (a returning guest!) that is mostly about an amazing project he and a few volunteers recently secured funding to go and deliver called Mini Switzerland in the Derbyshire hills. We often hear about how it's not possible to deliver high quality public transport because there simply aren't enough people to make it worthwhile. That makes a lot of people fee...
Challenger Cities EP82: The Purpose is Not the Function with Sam Peart 22.05.2026 57:52
One of the best people I met last year was Samantha Peart. We were in Copenhagen for a few days and of our fellows group, I have to say she asked the best questions. She’s also exceptionally good at getting you to question your assumptions or reflect on why you might think what you’re thinking. And that really comes through in this conversation, with real examples that have had a massive impact on...
Challenger Cities EP81: A Chair in the City and a Stool at the Rouge with Ken Greenberg 15.05.2026 1:08:42
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 the city and then took it to the likes of St. Paul and Boston in the US. We set up this episode to discuss work he's doing around the newly free'd up...
Challenger Cities EP80: The Materials of Cities with Saurabh Mangla 12.05.2026 45:31
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 of his materials lab and how he's working to explore how cities use their materials more effectively, efficiently and in many ways, delightfully is a g...
Challenger Cities EP79: The Best Practice Industrial Complex with Gerald Babel-Sutter 05.05.2026 53:47
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 managers in a room, not the communications directors, and ask them to talk honestly about what went wrong. In this conversation we cover how a frustrat...
Challenger Cities EP78: Saying Yes More with Jen Angel 01.05.2026 44:19
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 national organisation behind the Brick Works in Toronto and a portfolio of public space projects across the country — from school grounds transformatio...
Challenger Cities EP77: The Will To Build with Alex Bozikovic 28.04.2026 1:08:18
Alex Bozikovic is the architecture critic for the Globe and Mail, which in practice means he writes about everything from housing politics to the public realm to the quiet cultural erosion that happens when a city stops expecting much of itself. In this episode, Iain and Alex dig into why Toronto ... a city with extraordinary people, genuine sophistication and real financial muscle ... keeps faili...
Challenger Cities EP76: Urban Troubleshooting with Heath Gledhill & Tom Shield 23.04.2026 1:01:20
Exploring Urban Troubleshooting In this episode, Heath Gledhill and Tom Shield, founders of GledHill Shield, share their extensive experience navigating complex urban infrastructure projects. They discuss how early decision-making, constraints and collaborative design principles can transform city development. Whether you're an urbanist, engineer, architect, designer or planner, their insights cha...
Challenger Cities EP75: What a Rock Off a Rock Can Teach the Rest of Us with Tasha Freidus 21.04.2026 46:22
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...
Challenger Cities EP74: Embrace the Chaos with Bronwyn Williams 17.04.2026 44:57
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...
Challenger Cities EP73: Showing a City to Itself with Phil Tabah 14.04.2026 43:50
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 c...
Challenger Cities EP72: The Case for Civic Joy with Ilana Altman 07.04.2026 1:03:07
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...
Challenger Cities EP71: Welcome to Your Agentic City with Alistair Croll 30.03.2026 53:26
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 fi...
Challenger Cities EP70: Building a Village in the Sky with Anson Kwok 16.03.2026 54:21
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 designe...
Challenger Cities EP69: Designing for Intimacy with Paul Meyers 16.03.2026 47:13
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: • Wh...
Challenger Cities EP68: The Bus Deserves Better with Ray Stenning 03.03.2026 58:58
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 count...
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