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.
Koniecznie odwiedź stronę podcastu i wesprzyj twórcę: challengercities.substack.com
Autor
Iain Montgomery
Kategoria
Strona podcastu
Ostatni odcinek
27 paź 2026
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Odcinki
Challenger Cities EP107: Cities Are Ritual Factories with Lev Kushner 27.10.2026 52:20
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 runs Department of Here, comes from a family of rabbis, and describes city planning as his compromise between clergy and architecture. We talk about why bureaucracies are so bad at telling their own story, why cities are really ritua...
Challenger Cities EP106: The View from the Fish Counter with John Sills 15.10.2026 37:48
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 author of The Human Experience , spent the next six months hearing that CEO mention her by name. That story is where this conversation lives. John started out stamping cheques in an HSBC branch and was managing one when Northern R...
Challenger Cities EP105: Coming to Play with the Downtown Denver Partnership 05.10.2026 53:01
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 spent 48 hours in Montréal this year, studying how a city makes vibrant neighbourhoods through play. On their last morning, while I ran a workshop with the group, Greg Lindsay borrowed the microphone and pulled the three of them aside....
Challenger Cities EP104: Just Doing Our Thing with @JamesinSerbia 05.10.2026 50:11
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 of don't really notice that there's anything going on at the end of the road." After five years in Italy, ski seasons across the Alps and one brutal winter in Andorra, he flew to Serbia with one suitcase, a ski bag and his laptop....
Challenger Cities EP103: What Airports Know That Cities Don't with Philip Galway-Witham & Chris Belisle 24.09.2026 1:15:53
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 designed to last decades? Chris Belisle cut his teeth on airports in Asia in the mid-2000s, when the growth was so relentless that a firm would hand an entire airport to a designer barely out of school and tell him to get on with it...
Challenger Cities EP102: Getting to Yes with Laura Dean 21.09.2026 1:01:12
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 isn't a politician. She spent her career working out why the city says no, and how to get it to yes. We talk about why Toronto has so many ways to block things and so few to let them happen. We also cover the plans the city still...
Challenger Cities EP101: Chain Drain with Bryan Boyer & Greg Lindsay 15.09.2026 1:02:46
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 a pretty awesome feedback loop. But the urban realm doesn't work like that. There is a much longer and less responsive chain at play where the planners, developers, architects, engineers, construction firms, designers, financiers...
Challenger Cities EP100: How Big Things Get Done with Bent Flyvbjerg 08.09.2026 1:01:44
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 early on took a bit of a turn to have conversations about cities and infrastructure that didn't seem to be happening anywhere else … … the ones that fall between planners, architects, engineers, economists and what ‘regular’ peop...
Challenger Cities EP99: Bottom Up & Top Down Cultural Infrastructure with Jacquelyn West 01.09.2026 58:20
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 Montréal, by way of Toronto, where she spent much of her career working with artists, festivals and creative organisations. She watched the same cycle run several times over: artists move into a cheap neighbourhood, the neighbourh...
Challenger Cities EP98: Stations & Airports of the Future ... a Megacast 27.08.2026 1:16:43
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 session to stress test the thinking and bring their own — which is a rather Challenger way of doing it, and only really possible when you can have Tokyo, Boston, Toronto and London in the same room. Greg Dyson joins from Thailand...
Challenger Cities EP97: Developers as Citymakers with Stratton Townley 27.08.2026 1:09:05
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 work out whether they intended to spend anything. Stratton is at Woodcliffe Landmark Properties, a small, private, family-run developer that has been on the same Toronto street for thirty years. His stepfather founded it; his moth...
Challenger Cities EP96: The Paradox of Proximity with Ann-Britt Elvin Andersen and Jakob Norman-Hansen 11.08.2026 1:02:47
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 city" actually is. That's Jakob Norman-Hansen. Along with Ann-Britt Elvin Andersen, he's spent about a decade at BLOXHUB explaining Copenhagen to visiting delegations — and watching most of them decide it could never work back hom...
Challenger Cities EP95: The 5-to-9 Episode with Mo, Laura & Nick from Mosaic 04.08.2026 1:38:31
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 making this podcast. We're doing it because I loved what they did after I spoke. Several people from the team were invited to share what they do with thei...
Challenger Cities EP94: We Wunt Be Druv with John V Willshire 29.07.2026 1:00:55
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 has a gift for the metaphor that reframes everything. In this case, swapping the language of levers and control for gardening where you can't tell a p...
Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen 15.07.2026 1:04:07
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 engineering, economics and urbanism — but I've been converted. The unlikely converters are Florence Okin and Sam Cohen, who run a workshop called Know Thy...
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...
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