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Challenger Cities: Daily Summaries Delivered
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.
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- 2 days ago1h 8m
Challenger Cities EP108: The Front Room of the City with Sofia Song
Sofia Song, who leads cities research at the Gensler Research Institute, is back to talk through City Pulse 2026. It’s Gensler’s survey of 35,000 people across 75 cities and 133 business districts, and this year it’s all about downtowns.We get into the four kinds of downtown visitor, with reluctant visitors the biggest group at 42%. We look at why Cairo and Detroit top the stickiness rankings while New York and London miss the top ten, and how Newark ended up at number five. Sofia explains why the time people spend downtown matters more than how often they visit, why evenings and weekends drive vibrancy, and why people keep asking for markets, festivals and independent cafés over global brands.Along the way there’s La Défense, Calgary’s mountains, the front room versus the living room, and the idea of downtown as a “reputation engine” for the whole city.
- 1 weeks ago52 min
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 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 ritual factories, and what a kindergarten graduation in a public plaza could do for a place. Then we get into why even the best public art is a one-time visit, and why the real job now is teaching people how to leave the house again.Along the way Lev pulls apart my definition of play and my five tests for a playful city. We cover Brazilian beach football, Scotland fans in Boston, jazz versus pop, kids who won’t play without proper goals, and going mudlarking for the rituals already buried in your city. To finish, the biggest and smallest ideas, as always: stop trying to save everything, and go downtown with a ba
- 3 weeks ago37 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 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 Rock collapsed. Since then he has made a career of dragging executives out of the boardroom and into supermarket aisles, call centres and station platforms. We recorded in person in London and covered why feedback surveys and public consultation make leaders feel close to people without getting them there, how the same commuter becomes a different person at 11.30pm, and what airports, trains and cities could learn from Pizza Express. He finishes with a big idea for long-distance rail and a small step any transport boss could take tomorrow.
- Oct 5, 202653 min
Challenger Cities EP105: Coming to Play with the Downtown Denver Partnership
Challenger Cities EP105: Coming to Play with the Downtown Denver PartnershipKourtny 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.Kourtny, CEO of the Downtown Denver Partnership, explains why play became the headline of Denver's new downtown plan, and why her truest measure of success, after all the foot traffic data, is watching people's faces. "It's simply a feeling." Gretchen, executive director of Denver Arts & Venues, runs a city department that pays its own way through Red Rocks concerts and touring Broadway, which is how Greg came to call her the Robert Moses of the arts. "I would prefer to be from Toronto and the Jane Jacobs, but I am an American, so I guess I'm stuck with Robert Moses." Aisha, executive director of the Newman Center for the Performing Arts, talks about why cities default to public art, and what it takes to make performance happen again and again.In between, Greg and I compare notes on the workshop, honest pilots, and a 32-foot glowing-eyed blue horse called Blucifer.In this episode:Downtown as a venue, and where a city can start to bend the rulesWhat Montréal puts in the ground so organisers pay for the programme instead of the plumbing"Play is a tool, but the outcome is connection."Why public art gets a 1% budget and repeat performance gets nothingWould a forty-year-old do this without feeling stupid?How a once-creepy airport sculpture became a festival name nobody commissionedAisha's smallest thing: "Once you finally get through that first chance, the next time it's gonna be easier and easier until it becomes tradition and ritual."Greg, Lev Kushner, Jasmine Palardy and I will be in Denver on 5 and 6 November to turn all of this into something the city can go and do. If you're in Denver, we'd like to see you there.
- Oct 5, 202650 min
Challenger Cities EP104: Just Doing Our Thing with @JamesinSerbia
Challenger Cities EP104: Just Doing Our Thing with @JamesinSerbiaJames, 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. Within eight days he had an apartment in Novi Sad, a lawyer and the internet installed.We talk about what he found there: a country that doesn't pretend to be anywhere else. James explains inat, the Serbian word for "the more you tell me not to do something, the more I'm gonna do it", and why it might be the closest thing to a national Challenger mindset. We get into Serbia's marketing problem, Europe's borrowed identities, a map trick best done over rakija, and why so many Britons are sliding into his DMs asking whether Serbia really works.And there's Koptr, a coffee shop built around a seventies Soviet troop helicopter in a Novi Sad warehouse. "If it was anywhere else in the world, it wouldn't be allowed." The same permissive culture that let it happen may now let it vanish for a property deal, which led James to the smallest possible thing he could do about it.In this episode:Why Britain can feel like a cul-de-sac once you've left itInat, and confidence in who you are, flaws includedPlaces cosplaying as western Europe, and one that won'tPermission, and why an owner's judgement should count for somethingBeing a guest, and joining in instead of trying to change thingsJames's advice if you're curious: "Go to Belgrade, join in for a few days, and just see if you like it because you'll know very quickly."Find James on Instagram at @jamesinserbia.
- Sep 24, 20261h 15m
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 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. Think Hong Kong, India, the Philippines etc. I assume most architects spend their twenties detailing stairwells, so that’s quite the apprenticeship, and it shows in how he talks about terminals through the course of this conversation as much more than big buildings.Philip Galway-Witham is, in his own words, a fellow geographically confused Brit, which makes two of us in this chat. He’s a Resilience Leader for Gensler’s Northeast region, which I find a rather interesting title, because Gensler use that term ‘resilience’ where most firms probably still say ‘sustainability’. Capital-S Sustainability is a badge that doesn’t really say what it was a few years ago. You can’t just bolt some kind of green façade onto a building and lay claim to your sustainability creds in a press release.Obviously, that is a good thing, we have matured.Together, Phil and Chris co-lead Gensler’s aviation practice in Canada from Toronto. Gensler being the largest architecture firm on the planet, which means if you’ve flown anywhere lately there’s a fair chance you’ve sat, queued or watched the world go by in something they designed. I’ve spent a decent chunk of my recent working life on the future of stations and airports, so I’m rather pleased we’re doing a proper episode on airports in relation to cities.
- Sep 21, 20261h 1m
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 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 doesn't have, and her positive pitch for a city that's "better, easier and more beautiful". And she has a case for seeing the race as more than a two-horse contest.https://lauradeanformayor.ca/
- Sep 15, 20261h 2m
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 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 and clients do not have such rapid or sophisticated mechanisms of connection and communication.An architect can finish their work on a building before moving onto the next project. They don't have the right of return, access to the energy data of the finished project, may well have had the work adjusted in the process and aren't the ones experiencing what it's like to use it.It's what Bryan Boyer from Taubman College of Architecture + Urban Planning, University of Michigan and Greg Lindsay, newly installed Urbanist-in-Residence at School of Cities, University of Toronto call 'Chain Drain'.Think of the handoffs, where an architect might place a window, but a structural engineer needs a column exactly there, and the mechanical engineer needs a drain. One of them will likely win an argument, and the others will adapt. Multiply that by every handoff on every project and you get an industry where each job starts roughly where the last one started, and where value leaks out at every transition.That matters as US construction productivity has fallen something like ~30% since 1970, while productivity in the wider economy more than doubled. We are asking this sector to deliver housing, climate adaptation and the retrofit of trillions in stranded assets. That's a big ask when over the last half century, it's in some ways getting worse at building things in the first place.It's a properly good paper that I hope will bring the Challenger mindset to the people tasked with designing, planning, making, building and operating Cities and Place.Find the paper in full here: https://www.bryanboyer.com/chaindrain/Challenger Cities Summary: https://challengercities.substack.com/p/challenger-cities-ep101-chain-drain
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About 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.
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