Challenger Cities

por Iain Montgomery

Temporada 7

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

T7 · E14

15 sept 2026

1:02:46

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 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’ people want in cities. I didn't expect to still be at it, let alone to have talked my way through 100 guests to get here. I think Bent Flyvbjerg makes a fitting person to mark the occasion, having spent a career exploring perhaps one of the most consequential questions in the business of cities. How big things actually get done? And so often they aren't? --- At a time when so many cities and nations are discussing their need for new infrastructure, they are also often arguing over the cost and time required to build it. Bent, with Dan Gardner, pretty much wrote the book on why so many big infrastructure projects end up being so much more expensive than they should have been. We get into some of the principles in the book, along with some of what's missing when these big projects start out. His blunt takeaway after the data is that the biggest risk is ourselves as we systematically underestimate risk and assume our project is the exception. The remedy is to be a “realistic optimist,” keep a learning mindset and treat innovation as coming from learning. The episode frames this as fitting the podcast’s broader mission of examining how cities and infrastructure actually get built. Here's to the next 100 episodes!

T7 · E13

8 sept 2026

1:01:44

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 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 neighbourhood becomes desirable, and the people who made it desirable can no longer afford to be there. In this episode she and Iain Montgomery get into the parts of cultural infrastructure that rarely make a capital plan. Affordable creative workspace and production capacity. Third spaces where nobody has to buy anything. And governance, which decides whether any of the rest of it works. They also get into the money. Jacquelyn explains why the financing system produces the same four ground-floor tenants in every new podium, and what Toronto learned when it compelled developers to fund public art without building any stewardship around the requirement. Topics include the professionalisation of placemaking, where bottom up meets top down, Esplanade Tranquille as a third space that works, Montréal's idea of cohabitation in public space, why "play" is a hard word to fund, and how cycling infrastructure expands the cultural catchment of a city. 05:20 — What cultural infrastructure actually includes 07:52 — Culture needs places to be made, seen and belong 10:07 — Why the building is rarely the whole answer 14:26 — Placemaking, professionalised 18:06 — Where bottom up meets top down 22:41 — Empty community centres and overwhelmed small ones 36:07 — Culture as an infrastructure advantage 36:48 — Why the anchor leases decide the ground floor 38:26 — Toronto's public art mandates and what went wrong 43:02 — Programming, stewardship and Esplanade Tranquille 47:23 — Cohabitation, control and care 51:34 — Play, and why it's hard to fund 56:59 — Cycling and the cultural catchment of a city 1:01:34 — The smallest possible thing: count who's leaving https://challengercities.substack.com/p/challenger-cities-ep99-bottom-up

T7 · E12

1 sept 2026

58:20

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 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, late at night, to explain why most Japanese stations are visually drab and work anyway: wayfinding that never changes, platforms that never move, and amenity provided in inverse proportion to frequency. Three-minute trains, nowhere to sit. Hourly trains, a heated waiting room. Which is roughly the opposite of how we do it. Seth Hardy on reducing friction and increasing attachment, and the burger place in Copenhagen his family return to on every trip. Why familiarity beats spectacle, and why two of the most profitable Greggs in Britain are where they are. John Ozimec asks the hard one: Oakville GO, ten thousand people a day, four thousand parking spaces, being redesigned right now by people who've already decided nobody wants to be there. Charles Finley on why that persists — engineers doing engineering, architects doing architects, and nobody talking to anybody — and Greg on who actually owns the land around a station and gets to keep the value a good one creates. Also: what happens when an operator makes its stations too comfortable, why transit-oriented development might be the wrong way round, and Roundtree Post. The Anxiety Machine: https://challengercities.substack.com/p/the-anxiety-machine To being Challengers.

T7 · E11

27 ago 2026

1:16:43

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 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 mother runs it. He spent his first decade in brokerage and investment sales avoiding the family business entirely, on the strength of one job interview where he was told not to take the job. The thirty years is what this episode is really about. Woodcliffe kept Waterworks rather than registering the condos and moving on, which turned a real estate landlord into something closer to a hospitality operator — and gave them a feedback loop most developers never get. We talk about what that does to the design of the next building, why the city won't let him cut the grass in the park next door, heated pavements in Summerhill, silos in careers and buildings and government, and a Toronto waterfront that nobody will commit to beyond an electoral cycle. He is born and raised in Toronto, committed to it, and an optimist — which makes him better company on the city's problems than most. LINKS Woodcliffe Landmark Properties — https://www.woodcliffe.ca Waterworks Food Hall — https://waterworksfoodhall.com Shops of Summerhill — https://www.woodcliffe.ca/portfolio/shops-of-summerhill Read the write-up: https://challengercities.substack.com/publish/post/211069995 Challenger Cities — https://challengercities.substack.com

T7 · E10

27 ago 2026

1:09:05

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 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 home. Neither of them came to urbanism the usual way. Ann-Britt arrived through media and innovation, including a spell as an editor-in-chief in Japan. Jakob thought he'd spend his career in international development and started with two years in Ethiopia. Which might be exactly why they've gone after the one thing the profession has no filing cabinet for. As Ann-Britt puts it, loneliness doesn't normally land on an architect's desk, or an engineer's desk, or even a planner's desk for that matter. Their argument is that proximity was never doing the connecting. What counts is how much time we actually share, and whether we feel accepted and seen. In this episode: why the convenience economy is also a disconnection economy, and whether we've all been eating fast food for the brain. What happens when you point the attention economy at metro design. Why the benches and the barbecue never reach the people they're meant for, and how chronic loneliness changes the way you read a room. Why "lots of people turned up" is a lousy way to judge a public space. What a bridge built out into the water says about fixing your own mistakes. And why a delegation from Colombia asked the sharpest question anyone has put to them about liveability. Plus a turn few Copenhagen conversations take — both guests being properly rude about their own city. Too planned. Too alike. And on course to price out their own children.

T7 · E9

11 ago 2026

1:02:47

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 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 their passions in their 5-9 hours, i.e. outside of work. You're going to hear from Mo, who has a much sunnier disposition on Toronto than I. We'll even get into a bit of an agreeable disagreement. Where we do see eye to eye is we need more of a mindset for hospitality in urbanism. Then you're hear from Laura who will share her story of arriving in Canada, finding a great job at Mosaic and the connections required to make it real. She now pays it back too, solving a massive challenge in Canada as many people not from here need better opportunities. And lastly, we'll get into it with Nick who has created one of the coolest independent culture spaces in the city. As possible the world's most eclectic urbanism podcast, this is a properly eclectic episode! Check the Substack for various links. https://challengercities.substack.com/p/challenger-cities-ep95-the-5-to-9 https://www.mosaic.com/ https://threehorses.ca/ https://www.linkedin.com/company/notworking-to-networking/?originalSubdomain=ca

T7 · E8

4 ago 2026

1:38:31

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 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 plant what to do, you can only offer it a trellis and see what climbs. We get from there to Sussex, its improbable 2006-vintage "ancient" charter, and We Wunt Be Druv, a game about refusing the devolution you're handed and designing one that works round here instead. It's really a conversation about agency; why you only notice what you feel you could act on, why organisations don't care about things but people do, and why the smallest possible thing of a homemade game played in Thomas Paine's front room might be how the biggest possible future actually starts. And this is the piece that kicked off our conversation: https://buttondown.com/artefacts/archive/artefact-263/

T7 · E7

29 jul 2026

1:00:55

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 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 Thyself under their business The Twenty Six Collective, and who arrive at cities from completely outside the usual circles: the talent side of startups and the full entrepreneurial tour, plus an apprenticeship under two Dutch master coaches. Their premise, once you follow it through, is uncomfortable for our industry. Cold teams build cold places. The conversation runs from a survey that found people drowning in success and starved of fulfilment, through Sam's reframe of spirituality as "an antidote to control" — which stops being woo the moment you notice our whole profession is built on control and nobody's trained to hold value they can't yet measure — to the idea of a "spiritual board of directors" in rooms that currently have economists, engineers and everyone except the person responsible for why a place will be loved rather than merely used. Flo names the wound from the talent side: the waste of human potential she watched inside successful companies, brilliant people ground down into something far smaller than what they've got. It connects, in the end, to a lot of what guests keep circling on this podcast — Richard Fisher's monodisciplinary confidence, the human proposition that goes undesigned — only worked one layer deeper, inside the people doing the building. The through-line is that the maker is the medium: you can't design warm, human places with people who've been trained out of being warm and human themselves. As ever, we land on the biggest possible future — Flo's vision of helping people look inward rather than outsource the answers — and the smallest possible thing, Sam's deceptively tiny instruction to stop making if-then statements and just step forward. Whether you build railways, run a team, or just recognise yourself in the seven-figure misery, this one's worth your time. Then go and try it on yourself. https://knowthyself.onrender.com/

T7 · E6

15 jul 2026

1:04:07

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, 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, peaceful renderings we keep selling ourselves. This is a man who's built his whole life around cities and stays ahead of the curve by avoiding urbanists — going out of the bubble to talk to the venture capitalists and technologists who are quietly deciding what our streets and buildings become, whether or not the word "city" appears anywhere in their job title. We get into why Italy is secretly the master of sprawl rather than the piazza (and what the rest of us should be hiring Italians to teach us), why the future of cities is being written in Zurich and Stockholm rather than at the planning conference, and the idea that gives the episode its title: that cities are mental weapons, and the real work is citizen-making, not city-making. You don't need a big budget or an important title to change your patch of the world — you need to actually show up for the place you live. It's one of my favourite conversations of the series so far. Have a listen, and if it lands, come and be utopian with us in Turin this October.

T7 · E5

7 jul 2026

43:53

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