Challenger Cities

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?
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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!

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

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.

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

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.