Challenger Cities

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.

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

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/