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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.

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. 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.

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. 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.

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.

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/

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

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!

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.

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/

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/

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.