Challenger Cities

by Iain Montgomery

Season 7

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

S7 · E8

Aug 4, 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/

S7 · E7

Jul 29, 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/

S7 · E6

Jul 15, 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.

S7 · E5

Jul 7, 2026

43:53

Challenger Cities EP91: Expanding Your Luck Surface Area with Matt Ballantine

In this spirit of being the world's most eclectic podcast about cities and places, this episode is a bit random. Which is good, because it's with Matt Ballantine and he's written a book, called Random with Nick Drage. Some might say 120 short stories that can be shuffled into any order isn't actually a book, but I read it as one, and it's excellent. Plus many of the stories are about cities, places and people in them. In a world where we spend so much time filtering out opportunities for luck, serendipity or just the unplanned ... this is a conversation that is very important for dragging people that feel everything can be perfectly zoned or planned, back into the real world.

S7 · E4

Jul 2, 2026

47:31

Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik

This is an episode about a big, ambitious idea. Which is why people are quick to label it as crazy. But Britain, like many developed nations has a housing crisis. The country simply doesn't build enough good homes for the people who want to live there, and incremental approaches are going to solve for it. So along comes Shiv Malik, a journalist by trade, with an idea for a new city, not too far from Cambridge, becoming a place one million people will call home. Naturally, he's had a lot of scrutiny, but he's steadily winning people over. This conversation explores where the idea came from. why it's needed, the biggest challenges, and the reasons to believe something like this could actually happen. One of an incoming Prime Minister to consider perhaps!?

S7 · E3

Jun 29, 2026

1:04:03

Challenger Cities EP89: To Do, Not Just Be with Gil Penalosa

This episode is a zinger. Because Gil Penalosa came in ready to talk! He doesn't hold back as he discussed the issues with Toronto municipal projects, where the city could be amazing but is often found lacking in ambition. We explore ideas from the absolute basics of providing space to walk, why we might want to reframe the idea of the NIMBY to the one of the CAVE person - Citizens Against Virtually Everything!, and how rather than debating an idea to death ... maybe we just try it and see what happens. As Toronto comes up to the mayoral election, Brad Bradford or Olivia Chow might actually want to pay some attention.

S7 · E2

Jun 25, 2026

1:34:37

Challenger Cities EP88: The Neighbourhood is the Amenity with Alicia Pederson

Alicia Pederson went from a Renaissance literature PhD and a two-year stint as an au pair in Florence to becoming one of the best voices on a deceptively simple idea: the courtyard in the middle of apartments. After watching family friends priced out of Chicago one by one - not because they disliked the city, but because the only family housing on offer was a million-dollar house with a private yard - she started asking why North America builds apartments as huge, hotel-like buildings when European cities solved this centuries ago. Her answer is the courtyard block with apartments that live like houses, with a front door onto the street and a back door onto a shared green courtyard. It's a housing idea that's genuinely lovable, demonstrably doable and cheaper to build ... and, as we get into, almost entirely illegal to build in many North American cities. In this conversation we dig into why a shared courtyard somehow feels more private than a fenced backyard, why your kids don't actually want a yard (they want friends to play with), and why the amenity-stuffed apartment building — gym, dog wash, rooftop — is starving the very neighbourhood that should be the amenity. Alicia and Iain make the case that density is a feeling before it's a number, that the cities which kept their apartments are the ones that proved resilient, and that the fix isn't masterplanning but handing cities back their oldest tool: lay the streets, cut the right parcels, and let a hundred small builders fill them in. We also push on where it's hardest — the cold-start problem, who governs the shared space, the parking question — but suspect you will come away convinced this is a concept every Challenger City should be looking at as it reimagines the home, the street and the shape of a life.

S7 · E1

Jun 21, 2026

58:36

Season 6

Challenger Cities EP87: Bringing Sexy Back to Transit with Mark Salsberg and Jonathan English

Canada is about to spend more on transit and rail than the oil sands are worth, and it's doing it without a national rulebook, a training pipeline or much recent memory of how to build well. So is that a crisis, or the best shot a country has ever had at becoming a genuine transit Challenger? This episode is a double act with two people who think about this for a living. Mark Salsberg is co-founder of TRACCS (the Transit Rail Association for Canadian Contractors, Maintainers, Operators and Standards), and his mission is the unglamorous connective tissue Canada skipped: standards, training, and procurement assurance. Jonathan English leads Infrastory Insights, holds a doctorate in urban planning from Columbia, was previously policy director at the Toronto Region Board of Trade, and the person who reminds us of the "Toronto Model" ... the heretical idea that good service is what actually drives transit demand, not the other way round. It starts a little dry and then gets properly good. We get into why Canada is one of the most expensive places on earth to build, why benchmarking against the United States ("the worst in the developed world," per Jonathan) imports all the wrong lessons, and why we keep trying to force passenger rail into a freight-shaped hole. But this isn't a kicking. There's a real opportunity buried in here for Canada acting as a bridge between a mature-but-complacent Europe and a car-choked North America that badly needs another way for its cities to grow. What we get into: The three things Canada never built: standards, training, procurement assurance Why we "learn bad lessons" and never close the loop on projects The one genuinely remarkable thing Toronto did after the war — and still benefits from Infrastructure vs service, and why Canada has both problems "Is this an engineering problem, or a phone-call problem?" Bringing sexy back to transit: careers, signal engineers, and the passion the industry side-eyes The biggest possible future and the smallest possible thing — including just running the buses more often

S6 · E13

Jun 15, 2026

1:00:32

Challenger Cities EP86: How the Robocars Meet the Curb with Bern Grush

Good new Challenger Cities episode today, all about autonomous vehicles and the bit that our guest, Bern Grush, thinks cities need to be thinking about more now. Like them or not, robotaxis are coming to cities. And for all the spectacular technology that helps cars drive themselves, the have some meaty challenges ahead. One of them being what happens when they interact with the curb. We've already seen how fleets of autonomous cars can create new forms of congestion, and we've seen tragic accidents come about as people open doors into the likes of passing cyclists. A few years ago I was involved in a project for a big tech firm looking at this, but it was rather quickly mothballed as big automotive clients shooed them away from it. The hardest part though was the orchestration layer between the operators of autonomous vehicles (think the ridehailing firms minus drivers) and deliveries that are seeking to move away from having a human at the wheel too. It effectively means redesigning who can stop where, when, for how long, and normally monetising it in the same way on-street parking is done today. So if you want to stop on a busy road to pickup/dropoff ... well you're going to pay for that. And you might be incentivised to do so somewhere quieter, or even let that tempt you towards public transport instead. We have finite space in urban areas, so we're going to need to be clever to make sure autonomous driving doesn't choke the city.

S6 · E12

Jun 11, 2026

58:37

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