Published by Iain Montgomery
Iain Montgomery of Now or Never Ventures interviews urbanists, creatives, transit and development types to explore how cities can punch above their weight and create distinctive new futures outside of the tired playbooks.
Listen on Apple PodcastsThis 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.
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.
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!?
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.
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.
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
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.
Canada is, well might be, building a high speed train. At long last after 50 odd years of talking about doing so. But concerningly, there is much negative noise around the project as it seems it might not really be learning the lessons for how successful projects have been delivered elsewhere, and where projects for building fast trains have gone wrong. This podcast is with Michael Schabas, a Canadian, who knows all about how to make these projects successful. It's a really honest and open conversation about how to build HSR, what Canada is missing just now, and how we can hopefully influence Alto to ensure we actually learn from how it's been done elsewhere. If you like the idea of HSR, or even if you actually think it's a bad idea, well you should probably listen to this episode and get a feel for yourself. Michael's work is also available to be found here: https://www.highspeedrailcanada.com/p/all-canadian-hsr-studies.html
Two risk-management cultures looking at each other across a table, each waiting for the other to move. That's rail's relationship with venture capital. Iain talks to Richard Fisher, founder of Future Travel Studio, about why nobody would fund his Dream Suite flatbed seat for trains, even after InnovateUK had backed it and operators had tested it. About rail's proposition gap, the incumbents who monetise complexity rather than solve it, and why every discipline in the chain can be doing its job correctly while the sector as a whole still can't move. Plus what a transatlantic venture studio is trying to build instead.
This is a lovely episode with Thomas Ableman (a returning guest!) that is mostly about an amazing project he and a few volunteers recently secured funding to go and deliver called Mini Switzerland in the Derbyshire hills. We often hear about how it's not possible to deliver high quality public transport because there simply aren't enough people to make it worthwhile. That makes a lot of people feel quite clever in saying no to it. But then go an explain how Switzerland works then. If a nation that has some of the most challenging geography, and not particularly huge numbers of people, can deliver frequent, integrated, efficient and enjoyable transport to villages with as little as 300 people half-way up a mountain ... then I don't think we've got much excuse in the UK, US and Canada. We also talk quite a lot about trams, and how despite me really not being a fan of Andy Burnham, the fact a man that is probably best known for trams and yellow buses actually might make them an important topic for Westminster government to take more interest in.
One of the best people I met last year was Samantha Peart. We were in Copenhagen for a few days and of our fellows group, I have to say she asked the best questions. She’s also exceptionally good at getting you to question your assumptions or reflect on why you might think what you’re thinking. And that really comes through in this conversation, with real examples that have had a massive impact on projects and places. I’m such a fan of hers, that I even let her destroy the magic wand question. Because she makes an excellent point about it. So if you’re involved in any sort of urbanism, placemaking or infrastructure project. This really is one you need to have a listen to.
If you liked our episode with Ilana Altman about The Bentway, then you'll like this one with Ken Greenberg, because he's part of that origin story. Ken is a legend in Toronto urbanism circles, as someone who did pioneering work in his early career in the city and then took it to the likes of St. Paul and Boston in the US. We set up this episode to discuss work he's doing around the newly free'd up airport lands in Pickering, ON and his vision to turn this into a new part of the Rouge National Urban Park. It's a conversation that we hope can breathe life and optimism into the Toronto urban discourse, as many of the components of what Challenger Cities need is right there. It just needs unleashing.
This is a bit of a different episode because we're talking about what cities are made of, rather than how we make our cities. I had the pleasure of meeting Saurabh Mangla on a day where I was hot, tired and just wanted a beer. But getting the story of his materials lab and how he's working to explore how cities use their materials more effectively, efficiently and in many ways, delightfully is a good reviver. We talk about Singapore, India and how material resources can be an excellent way for cities to demonstrate their Challenger mindset.
Gerald Babel-Sutter is the founder of Urban Future, a 14-year-old event that has grown from a workshop for ten city officials in Graz to a gathering of 2,000 people from 290 cities in 48 countries. The premise hasn't changed: get the actual project managers in a room, not the communications directors, and ask them to talk honestly about what went wrong. In this conversation we cover how a frustrated city official's complaint over a beer became the founding logic of one of Europe's most distinctive urbanism events, why Oslo's deputy mayor told a room full of city planners to never call anything a car-free city centre, what Helsingborg's annual fuck-up of the year award reveals about institutional culture change, and why Istanbul — four religions, sixteen million people, a more open visa regime — is where Urban Future is heading in April 2027. Gerald also makes a case that the knowledge flows in urbanism run almost entirely in the wrong direction, and that who gets a visa to attend whose conference is one of the most consequential questions in the field that nobody is talking about. https://urban-future.org/
Jen Angel thinks Canada is closer to a moment of triumph in how it builds than it has been in her lifetime. The conditions are there. What's missing is enough people in positions of authority with the permission to say yes. Jen leads Evergreen, the national organisation behind the Brick Works in Toronto and a portfolio of public space projects across the country — from school grounds transformations in Halton and Winnipeg, to a Mi'kmaq Native Friendship Centre-led project in Halifax, to the Toronto ravines programme. Before Evergreen, she ran a Nova Scotia crown corporation that built the Halifax Waterfront, Peggy's Cove and Lunenburg Waterfront, alongside rural broadband and innovation hubs. She also sits on the Canadian Infrastructure Council, the ministerial-appointed arm's-length body writing Canada's first national infrastructure assessment. In this episode we get into: — Why "it's not that much harder to build a good one than a crappy one" might be the most damning line about Canadian infrastructure this year — The permission problem: why no has become the safe answer across our institutions, and what it costs us — Multi-benefit projects, and why our funding model is almost institutionally incapable of recognising them as legible — Why this particular moment — tariffs, geopolitical pressure, a public mood that actually wants things to be tried — might be a generational opportunity — What the East Coast knows about resilience that the rest of the country keeps forgetting — The Evergreen Conference at the Brick Works, May 6–7, theme: Cities Bursting with Life
Alex Bozikovic is the architecture critic for the Globe and Mail, which in practice means he writes about everything from housing politics to the public realm to the quiet cultural erosion that happens when a city stops expecting much of itself. In this episode, Iain and Alex dig into why Toronto ... a city with extraordinary people, genuine sophistication and real financial muscle ... keeps failing to act on what it already knows. We cover the Spadina Expressway and the identity it left behind, the Ontario Science Centre closure and what it reveals about the state of progressive urban politics, the suburbs as the real story of Toronto's diversity, and what a bar in a 1899 attic has to do with the soul of a city. Plus Montreal, Sugar Beach, the Sanaaq Centre, and why the best things in Toronto tend to happen despite the default settings rather than because of them.
Exploring Urban Troubleshooting In this episode, Heath Gledhill and Tom Shield, founders of GledHill Shield, share their extensive experience navigating complex urban infrastructure projects. They discuss how early decision-making, constraints and collaborative design principles can transform city development. Whether you're an urbanist, engineer, architect, designer or planner, their insights challenge conventional project setups and advocate for more intentional, purposeful city shaping. Key Topics: The importance of framing the core problem before designing solutions How constraints foster innovative and effective urban design The role of the business case in guiding project decisions and maintaining focus Challenges with briefs, approvals and stakeholder engagement in infrastructure projects The power of compromise and trade-offs in city development Embedding aspiration and community impact through creative public programs Cross-disciplinary integration as a necessity for successful urban projects The influence of cultural attitudes—Australia, Canada, the UK—on project delivery The potential of digital tools and visual artifacts to ground project vision Building trust and social license through transparency and stakeholder inclusion The value of humility, purpose and intentionality in urban planning