95 episodes
Challenger Cities EP93: The Maker is the Medium with Florence Okin and Sam Cohen
15/07/2026 | 1h 4 mins.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. Challenger Cities EP90: It Only Sounds Mad Because We Think Small with Shiv Malik
29/06/2026 | 1h 4 mins.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.
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About Challenger Cities
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.
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