
Lev Kushner sent me an email saying public art is rarely cool, not very good at attracting visitors, and kind of a waste of money. So we made a podcast out of it. Lev runs Department of Here, comes from a family of...


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.
Required Pod Score for this podcast. PitchCentric checks your profile against host openness, topical fit, and audience signals before you generate a pitch.
Contact path
Public web form
Booking probability
32%
Guest openness
Selective
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Signup to Generate a PitchIain 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.
Recent episodes include "Challenger Cities EP107: Cities Are Ritual Factories with Lev Kushner" (27 October 2026, 52 minutes), "Challenger Cities EP106: The View from the Fish Counter with John Sills" (15 October 2026, 38 minutes), and "Challenger Cities EP105: Coming to Play with the Downtown Denver Partnership" (5 October 2026, 53 minutes).
Challenger Cities publishes roughly weekly, with episodes averaging 62 minutes.
Booking probability for Challenger Cities is 32%, and the host is rated Selective on guests. Challenger Cities requires a Pod Score of 80 or higher. Challenger Cities's contact route on record: public web form.
The strongest fits for Challenger Cities are Architecture & Engineering and Property Management & Appraisal. Challenger Cities has an arts audience.
Challenger Cities is an arts podcast.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

Lev Kushner sent me an email saying public art is rarely cool, not very good at attracting visitors, and kind of a waste of money. So we made a podcast out of it. Lev runs Department of Here, comes from a family of...

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...

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 Montrรฉal this year, studying how a...

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...

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...

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...

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...

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...

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 Montrรฉal, by way of Toronto, where she spent much...

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...

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...

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...

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...

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...

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...

Challenger Cities
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...

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...

Episode #13
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...

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...

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...
Recent guests on Challenger Cities. Study who booked and why before you pitch.
BT Professor and Chair of Major Programme Management, University of Oxfordโs Saรฏd Business School
Principal Team Teach trainer, Great Bridge Battlefield and Waterways History Foundation
Copenhagenize Design Company
author, journalist, broadcaster and consultant specializing in food and drink, Tow Center for Digital Journalism at Columbia University
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