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PODCAST

Challenger Cities

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.

arts design

All Episodes

40:54

EP50: If a City Can’t Handle a Little Kink ... with...

Challenger Cities ·

2025/10/29

This one’s a little different. We sat down with Lady Valeska, a professional dominatrix now based in London, to talk about what cities, workplaces, and leaders could learn from the world of kink.It turns out, quite a lot!We talked about power, shame, permission, and trust, but not in the ways you’d expect. Lady Valeska’s version of dominance isn’t about control, rather it's about awareness. She reads people the way good designers read context: through signals, not assumptions.We got into:How

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65:21

Challenger Cities EP49: How the Screen Has Killed the...

Challenger Cities ·

2025/10/27

Iain Montgomery and Greg Lindsay explore the intersection of urbanism and technology, discussing how screens and AI are reshaping cities. They delve into the implications of surveillance, the concept of the 15-minute city, and the importance of social equity in urban planning. The discussion also touches on Estonia's digital governance model and the challenges posed by the Saudi urban experiment. Ultimately, they emphasize the need for community engagement and a reimagined approach to urban

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58:52

Challenger Cities EP48: Live, Move, Rest ... The...

Challenger Cities ·

2025/10/20

In this conversation, Iain Montgomery and Anupam Yog delve into the concept of urban mindfulness and its implications for city design. They explore how mindfulness can enhance urban living, the importance of community engagement, and the potential of lesser-known cities like Ramsgate as models for transformation. The discussion emphasizes the need for compassion in urban planning and the idea that cities should facilitate a balance between movement and stillness. Anupam shares insights from his

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56:25

Challenger Cities EP47: Cities on the Couch with...

Challenger Cities ·

2025/10/02

SummaryIn this conversation, Charles R. Landry discusses the concept of creative cities, emphasizing the importance of imagination, psychology, and human-centered design in urban planning. He explores how cities develop identities, the psychological complexities they face, and the impact of gentrification on urban evolution. Landry highlights the need for spaces that foster connection and the role of curiosity in understanding urban dynamics. He concludes with thoughts on the future of cities and

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52:53

Challenger Cities EP46: Stitching the Fragmented City...

Challenger Cities ·

2025/10/01

In this conversation, Iain Montgomery and Rashiq Fataar delve into the complexities of urbanism in South Africa, particularly focusing on Cape Town. Rashiq shares his journey from actuarial science to becoming a self-appointed urbanist, emphasizing the need for innovative urban solutions that address social and spatial inequalities. They discuss the current state of South African cities, the lessons learned from global urbanism, and the challenges faced in urban development. Rashiq highlights the

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43:13

Challenger Cities EP45: Utopian Hours - Turin’s...

Challenger Cities ·

2025/09/26

In this conversation, Iain Montgomery speaks with Luca Ballarini about Utopian Hours, a festival in Turin that celebrates urbanism and creativity. They discuss Luca's journey from architecture to graphic design, the challenges of transforming urban narratives, and the unique identity of Turin as a city. The conversation highlights the emotional connection people have with their cities and the importance of community engagement in urban development. Luca shares insights on the festival's diverse

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66:55

Challenger Cities EP44: Your City Isn’t Crowded, It’s...

Challenger Cities ·

2025/08/19

aniel Herriges joins us to explore one of the most underestimated levers for better cities: parking reform. A longtime Strong Towns writer and co-author of Escaping the Housing Trap, Daniel explains how the post-war American obsession with car storage has quietly shaped—and often strangled—urban life.From zoning codes that make beloved main streets illegal, to the $127 billion annual subsidy for “free” parking, Herriges walks through the cultural, financial, and environmental costs of designing

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61:52

Challenger Cities EP43: Daring To Be Different with...

Challenger Cities ·

2025/08/19

Andy Nulman is a man who’s seen Montreal through every era — and he’s not afraid to call out what’s gone wrong. In this no-holds-barred conversation, the Just for Laughs co-founder shares his frustrations with small-minded politics, lost ambition, and a city that’s forgotten how to dream big. We talk about Montreal’s golden ages, its identity crisis, and what it would take to fix the city’s flow, literally and metaphorically.From language laws to bike lanes, bad branding to bold leadership, this

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61:32

Challenger Cities EP42: Hauling Towards the Future...

Challenger Cities ·

2025/08/01

TakeawaysMichael Wexler's journey into urbanism began unexpectedly.He transitioned from cycling-focused projects to broader transit planning.Cargo bikes represent a gap in North American urban mobility.Infrastructure is crucial for increasing cycling and cargo bike usage.Copenhagen's cycling culture serves as an inspiration for Montreal.Mulo aims to fill the cargo bike market gap in Montreal.Community partnerships are essential for Mulo's success.E-bikes have transformed the cargo bike

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53:39

Challenger Cities EP41: Cities in Limbo with Diana Lind

Challenger Cities ·

2025/07/29

Exploring Urban Evolution with Diana LindJoin host Iain Montgomery in a captivating conversation with Diana Lind, renowned urbanist and author, as they delve into the complexities of modern cities. From the challenges of zoning reform to the potential of urban public education, this episode offers a thoughtful exploration of how cities can transform and thrive.Key Topics:The evolution of cities post-pandemic The role of Starbucks in urban development Zoning reform and its impact on housing The

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48:36

Challenger Cities EP40: Hovering Above the Status Quo...

Challenger Cities ·

2025/07/25

What if commuting from Niagara to Toronto didn’t mean hours in traffic or waiting on a slow, infrequent train? Erika Potrz thinks there’s a better way, and it involves a military‑grade hovercraft gliding across Lake Ontario in just 30 minutes.In this episode, we talk about why Hoverlink could change more than just the QEW commute: from making travel joyful again (yes, DJs on board), to giving people their time back, to rethinking the connection between transport, tourism, and housing. Erika also

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58:28

Challenger Cities EP39: A Public Service Steeped in...

Challenger Cities ·

2025/07/24

Northern has long been the UK’s biggest rail operator by stations—and one of its most under-loved. But under Alex Hornby, it’s getting a dose of something different: warmth, character, and a clear sense of purpose.In this episode, we talk to Alex about his journey from making buses in Burnley genuinely desirable to leading a railway that serves some of the North’s most complex and underserved places. We explore why he believes public transport should be treated like a product people love, not just a

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57:31

Challenger Cities EP38: The City Fixer's Guide to...

Challenger Cities ·

2025/07/24

Every city tells itself a story. In Kansas City, it’s one of manageability: there’s parking when you want it, space to drive, and just enough shine in a few key places to make it feel like things are ticking along. But scratch the surface—or take a walk down the streets that aren’t newly polished—and another story emerges. One of unrealised potential, oversized roads, empty sidewalks, and neighbourhoods running on a fraction of their former energy.In this episode, we sit down with Kevin Klinkenberg,

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62:28

Challenger Cities EP37: The Recipe Book for Cities...

Challenger Cities ·

2025/07/24

The City’s Recipe Book: Borrow the Technique, Use Your Own Ingredients with Guillermo BernalCities don’t work because of glossy plans or polished renderings. They work because people use them, reshape them, and often subvert them in ways no planner predicted.That’s the world Guillermo Bernal inhabits. A political scientist turned place-maker, Guillermo has spent the past decade helping communities across Mexico reclaim their public spaces — not through sweeping vision statements, but through small,

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61:36

Challenger Cities EP36: From Corporate Innovation to...

Challenger Cities ·

2025/07/24

What happens when you take someone fluent in corporate innovation and drop them into the world of council-led adult social care? A surprising amount of clarity on what actually counts as value.In this crossover episode, Iain Montgomery is joined by his usual SIDEBAR co‑conspirator, Charlie Rowat, to explore how innovation changes when you swap corporate executives for councillors, consumers for citizens, and quarterly shareholder updates for public accountability.Charlie has spent the past few

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57:06

Challenger Cities EP35: After Dark and Into the...

Challenger Cities ·

2025/07/24

What does it take to make a city work after dark?In this episode, we're speaking with Mathieu Grondin, Ottawa’s first-ever Nightlife Commissioner, about why nightlife isn’t just parties and late bars, it’s infrastructure.The conversation explores why Ottawa created this role, what mid-sized cities can teach their bigger siblings about cultural development, and how better policy can make cities safer, more vibrant, and more economically resilient. From public transit to zoning reform, and from the

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61:13

Challenger Cities EP34: The Magnetic, Messy, Cities...

Challenger Cities ·

2025/07/24

The Magnetic, Messy Cities People Don’t Leave — with Sofia SongWhat actually keeps people in cities? It isn’t just housing supply, transit plans, or economic growth. It’s something far less tangible, emotional connection.In this episode, we speak with Sofia Song, Head of Global Cities Research at Gensler, about the City Pulse study, one of the most ambitious looks at urban life anywhere in the world. Drawing on insights from 65 cities, 30 countries, and over 100,000 people, it explores what makes a

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52:49

Challenger Cities EP33: Riding Through Stories, Not...

Challenger Cities ·

2025/07/23

What if cycling policy wasn’t about bike lanes but about joy, dignity, and connection? In this episode of Challenger Cities, we sit down with Michela Grasso — Italian researcher, urbanist, and co-author of the Urban Cycling Manifesto — to explore how cities can rethink mobility through culture, inclusion, and imagination.We talk about:Why benches might matter more than bike lanes.How e-bikes are transforming independence for older riders.Mama Agatha’s migrant cycling lessons in Amsterdam.Bologna’s

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53:46

Challenger Cities EP32: How to Love a Town Back to...

Challenger Cities ·

2025/07/11

We talk a lot about fixing cities—but less about why we’ve let them decline in the first place. This conversation with civic pride expert Jeff Siegler is a deep, uncomfortable, and often inspiring look at how we got here and what it takes to turn it around.Jeff doesn’t believe in sugar-coating. He’s spent his life fighting against civic apathy and calling out the ways we’ve outsourced care, maintenance, and even meaning in our places. We talked about what happens when people stop seeing their city

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62:56

Challenger Cities EP31: Building Transit, Trust and...

Challenger Cities ·

2025/07/09

Russell King didn’t start out in transport. But somewhere between regenerating Battersea and reforming Sydney’s transit system, he became—by his own admission—“a transport tragic.”In this wide-ranging conversation, Russell shares what it actually takes to build infrastructure that shapes cities, why most governments lose the capability they’ve just built, and how our obsession with roads and cost-cutting gets in the way of good transport policy. We get into:– Why rail lines define what kind of city

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