Iain Montgomery
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.
Author
Iain Montgomery
Category
Podcast website
Latest episode
Jul 7, 2026
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Episodes
Challenger Cities EP67: Watching a World From Behind the Window with Füsun Aydın 25.02.2026 51:59
Füsun Aydın has spent twelve years reading people from a window in Amsterdam. Cities would be better places if the people planning them had half her instinct. Füsun is Turkish-born, a trans woman, a former sex worker, and now the madam of a bordello in Amsterdam's red light district. She came to the Netherlands as an asylum seeker at nineteen, having grown up in Istanbul where trans women have no...
Challenger Cities EP66: Urbanism Without the Excuses with Mikael Colville-Andersen 19.02.2026 1:03:38
In this episode of Challenger Cities , Iain Montgomery is joined by urban designer, filmmaker, and author Mikael Colville-Andersen for a wide-ranging conversation about why cities so often know what works, yet struggle to act on it. We start with train stations and the importance of arrival, before moving through cycling, design, experimentation, Nordic urbanism, and finally Mikael’s recent work i...
Challenger Cities EP65: Sitopia with Carolyn Steel 16.02.2026 1:21:36
Cities are usually explained through buildings, infrastructure, policy and planning. Food rarely gets a look-in. Which is strange, because for most of human history, cities existed in the first place because we learned how to feed ourselves at scale. Farming allowed settlement. Settlement allowed specialisation. Specialisation gave us civilisation. Long before zoning codes or masterplans, food dec...
Challenger Cities EP64: Tourism as a Stress Test with Maryam Siddiqi 10.02.2026 1:00:08
Tourism is big business. Cities spend vast sums attracting visitors, promoting landmarks and polishing their image. What they’re far less good at is thinking through the experience of actually being there. How a place works once you arrive. How you move around it. What makes sense, what doesn’t, and what quietly undermines the affection people might otherwise develop for a city. In this episode, I...
Challenger Cities EP63: The Pub Is a Public Service with Pete Brown 06.02.2026 49:15
In this episode of Challenger Cities , we've got Pete Brown, one of the UK’s most thoughtful writers on beer, pubs, and drinking culture. Pete has spent decades writing about pubs not as lifestyle accessories or nostalgic backdrops, but as places where history, behaviour, economics and everyday social life collide. We talk about why pubs weren’t designed, branded or planned into existence, but evo...
Challenger Cities EP62: Cities for People Who Want to Try Things with Patti Baston 02.02.2026 1:06:44
Most cities are designed around a surprisingly narrow idea of who gets to feel comfortable in public. In this episode of Challenger Cities , Iain Montgomery chats with Patti Baston , who runs a feminisation makeover service in Manchester. On the surface, her work might sound niche. In practice, it turns out to be a sharp and unexpected lens on how cities really work, who they quietly exclude, and...
Challenger Cities EP61: Sweat and the City with Glenn Auerbach 27.01.2026 50:55
Iain Montgomery talks with Glenn Auerbach about why sauna, bathing and cold-water culture has suddenly gone mainstream in cities around the world, and why the reasons go far beyond health trends or wellness hype. From floating saunas and mobile heat rooms to dawn swims in urban rivers and harbours, we explore how shared rituals of heat, cold and recovery are reintroducing forms of social connectio...
Challenger Cities EP60: Designing Cities in Pencil, Not Pen with Jasmine Palardy (again) 19.01.2026 49:54
We reconnect with Jasmine Palardy almost eighteen months after our very first conversation to reflect on what has changed in how we think and talk about cities, and what hasn’t. Exploring why real progress in cities comes not from imposing control but from embracing uncertainty, loosening the grip of over-planning and letting “accidental urbanists” and informal city builders shape change on the gr...
Challenger Cities EP59: Building Faster Than Memory with Ruchita Bansal 19.01.2026 53:41
Ruchita Bansal discusses what happens when modern infrastructure projects are built at speed but don’t connect with the deep, informal systems that make cities work. Drawing on her experience across Indian urban planning and large-scale delivery, we explore how cities in India are being transformed rapidly with metros, highways and ambitious timelines, yet often miss the connective tissue of every...
Challenger Cities EP58: The World's Best Cities with Chris Fair 19.01.2026 52:56
Chris Fair, CEO of Resonance and publisher of "World's Best Cities" talks about what really separates the world’s cities. As Chris explains, obsessively measured performance isn’t enough to explain why some cities feel magnetic and others feel interchangeable. We unpack the World’s Best Cities framework and how liveability, prosperity, and a often-overlooked dimension of lovability shape both the...
Challenger Cities EP57: Young People and the New Rules of Money with David Akermanis 19.01.2026 56:12
Researcher and strategist David Akermanis talks about how young people are navigating a world where traditional financial stability has eroded and cities themselves shape economic life. We explore why the familiar narratives about youth finance, savvy versus reckless, miss the deeper tension underneath. Across stories of early career precarity, the blending of gambling and investing, the limitatio...
Challenger Cities EP56: Why Empty Space Is Never Neutral with Evan Snow 19.01.2026 50:05
Evan Snow, co-founder of Zero Empty Spaces talks about why vacancy in cities isn’t a neutral pause but an active force shaping how we feel, move and connect in urban places. We explore how empty storefronts, abandoned commercial spaces and obsolete interiors drain confidence and disrupt movement, and how creative, low-risk activation can turn them into meaningful places without waiting for the “pe...
Challenger Cities EP55: Impossible City - Paris in the 21st Century with Simon Kuper 19.01.2026 47:55
In this episode of Challenger Cities , Iain Montgomery talks with journalist and author Simon Kuper about his book Impossible City: Paris in the Twenty-First Century and what modern Paris really is beneath its postcard reputation. We start with Simon’s accidental arrival in the city and the surprising affordability and vibrancy Paris once had, and then explore how it has changed into a global powe...
Challenger Cities EP54: Rethinking Ireland, the Too Often Misunderstood Challenger Country with Peter Ryan 19.01.2026 1:07:32
In this episode of Challenger Cities , Iain Montgomery is joined by economist and commentator Peter Ryan for a wide-ranging conversation about Ireland, a country that is often talked about but rarely understood. We dig into why Ireland’s global reputation, from tax haven clichés to headline GDP figures, obscures the lived reality on the ground. Peter unpacks how the country’s early post-independen...
Challenger Cities EP53: The Logic Beneath the Madness of Transport with Marcus Mayers 03.12.2025 48:48
Iain Montgomery and Marcus Mayers discuss the complexities of transport systems, focusing on the balance between passenger experience and operational efficiency. They explore the impact of government regulations, the role of technology, and the need for a mindset shift in transport management. The discussion emphasises the importance of understanding passenger needs, improving accessibility and re...
Challenger Cities EP52: Culture as a Form of Wealth with Paul Owens 24.11.2025 48:52
In this episode of Challenger Cities , we chat with Paul Owens, co-founder of BOP Consulting, long-time collaborator of Charles Landry, and one of the most quietly influential thinkers on culture and cities anywhere in the world. Paul has spent decades helping cities understand something most of them overlook: culture isn’t a sector or an industry, it’s an operating system of a place. It’s who you...
Challenger Cities EP51: Women Changing Cities with Melissa Bruntlett 10.11.2025 57:00
Melissa Bruntlett discusses her book 'Women Changing Cities' and the transformative role of women in urban mobility and planning. She emphasizes the importance of empathy, care, and community engagement in creating sustainable and equitable cities. The discussion covers various global cities, the challenges faced in transportation, and the impact of female leadership on urban change. Bruntlett sha...
EP50: If a City Can’t Handle a Little Kink ... with Lady Valeska 29.10.2025 40:54
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...
Challenger Cities EP49: How the Screen Has Killed the City with Greg Lindsay 27.10.2025 1:05:21
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....
Challenger Cities EP48: Live, Move, Rest ... The Conscious City with Anupam Yog 20.10.2025 58:52
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...
Challenger Cities EP47: Cities on the Couch with Charles Landry 02.10.2025 56:25
Summary In 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 rol...
Challenger Cities EP46: Stitching the Fragmented City with Rashiq Fataar 01.10.2025 52:53
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 lesso...
Challenger Cities EP45: Utopian Hours - Turin’s Festival of the Possible with Luca Ballarini 26.09.2025 43:13
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 impo...
Challenger Cities EP44: Your City Isn’t Crowded, It’s Just Full of Cars with Daniel Herriges 19.08.2025 1:06:55
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...
Challenger Cities EP43: Daring To Be Different with Andy Nulman 19.08.2025 1:01:52
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,...
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