Challenger Cities

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 legal discrimination protections and sex work on the street is both common and dangerous. The move wasn't idealism — it was survival arithmetic. In four years...

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 in Ukraine, where urbanism takes on a very different meaning.

We cover:

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 decided where cities formed, how power worked, and why empires survived or collapsed.

In this episode, I’m joined by architect and writer Carolyn Steel, whose books Hungry City and Sitopia have quietly reshaped how many people think about fo...

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, Iain Montgomery is joined by Maryam Siddiqui, a Toronto-based travel and culture journalist who came to travel writing sideways rather than by design. Starting out in PR before moving into business jour...

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 evolved slowly through circumstance, need, and habit. Why that matters for cities obsessed with masterplans and placemaking. And why attempts to “recreate” pub culture so often feel hollow.

Pete offers a...

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 how play, permission, and experimentation get designed out of adult life.

We talk about growing up without space to express yourself, getting ready in café toilets, the freedom c...

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 connection that cities have quietly lost.

Glenn traces sauna’s roots as everyday civic infrastructure rather than luxury amenity, reflects on the risks of gatekeeping and elitism as the scene grows, an...

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 ground.

Jasmine reframes urbanism as a messy, lived practice rather than a rigid discipline, and highlights how everyday friction and irritation are often the beginning of meaningful change.

This episode refram...

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 everyday life such as first-mile/last-mile walking, informal transport, street life and safety.

We dig into whether building faster actually deepens resilience or erodes memory, how imported models can misfit local context, and what it me...

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 experience of place and its global perception.

We explore the gap between performance and perception, why most cities lack resonance on the world stage, and how the interplay between infrastructure and experience may de...

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 limitations of traditional banking advice, and how mobility and access matter as much as income, we dig into how young people are improvising within a system that no longer feels trustworthy.

The conversation reframes stability, money, and the urban...

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 “perfect tenant” or a grant.

Evan’s work reframes empty space as opportunity, showing how activation builds momentum, restores “muscle memory” on streets, and creates social and economic life where there was none. This e...

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 powerhouse of luxury and culture while still maintaining a remarkable commitment to social housing and dense urban life.

Paris’s paradoxes become a lens for thinking about cities more broadly: its subu...

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-independence history shaped a cautious institutional culture, why Ireland’s real constraints are political and regulatory rather than natural or financial, and how GDP growth has failed to translate into housing, infrastructure, and everyday quality...

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 rethinking marketing strategies in the transport sector. The conversations leads to a call for a more human-centred approach to transport innovation that prioritises quality of life and effective communication.

Takeaways

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 are, where you come from, and how you imagine yourself collectively as a city.

We talk about:

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 shares insights on grassroots movements and the need for collaboration to drive positive change in urban environments.

Takeaways

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:

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 living.

Takeaways

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 experiences in Singapore and other cities, advocating for a new paradigm of urban living that prioritizes well-being and connection with nature.

Takeaways

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 role of curiosity in understanding urban dynamics. He concludes with thoughts on the future of cities and the importance of simplifying complex ideas without losing their essence.

Takeaways

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 importance of public spaces, transportation, and housing, while also envisioning a future where Cape Town can thrive as a model for urban living. The conversation concludes with...

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 speakers and topics, as well as his vision for a more accessible and imaginative approach to urbanism.

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 places around peak car demand. But more importantly, he makes a compelling case for a bottom-up approach to urban change: one that values s...

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 episode is about what happens when cities stop being bold … and how to bring...

Takeaways

Summary

In this conversation, Michael Wexler shares...

Exploring Urban Evolution with Diana Lind

Join 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 concept of co-living and its future The importance of urban public education

Guest...

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 shares her “magic wand” for making Canada bolder about big ideas and why sometimes...

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 utility they endure, and what Northern’s “30 by 30” plan means for...

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, architect-turned-place-maker and Executive Director of Midtown KC Now, who has sp...

The City’s Recipe Book: Borrow the Technique, Use Your Own Ingredients with Guillermo Bernal

Cities 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, tangible acts of change.

In this episode, we explore:

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 months working with councils in London and Essex on an adult social care innovation programme with Rainmaking and Thames Ga...

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 loss of mid-size venues to Canada’s image problem abroad, Grondin makes the case for treating nightlif...

The Magnetic, Messy Cities People Don’t Leave — with Sofia Song

What 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 city truly magnetic … and what drives people away.

We cover:

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:

Michela’s insi...

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 as theirs, why shame and pride are two si...

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 you get – The real reason most transit projects don’t integrate with housing – Lessons from London, Sydney, a...

Episode Description: Dave Cairns used to sell downtown towers. Then he left the city—and the real estate orthodoxy behind. In this episode, the former poker pro turned office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.

We talk about: – Why cities must now earn our presence – Atlassian and Pinterest as models for modern work – The slow death of co-working (and the lie of flexibility) – How mental health, AI, and autonomy are reshaping va...

Architect and urban planner Naama Blonder didn’t set out to be a suburban revolutionary. She’s raised her kids in a condo, doesn’t own a car, and rides her bike everywhere. But now she’s challenging the idea that suburbia has to be bad—and that density has to be boring.

In this episode, we dig into her award-winning Sub-Divillage project, why charm is a strategic tool (not a luxury), and how even transit-oriented developments suffer from car-first thinking.

We also cover:

If you’ve ever tumbled down a YouTube rabbit hole about public transportation, chances are you’ve come across Reece Martin — the sharp, relentless mind behind RMTransit. With over 1,000 videos filmed across dozens of cities, Reece has quietly become one of the most insightful, entertaining, and occasionally exasperated voices in the transit world.

In this episode, we talk about: