Challenger Cities

by 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.

Podcast episodes

  • Season 2

  • Challenger Cities EP 22: The Newcomer Perspective, What Works and What Could Be Better in Toronto with Arthur Smith

    Challenger Cities EP 22: The Newcomer Perspective, What Works and What Could Be Better in Toronto with Arthur Smith

    The Newcomer Perspective: What Works and What Could Be Better in Toronto with Arthur Smith In this episode, we flip the perspective and hear from a newcomer to Toronto—Arthur Smith. With a background in micro-mobility and a fresh set of eyes on the city, Arthur shares what drew him here, what he loves about Toronto, and where he sees untapped potential. What We Discussed: 🔹 Why Toronto? Arthur’s journey to the city and what made it an attractive place to call home. 🔹 Transit Strengths & Gaps – A love for Toronto’s streetcars, but a push for better right-of-way and pedestrian-prioritized streets. 🔹 Quietness as a Competitive Advantage – How Toronto’s lower noise levels make it stand out compared to major U.S. cities. 🔹 Waterfront Potential – What Toronto is getting right and how it could become an even greater urban asset, inspired by Lisbon. 🔹 Micro-Mobility & Infrastructure – What’s working, what’s missing, and how smart investments could unlock more adoption. 🔹 Supporting Small Businesses – Why walkability and vendor-friendly policies could transform local commerce. 🔹 A Bold Vision for Toronto – Arthur’s magic wand wish for a pedestrian-first downtown with thriving street life. Toronto is already a great city, but what could make it even better? Tune in for an insightful conversation on what’s working, what could improve, and how we can push for a bolder, more vibrant urban future.

  • Challenger Cities EP21: Learnings from 'the Soo' for Future Healthy Cities with Anna Foat

    Challenger Cities EP21: Learnings from 'the Soo' for Future Healthy Cities with Anna Foat

    In a world where healthcare systems strain under ageing populations, chronic diseases, and practitioner shortages, innovation has never been more critical. In this episode, we explore how cities can rethink health through the lessons of Sault Ste. Marie. Healthcare: The Urban Blindspot Healthcare often sits on the periphery of urban planning—a blindspot that Anna Foat, with her wealth of experience, helps illuminate. “People often think healthcare is free, but nothing’s truly free,” she begins, describing how systems designed decades ago are struggling to adapt. Longer lifespans, chronic diseases, and shifting practitioner roles have created a "rat’s nest" of challenges. Sault Ste. Marie: A Case Study in Creativity Historically a steel town, Sault Ste. Marie has faced significant healthcare challenges but also developed innovative solutions. “When the steel plant set up here, they established Group Health—a mini-hospital integrating doctors, nurses, nutritionists, and more,” Anna explains. The Northern Ontario School of Medicine (NOSM) complements this approach by training rural generalists equipped for diverse, high-pressure settings. This strategy helps prevent brain drain and fosters skills tailored to the region’s needs. The Case for Prevention “We don’t make the healthcare point when designing cities,” Anna argues. Active transportation—like walking and biking—boosts physical health and social connectivity. She points to initiatives where doctors prescribe nature passes or train tickets to get people moving. “It’s not fluffy—it’s fundamental to public health.” Breaking Down Barriers Anna critiques the inefficiencies within healthcare systems: “Most healthcare tech feels like the 1990s—nurses still transcribe notes by hand.” She advocates for basic tech improvements, like searchable PDFs and OCR, to reduce administrative burdens. Cultural shifts are equally crucial: “We create so much busy work. Patients end up in unnecessary appointments while others with acute needs wait.” Humanising Healthcare Healthcare is ultimately about people, not just systems. Anna underscores the need for clear, compassionate communication: “A third of terminal cancer patients don’t know they’re terminal. Doctors shy away from harsh news, leaving patients uninformed.” Despite the challenges, she shares positive anecdotes, like her son’s swift, well-communicated care after a broken arm—reminders that human touch often outweighs technological advancements. A New Vision for Cities Anna draws inspiration from the Netherlands' 'home-spital' model, which keeps patients comfortable at home and eases hospital strain. Looking ahead, she prioritises community-building to combat loneliness: “Cities can create events and spaces that bring people together. It’s not everything, but it’s a meaningful start.” Magic Wand Question: “If I had a magic wand, I’d tackle loneliness.” Anna’s belief is clear: healthcare innovation isn't just about new tools or buildings—it's about rethinking how we connect, care, and design our cities to foster well-being.

  • Challenger Cities EP20: Rethinking Cities Through Lessons from Music, Psychology and Engineering with Nick Tyler

    Challenger Cities EP20: Rethinking Cities Through Lessons from Music, Psychology and Engineering with Nick Tyler

    Urban design often focuses on hardcore infrastructure—but what about the people who use it? In this episode, we explore how psychology, neuroscience, and philosophy can make urban spaces work better for everyone. From Oboist to Urban Innovator “Musicians handle time—we take a note from the future, play it in the present, and it instantly becomes the past.” Nick Tyler’s journey into urban design began in an unconventional place: as a professional oboist. His musical background taught him to think creatively about time, space, and human experience—lessons that would later shape his innovative approach to city planning. After a master’s in transportation planning and time spent studying Brazilian bus systems, Nick saw how traditional engineering models often ignored human behavior. “Engineering is often about making up your mind. But real creativity lies in undoing your mind—being open to new ways of thinking.” PEARL: A Laboratory for Urban Change Nick leads PEARL, a cutting-edge facility at University College London that simulates urban environments to study how people react to light, sound, and space. Through this work, Nick and his team have uncovered fascinating insights, like the psychological conflict caused by floating bus stops. “Cyclists narrow their focus to stay upright, making them less aware of pedestrians. It’s not their fault; it’s just how the brain works.” The research showed how fear and unpredictability impact people’s perceptions, highlighting the need to design for both physical safety and emotional comfort. Designing for People, Not Codes Nick challenges the rigid standards in urban design: “Standards should serve people, not constrain creativity.” He advocates for outcome-based approaches—like lighting standards that ensure passengers can see a person in black at 200 meters rather than meeting abstract brightness metrics. This human-first mindset redefines accessibility as a mental state, not just a physical requirement. Rethinking Maslow’s Hierarchy of Needs “Maslow never intended his needs to be a hierarchy,” Nick reveals. Instead of a fixed pyramid, human needs are dynamic and context-dependent. Cities, therefore, should balance safety, community, and creativity to foster genuine well-being. Community at the Core of Urban Design “Social connectedness is essential for survival.” Nick envisions cities as places where human connection is easy and natural. His experiment—saying good morning to bus drivers—illustrated how simple social interactions can ripple through a community. Designing for these moments could reshape cities into spaces where people feel safe, seen, and connected. Magic Wand Question: “If I had a magic wand, I’d enable people to express their sociality in public spaces.” Nick’s vision is a world where cities are designed with the messiness of human behavior in mind—where psychology and engineering work hand in hand.

  • Challenger Cities EP19: Why Localism Fuels Challenger Cities with Mary Rowe

    Challenger Cities EP19: Why Localism Fuels Challenger Cities with Mary Rowe

    In this conversation, Iain Montgomery speaks with Mary Rowe, the head of the Canadian Urban Institute, about the importance of local engagement in urbanism, the challenges faced by cities, and the role of community in fostering resilience and innovation. They discuss the need for a ground-up approach to urban development, the significance of local economies, and the mission of the Canadian Urban Institute in connecting urban practices across the country. The conversation emphasizes the value of mutual aid, decentralized solutions, and the potential for revitalizing Main Streets as vital community hubs. takeaways Local engagement is crucial for urban resilience. Focusing on hyperlocal issues can provide a sense of agency. Community relationships are foundational for urban development. Public policy should adapt to local realities. Urban growth presents both challenges and opportunities. Local economies can drive innovation and sustainability. The Canadian Urban Institute aims to connect urban practices. Diverse public spaces can enhance community cohesion. Mutual aid and decentralized solutions foster innovation. Main Streets are vital for community identity and economy. titles Revitalizing Urban Spaces: A Local Approach The Power of Community in Urban Development Sound Bites "You give me so much hope." "I'm a ground up person." "Cities are about choice." Chapters 00:00Navigating Uncertainty in Today's World 03:44The Importance of Hyperlocal Engagement 06:44Personal Journey into Urbanism 09:14The Challenge of Large-Scale Solutions 11:56Local Solutions to Global Problems 15:04The Dynamics of Urban Life 17:47Resilience in Local Economies 20:26The Role of the Canadian Urban Institute 24:27Revitalizing Main Streets as Community Hubs 27:33Housing Opportunities Along Main Streets 28:25Canada's Urban Challenges and Political Decisions 31:13The Role of Geography in Urban Development 33:07Decentralization and Mutual Aid in Urban Spaces 35:14Innovative Use of Public Spaces and Markets 45:37Introduction to City Improvement Challenges 46:06The Importance of Experimentation in Urban Development

  • Challenger Cities EP18: How Downsview is redefining Toronto's future by shifting the centre of gravity with Chris Eby

    Challenger Cities EP18: How Downsview is redefining Toronto's future by shifting the centre of gravity with Chris Eby

    In this episode of Challenger Cities, host Iain Montgomery sits down with Chris Eby, Executive Vice President of Northcrest, to explore one of Toronto’s most ambitious urban redevelopment projects: the transformation of the Downsview lands (YZD). Chris shares the vision for this 520-acre project, which promises to shift Toronto’s center of gravity north, creating a network of vibrant, walkable neighborhoods centered around sustainability, public spaces, and transit integration. From reimagining a 2.1-kilometer runway into Toronto’s answer to New York’s Highline to tackling stormwater management with a groundbreaking “sponge city” approach, Chris explains how YZD is redefining what a city can be. Along the way, they discuss the challenges of urban planning in Toronto, the lessons learned from Sidewalk Labs, and the cultural factors that have held Canadian cities back from creating world-class public spaces. What You’ll Learn in This Episode: Why Toronto needs multiple hubs, not just one downtown, to thrive in the future. How the Downsview project is balancing bold vision with community engagement. The role of sustainability in creating a fully electric, future-proof urban center. What Toronto can learn from global cities like Copenhagen, New York, and Montreal. Why Canadian modesty has limited urban innovation—and how YZD is changing that. Memorable Quotes: “This is going to shift the center of gravity north. Downtown is great, but we need a variety of hubs.” “The success or failure of this project hinges on getting public spaces right.” “We will not be building any new fossil fuel infrastructure on the site.” “A lot of older Canadians have cottages, places up north or in the country. When they have free time, they leave the city. There’s never been a push on governments to build great public spaces in the city.” “We’ve got to stop being so unambitious about transit. You look at the map in London, New York, or Tokyo—ours just pales in comparison.”