Challenger Cities

Jen Angel thinks Canada is closer to a moment of triumph in how it builds than it has been in her lifetime. The conditions are there. What's missing is enough people in positions of authority with the permission to say yes.

Jen leads Evergreen, the national organisation behind the Brick Works in Toronto and a portfolio of public space projects across the country — from school grounds transformations in Halton and Winnipeg, to a Mi'kmaq Native Friendship Centre-led project in Halifax, to the Toronto ravines programme. Before Evergreen, she ran a Nova Scotia crown corporation that built the Halifax Waterfront, Peggy's Cove and Lunenburg Waterfront, alongside rural broadband and innovation hubs. She also sits on the Canadian Infrastructure Council, the ministerial-appointed arm's-length body writing Canada's first national infrastructure assessment.

In this episode we get into:

— Why "it's not that much harder to build a good one than a crappy one" might be the most damning line about Canadian infrastructure this year

— The permission problem: why no has become the safe answer across our institutions, and what it costs us

— Multi-benefit projects, and why our funding model is almost institutionally incapable of recognising them as legible

— Why this particular moment — tariffs, geopolitical pressure, a public mood that actually wants things to be tried — might be a generational opportunity

— What the East Coast knows about resilience that the rest of the country keeps forgetting

— The Evergreen Conference at the Brick Works, May 6–7, theme: Cities Bursting with Life

Alex Bozikovic is the architecture critic for the Globe and Mail, which in practice means he writes about everything from housing politics to the public realm to the quiet cultural erosion that happens when a city stops expecting much of itself. In this episode, Iain and Alex dig into why Toronto ... a city with extraordinary people, genuine sophistication and real financial muscle ... keeps failing to act on what it already knows.

We cover the Spadina Expressway and the identity it left behind, the Ontario Science Centre closure and what it reveals about the state of progressive urban politics, the suburbs as the real story of Toronto's diversity, and what a bar in a 1899 attic has to do with the soul of a city. Plus Montreal, Sugar Beach, the Sanaaq Centre, and why the best things in Toronto tend to happen despite the default settings rather than because of them.

Exploring Urban Troubleshooting

In this episode, Heath Gledhill and Tom Shield, founders of GledHill Shield, share their extensive experience navigating complex urban infrastructure projects. They discuss how early decision-making, constraints and collaborative design principles can transform city development. Whether you're an urbanist, engineer, architect, designer or planner, their insights challenge conventional project setups and advocate for more intentional, purposeful city shaping.

Key Topics:

• The importance of framing the core problem before designing solutions
• How constraints foster innovative and effective urban design
• The role of the business case in guiding project decisions and maintaining focus
• Challenges with briefs, approvals and stakeholder engagement in infrastructure projects
• The power of compromise and trade-offs in city development
• Embedding aspiration and community impact through creative public programs
• Cross-disciplinary integration as a necessity for successful urban projects
• The influence of cultural attitudes—Australia, Canada, the UK—on project delivery
• The potential of digital tools and visual artifacts to ground project vision
• Building trust and social license through transparency and stakeholder inclusion
• The value of humility, purpose and intentionality in urban planning

When the cod fishery collapsed in the nineties, Fogo Island lost its economy almost overnight. What came next — slowly, imperfectly and without a guarantee of success — became one of the most compelling stories in Canadian community development. Shorefast, the charity behind the Fogo Island Inn, wasn't built on the logic of charity. It was built on the logic of place. Every business decision, from the number of rooms in the inn to where every dollar gets spent, runs through a single question: does this strengthen the local economy?

Tasha Freidus, Shorefast's Director of Education and Entrepreneurship, joins Challenger Cities to unpack the model and what it means beyond Fogo. We talk economic nutrition labels, the forgotten community pillar of the economy, why local banking matters more than most people realise, and how a platform launching this spring is attempting to connect communities across Canada who are quietly doing the same thing, whether they know it or not.

Key Topics

• Fogo Island's history and economic transformation
• The role of Shorefast and Zeta Cobb in community development
• Asset-based community development principles
• Storytelling and social media in community building
• Economic nutrition labels and local spending
• Scaling community models to larger cities
• Challenges in local economic stewardship
• The importance of local banking and finance

Bronwyn Williams is a South African futurist and economist, a combination she'll tell you should not be the oxymoron most people assume it is. She's been doing sharp thinking about cities lately, and this conversation is a good example of why.

We get into South African cities as a lens for the future with Johannesburg and Cape Town as two very different experiments in what happens when you try to impose order on a place that has other ideas. We talk about why the cities that look like they're working are often the most troubling ones of all, and what Dubai, Brazil and China tell us about the limits of control as a city-building strategy.

We also get into AI and the data confidence problem including why shinier models don't mean better assumptions, just more expensive mistakes at greater scale. And we end up at the one question I always ask urban planners that they never quite know how to answer.

Bronwyn is a futurist-economist based in Johannesburg. She works at the intersection of foresight and economic analysis, and has done work with Metropolis and UN-Habitat among others.

Phil Tabah is the co-founder of The Main, Montreal's city magazine, and one of the most thoughtful people working on the question of how cities see themselves and tell their own story.

In this conversation we get into why Phil started The Main at 21 as a Twitter account and what it's become, the publications that used to do this job well and what happened to them, why Montreal is a city that has cracked culture but not confidence, the economics of being a springboard city, and what it would actually take for Montreal to claim what it's already built.

We also get into why the stories worth telling about a city are exactly the ones AI can't tell, and what a refined bullshit meter has to do with good editorial judgment.

The Main is at themain.com. Go subscribe.

Most cities debate their troubled infrastructure to a standstill. Toronto has been arguing about the Gardiner Expressway for decades. Ilana Altman didn't wait for that debate to resolve. As CEO of The Bentway — a public space and cultural platform built underneath Toronto's elevated waterfront highway — she's been proving that you don't have to tear something down, or wait for it to die, to embed new values in it.

In this conversation, Ilana and Iain cover the full arc: how the Bentway went from idea to open in under three years, what it actually takes to run a 24/7 public space underneath a working highway, and why the conservancy model it pioneered is still largely foreign to Canadian cities. They get into the practical constraints — maintenance access, lighting limits, the challenge of food and beverage on a linear site — and what those constraints have forced the team to do creatively. Including turning highway maintenance equipment into community mascots.

But the deeper conversation is about civic joy as a strategy. The Bentway's Dominoes project — 2.7 kilometres of oversized dominoes run through Toronto streets by 300 volunteers — became one of the city's most shared moments in recent memory. Ilana traces what that kind of project actually does: not just entertain, but rebuild the connective tissue of a city that's been losing its volunteers, its optimism, and its willingness to celebrate what it's accomplished.

With FIFA FanFest coming to the Bentway this summer and the full seven-kilometre Under Gardiner Public Realm Plan now approved by council, the window to get the rest of the corridor right is open. Ilana is clear-eyed about how short that window is.

In this episode:

• How the Bentway went from philanthropic idea to open public space in under three years
• What makes it genuinely different from the High Line and other post-industrial urban renewal projects
• The conservancy model and why it's still novel in Canada
• Shade as a climate virtue — and how the Bentway reframed it
• The Boom Buddies: turning maintenance constraints into public education
• Why volunteerism in Toronto is down 30% and what Dominoes did about it
• The urgency of the eastern Gardiner corridor and the window that's closing
• Toronto's self-confidence problem — and what it would take to fall back in love with the city

We have spent a lot of time on the podcast talking about physical cities as streets, buildings and the spaces between them. What we perhaps don't talk about enough is the digital layer underneath all of it, and how badly most cities are fumbling it. This week's guest has spent the last decade thinking about almost nothing else.

Alistair Croll runs FWD50, perhaps the biggest gathering of digital first public servants in the world. He also wrote the book on lean analytics, literally, with Ben Yoskovitz. And last year he published Just Evil Enough with Emily Ross, which is about recognising the systems you're inside and getting them to behave in ways their creators didn't intend. As it turns out, that's a pretty useful instinct when you're trying to drag government into the 21st century.

We talked about why digital government is slow ... and it's not the reason most people think, about what AI is about to do to the relationship between citizens and the state and why cities need to start thinking a lot weirder than they currently do.

Basically if you're into cities as one of the original forms of artificial intelligence more than you are the built environment, this is the conversation for you.

Anson Kwok has spent fourteen years building Canada's tallest tower at the foot of Yonge Street. As VP of Sales and Marketing at Pinnacle International, he's had a front row seat to how Toronto has transformed from a city of downtown parking lots to one of the most dense urban skylines in North America. We talk about what it actually takes to build a vertical city inside a city that wasn't designed for one, why the rules written for 20-storey buildings don't survive contact with a 106-storey one, and what patience has to do with getting any of it right.

At first glance, SPNKD might look like a BDSM venue. But Paul Meyers real focus is something deeper ... finding connection and creating intimacy.

We explore how intimacy is designed, why many people use kink to avoid connection rather than deepen it, and what the concept of creating an arena in BDSM can teach us about relationships, work and even how cities function.

Along the way we discuss:

• Why Paul created SPNKD after finding most kink venues “tacky dungeons”

• How BDSM spaces deliberately design trust, consent, and emotional safety

• Why many couples visit not because something is broken, but because they want to invest in their relationship

• The idea of the “arena” and what workplaces could learn from it

• Why four hours together changes how people interact

• How cities succeed or fail based on how they enable human interaction

• The difference between technical performance and real connection

This is a conversation about intimacy, but also about architecture, culture and subtle infrastructures that shape how we relate to each other.

In other words: what happens when you design spaces for connection rather than efficiency.