Challenger Cities

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.