Challenger Cities

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.

What if the problem with buses isn’t frequency, funding or technology ... but attitude?
In this episode, we're in person with Ray Stenning, founder of Best Impressions and arguably the most prolific bus livery designer in the world. For more than 40 years, Ray has been quietly reshaping how buses look, feel and function across the UK — from iconic interurban routes like the X43 and the 36 to countless urban fleets most people ride without ever knowing who shaped them.
But this isn’t a conversation about paint schemes.
It’s a conversation about dignity.
Ray argues that every rattling panel, every hard plastic bench, every grey-on-grey interior sends a message about who the passenger is assumed to be. When we design buses like cattle trucks, people behave accordingly. When we design them like shared public rooms, behaviour shifts.
We explore:
Why anxiety — not speed — is the real barrier to bus use
The psychology of reassurance in public transport
How small design details change passenger behaviour
Why manufacturers optimise spreadsheets instead of humans
The hidden importance of noise, seat spacing and eye-lines
Why drivers are always “on stage”
The missed opportunity of electric buses that still feel like diesel punishment
And why a bus is closer to a café than a car
Ray makes a simple but uncomfortable point: buses have been treated as the lowest common denominator because the people who use them are assumed to be the lowest common denominator.
If we want more people on public transport, we don’t just need better timetables. We need better environments. Better hospitality. Better ambition.
Because public transport isn’t just about moving bodies. It’s about how we choose to treat one another in shared space.