This was never meant to be a podcast with a “Series 3.”

Challenger Cities started as a bit of a rant, with a hint structure. I was living in Toronto, feeling stuck. Not just physically, but mentally. Stuck in a city full of potential but seemingly allergic to risk, creativity, or even a dash of novelty. A city that calls itself “world-class” while making it nearly impossible to build homes, run transit, or try something new without a multi-year process and a public consultation full of professional naysayers.

So I hit record. I found some unconventional voices. And to my surprise, people started listening.

Since then, it’s grown into a wider conversation, a bit of a playbook and maybe even a slow-burn manifesto. Series 2 took us beyond Toronto, and Series 3 is going further still: to cities you’ve heard of, and a few you definitely haven’t, but should have.

This short episode is a reflection. A little thank-you to the people who’ve been listening, reading, sharing and a bit of a rallying cry for what comes next.

We’re not trying to make clones of Amsterdam. We’re trying to be better, bolder, and interestingly less wrong.

Series 3 starts now.

Policy may not be sexy. But it is what shapes your city — or keeps it stuck.

In this episode, I talk with Tom Goldsmith, one of the sharpest minds on innovation and public policy in Canada, and the writer behind Orbit Policy’s must-read Deep Dives. Together, we explore why cities can’t just wait for permission — they need to start shaping policy on their own terms.

Tom cuts through the usual fog, arguing that good policy lives at the messy intersection of evidence, politics, and money. It’s not just about having the right ideas — it’s about getting them done, in the real world, where compromise is constant and perfection is a mirage.

We get into why:

• Policy isn’t what’s written — it’s what actually gets done (or avoided).
• Inaction is a choice. Usually a bad one.
• Governments fear failure so much they only “experiment” with what they already know.
• The state has been hollowed out — and now it struggles to deliver the things we desperately need.
• Cities are innovation engines, but rarely funded or empowered like they are.

KEY QUOTES:

“There are plenty of examples of good policies that failed because the harm was pointed — and the benefit was diffuse.”

“The connective tissue is often missing. Step 1: throw money. Step 3: world-class outcomes. Step 2? Dot-dot-dot.”

“There’s been a conscious dismantling of the state’s capacity since the '80s and '90s.”

“Cities shouldn’t just be delivery vehicles for federal strategy. They should be authors of their own policy futures.”

“We don’t need perfect policies. Just ones that are more interestingly less wrong.”

LISTEN FOR INSIGHTS ON: 📜 How Challenger Cities can get bolder about writing their own rules 🏗️ Why experimentation should be normal in city governance 🗳️ The political psychology behind policy paralysis 🌎 Why a one-size-fits-all national strategy rarely works in Canada 🔧 The mindset shift from “more perfect” to “more possible”

This one’s for the urbanists, policymakers, and troublemakers who know that real leadership starts not with permission, but with momentum.

When we think about building better cities, nature rarely gets top billing. Jan Sumner wants to fix that.

As Executive Director of the Wildlands League, Jan makes a powerful case that urban nature isn’t just nice to have — it’s critical infrastructure. From wetlands that reduce flood risk to green corridors that support biodiversity and mental health, she’s helping cities across Canada reconnect with the natural world, one park, prairie, and paddling trip at a time.

In this episode, we explore how National Urban Parks are becoming a unifying thread for a fragmented country — and why we should stop seeing development and nature as being at odds. We dig into what went wrong at Ontario Place, what went right at the Rouge, and how to build momentum with both legislation and joy.

Jan explains why:

• Nature is infrastructure. Trees, wetlands and green corridors are as vital as roads and pipes.
• Biodiversity loss is an urban problem — because that’s where species are disappearing fastest.
• Public joy can be a powerful policy lever (“700 people paddling the Rouge can do more than a white paper.”)
• Rewilding cities isn't anti-growth — it’s a smarter way to grow.
• Developers don’t have to be the enemy — they can be part of the solution.

KEY QUOTES:

“You can't halt biodiversity loss if you're not prepared to go where we’re losing the most species — and that’s in our urban and rural areas.”

“Windsor is the flood capital of Canada. You can’t get flood insurance in many places anymore — but green infrastructure acts like a sponge.”

“Not every bird makes it to the end of the migration. Cities have to be part of that journey.”

“If we connected all of this — cities wouldn’t feel isolated. And this would explode.”

“Nature is not the opposite of progress. It’s what makes progress possible.”

MENTIONS & CASE STUDIES: 🌳 Rouge National Urban Park 🚣 Paddle the Rouge initiative 🏞️ Green Infrastructure Ontario 🌊 Marine protected area on Ontario’s north coast 🏙️ 25+ cities now asking for their own National Urban Parks

LISTEN IF YOU’RE INTO: 🌿 Urban nature and rewilding 🌆 Climate resilience in cities 📣 Environmental advocacy that builds public support 🛠️ Smart, green development 🦅 Turning forgotten parks into national assets

What if your city’s most underused asset wasn’t a park or a waterfront—but an office tower?

In this episode, I talk with Steven Paynter, Global Lead for Building Transformation and Adaptive Reuse at Gensler, who’s made it his mission to turn tired, half-vacant office blocks into vibrant places to live. Before "Is Downtown Dead?" became a post-pandemic cliché, Steven and his team were building the model that could help bring it back to life.

From Calgary to Baton Rouge, they’ve studied over 2,000 buildings in 150 cities, mapping which ones are ripe for conversion—and which aren’t worth the effort. But this isn't just about fixing vacancy stats. It’s about redesigning downtowns around people, not just companies.

Steven explains why:

• Cities need to treat buildings like living systems, not museum pieces
• We should stop waiting for perfect and start building for someone
• Urban reinvention is more likely in overlooked places than poster cities
• Conversions can be beautiful—if you know what to reveal, not just what to add
• The best results come when cities concentrate effort, not spread it like butter

We dig into why Toronto is still dragging its feet, how Calgary is showing what’s possible, and what lessons Detroit offers on how to rebuild after hitting rock bottom. We also get into his next big obsession: what happens when even conversion isn’t an option?

KEY QUOTES:

“We get so worried about protecting what we have that we forget cities are supposed to evolve.”

“If a building doesn’t work as an office and doesn’t work as housing—then what do you do? That’s the next problem I want to solve.”

“Let’s stop letting perfect get in the way of actually achieving anything.”

“You don’t need billionaires to revitalize a city. Cities can do that if they choose to.”

“Wouldn’t it be cool if downtown was completely different and better?”

FEATURED PROJECTS:

• Rivermark Centre, Baton Rouge
• Pearl House, NYC Financial District
• Gensler’s national office-to-residential model
• Sidewalk Labs prefab and mass timber R&D (getting a second wind)

LISTEN IF YOU’RE INTO: 🏙️ Adaptive reuse and city transformation 📉 Fixing office vacancy with actual humans 🏗️ Data-driven design that isn’t soul-crushing 📦 Prefab, mass timber, and the next urban frontier ⚡ Starting before the market’s ready

Rik Adamski doesn’t believe in big, dusty plans. He believes in action.

In this episode, we sit down with the unorthodox but deeply practical urban planner and designer Rik Adamski, who’s made a career out of helping cities do rather than just plan. His approach? Start small. Start now. Test it. Prove it. Then go big.

Rik shares stories from his journey—from growing up in walkable Midwest neighbourhoods, to working with the Congress for the New Urbanism, to transforming a dollar store in DeSoto, Texas into a thriving micro-business hub. He champions tactical urbanism and sees policy inertia as something to be poked with pizza and pilot projects.

Along the way, Rik explains why:

• Most planning documents are "300 pages of nothing"
• The simplest act—cleaning a street and feeding people—can kickstart transformation
• Cities must treat downtowns like complex systems, not complicated ones
• Pedestrianisation needs testing, not top-down mandates
• Progress comes from “What’s the smallest thing we can do today?”

This one’s a must-listen for anyone tired of endless consultation loops and looking for momentum, not just vision.

KEY QUOTES:

“We’ve become too clever by half. We write 300-page reports that say nothing.”

“The most transformative thing we did was buy pizza and clean up the street.”

“A street is complex. You don’t know what will happen when you change something—so start simply.”

“I gave a mayor a plan once and he said, ‘Well, we could do that,’ as if it was a bad thing.”

MENTIONS:

• Grow DeSoto Marketplace
• Congress for the New Urbanism
• Center for Neighborhood Technology
• Chuck Marohn and Strong Towns
• Tactical Urbanism movement
• Interview with Mary Rowe (CUI)

LISTEN IF YOU’RE INTERESTED IN: ✨ Tactical urbanism 🛠️ Doing before planning 🏙️ How to spark momentum in cities 🌭 Urban design with a side of pizza

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.

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.

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.