Episode Description: Dave Cairns used to sell downtown towers. Then he left the city—and the real estate orthodoxy behind. In this episode, the former poker pro turned office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.

We talk about: – Why cities must now earn our presence – Atlassian and Pinterest as models for modern work – The slow death of co-working (and the lie of flexibility) – How mental health, AI, and autonomy are reshaping value – What Canadian cities still get wrong

Architect and urban planner Naama Blonder didn’t set out to be a suburban revolutionary. She’s raised her kids in a condo, doesn’t own a car, and rides her bike everywhere. But now she’s challenging the idea that suburbia has to be bad—and that density has to be boring.

In this episode, we dig into her award-winning Sub-Divillage project, why charm is a strategic tool (not a luxury), and how even transit-oriented developments suffer from car-first thinking.

We also cover:

• Why Toronto’s biggest TODs feel like vertical suburbs
• The myth that midrise is always the best compromise
• Why towers aren’t the problem—it’s what we do at street level
• How to push bold designs through a system built to say no
• The emotional energy tax of public consultations
• What Naama would do with a magic wand (hint: it’s about speed)

“Even people who love driving still appreciate walkability.” “We don’t have a charm crisis—but we’ve stopped even asking for charm.”

This is a conversation about better tactics, not just bigger ideas. Because if you want people to live with less, you’d better give them more to love.

https://smartdensity.com/subdivillage/

If you’ve ever tumbled down a YouTube rabbit hole about public transportation, chances are you’ve come across Reece Martin — the sharp, relentless mind behind RMTransit. With over 1,000 videos filmed across dozens of cities, Reece has quietly become one of the most insightful, entertaining, and occasionally exasperated voices in the transit world.

In this episode, we talk about:

• Why North America — and Toronto in particular — keeps getting transit so wrong
• The difference between places that treat transit like infrastructure vs. places that treat it like an expensive hobby
• How insecure leadership stops smart people from fixing obvious problems
• Why signage, governance, and shelters are more broken than you think
• What we can learn from Singapore, Germany, and even the SkyTrain in Vancouver
• The one change Reece would make if he was handed a magic wand

We also cover Reece’s personal journey — how a COVID-era side project became a global platform — and the two RMTransit videos he’s still most proud of.

This is a conversation about imagination, urgency, and doing the damn thing.

Because at some point, you have to stop planning and start building.

Watch Reece’s Vancouver video: I Went to Every SkyTrain Station in Vancouver

Explore RMTransit on YouTube: https://www.youtube.com/@RMTransit

In this conversation, Iain Montgomery interviews Mike Schreiner, the leader of the Ontario Greens, focusing on the pressing issue of housing in Ontario. They discuss the challenges of housing affordability, the Ontario Greens' comprehensive housing policy, and the importance of community engagement in addressing these issues. Mike emphasizes the need for a multi-faceted approach that includes both market and non-market solutions, as well as the role of infrastructure in housing development. The conversation highlights the necessity of public consultation and the importance of local economies in creating sustainable housing solutions. Mike also shares his vision for the future of housing in Ontario and encourages public engagement to drive change.

takeaways

• Housing affordability is primarily driven by the housing crisis.
• The Ontario Greens have been recognized for having the best housing plan in Canada.
• Community engagement is crucial for successful housing development.
• Legalizing gentle density can help increase housing supply.
• Public consultation needs to include voices from outside the neighborhood.
• Infrastructure repair is a significant cost for municipalities.
• Local economies benefit from diverse housing options.
• Government investment in co-op and supportive housing is essential.
• Political courage is needed to overcome NIMBYism.
• Engaging the public can lead to meaningful change in housing policy.

titles

• Housing Crisis in Ontario: A Conversation with Mike Schreiner
• The Ontario Greens' Vision for Affordable Housing

Sound Bites

• "Housing is one of my favorite topics."
• "The Ontario Greens have the best housing plan."
• "Housing stability is mission critical."

Chapters

00:00Introduction to Housing Challenges in Ontario

08:27Mike Schreiner's Background and Political Journey

13:57The Ontario Greens' Housing Plan

20:32Market Reactions and Political Dynamics

28:07Community Engagement and Public Consultation

32:47Urban Development and Neighborhood Evolution

35:21Challenges in Housing Development

37:36The Fiscal Framework and Infrastructure Costs

40:04The Impact of Urban Sprawl

43:03Building Strong Local Economies

46:22Adapting Solutions for Diverse Communities

49:58Magic Wand Solutions for Housing Crisis

54:08Empowering Community Action for Change

57:15Introduction to Challenger Cities Podcast

57:39Engagement and Community Feedback

57:51New Chapter

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