We talk a lot about fixing cities—but less about why we’ve let them decline in the first place. This conversation with civic pride expert Jeff Siegler is a deep, uncomfortable, and often inspiring look at how we got here and what it takes to turn it around.

Jeff doesn’t believe in sugar-coating. He’s spent his life fighting against civic apathy and calling out the ways we’ve outsourced care, maintenance, and even meaning in our places. We talked about what happens when people stop seeing their city as theirs, why shame and pride are two sides of the same coin, and how to rebuild not just infrastructure, but belief.

This episode is full of insights on:

• Why placelessness is a symptom of deeper dysfunction
• The dangers of design without stewardship
• The real cost of our maintenance gap
• How cities can rekindle civic love—not through slogans, but through action

As Jeff says: “The opposite of love isn’t hate. It’s indifference. And that’s what’s killing our cities.”

Russell King didn’t start out in transport. But somewhere between regenerating Battersea and reforming Sydney’s transit system, he became—by his own admission—“a transport tragic.”

In this wide-ranging conversation, Russell shares what it actually takes to build infrastructure that shapes cities, why most governments lose the capability they’ve just built, and how our obsession with roads and cost-cutting gets in the way of good transport policy. We get into:

– Why rail lines define what kind of city you get – The real reason most transit projects don’t integrate with housing – Lessons from London, Sydney, and Madrid on what to and not to do – Why the road lobby is winning—and how to push back – The hidden subsidies no one talks about (hint: it’s not just transit) – What happens when the political stars align—and why it rarely lasts

A must-listen if you care about cities, infrastructure, or just want to know how good ideas actually get delivered.

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office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.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.