Challenger Cities EP32: How to Love a Town Back to Life with Jeff Siegler
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 dysfunctionThe dangers of design without stewardshipThe real cost of our maintenance gapHow cities can rekindle civic love—not through slogans, but through actionAs Jeff says: “The opposite of love isn’t hate. It’s indifference. And that’s what’s killing our cities.”
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Challenger Cities EP31: Building Transit, Trust and Capability with Russell King
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 lastsA must-listen if you care about cities, infrastructure, or just want to know how good ideas actually get delivered.
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Challenger Cities EP30: Is the On-Site, the New Off-Site? Real Estate, Remote Work and Reinventing Cities with Dave Cairns
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
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Challenger Cities EP29: The Charming Housing Rebellion with Naama Blonder
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 suburbsThe myth that midrise is always the best compromiseWhy towers aren’t the problem—it’s what we do at street levelHow to push bold designs through a system built to say noThe emotional energy tax of public consultationsWhat 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/
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Challenger Cities EP28: Why North American Transit is Mediocre ... and How to Make it Actually Good with Reece Martin
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 wrongThe difference between places that treat transit like infrastructure vs. places that treat it like an expensive hobbyHow insecure leadership stops smart people from fixing obvious problemsWhy signage, governance, and shelters are more broken than you thinkWhat we can learn from Singapore, Germany, and even the SkyTrain in VancouverThe one change Reece would make if he was handed a magic wandWe 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 VancouverExplore RMTransit on YouTube: https://www.youtube.com/@RMTransit
Iain Montgomery of Now or Never Ventures interviews urbanists, creatives, transit and development types to explore how cities can punch above their weight and create distinctive new futures outside of the tired playbooks.
New Zealand