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office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.We talk about: – Why cities must now earn our presence – Atlassian and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
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Challenger Cities EP27: A Housing Plan for Ontario with Mike Schreiner
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.takeawaysHousing 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.titlesHousing Crisis in Ontario: A Conversation with Mike SchreinerThe Ontario Greens' Vision for Affordable HousingSound Bites"Housing is one of my favorite topics.""The Ontario Greens have the best housing plan.""Housing stability is mission critical."Chapters00:00Introduction to Housing Challenges in Ontario08:27Mike Schreiner's Background and Political Journey13:57The Ontario Greens' Housing Plan20:32Market Reactions and Political Dynamics28:07Community Engagement and Public Consultation32:47Urban Development and Neighborhood Evolution35:21Challenges in Housing Development37:36The Fiscal Framework and Infrastructure Costs40:04The Impact of Urban Sprawl43:03Building Strong Local Economies46:22Adapting Solutions for Diverse Communities49:58Magic Wand Solutions for Housing Crisis54:08Empowering Community Action for Change57:15Introduction to Challenger Cities Podcast57:39Engagement and Community Feedback57:51New Chapter
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Challenger Cities Interlude: One Year Later ... Still a Podcast, but Maybe Something Bigger?
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.
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.
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