Challenger Cities EP26: The Policy Playbook for Challenger Cities with Tom Goldsmith
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.
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Challenger Cities EP25: How Nature Can Make Our Cities Thrive with Jan Sumner
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 ParksLISTEN 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
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Challenger Cities EP24: Reinventing Cities, through Office to Residential Conversions with Steven Paynter
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 piecesWe should stop waiting for perfect and start building for someoneUrban reinvention is more likely in overlooked places than poster citiesConversions can be beautiful—if you know what to reveal, not just what to addThe best results come when cities concentrate effort, not spread it like butterWe 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 RougePearl House, NYC Financial DistrictGensler’s national office-to-residential modelSidewalk 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
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Challenger Cities EP23: Fixing Cities Through Momentum, Not Just Masterplans with Rik Adamski
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 transformationCities must treat downtowns like complex systems, not complicated onesPedestrianisation needs testing, not top-down mandatesProgress 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 MarketplaceCongress for the New UrbanismCenter for Neighborhood TechnologyChuck Marohn and Strong TownsTactical Urbanism movementInterview 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
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Challenger Cities EP 22: The Newcomer Perspective, What Works and What Could Be Better in Toronto with Arthur Smith
The Newcomer Perspective: What Works and What Could Be Better in Toronto with Arthur SmithIn 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.
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