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