Challenger Cities

Every city tells itself a story. In Kansas City, it’s one of manageability: there’s parking when you want it, space to drive, and just enough shine in a few key places to make it feel like things are ticking along. But scratch the surface—or take a walk down the streets that aren’t newly polished—and another story emerges. One of unrealised potential, oversized roads, empty sidewalks, and neighbourhoods running on a fraction of their former energy.

In this episode, we sit down with Kevin Klinkenberg, architect-turned-place-maker and Executive Director of Midtown KC Now, who has spent years in the guts of Kansas City figuring out how to shift that story—not through glossy master plans, but by making blocks work better. Then another. And another.

We talk about:

• Why “big visions” rarely survive contact with reality
• How a three-block art walk (The Artery) is sparking collaboration across Kansas City
• The overlooked power of roundabouts, backyard cottages, and other suburban fixes
• Why charm often comes from what’s been left alone, not designed from scratch
• How small, scrappy interventions—a tricycle in the street, a few trees—can create real momentum

As Kevin says: “Pick the thing that annoys you, and fix that.”

If you’ve ever wondered how to get your city unstuck—or how to make a meaningful difference without waiting for permission—this conversation is for you.

The City’s Recipe Book: Borrow the Technique, Use Your Own Ingredients with Guillermo Bernal

Cities don’t work because of glossy plans or polished renderings. They work because people use them, reshape them, and often subvert them in ways no planner predicted.

That’s the world Guillermo Bernal inhabits. A political scientist turned place-maker, Guillermo has spent the past decade helping communities across Mexico reclaim their public spaces — not through sweeping vision statements, but through small, tangible acts of change.

In this episode, we explore:

• Why cookbook urbanism (copying the look of other cities) fails without understanding the “ingredients” that make it work
• How Mexico City thrives on improvisation, adaptation, and citizen-led transformation
• The risks of chasing authenticity until it becomes a product — and what happens when places lose their soul
• Why trusting citizens with public spaces leads to more vibrant, cared-for cities

Guillermo reminds us that the best cities aren’t perfect or polished. They’re unfinished, alive, and constantly rewriting their own rules.

What happens when you take someone fluent in corporate innovation and drop them into the world of council-led adult social care? A surprising amount of clarity on what actually counts as value.

In this crossover episode, Iain Montgomery is joined by his usual SIDEBAR co‑conspirator, Charlie Rowat, to explore how innovation changes when you swap corporate executives for councillors, consumers for citizens, and quarterly shareholder updates for public accountability.

Charlie has spent the past few months working with councils in London and Essex on an adult social care innovation programme with Rainmaking and Thames Gateway — an area that consumes roughly 40% of local government budgets and still isn’t enough. It’s a space where “innovation” isn’t a buzzword but a lifeline: prediction over reaction, prevention over crisis, survival before strategy.

We discuss: – Why corporate and civic notions of “value” are worlds apart – How urgency and constraint shape innovation in public life – Why planning consultations are broken (and how imagination could fix them) – What Shoreditch teaches us about regenerating cities like Bradford – The courage it takes for councils to make change that can’t be ignored

“Lots of will, lots of appetite, no real budget. I mean, literally they are struggling to keep the lights on.”

This one’s about guts, trade‑offs, and what it really means to innovate when the stakes are human.

What does it take to make a city work after dark?

In this episode, we're speaking with Mathieu Grondin, Ottawa’s first-ever Nightlife Commissioner, about why nightlife isn’t just parties and late bars, it’s infrastructure.

The conversation explores why Ottawa created this role, what mid-sized cities can teach their bigger siblings about cultural development, and how better policy can make cities safer, more vibrant, and more economically resilient. From public transit to zoning reform, and from the loss of mid-size venues to Canada’s image problem abroad, Grondin makes the case for treating nightlife as a vital part of urban life, not a nuisance.

In this episode:

• Why Ottawa of all places is leading on nightlife governance
• The link between nightlife, safety, and economic growth
• How mid-sized cities are driving Canada’s cultural experimentation
• What happens when you lose the “middle class” of culture
• Why cities need projects, not just ideas

Challenger Cities explores how places defy expectations, take risks, and build something better — and why that matters for everyone who lives, works, and plays there.

The Magnetic, Messy Cities People Don’t Leave — with Sofia Song

What actually keeps people in cities? It isn’t just housing supply, transit plans, or economic growth. It’s something far less tangible, emotional connection.

In this episode, we speak with Sofia Song, Head of Global Cities Research at Gensler, about the City Pulse study, one of the most ambitious looks at urban life anywhere in the world. Drawing on insights from 65 cities, 30 countries, and over 100,000 people, it explores what makes a city truly magnetic … and what drives people away.

We cover:

• Why people move for practicality but stay for feeling
• The underestimated power of emotional infrastructure
• How second-tier cities risk losing their magic
• Why boredom is the biggest predictor of whether someone stays
• What it takes to design places people can’t imagine leaving

https://www.gensler.com/press-releases/city-pulse-magnetic-city-2025

What if cycling policy wasn’t about bike lanes but about joy, dignity, and connection? In this episode of Challenger Cities, we sit down with Michela Grasso — Italian researcher, urbanist, and co-author of the Urban Cycling Manifesto — to explore how cities can rethink mobility through culture, inclusion, and imagination.

We talk about:

• Why benches might matter more than bike lanes.
• How e-bikes are transforming independence for older riders.
• Mama Agatha’s migrant cycling lessons in Amsterdam.
• Bologna’s 30 km/h revolution — and how small policy shifts save lives.
• Why she’d let children redesign our cities.

Michela’s insights challenge the way we think about cycling and urban design — shifting the focus from infrastructure to experience.

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/