aniel Herriges joins us to explore one of the most underestimated levers for better cities: parking reform. A longtime Strong Towns writer and co-author of Escaping the Housing Trap, Daniel explains how the post-war American obsession with car storage has quietly shaped—and often strangled—urban life.

From zoning codes that make beloved main streets illegal, to the $127 billion annual subsidy for “free” parking, Herriges walks through the cultural, financial, and environmental costs of designing places around peak car demand. But more importantly, he makes a compelling case for a bottom-up approach to urban change: one that values small bets, local agency, and a return to permission-based development.

This is not a podcast about technical policy. It’s about rediscovering momentum. And why cities that want to become more livable, walkable, and resilient need to focus on being more interestingly, less wrong.

💬 In This Episode: – Why parking is the “dark matter” of North American cities – The hidden cost of “free” parking – How zoning codes ban the kinds of places people love – Why most people don’t hate new neighbours—they hate traffic – The importance of small-scale experimentation – Why “let people do things” might be the best policy of all – How bottom-up momentum outperforms masterplans – Reframing density for public understanding – The power of getting it less wrong over time

Andy Nulman is a man who’s seen Montreal through every era — and he’s not afraid to call out what’s gone wrong. In this no-holds-barred conversation, the Just for Laughs co-founder shares his frustrations with small-minded politics, lost ambition, and a city that’s forgotten how to dream big. We talk about Montreal’s golden ages, its identity crisis, and what it would take to fix the city’s flow, literally and metaphorically.

From language laws to bike lanes, bad branding to bold leadership, this episode is about what happens when cities stop being bold … and how to bring the swagger back.

Takeaways

• Michael Wexler's journey into urbanism began unexpectedly.
• He transitioned from cycling-focused projects to broader transit planning.
• Cargo bikes represent a gap in North American urban mobility.
• Infrastructure is crucial for increasing cycling and cargo bike usage.
• Copenhagen's cycling culture serves as an inspiration for Montreal.
• Mulo aims to fill the cargo bike market gap in Montreal.
• Community partnerships are essential for Mulo's success.
• E-bikes have transformed the cargo bike experience.
• The political landscape significantly impacts urban mobility initiatives.
• A multi-faceted approach is needed for sustainable urban transportation.

Summary

In this conversation, Michael Wexler shares his unique journey into urbanism, highlighting his experiences with cycling infrastructure and transit planning. He discusses the rise of cargo bikes as a sustainable urban mobility solution, the cultural differences in their adoption, and the importance of infrastructure in promoting cycling. Wexler emphasizes the need for community engagement and local partnerships in launching initiatives like Mulo, Montreal's first cargo bike share system. He also addresses the challenges of urban transit and the political landscape affecting mobility projects, ultimately advocating for a multi-faceted approach to creating better urban environments.

Chapters

00:00 Introduction and Background of Michael Wexler

02:47 Transitioning from Cycling to Transit Planning

05:59 The Rise of Cargo Bikes in Urban Mobility

09:11 Cultural Differences in Cargo Bike Adoption

11:56 Infrastructure and Its Impact on Cycling

15:03 Encouraging the Use of Cargo Bikes

18:07 Types of Cargo Bikes and Their Uses

20:57 Mulo's Initial Launch and Community Engagement

23:42 Future Aspirations and Expansion Plans

27:03 Operational Challenges and Solutions

29:56 The Role of E-Bikes in Urban Mobility

32:50 The Importance of Local Partnerships

36:08 The Future of Cargo Bikes in Urban Areas

38:56 The Need for Better Transit Systems

42:02 The Political Landscape of Urban Mobility

44:54 The Vision for a Better Urban Future

47:47 Conclusion and Final Thoughts

Exploring Urban Evolution with Diana Lind

Join host Iain Montgomery in a captivating conversation with Diana Lind, renowned urbanist and author, as they delve into the complexities of modern cities. From the challenges of zoning reform to the potential of urban public education, this episode offers a thoughtful exploration of how cities can transform and thrive.

Key Topics:

The evolution of cities post-pandemic The role of Starbucks in urban development Zoning reform and its impact on housing The concept of co-living and its future The importance of urban public education

Guest: Diana Lind, author of "Brave New Home" and writer of "The New Urban Order" on Substack.

Don't miss this insightful discussion on the future of urban living. Subscribe now to the Challenger Cities podcast for more engaging episodes.

#Urbanism #CityPlanning #ZoningReform #PublicEducation #Podcast

What if commuting from Niagara to Toronto didn’t mean hours in traffic or waiting on a slow, infrequent train? Erika Potrz thinks there’s a better way, and it involves a military‑grade hovercraft gliding across Lake Ontario in just 30 minutes.

In this episode, we talk about why Hoverlink could change more than just the QEW commute: from making travel joyful again (yes, DJs on board), to giving people their time back, to rethinking the connection between transport, tourism, and housing. Erika also shares her “magic wand” for making Canada bolder about big ideas and why sometimes, it takes an unconventional outsider to get things moving.

This isn’t just a ferry service. It’s a challenge to the way Ontario thinks about mobility, growth, and what’s possible.

Northern has long been the UK’s biggest rail operator by stations—and one of its most under-loved. But under Alex Hornby, it’s getting a dose of something different: warmth, character, and a clear sense of purpose.

In this episode, we talk to Alex about his journey from making buses in Burnley genuinely desirable to leading a railway that serves some of the North’s most complex and underserved places. We explore why he believes public transport should be treated like a product people love, not just a utility they endure, and what Northern’s “30 by 30” plan means for the region.

From asking “what if IKEA ran our stations?” to empowering staff with handwritten notes during disruption, Alex shares how small, thoughtful changes add up to big cultural shifts. This is an episode about public service as choreography—turning trains, stations, and timetables into something that moves people, not just moves them around.

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.