Challenger Cities (Iain Montgomery)

In this episode of Challenger Cities, host Iain Montgomery sits down with Chris Eby, Executive Vice President of Northcrest, to explore one of Toronto’s most ambitious urban redevelopment projects: the transformation of the Downsview lands (YZD). Chris shares the vision for this 520-acre project, which promises to shift Toronto’s center of gravity north, creating a network of vibrant, walkable neighborhoods centered around sustainability, public spaces, and transit integration.

From reimagining a 2.1-kilometer runway into Toronto’s answer to New York’s Highline to tackling stormwater management with a groundbreaking “sponge city” approach, Chris explains how YZD is redefining what a city can be. Along the way, they discuss the challenges of urban planning in Toronto, the lessons learned from Sidewalk Labs, and the cultural factors that have held Canadian cities back from creating world-class public spaces.

What You’ll Learn in This Episode:

• Why Toronto needs multiple hubs, not just one downtown, to thrive in the future.
• How the Downsview project is balancing bold vision with community engagement.
• The role of sustainability in creating a fully electric, future-proof urban center.
• What Toronto can learn from global cities like Copenhagen, New York, and Montreal.
• Why Canadian modesty has limited urban innovation—and how YZD is changing that.

Memorable Quotes:

• “This is going to shift the center of gravity north. Downtown is great, but we need a variety of hubs.”
• “The success or failure of this project hinges on getting public spaces right.”
• “We will not be building any new fossil fuel infrastructure on the site.”
• “A lot of older Canadians have cottages, places up north or in the country. When they have free time, they leave the city. There’s never been a push on governments to build great public spaces in the city.”
• “We’ve got to stop being so unambitious about transit. You look at the map in London, New York, or Tokyo—ours just pales in comparison.”

The Newcomer Perspective: What Works and What Could Be Better in Toronto with Arthur Smith

In 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.

In this episode of Challenger City TO, we sit down with Antoine, a seasoned transit professional with global experience, to dive deep into the complexities of Toronto's transit system. Antoine shares his unique insights into the city's current challenges and opportunities, drawing on examples from his work across Europe and North America.

Key Topics Discussed:

• Toronto's Identity Crisis: Antoine discusses why Toronto needs to embrace its unique character rather than constantly comparing itself to other global cities.
• Governance and Accountability: The conversation explores the fragmented nature of Toronto's transit governance and the urgent need for a unified leader or entity to take charge of transportation outcomes.
• The Role of Cars and the Future of Transit: Antoine explains why cars will continue to play a role in Toronto but stresses the importance of planning for a future where transit, cycling, and walking are prioritized.
• Optimizing Streetcars: Antoine suggests "LRT-izing" Toronto's streetcars, drawing inspiration from European cities like Prague, where streetcars are seamlessly integrated into both new and historic urban areas.
• Importance of User Experience: The episode delves into the need for transit systems to respect and attract passengers, highlighting improvements in bus services and the potential of cycling infrastructure.
• Progress in Infrastructure: Antoine points out successes like the Finch and Hazel McCallion Lines, as well as new GO train infrastructure, showing that Toronto can learn from past challenges like the Eglinton Line.

Memorable Quotes:

• "Toronto is just Toronto. It’s not New York or Switzerland—it’s unique, and that’s why we need to love it."
• "Everybody's in charge of something, but nobody's in charge of the whole."
• "A streetcar is a subway that stops for cars."
• "The bus is magical; we need to make it clean, efficient, and a respected part of the transit system."

Final Thoughts: Antoine leaves us with a call for Toronto to stop looking outward and start focusing on its own potential. With the right leadership and a commitment to long-term planning, Toronto can transform its transit system into one that is reliable, user-friendly, and fully integrated.

In this episode of Challenger City TO, we sit down with Chris Burchett, a telecommunications expert turned transit visionary, to explore the transformative potential of train stations. Chris shares his journey from Wi-Fi to transit hubs, highlighting the often-overlooked importance of stations in shaping the overall passenger experience. He discusses the challenges of the engineering-centric approach in transit agencies and the untapped economic potential of integrating retail and real estate into station designs. Discover how rethinking land use and adding unique amenities can turn stations into vibrant, multi-functional urban hubs.

Key Topics Discussed:

• The Importance of Stations: Chris explains why stations are critical components of the transit experience, forming the first and last impressions of any trip.
• Engineering-Centric Challenges: The tendency of transit agencies to focus on engineering solutions at the expense of passenger experience.
• Swallowing the 'Orange Pill': Chris’s epiphany about the potential of reimagined transit, inspired by the Netherlands’ advanced transit systems.
• Economic Opportunities: How integrating retail and real estate into stations can generate significant non-fare revenue and ease political challenges around transit funding.
• Better Use of Space: Ideas for repurposing ticket halls and other underutilized spaces in stations to enhance functionality and revenue.
• Urban Planning Insights: The impact of better transit planning on overall urban livability, including benefits for drivers and reducing dependency on cars.
• Innovative Thinking: The need for creative approaches, like those championed by Rory Sutherland, to make transit more appealing and boost urban vibrancy.
• Enhancing Station Amenities: Practical suggestions for adding amenities like soundproof booths for video calls to make stations more useful and enjoyable.

Quotes Highlighted:

• "Stations are the bookends of every trip. They form your first and last impressions."
• "We discovered that nobody’s really talking about stations. They’re a critical part of the journey."
• "Amsterdam Central has transformed into a hub with reasons to visit beyond transit—it's a model for what stations can achieve."
• "It’s about rethinking land use to make stations integral parts of their communities."

Iain Montgomery sits down with Chris Bruntlett of the Dutch Cycling Embassy to explore how cycling infrastructure can transform urban life. Chris shares insights from the Netherlands, where bikes are seamlessly integrated into daily life, and discusses how other cities can adapt these principles to their unique contexts. From leadership lessons to e-bike revolutions, this conversation uncovers what it takes to build cities that are healthier, happier, and more livable.

What We Cover in This Episode:

• Chris’s journey from advocating for bike lanes in Vancouver to working with the Dutch Cycling Embassy in Delft.
• Why cycling isn’t just about bikes—it’s about livability, inclusivity, and prosperity.
• The importance of cohesive cycling networks versus piecemeal infrastructure.
• How bold leadership, particularly female leaders like Anne Hidalgo in Paris, drives transformative change.
• The game-changing potential of e-bikes and intermodal transportation.
• Challenges like weather and cultural perceptions—and how to overcome them.
• Why even car-centric companies like Walmart are embracing cycling.

Notable Quotes:

• “It’s not just about bikes. It’s about livability, inclusivity, prosperity—all the things that getting more people cycling can do for your city.”
• “The bicycle has a range problem, and public transport has a convenience problem. Combine the two, and you’ve got a real alternative to the car.”
• “Bold decisions aren’t always popular at first, but when streets become safer and cities more livable, the results speak for themselves.”

Resources and Links:

• Learn more about the Dutch Cycling Embassy.
• Follow Chris Bruntlett on LinkedIn.
• Stay tuned for Chris and Melissa Bruntlett’s upcoming book on female leadership and urban transformation, releasing in 2025.

What some cities get so right about transportation, why others get it so wrong, and how we can make the whole thing much better.

In this episode of Challenger Cities, Thomas Ableman, a leading voice in transportation innovation, takes us on a journey through the world of urban mobility. From the seamless efficiency of Swiss trains to Oslo’s ambitious integration of electrification and autonomy, Thomas shares lessons from cities that are getting transportation right—and the pitfalls of those that aren’t.

We dive into:

🚉 Why public transport isn’t just about moving people, but creating places where they want to be.

🏙️ London’s success stories, like Golders Green and Walthamstow, and how strategic planning shaped their growth.

🇨🇭 What makes Swiss Federal Railways a gold standard, from punctuality driven by pride to intelligent funding mechanisms.

🌍 Oslo’s pioneering work in electrification and autonomous vehicles as part of public transit—not just private luxury.

🛤️ Why trains feel more trustworthy than buses and how simple design changes can dramatically improve the rider experience.

🗳️ The political fear that stalls bold ideas—and why leaders who embrace change often win bigger than expected.

🛑 Hidden car subsidies like free parking that distort the true cost of driving.

✨ Thomas’s vision for making public transport so good that driving feels irrational.

Key Takeaway: Bold leadership and smart design can transform transportation systems into something that not only moves people but inspires them. "If the Swiss can do it, so can we. We just need to believe it’s possible," says Thomas.

You can find more from Thomas here:

https://www.freewheeling.info/

https://www.linkedin.com/in/thomasableman/

https://www.youtube.com/watch?v=-b8grwoUqvo&pp=ygUOVGhvbWFzIGFibGVtYW4%3D

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 pieces
• We should stop waiting for perfect and start building for someone
• Urban reinvention is more likely in overlooked places than poster cities
• Conversions can be beautiful—if you know what to reveal, not just what to add
• The best results come when cities concentrate effort, not spread it like butter

We 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 Rouge
• Pearl House, NYC Financial District
• Gensler’s national office-to-residential model
• Sidewalk 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

Episode Description

In this episode, we sit down with Laura Manes, a strategic change agent with over 20 years of experience in retail and consumer brand innovation. Laura shares her insights on how Toronto can reclaim its status as a Challenger City. We discuss the importance of human-centric design, the need to focus on often overlooked stakeholders, and how vibrant local neighborhoods can foster community engagement. Laura also highlights successful urban planning examples from other cities and offers her vision for a more dynamic and inclusive Toronto.

Key Topics:

• Toronto’s Transition: How the city lost its way with the overdevelopment of sterile condo towers.
• Human-Centric Design: The importance of focusing on children, families, and lower-income residents to create vibrant urban spaces.
• School Streetscapes: Benefits for the whole neighborhood and the challenge of convincing parents.
• Vibrant Neighborhoods: The contrast between Toronto’s older neighborhoods and new developments.
• Retail and Condo Development Disconnect: How retail becomes a no man’s land in condo developments.
• Success Stories: Assembly Square on the Mystic River as a model for urban planning.
• Pedestrian Streets: The benefits of pedestrianizing streets like King Street.
• Reviving Yonge Street: Reopening store entrances to create a more inviting streetscape.
• Improving Suburban Connectivity: The need for efficient park-and-ride systems.

Quotes:

• “Toronto used to be a great Challenger City, but we've lost our way through the overdevelopment of sterile condo towers.”
• “A good human-centric city focuses on the least loud stakeholders—children, families, and lower-income people. If you build for them, the rest takes care of itself.”
• “Our skyline is becoming monotonous. We need to push beyond condo-centric development and foster a more diverse, engaging urban fabric.”
• “Imagine if King Street was pedestrianized. In Europe, trams and pedestrians coexist. Designing like this enables great retail, patios, and cafes.”

Actionable Takeaways:

• Design retail spaces that invite curiosity and community engagement.
• Enhance downtown transit options to reduce car dependency.
• Allow commercial units on residential corners to foster local engagement.

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

In this conversation, Iain Montgomery speaks with Mary Rowe, the head of the Canadian Urban Institute, about the importance of local engagement in urbanism, the challenges faced by cities, and the role of community in fostering resilience and innovation. They discuss the need for a ground-up approach to urban development, the significance of local economies, and the mission of the Canadian Urban Institute in connecting urban practices across the country. The conversation emphasizes the value of mutual aid, decentralized solutions, and the potential for revitalizing Main Streets as vital community hubs.

takeaways

• Local engagement is crucial for urban resilience.
• Focusing on hyperlocal issues can provide a sense of agency.
• Community relationships are foundational for urban development.
• Public policy should adapt to local realities.
• Urban growth presents both challenges and opportunities.
• Local economies can drive innovation and sustainability.
• The Canadian Urban Institute aims to connect urban practices.
• Diverse public spaces can enhance community cohesion.
• Mutual aid and decentralized solutions foster innovation.
• Main Streets are vital for community identity and economy.

titles

• Revitalizing Urban Spaces: A Local Approach
• The Power of Community in Urban Development

Sound Bites

• "You give me so much hope."
• "I'm a ground up person."
• "Cities are about choice."

Chapters

00:00Navigating Uncertainty in Today's World

03:44The Importance of Hyperlocal Engagement

06:44Personal Journey into Urbanism

09:14The Challenge of Large-Scale Solutions

11:56Local Solutions to Global Problems

15:04The Dynamics of Urban Life

17:47Resilience in Local Economies

20:26The Role of the Canadian Urban Institute

24:27Revitalizing Main Streets as Community Hubs

27:33Housing Opportunities Along Main Streets

28:25Canada's Urban Challenges and Political Decisions

31:13The Role of Geography in Urban Development

33:07Decentralization and Mutual Aid in Urban Spaces

35:14Innovative Use of Public Spaces and Markets

45:37Introduction to City Improvement Challenges

46:06The Importance of Experimentation in Urban Development

In this enlightening episode, we sit down with Ramy Nassar, a leading expert in foresight and urban innovation, to discuss his vision for Toronto as a Challenger City. Drawing inspiration from his favourite movie Back to the Future, Ramy shares his thoughts on why foresight is essential for shaping the future we want rather than having it imposed on us. From tackling AI fatigue to addressing the city’s affordability and transit issues, Ramy offers a comprehensive blueprint for making Toronto a more liveable and innovative city.

Key Topics Discussed:

1. Introduction to Ramy Nassar:
   • Ramy’s inspiration from Back to the Future.
   • The importance of foresight in shaping the future.
2. AI Fatigue and Emerging Technologies:
   • Ramy’s decade-long experience with AI.
   • His current focus on quantum computing and other emerging technologies.
3. The Essence of Challenger Cities:
   • What it means to be a Challenger City.
   • The need for Toronto to think and act differently.
4. Affordability Issues in Toronto:
   • Comparison of housing costs in Toronto versus international cities.
   • The broader problem of affordability in Canadian cities.
5. Challenges with Toronto’s Transit System:
   • Ramy’s critique of the TTC and GO train.
   • Lessons from Copenhagen’s cycling culture.
6. The Problem with Emulating Other Cities:
   • Why Toronto shouldn’t try to be “Silicon Valley North.”
   • The pitfalls of copying concepts like “Toronto vs. Everybody.”
7. Limitations of AI in Solving Urban Problems:
   • AI’s role in optimization but not in addressing fundamental issues.
   • The need to focus on solving the right problems.
8. Economic Trade-offs and Decision Making:
   • The importance of understanding and making trade-offs.
   • The role of foresight in preparing for future challenges.
9. Ramy’s Magic Wand Wish for Toronto:
   • Revisiting the Sidewalk Labs project with a citizen-first approach.
   • The potential for bold and transformative urban development.

Quotes:

• "I’ve always wished I could go to the future, and that’s what inspires my work in foresight."
• "The essence of a Challenger City is to do things differently, not just follow the trend."
• "Affordability is a massive problem here in Toronto, and it’s not going in the right direction compared to international cities."
• "The highest compliment I can pay our transit system is that it mostly works. It’s not pleasant, fast, or reliable."
• "AI can optimize certain challenges, but it won’t solve the fundamental problems. We need to focus on solving the right problems."
• "We all have to make trade-offs. Understanding these trade-offs is crucial for making better decisions."
• "Foresight is about identifying weak signals and trends that point to a different future and preparing for that world."
• "If I had a magic wand, I’d go back in time and get the Sidewalk Labs project right by focusing on citizen needs first."

Summary

In this conversation, Iain and Nick Tyler explore the intricate relationship between urban design, human behavior, and well-being. They discuss how cities can be designed not just for efficiency but for human flourishing, emphasizing the importance of empathy and social connectivity in urban planning. Nick shares insights from his background in music and engineering, illustrating how these disciplines intersect to create better urban environments. The discussion also delves into the psychological aspects of urban spaces, the challenges of mobility, and the need for innovative solutions that prioritize human experiences.

Takeaways

• Urban design impacts mental well-being and social connectivity.
• Empathy is crucial in creating urban spaces that work for everyone.
• Understanding human perception can improve urban safety.
• The brain adapts to its environment, influencing behavior.
• Social interactions can enhance community well-being.
• Innovative urban solutions require interdisciplinary collaboration.
• Designing for humans means considering emotional responses.
• Mobility systems should prioritize human experiences over efficiency.
• Community involvement is essential in urban planning.
• A simple greeting can foster social connections and improve happiness.

Chapters

00:00 Introduction to Nick Tyler's Journey

07:19 The Intersection of Music and Engineering

12:52 Understanding Pearl: A New Approach to Urban Design

20:07 The Psychology of Fear in Urban Spaces

29:24 Rethinking Mobility and Urban Infrastructure

40:51 Building Community Through Conversation

42:17 The Importance of Social Connectedness

43:39 Understanding Human Behavior in Mobility Systems

46:55 The Complexity of Human Movement

49:42 Musicians and the Art of Listening

51:55 Understanding Neurodiversity in Transportation

54:49 Bridging Psychology and Engineering

01:07:36 The Magic Wand for Social Connectivity

01:13:33 The Importance of Collaborative Urban Development

01:14:36 New Chapter

In this episode of Challenger City TO, host Iain sits down with Chris Spoke, a partner at Toronto Standard and a vocal advocate for smarter urban development. Chris shares his journey from the world of software to real estate, diving deep into the challenges and opportunities facing Toronto's housing market. The discussion covers a range of critical topics, including the impact of restrictive zoning laws, the need for bold leadership in city planning, and the importance of simplifying Toronto’s official plan and zoning bylaw to foster more inclusive growth.

Chris also offers his vision for the future of Toronto, touching on how the city can learn from global examples, particularly in how regulations impact housing accessibility and design. From the concept of Toronto as a "Potemkin city" to the challenges of building viable infill projects, this episode is packed with insights for anyone interested in the future of urban living.

Key Topics Discussed:

• Chris Spoke's unconventional path into real estate development.
• The paradox of Toronto’s development: dense downtown, stagnant neighborhoods.
• The need to simplify Toronto’s official plan and zoning bylaw.
• The impact of North American vs. European building regulations on housing.
• Why bold, early-term leadership is essential for meaningful change.
• Recent policy changes in Toronto and their potential impact on housing.
• Chris’s vision for a more inclusive, accessible, and vibrant Toronto.

Top Quotes:

• "Toronto is like a seven-foot basketball player who can't dunk. It's got all the potential in the world and just needs to learn how to dunk."
• "We've halted natural growth through zoning. We skipped all the steps of development in between."
• "Our elevators are generally much larger, but what happens in practice is we just have fewer elevators, more walk-up apartments, which is bad for accessibility."

Iain Montgomery of Now or Never Ventures speaks with Paul Kalbfleisch, author of The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society.

Paul shares his unique journey from marketing executive to accidental urbanist and his mission to reimagine cities as spaces for connection, joy, and belonging. Drawing from his experiences in Ontario’s Waterloo Region and beyond, Paul offers fresh perspectives on the transformative power of public spaces and why cities that prioritize play are the key to building stronger, more resilient communities.

What You'll Learn in This Episode

• How Paul’s background in branding led to his work in urbanism.
• Why mid-sized cities are uniquely positioned to become "challenger cities" and lead innovation.
• The power of “play, live, work” as a new framework for designing cities.
• Real-world examples of public art and play fostering community, like Meander in Cambridge, Ontario.
• Why joy is not just an emotion but a practical tool for city building and social resilience.
• How everyday people can influence their cities and advocate for joyful, engaging spaces.

Key Quotes from Paul

• “Cities that know how to play, that's where we start this healing. We will change the world by how we change cities.”
• “Play is the most complex social activity humans do. It’s where we learn to collaborate, see differences as assets, and celebrate together.”
• “We will not solve the problems of the world by using grim determination to tackle grim problems. If we double down on grim, people will feel society is failing.”
• “A city should make you happy. It should make you feel like you belong to something.”

Links and Resources

• Paul’s Book: The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society
• Connect with Paul: [LinkedIn/Profile Link]
• Mentioned Projects:
  • Meander installation in Cambridge, Ontario
  • The Bentway in Toronto

Actionable Takeaways

1. Engage with your city: Attend events, visit public spaces, and participate in community-driven activities.
2. Advocate for joy: Let your city officials know you value joyful, engaging public spaces—and celebrate them when they’re created.
3. Think differently about public spaces: Consider how parks, benches, and plazas can foster connection and play, not just quiet retreat.

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.

In this episode of "Challenger Cities," host Iain Montgomery sits down with two influential figures in Toronto's creative landscape: Tabassum Siddiqui, a freelance journalist and communications specialist, and Faisal Siddiqui, founder of the Creative Business Company. Together, they delve into the strengths, challenges, and future prospects of Toronto's vibrant arts and culture scene.

Key Topics:

• Toronto's Vibrant Arts Scene: Tabassum highlights how Toronto excels in hosting a plethora of cultural events at all cost levels, driven by its diversity. "This is what people flock to cities for," she notes.
• Threats to Creativity: The discussion touches on the closure of venues across the city, which act as vital incubators for the arts. "Venues have closed right across the city in a really, really major way in the last sort of 10 to 15 years," Tabassum points out.
• Digital vs. In-Person Experiences: Despite the rise of digital platforms, the pandemic underscored our craving for the energy of live events. "We crave coming together and there's nothing like live music in the sense of having all those people in a room," says Tabassum.
• Scaling Up Creativity: Faisal discusses the challenge of scaling up creative ventures in Toronto and expresses excitement about micro-retail spaces. "I think the Gerard Street example where you have developers working in conjunction with...a public and private model...gives the best chance for a lot of these companies to grow," he says.
• The High Cost of Living: A 2019 Toronto Arts Council report revealed that 70% of artists are considering leaving the city due to high living costs. "How do you sustain a creative city when your artists can't afford to live here?" Tabassum questions.
• Toronto’s Unique Story: Both guests suggest creating a Chief Creative or Culture Officer to craft and tell Toronto's unique story. Faisal provocatively suggests, "Don't give a fuck about Tim Hortons and hockey... be more than a Bennetton commercial mixed with a Tim Hortons one."
• A Call to Action: As the episode concludes, Faisal and Tabassum urge Torontonians to recognize that their story is far from finished. "Come up here and finish the story," Faisal invites.
• "Venues have closed right across the city in a really, really major way in the last sort of 10 to 15 years." - Tabassum Siddiqui
• "We crave coming together and there's nothing like live music in the sense of having all those people in a room." - Tabassum Siddiqui
• "I think the Gerard Street example where you have developers working in conjunction with... a public and private model... gives the best chance for a lot of these companies to grow." - Faisal Siddiqui
• "Toronto Arts Council and Foundation in 2019 put out a research report... 70% of the several thousand artists that they surveyed said they were considering leaving Toronto in the coming years. And why was that? Simply cost of living." - Tabassum Siddiqui
• "This is the place where who you were has no bearing on who you can be. That's ambitious, future-facing, and exciting." - Faisal Siddiqui
• "Why do people come to live in Toronto? For food and culture, not to live in a glass condo." - Faisal Siddiqui
• "We've come so far from 'Toronto the Good'... we're absolutely not that anymore." - Tabassum Siddiqui
• "Don't give a fuck about Tim Hortons and hockey... be more than a Bennetton commercial mixed with a Tim Hortons one." - Faisal Siddiqui
• "Come up here and finish the story." - Faisal Siddiqui
• "Toronto has to act now or the chance will be gone." - Faisal Siddiqui

In this episode of Challenger City TO, host Iain Montgomery sits down with Alex Tribe to discuss Toronto's transformation from a vibrant entertainment hub to a growing global city. They explore the city's evolving challenges, including housing affordability, risk aversion, and cultural mediocrity. Alex shares his unique insights from his journey as a DJ turned entrepreneur and small business consultant, highlighting the need for clear vision and ambitious leadership to navigate Toronto's growing pains and unlock its full potential.

Key Topics Discussed:

• Alex's Background:
  • Transition from DJ to entrepreneur.
  • The value of experimentation and taking risks in career and business.
• Evolution of Toronto’s Entertainment District:
  • Changes from a nightlife hotspot to a more residential area.
  • Impact of these changes on the city's cultural landscape.
• Toronto’s Growing Pains:
  • The city’s transition into a global city and the associated discomfort.
  • Challenges of applying old solutions to new problems.
• Cultural Mindset:
  • Tendency to choose mediocrity and avoid bold decisions.
  • Impact on the city's development and problem-solving.
• Affordability and Risk-Taking:
  • Economic realities forcing creative and entrepreneurial talent out of the city.
  • The alarming trend of people leaving Toronto for more affordable areas.
• Perception and Real Change:
  • The overwhelming focus on housing affordability overshadowing other critical issues.
  • Importance of perception and culture in driving real change.
• Clear Vision and Leadership:
  • The need for ambitious leadership with a clear vision for the city's future.
  • How solving housing and transit issues could unlock Toronto's potential.

Notable Quotes:

• "I'm a firm believer that just doing stuff for the sake of it and seeing where that takes you is one of the biggest launching pads for the best opportunities."
• "Toronto is kind of becoming a grown-up city... with a bunch of people who I think are reluctant to the idea or fail to recognize that we're becoming a global city."
• "We seem to just choose the middle of the road... it creates a culture of kind of, I guess, good enough or tolerate mediocrity."
• "Places that are less expensive are where experiments can be made because the risk of failure is lower."
• "Nine and a half out of ten conversations I have with people my age somehow get brought back to housing. I'm sick of talking about housing. I want to talk about way more interesting things than housing."
• "If we solve housing affordability and transit, it allows us to change the conversation to something higher leverage."

In this episode, futurist Nik Badminton shares his insights on the future of cities, emphasizing the need for human-centric, community-focused urban planning. Drawing from his global experiences, Nik discusses the challenges of balancing legacy systems with innovative solutions and highlights the importance of creating resilient, vibrant cities like Toronto.

Key Topics Discussed:

1. Introduction to Nik Badminton:
   • Background and experience in futurism and strategic planning.
   • Nik's travels and comparisons between cities like Toronto and Vancouver.
2. Challenger Cities Concept:
   • Definition and importance of Challenger Cities.
   • The need for cities to be more human-centric and community-focused.
3. Accretive Legacy Systems:
   • Explanation of how cities are built on historical infrastructures.
   • The constant challenge of updating and transforming old systems.
4. Rethinking Urban Planning:
   • Critique of using outdated templates for future cities.
   • Examples of successful urban planning from cities like Barcelona.
5. Facing Dystopian Futures:
   • Importance of considering both positive and dystopian futures.
   • Specific examples of dystopian elements in current cities.
6. Challenges and Opportunities for Toronto:
   • Issues with unchecked construction and the loss of community value.
   • The need for green spaces and community meeting areas.
7. Balancing Economic Growth with Community Cohesion:
   • The dangers of focusing solely on economic growth.
   • The importance of creating spaces that enhance quality of life.
8. Learning from Other Cities:
   • The benefits and pitfalls of copying urban designs from other cities.
   • The unique culture and hidden gems of Toronto.
9. Vision for Toronto’s Future:
   • Nik’s proposals for improving Toronto’s urban planning.
   • Emphasis on human-centric development and community cohesion.

Quotes from Nik Badminton:

• "Every time I traveled to Toronto, there was a real humanity to it, a real old-school feel."
• "Challenges cities need to buck the trend of being built around cars and trucks."
• "We need to rethink food, energy, water, and community systems."
• "Barcelona's superblocks are a great example of urban innovation."
• "We kind of live in a dystopian world that's rather strange."
• "Unchecked development leads to empty high-rises and lost community value."
• "We're like the algorithmic city... need to come back to human focus."
• "Most cities lack a comprehensive strategy beyond building more infrastructure."
• "Toronto is a tapestry of diverse neighborhoods and hidden gems."
• "Economic growth should be balanced with relentless community cohesion."

In this episode of Challenger City TO, Iain welcomes Jordan Ostapchuk, a pioneering capital designer, to explore the transformative role of capital design in urban investment. Jordan, who often finds himself as the "token capitalist in a room full of designers" and the "token designer in a room full of capitalists," shares his unique perspective on integrating creative thinking with traditional finance to address the complexities of modern urban challenges.

Key Discussion Points:

• Introduction to Capital Design:
  • Jordan explains the concept of capital design, blending the rigor of investment with the creative logic of design.
  • The importance of framing problems correctly to develop effective solutions.
• Role of Institutional Capital:
  • How institutional capital, encompassing over a hundred trillion dollars globally, influences urban development.
  • The need for design to help risk-averse and conservative investors adapt to new challenges with modern tools.
• Challenges and Innovations:
  • The mismatch between traditional asset classes and the modern world.
  • Jordan's experiences in driving innovation at a major real estate developer in Toronto during the rise of WeWork.
  • The example of APG changing their definition of infrastructure to include equality and quality of life.
• Toronto as a Challenger City:
  • The potential for Toronto to become a Challenger City by articulating clear aspirations and leveraging its strengths.
  • The role of institutional capital in contributing to the city's long-term viability and vibrancy.
  • Jordan's vision of a future where Toronto's decision-making processes are inclusive and future-oriented, with an Office for the Future dedicated to strategic planning.
• Designing Better Decision-Making Systems:
  • The need to improve the consultation process in urban planning.
  • The potential of innovative decision-making processes like quadratic voting.
  • Balancing top-down and bottom-up approaches in urban planning, drawing inspiration from natural systems.
• Toronto's Unique Position:
  • Toronto as a leading hub for pension investors, known for the Maple model.
  • The opportunity for Toronto to leverage its strengths and innovate, despite a tendency towards complacency.
• Future Outlook:
  • Jordan's speculation on where we might be in 10 years, potentially discussing urban investment in the headquarters of the Toronto Civic Strategic Sensing Centre.
  • His hope for a city that looks more like a thriving forest than a rigid Lego set.

Quotes:

• "If we can frame the problem correctly, I think we're 80% of the way there to solving it."
• "Institutional capital will be the most transformative force of the 21st century."
• "A Challenger City has a distinct aspiration for what it wants to be and a strategy to achieve it."
• "We're sitting in the headquarters of the Toronto Civic Strategic Sensing Centre, where we have a robust process for thinking about the future and incorporating multiple voices and perspectives and constantly adapting."
• "I hope that we can say the city looks a lot more like a forest than it does a Lego."

Summary

In this conversation, Iain interviews Jasmine about the concept of Challenger City and how cities can embrace this mindset to drive innovation and growth. They discuss the unique challenges and opportunities for cities in Canada, particularly smaller and mid-sized cities. They also explore the current state of Toronto and the need for the city to redefine itself and create a more vibrant and accessible downtown. Jasmine suggests the idea of a Challenger City accelerator to bring together stakeholders and drive action towards a shared vision. They also discuss the importance of creating diverse and inclusive spaces in cities to foster innovation and a sense of belonging.

Takeaways

• Challenger City is a mindset that involves embracing innovation and taking bold actions to redefine a city's identity and drive growth.
• Smaller and mid-sized cities in Canada are experiencing growing pains and are ripe for transformation and reimagining.
• Cities need to focus on creating vibrant and accessible downtown areas that offer unique experiences and cater to diverse demographics.
• A Challenger City accelerator could bring together stakeholders from various sectors to build capacity, define a shared vision, and drive action towards city-defining projects.
• Creating diverse and inclusive spaces in cities is crucial for fostering innovation, a sense of belonging, and a vibrant urban environment.

Sound Bites

• "A challenger city is a city that knows itself, that doubles down, that thinks about its critical stats in a new way, that's going to be bold around its story."
• "A challenger city is one that says, this is what we stand for. These are our strengths. These are the things we are not. And we're going to be really bold and ambitious around city-defining projects."
• "You can't manage a city by a spreadsheet because a city is a living thing."

In this enlightening episode of Challenger City TO, host Iain Montgomery sits down with Aileen Nandy, an expert in digital marketing, community building, and former journalist. Recorded amid the tranquil sounds of a camping trip, the conversation delves deep into what makes a city truly family-friendly and how Toronto can rise to the challenge. Aileen shares her unique perspective on urban development, the importance of affordable housing, and the concept of "extroverted spaces" that foster community interaction. Tune in to explore the complexities and possibilities of designing a city that supports families, and gain valuable insights on urban planning and community building.

Key Topics Discussed:

• Aileen Nandy's journey from journalism to community building
• Defining a Challenger City and its relevance to Toronto
• Balancing the core of the city with its suburbs
• The housing dilemma: affordability and availability for families
• Creating extroverted spaces that encourage community interaction
• Criticisms of Toronto's Vision Zero initiative and street safety
• The critical role of community programming and services
• A call for inclusive urban planning and redesigning housing
• Addressing Toronto's car-centric culture and its impact on walkability

Notable Quotes:

• "A Challenger City is one that thinks about what kind of communities or society they want to build and is not shackled by just building block upon block."
• "We end up with a profoundly family-unfriendly city that a lot of people can't afford to live in."
• "Cities should be designed to be extroverted. They should be designed to be easy to read and easy to understand and easy for lots of different people to engage with."
• "You need enough affordable housing that you have teachers who can work in the schools and not have totally ridiculous commutes because they can't afford to live in the city."
• "Only in the face of abject tragedy does it seem like we get any meaningful progress on Toronto's Vision Zero."

In a world where healthcare systems strain under ageing populations, chronic diseases, and practitioner shortages, innovation has never been more critical. In this episode, we explore how cities can rethink health through the lessons of Sault Ste. Marie.

Healthcare: The Urban Blindspot

Healthcare often sits on the periphery of urban planning—a blindspot that Anna Foat, with her wealth of experience, helps illuminate. “People often think healthcare is free, but nothing’s truly free,” she begins, describing how systems designed decades ago are struggling to adapt. Longer lifespans, chronic diseases, and shifting practitioner roles have created a "rat’s nest" of challenges.

Sault Ste. Marie: A Case Study in Creativity

Historically a steel town, Sault Ste. Marie has faced significant healthcare challenges but also developed innovative solutions. “When the steel plant set up here, they established Group Health—a mini-hospital integrating doctors, nurses, nutritionists, and more,” Anna explains. The Northern Ontario School of Medicine (NOSM) complements this approach by training rural generalists equipped for diverse, high-pressure settings. This strategy helps prevent brain drain and fosters skills tailored to the region’s needs.

The Case for Prevention

“We don’t make the healthcare point when designing cities,” Anna argues. Active transportation—like walking and biking—boosts physical health and social connectivity. She points to initiatives where doctors prescribe nature passes or train tickets to get people moving. “It’s not fluffy—it’s fundamental to public health.”

Breaking Down Barriers

Anna critiques the inefficiencies within healthcare systems: “Most healthcare tech feels like the 1990s—nurses still transcribe notes by hand.” She advocates for basic tech improvements, like searchable PDFs and OCR, to reduce administrative burdens. Cultural shifts are equally crucial: “We create so much busy work. Patients end up in unnecessary appointments while others with acute needs wait.”

Humanising Healthcare

Healthcare is ultimately about people, not just systems. Anna underscores the need for clear, compassionate communication: “A third of terminal cancer patients don’t know they’re terminal. Doctors shy away from harsh news, leaving patients uninformed.”

Despite the challenges, she shares positive anecdotes, like her son’s swift, well-communicated care after a broken arm—reminders that human touch often outweighs technological advancements.

A New Vision for Cities

Anna draws inspiration from the Netherlands' 'home-spital' model, which keeps patients comfortable at home and eases hospital strain. Looking ahead, she prioritises community-building to combat loneliness: “Cities can create events and spaces that bring people together. It’s not everything, but it’s a meaningful start.”

Magic Wand Question:

“If I had a magic wand, I’d tackle loneliness.”

Anna’s belief is clear: healthcare innovation isn't just about new tools or buildings—it's about rethinking how we connect, care, and design our cities to foster well-being.

In this conversation, Iain and Hayden discuss the complexities of urban transit systems, the historical context of public transportation in North America, and the political dynamics that affect transit development. They explore case studies like La Sombrita, the need for reform in institutions, and the importance of public trust in transit systems. The discussion also touches on international comparisons, the role of the private sector, and the vision for future transit systems that are interconnected and efficient. Ultimately, they emphasize the need for a new democratic urban agenda that prioritizes building and delivering effective transit solutions.

https://thetransitguy.substack.com/p/10-principles-for-a-new-democratic

takeaways

• Transformative transit is essential for urban development.
• Historical governance issues have led to poor transit systems in North America.
• Public trust is crucial for the success of transit projects.
• Reforming institutions can lead to better transit outcomes.
• International examples show the benefits of interconnected transit systems.
• The private sector has a significant role in urban development.
• Political dynamics often hinder effective transit solutions.
• Case studies can provide valuable lessons for future projects.
• A new democratic urban agenda is needed to prioritize building.
• We must shift from studying to implementing transit solutions.

titles

• Reimagining Urban Transit: A Conversation with Hayden Clarkin
• The Future of Public Transportation: Challenges and Solutions

Sound Bites

• "We need to rebuild these institutions."
• "Stop studying. Just do."
• "We need a housing industrial complex."

Chapters

00:00Introduction to The Transit Guy

04:53The Evolution of Public Transit in America

07:45The Impact of World War II on Urban Development

10:24The Challenges of Rebuilding Transit Systems

13:30La Sambrita: A Case Study in Transit Failures

16:09Political Trust and Institutional Failures

18:59The Need for Institutional Reform

21:37Comparative Analysis of Global Transit Systems

24:33The Importance of Incremental Development

27:23Public Perception and the Future of Transit

32:51The Experience Beyond the Stadium

36:41Zoning and Urban Design Challenges

40:50Homeowner vs. Renter Dynamics

46:29The Inefficiency of Government Processes

51:44Political Vision and Local Governance

53:41A National Vision for Transportation

55:51Introduction to Urban Challenges

Episode Summary:

In this episode of Challenger City TO, we sit down with Hans Bathija, a seasoned consultant with a rich history in Toronto. Hans shares his insights on the city's evolving identity, the impact of amalgamation, the importance of public safety, and the need for a renewed focus on arts and culture. Join us as we explore what it means for Toronto to be a Challenger City and how it can reclaim its status as a dynamic, innovative, and inclusive urban center.

Key Topics Discussed:

1. Hans' Journey to Toronto:
   • Moving from London to Toronto in 1975
   • Early experiences in Scarborough and working in the photo finishing industry
   • Transition to banking and consulting
2. Toronto's Evolution:
   • The city's innovative past in banking and technology
   • Impact of bank mergers and the end of antitrust acts
   • Shifts in local leadership and corporate focus
3. Amalgamation and Its Consequences:
   • Hans' run for mayor during the amalgamation period
   • Dilution of local leadership and competition
   • The need for accessible and responsive local governance
4. Public Safety and Infrastructure:
   • Issues in Liberty Village: traffic and emergency access
   • Bureaucratic indifference to local problems
   • Importance of public safety as a cornerstone of urban life
5. The Role of Arts and Culture:
   • Loss of Toronto's vibrant arts scene due to condo-ization
   • Need for protected artistic spaces
   • Toronto's rich musical heritage and cultural identity
6. Grassroots Initiatives:
   • Hans' involvement in the Toronto Dollar project
   • Challenges of sustaining grassroots initiatives
   • Importance of community engagement and local projects
7. Leadership and Vision:
   • The need for a blueprint for Toronto's future
   • Involving private sector leaders, academia, and the community
   • Defining what it means to be Canadian and ensuring a thriving urban environment

Memorable Quotes:

• "Up to maybe 20 years ago, Toronto was a very innovative place... The problem with that is you have organisations that are no longer Toronto-centric or Toronto-focused in terms of where they live and work and play."
• "Policies were designed to look after local taxpayers... We need accessible and responsive local governance."
• "Liberty Village is a 'disaster zone' with severe traffic and emergency access issues... I get told, 'Oh, studies have been done, there is no issue.' Well, 10 years later, it's gotten worse."
• "The culture that defined Toronto before is disappearing very rapidly... Maybe we need a place in Toronto that's protected and arts can go there."
• "We need to have a blueprint for the city... We need to demand more of the elders. Your grandchildren need your help. You can't just flitter off somewhere and have a good time and have your pina coladas while everything's burning around you."

Conclusion:

Hans Bathija's insights offer a compelling vision for Toronto's future as a Challenger City. His call for grassroots involvement, a renewed focus on public safety, and a commitment to preserving the city's cultural heritage resonates with the challenges and opportunities facing Toronto today. As the city navigates its evolving identity, Hans' perspective serves as a reminder of the importance of leadership, community, and a shared vision for a better future.

Urban design often focuses on hardcore infrastructure—but what about the people who use it? In this episode, we explore how psychology, neuroscience, and philosophy can make urban spaces work better for everyone.

From Oboist to Urban Innovator

“Musicians handle time—we take a note from the future, play it in the present, and it instantly becomes the past.”

Nick Tyler’s journey into urban design began in an unconventional place: as a professional oboist. His musical background taught him to think creatively about time, space, and human experience—lessons that would later shape his innovative approach to city planning.

After a master’s in transportation planning and time spent studying Brazilian bus systems, Nick saw how traditional engineering models often ignored human behavior. “Engineering is often about making up your mind. But real creativity lies in undoing your mind—being open to new ways of thinking.”

PEARL: A Laboratory for Urban Change

Nick leads PEARL, a cutting-edge facility at University College London that simulates urban environments to study how people react to light, sound, and space. Through this work, Nick and his team have uncovered fascinating insights, like the psychological conflict caused by floating bus stops. “Cyclists narrow their focus to stay upright, making them less aware of pedestrians. It’s not their fault; it’s just how the brain works.”

The research showed how fear and unpredictability impact people’s perceptions, highlighting the need to design for both physical safety and emotional comfort.

Designing for People, Not Codes

Nick challenges the rigid standards in urban design: “Standards should serve people, not constrain creativity.”

He advocates for outcome-based approaches—like lighting standards that ensure passengers can see a person in black at 200 meters rather than meeting abstract brightness metrics. This human-first mindset redefines accessibility as a mental state, not just a physical requirement.

Rethinking Maslow’s Hierarchy of Needs

“Maslow never intended his needs to be a hierarchy,” Nick reveals. Instead of a fixed pyramid, human needs are dynamic and context-dependent. Cities, therefore, should balance safety, community, and creativity to foster genuine well-being.

Community at the Core of Urban Design

“Social connectedness is essential for survival.”

Nick envisions cities as places where human connection is easy and natural. His experiment—saying good morning to bus drivers—illustrated how simple social interactions can ripple through a community. Designing for these moments could reshape cities into spaces where people feel safe, seen, and connected.

Magic Wand Question:

“If I had a magic wand, I’d enable people to express their sociality in public spaces.”

Nick’s vision is a world where cities are designed with the messiness of human behavior in mind—where psychology and engineering work hand in hand.

In this insightful episode of "Challenger City TO," Iain Montgomery sits down with Hilton Barber, a seasoned marketer and thought leader, to explore the transformative power of culture in shaping Toronto’s future. Hilton discusses the critical role that bold, courageous decisions play in driving cultural change, emphasising the need for Toronto to shift from a mindset of playing it safe to one of striving for greatness. He shares his thoughts on what it means to have a winning strategy, how culture impacts execution, and why defining Toronto’s unique version of “gold” is essential for the city's success.

Key Topics Discussed:

• The importance of culture in organisational and urban success
• Hilton’s career journey and insights on cultural impact
• Why curiosity alone isn’t enough—execution is key
• The need for safety and bravery in decision-making
• Examples of strong corporate culture, including Izzy Sharpe and Four Seasons
• Toronto’s current cultural landscape and the call for greater ambition
• The concept of playing to win versus playing to not lose
• The role of leadership in setting and executing grand ambitions
• Personal responsibility and collective effort in driving Toronto’s transformation
• The importance of storytelling in creating a shared vision for the city

Quotes to Remember:

• "Strategy is one thing. Execution is the game."
• "What is the size of our ambition? If we have a grand ambition, do we have the courage, the fortitude, the comfort with failing along that journey?"
• "If we don’t create a compelling story that brings people along, that engages them and says, 'Imagine this better future for Toronto,' we’re dead in the water."

Actionable Takeaways:

• Toronto must define its unique version of success and aim for it with boldness.
• Leaders need to create a culture that supports ambitious, transformative decisions.
• Personal and collective responsibility is crucial for Toronto’s progress.

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 transformation
• Cities must treat downtowns like complex systems, not complicated ones
• Pedestrianisation needs testing, not top-down mandates
• Progress 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 Marketplace
• Congress for the New Urbanism
• Center for Neighborhood Technology
• Chuck Marohn and Strong Towns
• Tactical Urbanism movement
• Interview 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