Challenger Cities – Details, episodes & analysis

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Challenger Cities

Iain Montgomery

Arts

Society & Culture

Frequency: 1 episode/9d. Total Eps: 98

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.

Recent rankings

Latest chart positions across Apple Podcasts and Spotify rankings.

Apple Podcasts

🇨🇦 Canada - design
21/08/2026
#84
🇫🇷 France - design
20/08/2026
#85
🇫🇷 France - design
19/08/2026
#76
🇫🇷 France - design
18/08/2026
#66
🇨🇦 Canada - design
17/08/2026
#88
🇫🇷 France - design
17/08/2026
#50
🇨🇦 Canada - design
16/08/2026
#85
🇫🇷 France - design
16/08/2026
#38
🇨🇦 Canada - design
15/08/2026
#95
🇫🇷 France - design
15/08/2026
#32

Spotify

No recent rankings available

Shared links between episodes and podcasts

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https://urban-future.org/
2 shares
https://www.freewheeling.info/
2 shares
https://thetransitguy.substack.com/p/10-principles-for-a-new-democratic
2 shares

https://www.youtube.com/@RMTransit
2 shares
https://www.youtube.com/watch?v=-b8grwoUqvo&amp
2 shares
https://www.youtube.com/watch?v=baDR_fBRpBI
1 share

https://www.linkedin.com/in/thomasableman/
2 shares
https://www.linkedin.com/company/notworking-to-networking/?originalSubdomain=ca
2 shares
https://linkedin.com
1 share

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RSS feed quality

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Score global : 62%

Publication history

Monthly episode publishing history over the past years.

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Latest published episodes

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Challenger City TO EP13: Envisioning Future Housing with Chris Spoke

Season 1 · Episode 13

Monday, August 19, 2024 • Duration 44:54

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."

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Challenger City TO EP12: Governance to Growth in Transportation with Antoine Belaieff

Season 1 · Episode 12

Monday, August 12, 2024 • Duration 54:31

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."

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.

Challenger City TO EP3: Toronto's Growing Pains with Alex Tribe

Season 1 · Episode 3

Tuesday, July 16, 2024 • Duration 34:10

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."

Challenger City TO EP2: Rekindling Toronto’s status through the eyes of a retailer with Laura Manes

Season 1 · Episode 2

Friday, July 12, 2024 • Duration 50:32

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.”

Challenger City TO EP1: Embracing the Challenger City spirit with Jasmine Palardy

Season 1 · Episode 1

Tuesday, July 9, 2024 • Duration 39:35

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."

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Challenger City TO EP11: Developing Toronto's Winning Culture for a Golden Future with Hilton Barbour

Season 1 · Episode 11

Friday, August 9, 2024 • Duration 50:49

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.

Challenger City TO EP10: Future Family-Friendly Cities with Aileen Nandy

Season 1 · Episode 10

Wednesday, August 7, 2024 • Duration 45:25

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."

Challenger City TO EP9: The Role of Capital Design in Better, Future Cities with Jordan Ostapchuk

Season 1 · Episode 9

Monday, August 5, 2024 • Duration 50:03

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.

Challenger City TO EP8: A blueprint for a better future through Safety, Leadership & Culture with Hans Bathija

Season 1 · Episode 8

Wednesday, July 31, 2024 • Duration 54:39

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:

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
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
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
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
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
Grassroots Initiatives:
- Hans' involvement in the Toronto Dollar project
- Challenges of sustaining grassroots initiatives
- Importance of community engagement and local projects

Challenger City TO EP7: Balancing the best of tradition and big futures for city planning with Nik Badminton

Season 1 · Episode 7

Friday, July 26, 2024 • Duration 39:00

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:

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

Challenger Cities – Details, episodes & analysis

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Challenger Cities – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other17

Youtube3

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RSS feed quality and score

Publication history

Latest published episodes

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Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Other17

Youtube3

LinkedIn3

Apple Podcasts

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