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PODCAST

Challenger Cities

Iain Montgomery

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.

arts design

All Episodes

56:16

Challenger Cities EP17: Cycling, Leadership and the...

Challenger Cities ·

2024/12/19

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

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56:30

Challenger Cities EP16: Red Tape to Results;...

Challenger Cities ·

2024/12/17

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

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61:48

Challenger Cities EP15: Trains, Pains and Automobiles...

Challenger Cities ·

2024/12/13

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

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67:32

Challenges Cities EP14: Exploring Joyful Cities with...

Challenger Cities ·

2024/11/25

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

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44:54

Challenger City TO EP13: Envisioning Future Housing...

Challenger Cities ·

2024/08/19

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

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54:31

Challenger City TO EP12: Governance to Growth in...

Challenger Cities ·

2024/08/12

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

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50:49

Challenger City TO EP11: Developing Toronto's Winning...

Challenger Cities ·

2024/08/09

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

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45:25

Challenger City TO EP10: Future Family-Friendly...

Challenger Cities ·

2024/08/07

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

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50:03

Challenger City TO EP9: The Role of Capital Design in...

Challenger Cities ·

2024/08/05

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

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54:39

Challenger City TO EP8: A blueprint for a better...

Challenger Cities ·

2024/07/31

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'

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39:00

Challenger City TO EP7: Balancing the best of...

Challenger Cities ·

2024/07/26

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

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39:28

Challenger City TO EP6: Swallowing the Orange Pill...

Challenger Cities ·

2024/07/25

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

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51:35

Challenger City TO EP5: Going beyond 'Toronto the...

Challenger Cities ·

2024/07/22

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

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38:19

Challenger City TO EP4: Foresight-led Future with...

Challenger Cities ·

2024/07/22

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

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34:10

Challenger City TO EP3: Toronto's Growing Pains with...

Challenger Cities ·

2024/07/16

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

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50:32

Challenger City TO EP2: Rekindling Toronto’s status...

Challenger Cities ·

2024/07/12

Episode DescriptionIn 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

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39:35

Challenger City TO EP1: Embracing the Challenger City...

Challenger Cities ·

2024/07/09

SummaryIn 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

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