Challenger Cities
Episodes
Challenger Cities EP71: Welcome to Your Agentic City with Alistair Croll
30 Mar 2026
Contributed by Lukas
We have spent a lot of time on the podcast talking about physical cities as streets, buildings and the spaces between them. What we perhaps don't talk...
Challenger Cities EP70: Building a Village in the Sky with Anson Kwok
16 Mar 2026
Contributed by Lukas
Anson Kwok has spent fourteen years building Canada's tallest tower at the foot of Yonge Street. As VP of Sales and Marketing at Pinnacle Internationa...
Challenger Cities EP69: Designing for Intimacy with Paul Meyers
16 Mar 2026
Contributed by Lukas
At first glance, SPNKD might look like a BDSM venue. But Paul Meyers real focus is something deeper ... finding connection and creating intimacy.We ex...
Challenger Cities EP68: The Bus Deserves Better with Ray Stenning
03 Mar 2026
Contributed by Lukas
What if the problem with buses isn’t frequency, funding or technology ... but attitude?In this episode, we're in person with Ray Stenning, founder o...
Challenger Cities EP67: Watching a World From Behind the Window with Füsun Aydın
25 Feb 2026
Contributed by Lukas
Füsun Aydın has spent twelve years reading people from a window in Amsterdam. Cities would be better places if the people planning them had half her...
Challenger Cities EP66: Urbanism Without the Excuses with Mikael Colville-Andersen
19 Feb 2026
Contributed by Lukas
In this episode of Challenger Cities, Iain Montgomery is joined by urban designer, filmmaker, and author Mikael Colville-Andersen for a wide-ranging c...
Challenger Cities EP65: Sitopia with Carolyn Steel
16 Feb 2026
Contributed by Lukas
Cities are usually explained through buildings, infrastructure, policy and planning. Food rarely gets a look-in.Which is strange, because for most of ...
Challenger Cities EP64: Tourism as a Stress Test with Maryam Siddiqi
10 Feb 2026
Contributed by Lukas
Tourism is big business. Cities spend vast sums attracting visitors, promoting landmarks and polishing their image. What they’re far less good at is...
Challenger Cities EP63: The Pub Is a Public Service with Pete Brown
06 Feb 2026
Contributed by Lukas
In this episode of Challenger Cities, we've got Pete Brown, one of the UK’s most thoughtful writers on beer, pubs, and drinking culture.Pete has spe...
Challenger Cities EP62: Cities for People Who Want to Try Things with Patti Baston
02 Feb 2026
Contributed by Lukas
Most cities are designed around a surprisingly narrow idea of who gets to feel comfortable in public.In this episode of Challenger Cities, Iain Montgo...
Challenger Cities EP61: Sweat and the City with Glenn Auerbach
27 Jan 2026
Contributed by Lukas
Iain Montgomery talks with Glenn Auerbach about why sauna, bathing and cold-water culture has suddenly gone mainstream in cities around the world, and...
Challenger Cities EP60: Designing Cities in Pencil, Not Pen with Jasmine Palardy (again)
19 Jan 2026
Contributed by Lukas
We reconnect with Jasmine Palardy almost eighteen months after our very first conversation to reflect on what has changed in how we think and talk abo...
Challenger Cities EP59: Building Faster Than Memory with Ruchita Bansal
19 Jan 2026
Contributed by Lukas
Ruchita Bansal discusses what happens when modern infrastructure projects are built at speed but don’t connect with the deep, informal systems that ...
Challenger Cities EP58: The World's Best Cities with Chris Fair
19 Jan 2026
Contributed by Lukas
Chris Fair, CEO of Resonance and publisher of "World's Best Cities" talks about what really separates the world’s cities. As Chris explains, obsessi...
Challenger Cities EP57: Young People and the New Rules of Money with David Akermanis
19 Jan 2026
Contributed by Lukas
Researcher and strategist David Akermanis talks about how young people are navigating a world where traditional financial stability has eroded and cit...
Challenger Cities EP56: Why Empty Space Is Never Neutral with Evan Snow
19 Jan 2026
Contributed by Lukas
Evan Snow, co-founder of Zero Empty Spaces talks about why vacancy in cities isn’t a neutral pause but an active force shaping how we feel, move and...
Challenger Cities EP55: Impossible City - Paris in the 21st Century with Simon Kuper
19 Jan 2026
Contributed by Lukas
In this episode of Challenger Cities, Iain Montgomery talks with journalist and author Simon Kuper about his book Impossible City: Paris in the Twenty...
Challenger Cities EP54: Rethinking Ireland, the Too Often Misunderstood Challenger Country with Peter Ryan
19 Jan 2026
Contributed by Lukas
In this episode of Challenger Cities, Iain Montgomery is joined by economist and commentator Peter Ryan for a wide-ranging conversation about Ireland,...
Challenger Cities EP53: The Logic Beneath the Madness of Transport with Marcus Mayers
03 Dec 2025
Contributed by Lukas
Iain Montgomery and Marcus Mayers discuss the complexities of transport systems, focusing on the balance between passenger experience and operational ...
Challenger Cities EP52: Culture as a Form of Wealth with Paul Owens
24 Nov 2025
Contributed by Lukas
In this episode of Challenger Cities, we chat with Paul Owens, co-founder of BOP Consulting, long-time collaborator of Charles Landry, and one of the ...
Challenger Cities EP51: Women Changing Cities with Melissa Bruntlett
10 Nov 2025
Contributed by Lukas
Melissa Bruntlett discusses her book 'Women Changing Cities' and the transformative role of women in urban mobility and planning. She emphasizes the i...
EP50: If a City Can’t Handle a Little Kink ... with Lady Valeska
29 Oct 2025
Contributed by Lukas
This one’s a little different. We sat down with Lady Valeska, a professional dominatrix now based in London, to talk about what cities, workplaces, ...
Challenger Cities EP49: How the Screen Has Killed the City with Greg Lindsay
27 Oct 2025
Contributed by Lukas
Iain Montgomery and Greg Lindsay explore the intersection of urbanism and technology, discussing how screens and AI are reshaping cities. They delve i...
Challenger Cities EP48: Live, Move, Rest ... The Conscious City with Anupam Yog
20 Oct 2025
Contributed by Lukas
In this conversation, Iain Montgomery and Anupam Yog delve into the concept of urban mindfulness and its implications for city design. They explore ho...
Challenger Cities EP47: Cities on the Couch with Charles Landry
02 Oct 2025
Contributed by Lukas
SummaryIn this conversation, Charles R. Landry discusses the concept of creative cities, emphasizing the importance of imagination, psychology, and hu...
Challenger Cities EP46: Stitching the Fragmented City with Rashiq Fataar
01 Oct 2025
Contributed by Lukas
In this conversation, Iain Montgomery and Rashiq Fataar delve into the complexities of urbanism in South Africa, particularly focusing on Cape Town. R...
Challenger Cities EP45: Utopian Hours - Turin’s Festival of the Possible with Luca Ballarini
26 Sep 2025
Contributed by Lukas
In this conversation, Iain Montgomery speaks with Luca Ballarini about Utopian Hours, a festival in Turin that celebrates urbanism and creativity. The...
Challenger Cities EP44: Your City Isn’t Crowded, It’s Just Full of Cars with Daniel Herriges
19 Aug 2025
Contributed by Lukas
aniel Herriges joins us to explore one of the most underestimated levers for better cities: parking reform. A longtime Strong Towns writer and co-auth...
Challenger Cities EP43: Daring To Be Different with Andy Nulman
19 Aug 2025
Contributed by Lukas
Andy Nulman is a man who’s seen Montreal through every era — and he’s not afraid to call out what’s gone wrong. In this no-holds-barred conver...
Challenger Cities EP42: Hauling Towards the Future with Michael Wexler
01 Aug 2025
Contributed by Lukas
TakeawaysMichael Wexler's journey into urbanism began unexpectedly.He transitioned from cycling-focused projects to broader transit planning.Cargo bik...
Challenger Cities EP41: Cities in Limbo with Diana Lind
29 Jul 2025
Contributed by Lukas
Exploring Urban Evolution with Diana LindJoin host Iain Montgomery in a captivating conversation with Diana Lind, renowned urbanist and author, as the...
Challenger Cities EP40: Hovering Above the Status Quo with Erika Potrz
25 Jul 2025
Contributed by Lukas
What if commuting from Niagara to Toronto didn’t mean hours in traffic or waiting on a slow, infrequent train? Erika Potrz thinks there’s a better...
Challenger Cities EP39: A Public Service Steeped in Northern Soul with Alex Hornby
24 Jul 2025
Contributed by Lukas
Northern has long been the UK’s biggest rail operator by stations—and one of its most under-loved. But under Alex Hornby, it’s getting a dose of...
Challenger Cities EP38: The City Fixer's Guide to Messy Momentum with Kevin Klinkenberg
24 Jul 2025
Contributed by Lukas
Every city tells itself a story. In Kansas City, it’s one of manageability: there’s parking when you want it, space to drive, and just enough shin...
Challenger Cities EP37: The Recipe Book for Cities with Guillermo Bernal
24 Jul 2025
Contributed by Lukas
The City’s Recipe Book: Borrow the Technique, Use Your Own Ingredients with Guillermo BernalCities don’t work because of glossy plans or polished ...
Challenger Cities EP36: From Corporate Innovation to Council Budgets with Charlie Rowat
24 Jul 2025
Contributed by Lukas
What happens when you take someone fluent in corporate innovation and drop them into the world of council-led adult social care? A surprising amount o...
Challenger Cities EP35: After Dark and Into the Future with Mathieu Grondin
24 Jul 2025
Contributed by Lukas
What does it take to make a city work after dark?In this episode, we're speaking with Mathieu Grondin, Ottawa’s first-ever Nightlife Commissioner, a...
Challenger Cities EP34: The Magnetic, Messy, Cities People Don’t Leave with Sofia Song
24 Jul 2025
Contributed by Lukas
The Magnetic, Messy Cities People Don’t Leave — with Sofia SongWhat actually keeps people in cities? It isn’t just housing supply, transit plans...
Challenger Cities EP33: Riding Through Stories, Not Just Spaces with Michela Grasso
23 Jul 2025
Contributed by Lukas
What if cycling policy wasn’t about bike lanes but about joy, dignity, and connection? In this episode of Challenger Cities, we sit down with Michel...
Challenger Cities EP32: How to Love a Town Back to Life with Jeff Siegler
11 Jul 2025
Contributed by Lukas
We talk a lot about fixing cities—but less about why we’ve let them decline in the first place. This conversation with civic pride expert Jeff Sie...
Challenger Cities EP31: Building Transit, Trust and Capability with Russell King
09 Jul 2025
Contributed by Lukas
Russell King didn’t start out in transport. But somewhere between regenerating Battersea and reforming Sydney’s transit system, he became—by his...
Challenger Cities EP30: Is the On-Site, the New Off-Site? Real Estate, Remote Work and Reinventing Cities with Dave Cairns
09 Jun 2025
Contributed by Lukas
Episode Description: Dave Cairns used to sell downtown towers. Then he left the city—and the real estate orthodoxy behind. In this episode, the form...
Challenger Cities EP29: The Charming Housing Rebellion with Naama Blonder
06 Jun 2025
Contributed by Lukas
Architect and urban planner Naama Blonder didn’t set out to be a suburban revolutionary. She’s raised her kids in a condo, doesn’t own a car, an...
Challenger Cities EP28: Why North American Transit is Mediocre ... and How to Make it Actually Good with Reece Martin
28 May 2025
Contributed by Lukas
If you’ve ever tumbled down a YouTube rabbit hole about public transportation, chances are you’ve come across Reece Martin — the sharp, relentle...
Challenger Cities EP27: A Housing Plan for Ontario with Mike Schreiner
22 May 2025
Contributed by Lukas
In this conversation, Iain Montgomery interviews Mike Schreiner, the leader of the Ontario Greens, focusing on the pressing issue of housing in Ontari...
Challenger Cities Interlude: One Year Later ... Still a Podcast, but Maybe Something Bigger?
20 May 2025
Contributed by Lukas
This was never meant to be a podcast with a “Series 3.”Challenger Cities started as a bit of a rant, with a hint structure. I was living in Toront...
Challenger Cities EP26: The Policy Playbook for Challenger Cities with Tom Goldsmith
21 Apr 2025
Contributed by Lukas
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...
Challenger Cities EP25: How Nature Can Make Our Cities Thrive with Jan Sumner
21 Apr 2025
Contributed by Lukas
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...
Challenger Cities EP24: Reinventing Cities, through Office to Residential Conversions with Steven Paynter
21 Apr 2025
Contributed by Lukas
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 L...
Challenger Cities EP23: Fixing Cities Through Momentum, Not Just Masterplans with Rik Adamski
21 Apr 2025
Contributed by Lukas
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 p...
Challenger Cities EP 22: The Newcomer Perspective, What Works and What Could Be Better in Toronto with Arthur Smith
19 Feb 2025
Contributed by Lukas
The Newcomer Perspective: What Works and What Could Be Better in Toronto with Arthur SmithIn this episode, we flip the perspective and hear from a new...
Challenger Cities EP21: Learnings from 'the Soo' for Future Healthy Cities with Anna Foat
18 Feb 2025
Contributed by Lukas
In a world where healthcare systems strain under ageing populations, chronic diseases, and practitioner shortages, innovation has never been more crit...
Challenger Cities EP20: Rethinking Cities Through Lessons from Music, Psychology and Engineering with Nick Tyler
18 Feb 2025
Contributed by Lukas
Urban design often focuses on hardcore infrastructure—but what about the people who use it? In this episode, we explore how psychology, neuroscience...
Challenger Cities EP20: Rethinking Cities Through Lessons from Music, Psychology and Engineering with Nick Tyler
22 Jan 2025
Contributed by Lukas
SummaryIn this conversation, Iain and Nick Tyler explore the intricate relationship between urban design, human behavior, and well-being. They discuss...
Challenger Cities EP19: Why Localism Fuels Challenger Cities with Mary Rowe
13 Jan 2025
Contributed by Lukas
In this conversation, Iain Montgomery speaks with Mary Rowe, the head of the Canadian Urban Institute, about the importance of local engagement in urb...
Challenger Cities EP18: How Downsview is redefining Toronto's future by shifting the centre of gravity with Chris Eby
07 Jan 2025
Contributed by Lukas
In this episode of Challenger Cities, host Iain Montgomery sits down with Chris Eby, Executive Vice President of Northcrest, to explore one of Toronto...
Challenger Cities EP17: Cycling, Leadership and the Future of Urban Living with Chris Bruntlett
19 Dec 2024
Contributed by Lukas
Iain Montgomery sits down with Chris Bruntlett of the Dutch Cycling Embassy to explore how cycling infrastructure can transform urban life. Chris shar...
Challenger Cities EP16: Red Tape to Results; Rethinking Governance for Better Cities with Hayden Clarkin
17 Dec 2024
Contributed by Lukas
In this conversation, Iain and Hayden discuss the complexities of urban transit systems, the historical context of public transportation in North Amer...
Challenger Cities EP15: Trains, Pains and Automobiles with Thomas Ableman
13 Dec 2024
Contributed by Lukas
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 Cha...
Challenges Cities EP14: Exploring Joyful Cities with Paul Kalbfleisch
25 Nov 2024
Contributed by Lukas
Iain Montgomery of Now or Never Ventures speaks with Paul Kalbfleisch, author of The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided...
Challenger City TO EP13: Envisioning Future Housing with Chris Spoke
19 Aug 2024
Contributed by Lukas
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 deve...
Challenger City TO EP12: Governance to Growth in Transportation with Antoine Belaieff
12 Aug 2024
Contributed by Lukas
In this episode of Challenger City TO, we sit down with Antoine, a seasoned transit professional with global experience, to dive deep into the complex...
Challenger City TO EP11: Developing Toronto's Winning Culture for a Golden Future with Hilton Barbour
09 Aug 2024
Contributed by Lukas
In this insightful episode of "Challenger City TO," Iain Montgomery sits down with Hilton Barber, a seasoned marketer and thought leader, to explore t...
Challenger City TO EP10: Future Family-Friendly Cities with Aileen Nandy
07 Aug 2024
Contributed by Lukas
In this enlightening episode of Challenger City TO, host Iain Montgomery sits down with Aileen Nandy, an expert in digital marketing, community buildi...
Challenger City TO EP9: The Role of Capital Design in Better, Future Cities with Jordan Ostapchuk
05 Aug 2024
Contributed by Lukas
In this episode of Challenger City TO, Iain welcomes Jordan Ostapchuk, a pioneering capital designer, to explore the transformative role of capital de...
Challenger City TO EP8: A blueprint for a better future through Safety, Leadership & Culture with Hans Bathija
31 Jul 2024
Contributed by Lukas
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 shar...
Challenger City TO EP7: Balancing the best of tradition and big futures for city planning with Nik Badminton
26 Jul 2024
Contributed by Lukas
In this episode, futurist Nik Badminton shares his insights on the future of cities, emphasizing the need for human-centric, community-focused urban p...
Challenger City TO EP6: Swallowing the Orange Pill and Rethinking Train Stations with Chris Burchett
25 Jul 2024
Contributed by Lukas
In this episode of Challenger City TO, we sit down with Chris Burchett, a telecommunications expert turned transit visionary, to explore the transform...
Challenger City TO EP5: Going beyond 'Toronto the good' to discover a city's new cultural identity with Faisal and Tabassum Siddiqui
22 Jul 2024
Contributed by Lukas
In this episode of "Challenger Cities," host Iain Montgomery sits down with two influential figures in Toronto's creative landscape: Tabassum Siddiqui...
Challenger City TO EP4: Foresight-led Future with Ramy Nassar
22 Jul 2024
Contributed by Lukas
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 TO EP3: Toronto's Growing Pains with Alex Tribe
16 Jul 2024
Contributed by Lukas
In this episode of Challenger City TO, host Iain Montgomery sits down with Alex Tribe to discuss Toronto's transformation from a vibrant entertainment...
Challenger City TO EP2: Rekindling Toronto’s status through the eyes of a retailer with Laura Manes
12 Jul 2024
Contributed by Lukas
Episode DescriptionIn this episode, we sit down with Laura Manes, a strategic change agent with over 20 years of experience in retail and consumer bra...
Challenger City TO EP1: Embracing the Challenger City spirit with Jasmine Palardy
09 Jul 2024
Contributed by Lukas
SummaryIn this conversation, Iain interviews Jasmine about the concept of Challenger City and how cities can embrace this mindset to drive innovation ...