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 Siegler is a deep, uncomfortable, and often inspiring look at how we got here and what it takes to turn it around.

Jeff doesn’t believe in sugar-coating. He’s spent his life fighting against civic apathy and calling out the ways we’ve outsourced care, maintenance, and even meaning in our places. We talked about what happens when people stop seeing their city as theirs, why shame and pride are two sides of the same coin, and how to rebuild not just infrastructure, but belief.

This episode is full of insights on:

• Why placelessness is a symptom of deeper dysfunction
• The dangers of design without stewardship
• The real cost of our maintenance gap
• How cities can rekindle civic love—not through slogans, but through action

As Jeff says: “The opposite of love isn’t hate. It’s indifference. And that’s what’s killing our cities.”

Russell King didn’t start out in transport. But somewhere between regenerating Battersea and reforming Sydney’s transit system, he became—by his own admission—“a transport tragic.”

In this wide-ranging conversation, Russell shares what it actually takes to build infrastructure that shapes cities, why most governments lose the capability they’ve just built, and how our obsession with roads and cost-cutting gets in the way of good transport policy. We get into:

– Why rail lines define what kind of city you get – The real reason most transit projects don’t integrate with housing – Lessons from London, Sydney, and Madrid on what to and not to do – Why the road lobby is winning—and how to push back – The hidden subsidies no one talks about (hint: it’s not just transit) – What happens when the political stars align—and why it rarely lasts

A must-listen if you care about cities, infrastructure, or just want to know how good ideas actually get delivered.

Episode Description: Dave Cairns used to sell downtown towers. Then he left the city—and the real estate orthodoxy behind. In this episode, the former poker pro turned office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.

We talk about: – Why cities must now earn our presence – Atlassian and Pinterest as models for modern work – The slow death of co-working (and the lie of flexibility) – How mental health, AI, and autonomy are reshaping value – What Canadian cities still get wrong