Challenger Cities EP30: Is the On-Site, the New Off-Site? Real Estate, Remote Work and Reinventing Cities with Dave Cairns
Update: 2025-06-09
Description
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office space contrarian explains why remote work is not a trend but a paradigm shift, how most cities are clinging to outdated myths, and why the real challenge isn't return-to-office—it's return to relevance.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
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