Madison McVeigh/CityLab

On Episode 3 of the podcast Technopolis, we wrestle with the legacy of Uber, Lyft, and Airbnb on how startups engage with government.

Listen and subscribe to Technopolis: Apple Podcasts / Stitcher / Google Play / Spotify

Walk the streets of some cities over the past few months and you'll find a new phenomenon in full force. Professionals in suits glide down bike lanes on skinny strips of plastic. Tourists gleefully teeter through their first scooter ride on crowded sidewalks.

For some, the quick adoption of the dockless electric scooter by city residents is an exciting development of new sustainable mobility options. But for every enthusiastic rider, there are also outraged pedestrians climbing over piles of scooters on the sidewalk, or cars veering to avoid a scooter in traffic. And a lack of clear rules and often, helmets, means that a lot of riders are ending up injured, sometimes finding themselves in the emergency room.

The rollout of scooters without new rules of the road has provoked a strong emotional response. And it’s not just the scooters. When new innovations like ride-hailing (e.g. Uber/Lyft), home-sharing (e.g. Airbnb), or home-cooking (e.g. Josephine) show up, the startups behind them don't always ask the cities where they're appearing for permission to be there. This is in part because they suspect a lot of cities probably wouldn’t give permission—at least not on the sped-up timelines those companies are seeking. And when companies don't ask for or get permission, they're unconstrained by rules—at least temporarily.

In the past, that "disruptive" rule-breaking quality has been a point of pride for some startups, while for others it’s been a source of embarrassment, and in a few cases just a reflection of their own obliviousness. Regardless of their intent, companies risk pissing off more city officials than they win over. Which poses a big strategic question: Is it better for startups to ask for permission or beg for forgiveness from the cities they’re trying to disrupt? And where does all of this leave the ordinary city resident who just wants to use a scooter—or avoid being run over by one?

These are the questions we ask on this week’s episode of Technopolis, the new podcast from CityLab about how technology is disrupting, remaking, and sometimes overrunning our cities.

We talk with an early political advisor to Uber, Bradley Tusk, who now advises scooter and drone startups on this very question. We also talk with the head of Los Angeles’ Department of Transportation, Seleta Reynolds, about her experience negotiating with the wild world of mobility disruptors. And we hear what it’s like for one city on the ground from Austin Chronicle reporter Nina Hernandez.

Nowhere are we seeing these city-startup dynamics play out more right now than in the e-scooter wars. But there’s one thing about working with cities: There are a lot of them, and they’re all pretty different. Figuring out the right way to launch a new urban technology may be more complicated—both for the businesses and the cities that regulate them—than you think.

Listen and subscribe to Technopolis: Apple Podcasts / Stitcher / Google Play / Spotify

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