Exploring the city Google couldn’t buy

Quayside proposal
Josh O'Kane's new book unpacks the Toronto boondoggle that captured the world's attention.

We cover a lot of different types of stories on BetaKit.

Stories we chase down, stories that smack us in the face, stories that we can’t escape.

Rarely do those stories attract global attention from all corners of politics, society, and tech. So much attention that no one seemed to agree on what the story was.

Such was the case with Sidewalk Toronto – the unholy merger of Waterfront Toronto and Sidewalk Labs that put one of the world’s largest tech companies in Toronto’s backyard, looking to build a pretty big treehouse.

“This is the rise and fall of a company that had hundreds of millions of dollars to play with and nothing left to say about it.”
– Josh O’Kane

It’s a story that BetaKit covered extensively from 2017 to the project’s ignominious shuttering in 2020 during COVID-19. We broke some news during that time, like Sidewalk Labs pulling its commitment to Quayside Venture Partners, and as you’ll hear on this podcast, a story on some comments from Toronto Mayor John Tory that prompted a “frustrated” email response from Sidewalk Labs CEO Dan Doctoroff.

But to be honest, it’s a story BetaKit struggled with – trying to set all of its writhing tendrils in context for our audience.

Turns out we weren’t the only journalists struggling. Globe and Mail reporter Josh O’Kane got hit with the bug so hard that he decided to write a book about the whole thing, called Sideways: The City Google Couldn’t Buy.

O’Kane joins us on the podcast this week, along with BetaKit Senior Editor Meagan Simpson, to relive the highs and lows and discuss the lessons learned from a local boondoggle that captured the world’s attention.

Let’s dig in.

Interested in catching the Sidewalk Toronto panel conversation moderated by Josh O’Kane at Elevate? Use the code ELEVATEFESTBK for 20 percent off your ticket.

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The BetaKit Podcast is hosted by Douglas Soltys & Rob Kenedi. Edited by Kattie Laur. Sponsored by SAAS NORTH.

Douglas Soltys

Douglas Soltys

Douglas Soltys is the Editor-in-Chief of BetaKit and founder of BetaKit Incorporated. He has worked for a few failed companies and written about many more. He spends too much time on the Internet.

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