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The City Google Couldn’t Buy is a study of the power and limits of Big Tech by author Josh O’KaneHandout

Josh O’Kane spent more than two years covering Google affiliate Sidewalk Labs’ controversial “smart city” in Toronto for The Globe and Mail. On Sept. 13, Random House Canada will publish Sideways: The City Google Couldn’t Buy, his book revealing the inside story of the failed project and the company’s collapse. The following is an exclusive excerpt from the book.

When people walked into the blue-splashed building at 307 Lake Shore Boulevard East for the first time, they were bound to find something to fill them with awe. Depending on the day, as they passed through the lake-facing doors and into Sidewalk Labs’ central showroom, they might have zeroed in on the floor laden with wooden prototypes of its hexagonal paving tiles. Maybe the vast models of a neighbourhood of wood-framed buildings would make them smile, or the walls plastered with city-building ideas scribbled by members of both Sidewalk and the public.

It conferred the impression of a welcoming oasis in a part of town that was not particularly welcoming. Sidewalk’s Toronto headquarters sat at the long-ignored post-industrial foot of Parliament Street, wedged between Lake Ontario and a raised expressway, right in the elbow of Quayside – the 12-acre plot of land it was hoping to turn into a beacon for the future of cities. Natural light flooded through windows onto gleaming white walls, which were occasionally obstructed by wooden-beam prototypes that looked like what the company some day wanted to use at the core of innovative “tall timber” skyscrapers. The 307 Lake Shore space was designed to be a symbol of optimism and opportunity. It was supposed to be a glimpse of the bright future Sidewalk wanted to build for Toronto, starting on that very site.

The blue paint made the office stand out among the monochromatic low-rise commercial buildings that lined the block. This deliberate symbolism pulled in optimists from all over Toronto. But it was just a coat of paint. Underneath, it was just as old and grey. Some people cried with joy when the company offered them a job. Some cried when they realized Sidewalk wasn’t the company they’d thought it was.

The Toronto office opened in the middle of 2018, and Sidewalk filled it with fresh-faced new recruits. They had quit careers at investment banks, tech companies and governments, and often marvelled at how freely money flowed as they flew back and forth to Hudson Yards to plot out an inclusive neighbourhood of the future. Some staff were surprised by what they viewed as arrogance, sometimes verging on aggression, from some of the New Yorkers who’d fly into Toronto. Their confidence struck the Canadians as bordering on a saviour complex, with Quayside as their plan to turn some backwater Canadian village into the next Hudson Yards. Even the New Yorkers’ mannerisms could feel abrasive, such as when they started meetings or e-mails by going straight to business instead of with friendly small talk. The local staff weren’t sure if it was a New York thing, an American thing, or a Bloomberg administration thing, but the culture clash grew exhausting.

Tensions became so severe by the late summer that the company agreed to hold presentations on Canadian culture for each office. Dozens of people showed up to them. They were led by a former City of Toronto media relations officer named Giannina Warren, who had gone on to do a PhD in the branding of places. She walked the staff through the countries’ divergent histories, and how the city’s angst over the Quayside project was rooted, at least in part, in Canadian resistance to American hegemony. Giants of corporate America had failed in Canada before, she told Sidewalkers, pointing to the department-store chain Target, which had pulled out of the country after only a couple of years in the market. She also explained Canada’s affection for the gravy-covered, french-fry-and-cheese-curd delicacy of poutine, a Molson beer ad campaign titled “I Am Canadian,” and the Tragically Hip – a shining example of a pop culture phenomenon that succeeded without America’s warm embrace.

Though some Toronto staff thought it was a cringe-worthy exercise, others were glad to finally have someone explain to their superiors that they were not in New York. When Warren then gave the presentation to the New York office – whose staffers probably needed the education more – people voiced their appreciation but flitted in and out regularly, and most left abruptly at the end. Some people who were there don’t recall CEO Dan Doctoroff attending; a company spokesman says he attended “parts of these sessions” (and insists that they were not a response to any tensions within the company).

Building in Toronto depended on gaining the trust of Torontonians, but secrecy was baked into Sidewalk’s DNA, stretching back to the days of exploring Larry Page’s fantasy of a regulation-free city on the sea. Not only did this culture make it hard for some employees to trust the company, it left them struggling to do their jobs.

As staff received the public at 307 Lake Shore, they were often asked what the company’s business model was, or how the project would be funded. But responding to those questions was a problem: Sidewalk hadn’t given its staff all the answers. Even a map was hard to find, leaving some staff to speculate that the company didn’t want to remind people they had the right to only 12 acres. All of this put the once-enthusiastic Canadians in an awkward position. The National Observer once reported that in some instances, staff were told to answer simply: “It’s way above my pay grade.”

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Some employees began to doubt whether the company itself knew what its business model was. In interviews and public appearances, Doctoroff had begun to rhyme off combinations of real estate investment, infrastructure investment and, sometimes, tech development – the company hoped to make money from one or all of these. After a number of staff complained about the uncertainty, the company sat them down to explain the model, only to give them a variation of the same answer. This was not what staff were looking for. They needed more to win Toronto over, especially as opposition to the project rose throughout 2018.

The public still cycled through the showroom, leaving ideas on cards that would be affixed to a wall, and Sidewalk counted every single person so they could say how many Torontonians the company had consulted. Sidewalk said that number eventually exceeded 11,000, though one person at 307 Lake Shore says it couldn’t have topped 5,000. And all those people’s ideas – just like the brainstorming of the experts consulted for the Yellow Book – didn’t appear to matter. “None of that information went anywhere,” one former Sidewalker says. “It didn’t mean anything.”

This was a common theme in Sidewalk’s history. Doctoroff liked to make people feel important by giving them a seat at the table; he could get his own work done more easily that way, even if he didn’t always pay attention to the people he’d invited. When he campaigned to bring the Olympics to New York decades earlier, he included staff from several city agencies on his facilities advisory board. “As a result, the territorial jockeying that can occur when public officials believe an outsider is attempting to do their jobs for them was minimized,” he later recounted in his memoir. Toward the end of his time at City Hall, as New York developed a long-term sustainability and economic plan, he perfected his seat-at-the-table scheme. Reveal a project’s goals, get feedback from people and politicians, then add details. That way, he said, “people would feel some ownership of the plan,” lowering the likelihood of dissent.

This was a tactic he’d used at Sidewalk, too, in 2015, splashing the names of dozens of luminaries like Richard Florida and Janette Sadik-Khan across the back page of the Yellow Book. Doctoroff wanted to do the same in Toronto, but the government agency he was ostensibly partnering with, Waterfront Toronto, had warned him against it. Those kinds of meetings were both too exclusive for the government agency’s comfort, and possibly broke the terms of the agreement signed in the summer of 2018. Sidewalk decided to disregard Waterfront’s warnings.

Doctoroff and a close circle of staff began compiling a list of influential names who could help spread Sidewalk’s gospel. It totalled nearly 70 people: urbanists, not-for-profit champions, executives and at least one former mayor.

They were invited that fall to a private lunch at 307 Lake Shore, where Doctoroff was planning to pitch them personally. Staff were tasked with transforming 307 Lake Shore as the CEO seemed to sweat every detail: the chairs, the tables, the place settings, the floral centrepieces. His obsession with pulling off the perfect day seemed to carry once-in-a-lifetime stakes. Behind his back, some of his employees called the meeting “Dan’s wedding.”

On a cloudy October 17, a fleet of cabs, Ubers and luxury cars delivered the CEO’s hand-picked group of luminaries to the doors of bright-blue 307 Lake Shore. They were greeted by a sea of familiar faces – the same crew of power brokers that usually showed up to rubber-chicken dinners hosted by the Toronto Region Board of Trade and the Canadian Club. The guests sat down at their tables, each with a Sidewalk staffer there to collect their ideas.

Doctoroff soon stood up, called Toronto his “second home,” then launched into scripted remarks, which included a joke about how recreational marijuana becoming legal in Canada – that very day – made Toronto an even more enticing host city. He ran through Sidewalk’s origin story, calling the company an “essential catalyst” for Waterfront Toronto’s dream of a better, more sustainable future.

The CEO tried to add some clarity to the business model questions that had plagued the company. Sidewalk would invest in infrastructure – an advanced electrical grid, stormwater management – and new technologies to manage traffic, buildings’ energy use and the delivery of social services. The company wanted to prove it was possible to build skyscrapers with wood-based structures. The ideas were so wide-ranging that he sounded like he was playing startup whack-a-mole. He also hinted at his grand vision beyond Quayside: “To create this new community will require substantial development on parcels of land that have laid fallow for decades,” he said.

The CEO got defensive, too, hinting at the Quayside pushback that had ramped up over the past year. “There are times when the prejudgment of what we will propose – and assumptions of ill intent – have taken me by surprise,” he said. “But I can tell you there is nothing more behind the curtain than what I have shared with you today.”

Doctoroff was trying to create the perception that everything was under control, even when it clearly wasn’t. People kept seeing his choices, and the choices of the company he’d built, much differently than he did – including those in the room around him.

As one attendee took his seat, he couldn’t help but notice that the rented chairs, centrepieces and room arrangement seemed familiar. There even seemed to be a head table for VIPs. “Hey,” he whispered to the person next to him. “This feels like a wedding.”

Excerpted from Sideways by Josh O’Kane. Copyright © 2022 Josh O’Kane. Published by Random House Canada, a division of Penguin Random House Canada Limited. Reproduced by arrangement with the Publisher. All rights reserved.

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