Sidewalk Labs believes its dual expertise in technology and urban design makes it different. The company is based in New York rather than Silicon Valley to distill a sense of city living in its employees. That DNA also shaped its bid and, consequently, the ideas that it's pushing forward for Quayside. The buildings, for instance, will use a modular design that's cheaper and faster to build. Some of them will utilize Loft, a minimalistic interior that means they can be quickly repurposed. In this scenario, a parking lot could be converted into an office as more people start to embrace electric and autonomous ride-sharing options.
Buildings will be made from eco-friendly buildings materials, including tall timber skeletons and mycelium insulation, and powered by renewable energy sources, including roof and wall-mounted solar panels. They'll be warmed and cooled by a thermal grid that leverages waste heat from sewers and buildings as well as geothermal sources and nearby lakes. Homes will also be LEED (Leadership in Energy and Environmental Design) certified and meet the energy-efficient Passive House standard developed by two professors in Germany (where it's known as Passivhaus) in the early 1990s.
"By far the most important issue is affordability."
Sidewalk is committed to affordability and avoiding Songdo's reputation as a half-empty city for the rich. It's banking on a blend of simple and old-fashioned pricing models, including social tenants, private renters, subsidized renters and full-fledged homeowners. "A partial homeownership program might be a perfect fit for a family looking to settle down, whereas a retiree on a fixed income may require a rental subsidy," the company explained. "Sidewalk proposes to make Quayside a living laboratory for housing policy innovation that delivers a mixed- occupancy community that mirrors Toronto's socioeconomic diversity."
Doctoroff pushed this point at a community town hall meeting last November. "By far the most important issue is all about affordability," he said. "We certainly see everyday people, middle class, lower-middle and lower-income people, being priced out of areas, suffering from the incapacity to get opportunities because distances are too great or the costs are too great. If we don't fundamentally address that issue, the fabric of society and the whole notion of this being an inclusive community begins to fray."

Sidewalk Labs is serious about ditching cars too. The team wants the Eastern Waterfront to be the first district in Toronto where only shared and self-driving vehicles are allowed. Non-emergency vehicles will be banned from "a large portion" of the neighborhood, giving space back to pedestrians and cyclists. A "transition zone" will exist for people who need to travel beyond Quayside, but the idea is to promote a walking, cycling and public transit culture in the center.
The absence of private cars should make the roads feel quieter and safer. It will also eliminate the need for curbside parking, freeing up crucial space for sidewalks and stores. "It's all about getting rid of stationary cars," Alan Penn, a professor in Architectural and Urban Computing at UCL, said. "That can transform what somewhere feels like."
Sidewalk plans to extend Toronto's existing bike-share scheme into Quayside. It's also considering an LED system that can create, widen and narrow temporary bike lanes on the road. The latter is experimental but perhaps unnecessary. Michael Seth Wexler, an urban designer at cycling consultancy Copenhagenize, said permanent, protected cycleways will be critical if the city wants to get more people on two wheels. If they disappear or they're few and far between, people won't be able to rely on them -- and casual cyclists will default to other forms of transportation.
"It's all about getting rid of stationary cars. That can transform what somewhere feels like."
"To know that there's always going to be a protected path that you can take down the main street," Wexler explained, "before any modern technology is implemented, that's a baseline that will create a sense of reliability in the transport system."
Above all, people want to feel safe. "They won't feel safe unless they have a separation from other modes of transport," Wexler added. "You don't want to be cycling slowly with a tram zooming right by you and then you have to duck out of the way of a transport truck or even an automated vehicle." It's worrying, he said, that none of the illustrations in the Sidewalk Labs pitch document show a protected cycleway.
Wexler welcomes technology, however, and how it could make cycling a more efficient and attractive option in Quayside. Sidewalk Labs will pilot an "adaptive traffic light" concept that can detect and prioritize cyclists at busy intersections. It would be similar to the green-wave system in Copenhagen, which ensures that cyclists traveling at 20KMH hit green lights all the way into the city center. The company has some new ideas, too, such as automatic, retractable canopies and heated bike paths that melt snow in the winter.
Technologists vs. urbanists
Doctoroff was brought onboard to bring urban planning and design expertise to Google's traditionally technological background. Blending these two worlds hasn't been easy though. Developers will often use A/B testing, for instance -- two versions of the same software, quietly distributed to different users -- to see which solution works best. In a city, however, that's often not an option. You can't A/B test a traffic light system if there's a chance one of them will cause accidents on the road. Similarly, "fail fast, fail often" is a bad ethos when lives are at risk.
Urbanists act more deliberately but can often see solutions as unchangeable. When a home is built or a cycle path is put in place, they see it as a semipermanent development. Sidewalk Labs found it "difficult" to balance these two cultures in its first year of operations. "It led to some conflicts," said Rit Aggarwala, chief policy officer at Sidewalk Labs. "It led to a bunch of misunderstandings where it wasn't an intentional conflict. We just realized we weren't speaking the same language with each other."
The urbanists had to be more explicit about the risks they were identifying, and the technologists had to be more attuned to where something could go wrong. Similarly, the developers needed to retain their enthusiasm and speed while protecting the values that urbanists believe are important.
Sidewalk Labs is envisioning Quayside as a series of layers. At the bottom is a network of tunnels, or utility channels, which serves as the city's near-invisible infrastructure. Above is the public realm, or street level, which serves as a foundation for its mobility and building concepts. At the highest level is the digital layer, which combines a network of sensors, a detailed map of the neighborhood, simulation software and a platform where citizens can log in and manage their public and private data.
Google makes its money by tracking internet users and serving them highly targeted ads. It's the revenue engine for Alphabet that, in turn, allows Sidewalk Labs to operate so freely. As a result, people are worried about Quayside and how residents' data will be treated. Will Sidewalk Labs have full access to the information collected by its sensors? How will data be shared with the company's partners? Will citizens be able to opt out of certain programs, and if so, how will it affect their quality of life in the city?
People are worried about Quayside and how residents' data will be treated.
Aggarwala is promising a privacy-by-design approach. That means limiting data capture to the "bare minimum" throughout the city. The company's internal Sense Lab, for instance, is developing a camera system that strips surveillance footage down to a series of faint outlines. "We don't need an image of you," Aggarwala said. "What we need is your outline, because then the computer can tell, 'Oh, that's a human. That's a person walking.' If all I do is outline your body and there's no face, no color, no nothing, then there's no way I can identify you. I've eliminated the privacy issue, but I've accomplished the goal."
Not everyone is convinced. To make a service smarter, or more user-friendly, you generally need more information. Let's say someone clambers into an elevator; with a motion sensor you can detect their presence and light up a control panel. If you know who they are, however, you can also play their favorite song or take them to their hotel room automatically. "They can anonymize the information," Cerrudo explained, "but in the end, the less they anonymize it, the more functionality they can give to the end user."
Part of the solution is a simulation platform called Model. It will be "metro area scale" and cover the movement of every Quayside resident who might wander through its virtual net. Sidewalk Labs will use this data to test possible changes to roadway pricing, ride-sharing and its multiuse buildings. It will also accept data collected by the Sense Lab team to simulate what will happen in the next five, 15 and 30 minutes. Over time, the company will use the platform to test long-term changes to water, energy and other public infrastructure. It will also grow more accurate and sophisticated with use, to the point where someone could ask, "Where were the 20 people on this bus really starting from, and where were they really going?"

Rit Aggarwala, chief policy officer at Sidewalk Labs
"It's a tool that doesn't exist," Aggarwala said. "We need to build it because the state-of-the-art equivalents right now are very expensive, very slow and very coarse in terms of their analysis."
It seems inevitable, though, that Sidewalk Labs will need to change or upgrade one of its services in the future. When that happens, the company will have to survey Quayside residents or ask them for approval, just like developers do now with user agreements in the App Store. Cerrudo suspects the company will introduce an "end-citizen" agreement that includes automatic approval for all technological changes in the city. Otherwise, "the challenge is to find a way to easily ask people for feedback and get an answer," Cerrudo said, "and then decide what to do."
Consultations will be a political and democratic problem as much as a privacy and security issue. Decisions will need to be backed by Quayside citizens as well as local and national government. "It could be very bureaucratic," Cerrudo said. Sidewalk Labs, however, thinks it's a question of trust. If its policies are transparent enough and there are robust safeguards to protect user data, residents will slowly give Doctoroff and his team the benefit of the doubt. "If not, then frankly we've made a mistake, because we have to earn that trust," Aggarwala said.
"There should be a whole chapter on privacy and security. There shouldn't just be one reference."
To do so, Sidewalk Labs will be asking for help from independent cybersecurity experts. Ann Cavoukian, a former information and privacy commissioner for Ontario and now executive director of the Privacy and Big Data Institute at Ryerson University, has agreed to serve on the company's advisory board. It's a positive step, though Cerrudo is still concerned about the company's commitment to security. In the pitch document, for instance, "I looked for 'security' and there are just two mentions of security, on two pages," he said. "There should be a whole chapter on privacy and security. There shouldn't just be one reference."
Trust will also hinge on the people that Sidewalk Labs is able to attract to the area. The company wants the community to be multigenerational, mixed-income and diverse. If all of its residents are Google employees or Silicon Valley developer types, the project may be seen by many as a failure. That doesn't mean Quayside will be for everyone, however. A major opportunity, Aggarwala said, will be attracting people who are open to urban innovation.
The company is thinking about a Smart Chute system, for instance, that tracks how much waste people are throwing away. It would then be possible to charge residents per bag, promoting waste reduction and generating cash for city refurbishments. Such a move would also help Quayside to reduce its environmental impact and the amount of traffic running through its underground tunnels. To be effective, though, Sidewalk Labs needs residents who can understand and embrace the long-term benefits. If a path is widened or a canopy is moved, citizens need to trust that it's for the greater good.
"My strong belief is that we're going to find it's an attitude that cuts across age, gender, income, background -- all sorts of things," Aggarwala said.
Waterfront Toronto has recognized the importance of privacy and data governance too. In a memo, Kristina Verner, vice president of innovation, sustainability and prosperity at Waterfront Toronto, said Cavoukian's help and privacy by design were "not sufficient to ensure legal compliance with relevant legislation." The organization will, therefore, create an independent Digital Strategy Advisory Panel to assist on the project. Members will be plucked from the academic, legal and civic technology communities and help Waterfront Toronto shape its digital-governance requirements.

Sidewalk Labs owns Intersection, one of the companies behind the LinkNYC WiFi kiosks.
Sidewalk Labs is an offshoot of Alphabet, but it's also experimenting with a subsidiary structure of its own. That's unusual; most of Google's acquisitions are quickly absorbed into one of its existing businesses. In June 2015, Doctoroff and his team led a consortium in the acquisition of Control Group, a New York-based technology and design consultancy firm, and advertising agency Titan. The pair were combined and rebranded as Intersection, a standalone company that has since turned thousands of old pay phones into free, gigabit-speed WiFi kiosks.
On February 1st, 2018, Sidewalk Labs announced another spin-off called Coord. The company is developing a platform with APIs that relate to road tolls, curbs and parking. It's a small but important piece in the development of a smart city. With a custom surveyor app, for instance, Coord employees can quickly photograph parking signs and other curbside information, digitizing road regulations in minutes. Developers can then access that information as an API and use it to improve their navigation apps and software. If you run a delivery truck business, for example, you need to know where it's OK to park and unload. Similarly, taxi drivers want to find the best places to pick up and drop off customers.
In the future, Coord will help self-driving vehicles adjust their routes in real time, preventing congestion, double-parking and unwanted toll fees. Google Maps has already integrated Coord so that drivers can find available parking near their destination. "By giving people full insight into all of their trip choices -- and seamless door-to-door service -- tools like this one can lead to better mobility outcomes for cities," Stephen Smyth, CEO of Coord, said in a blog post.
It's not clear if or how Coord and Intersection will work on Sidewalk Toronto. But a distribution of expertise could help Doctoroff's company to focus and solve specific problems.

Toronto's Eastern Waterfront
In many respects, Sidewalk Labs is building Quayside from scratch. The coastline area already exists, but the company is imagining a complete revamp that includes roads, buildings and public areas. It's an opportunity for the company -- a chance to implement large, experimental infrastructure from the outset -- but also a great challenge. The more options that you have, the harder it is to make decisions and prove that a single component or change is having a positive impact. Penn calls it a "combinatorial explosion." "People often think that a clean slate is an easier thing to handle in design," he said. "In fact it's not. It's much, much harder."
Most designers circumvent this problem by creating artificial constraints. They'll look at real-world examples and choose a small selection as possible solutions. Or they'll settle on a particular style that drastically reduces the possibilities in an urban area. Penn said, "You can say, 'Well, actually, I'm going to build a city in a big green field.' But how do you decide anything? Where do you start? So the first thing you do is invent constraints or you look at what constraints there are in the world. That narrows the possibilities down to the point at which you have a starting point."
It's also inaccurate to call Quayside a clean slate, because it sits within the larger context of Toronto. It's part of an old, established city that has its own culture and expectations. Many citizens, for instance, use cars to run errands and get to work. If the Eastern Waterfront has a complete ban on private vehicles, that will make it a difficult place to visit -- a futuristic but isolated community. That's why the company is thinking about a transition zone. Aggarwala compares it to Canary Wharf, a business district in London that was originally served by the DLR train line exclusively. It felt remote until an underground station was added as part of the 1999 Jubilee Line extension.
"All of a sudden it felt like, 'Oh, that's part of the city because that's part of what the rest of the city does.'"