Skip to content

Canada's Business and Tech Newsroom

  • Professional Subscription
  • Partnerships & Advertising
  • Licensing & Syndication
Log In Subscribe
Welcome,
  • My Account
  • Log Out
  • Business
  • Tech
  • National
  • The Big Read
  • Briefings
  • Commentary
Search
Log In Subscribe
Welcome,
  • My Account
  • Log Out
Exclusive

Sidewalk Labs and Plaza Ventures planning Toronto-based venture fund focused on smart-city technology

Sidewalk Labs and Plaza Ventures plan to launch a venture capital fund focused on smart-city technology, The Logic has learned. Expected to be between $20 million and $30 million, it would focus on high-risk investments in early-stage companies with the goal of establishing Toronto as a “global center” for smart-city tech—but is contingent on Waterfront Toronto moving ahead with Sidewalk as a partner in a controversial development on the city’s lakeshore.

Exclusive

Sidewalk Labs and Plaza Ventures planning Toronto-based venture fund focused on smart-city technology

By Amanda Roth and Catherine McIntyre
Sidewalk Labs’ office at 307 Lakeshore Blvd. E. Photo: Amanda Roth
Nov 21, 2019
A A
A Small A Medium A Large
Share

Gift

Share

Sidewalk Labs and Plaza Ventures plan to launch a venture capital fund focused on smart-city technology, The Logic has learned. Expected to be between $20 million and $30 million, it would focus on high-risk investments in early-stage companies with the goal of establishing Toronto as a “global center” for smart-city tech—but is contingent on Waterfront Toronto moving ahead with Sidewalk as a partner in a controversial development on the city’s lakeshore.

Talking Point

The Urban Technology Venture Fund would target companies that solve urban problems around mobility, affordability and sustainability. According to an investor deck obtained by The Logic, this could include technology to improve waste management, energy-efficiency in buildings, air and water quality and last-mile delivery.

The Urban Technology Venture Fund would be led by Sidewalk’s director of investments, Nicole LeBlanc, and Plaza general partner Matthew Leibowitz, according to an investor presentation deck obtained by The Logic.

Sidewalk and its parent company Alphabet have already committed $10 million to the fund, according to the deck. Other participants would have to contribute a minimum of $2 million. The fund would make investments of around $1 million in companies at the seed and Series A stages; investments could be as small as $200,000 “to capture companies in the ecosystem early, while follow-on and later-stage investments [could provide] companies the needed dry powder for continuous growth.” The fund has set an investment term of 10 years, with a designated investment period of 18 to 24 months. Sidewalk and Plaza would leverage their networks to help scale the companies in which the fund invests, the deck says.

Sidewalk and Plaza are targeting companies that solve problems around mobility, affordability and sustainability in cities. According to the investor deck, that could include technology to improve waste management, energy-efficiency in buildings, air and water quality and last-mile delivery. 

“Urban tech startups today face numerous challenges such as long pilot and procurement cycles, higher financing needs due to hardware requirements, lack of standardization making implementation bespoke, and data silos that make scaling difficult,” Leibowitz told The Logic. “We are looking forward to partnering with Sidewalk Labs on the establishment of this fund to support Canadian urban technology companies, build the ecosystem and transform Toronto and Canada into the global urban technology hub.”

The portfolio companies’ technology could be used in Sidewalk Labs’ planned development for a section of Toronto’s eastern waterfront, according to the deck: “The Fund will complement Sidewalk Labs’ proposal to transform the Quayside neighbourhood. Portfolio companies could assist in developing key technologies required to recreate the neighbourhood.” The presentation is dated September 2019, a month before Sidewalk and Waterfront reached an agreement on some contentious issues in their partnership, including the scale of the development; the deal announced October 31 was dramatically reduced from Sidewalk’s proposed 190-acre plan, restricting it to the 12-acre Quayside neighbourhood for which Waterfront initially issued a request for proposals in March 2017.

In Sidewalk’s Master Innovation and Development Plan for the project, released in June, it said it would commit $10 million to a venture fund that would invest in local startups contributing to urban innovation. In October, The Globe and Mail reported that Sidewalk was meeting with members of Canada’s venture capital community. 

“The venture fund is in our proposal for Quayside and we said we would move forward with if the Sidewalk Toronto project is approved by Waterfront Toronto and governments,” Sidewalk spokesperson Keerthana Rang told The Logic Thursday. “In the meantime, we have started reaching out to Toronto’s tech sector.”

Sidewalk provided more detail about the potential fund in its Digital Innovation Appendix, released November 15. 

“Over the last 18 months, Sidewalk Labs has engaged with over 300 Canadian urban tech companies, helping inform the fund’s emerging investment thesis,” that document reads.

The appendix says Sidewalk Labs would not take ownership of portfolio companies’ intellectual property (IP): “Our investment thesis rests on the assumption that retaining IP will be integral to the success of Canadian companies, and this is foundational to the fund’s practice.”

It says the fund’s “advisory network” would provide support in the companies’ IP strategies. It does not name Plaza Ventures as a partner in the fund. 

Andrew Tumilty, a spokesperson for Waterfront Toronto, said the agency was aware Sidewalk and Plaza were discussing a venture fund. The initiative is in keeping with the RFP, said Tumilty, which asked the successful bidder to “consider the feasibility of a catalyst fund to invest in emerging companies engaged in the project.”

The fund hinges on the deal between Sidewalk and Waterfront Toronto moving ahead, Tumilty confirmed: “Sidewalk Labs has indicated that the establishment of the fund is contingent on the Quayside proposal moving ahead to implementation, a decision which will be made by Waterfront Toronto, our Board of Directors, and our government partners.”

Plaza Ventures is the venture capital division of Plazacorp Investments, a real estate investment firm that leased Sidewalk Labs the land for its Toronto office at 307 Lakeshore Blvd. E. in March 2018.

Plaza has experience investing in early- and growth-stage technology companies, including Kitchener-Waterloo-based traffic-technology company Miovision Technologies. Miovision’s CEO, Kurtis McBride, has been a member of Waterfront Toronto’s digital strategy panel throughout the agency’s partnership with Sidewalk Labs, and helped launch the Open City Network, a non-profit Canadian tech coalition aiming to establish best practices around data collection in smart cities.

“I support any initiative that grows Canadian owned technology companies and keeps Canadian intellectual property, and the national economic benefits that flow from it, in the country,” McBride told The Logic. 

The proposed Urban Technology Venture Fund’s cheque sizes are relatively small. Radical Ventures, another Toronto VC firm that invests in early-stage artificial intelligence companies, including those working on smart-city technology, typically cuts cheques for between $5 million and $10 million, according to Salim Teja, a partner at the firm. 

Alphabet has its own venture capital investment arm called GV (formerly Google Ventures), which also focuses its investments on early- and growth-stage technology companies. It lists Uber, Slack and Medium among its portfolio companies.

Gift the full article

In August, Sidewalk Labs, Alphabet and the Ontario Teachers’ Pension Plan launched an infrastructure holding company called Sidewalk Infrastructure Partners (SIP). SIP was spun out of Sidewalk to make investments focused on North American technology-enabled projects. Earlier this month, SIP announced its first investment in AMP Robotics, a Denver-based startup that makes recycling robots. 

The next major deadline for Sidewalk Labs and Waterfront Toronto’s Quayside project is March 31, 2020, by which time the parties will need to agree on a development plan to move ahead with the project. They are currently working together to create a new innovation plan for the neighbourhood. It will draw some ideas from Sidewalk’s initial proposal, but incorporate the new principles agreed upon in October.

#Plaza Ventures #Sidewalk Labs

Sponsored Content

The real-world economic offshoots of sovereign AI

By Deborah Aarts
Illustration of a plane flying above a mailbox

Increasing healthcare access across Canada

By Deborah Aarts

What it takes to lead a frontier firm

By Deborah Aarts
Paid promotional content

Loading...

Thanks for sharing!

You have shared 5 articles this month and reached the maximum amount of shares available.

Close
This account has reached its share limit.

If you would like to purchase a sharing license please contact The Logic support at [email protected].

Close
Want to share this article?

Upgrade to all-access now

Close
Gift the full article!

You have gifted 0 article(s) this month and have 5 remaining.

Copy link and gift
Copy Link
Email to a friend
Send Email
Gift on Social Media

Recipients will be able to read the full text of the article after submitting their email address. They will not have access to other articles or subscriber benefits.

Photo: Amanda Roth

Most Popular This Week

A man walks across a large greenhouse with large glass ceilings. He is walking on a white path through rows of green lettuce growing on the ground.
News

Canadian businesses were bracing for a wave of retirees. Then along came AI

By Anita Balakrishnan
An image of a man wearing a dark suit jacket and tie. He is wearing a mic and looking slightly away from the camera.
News

Brookfield and Cohere execs among high-profile guests at CVCA summit

By Catherine McIntyre
In this photo illustration the Moneris logo is seen displayed on a smartphone.
News

U.S. private equity is buying Canada’s biggest payments processor. Some people are worried about sovereignty

By Claire Brownell
A silhouette of the Empire State Building against a blue sky.
News

Takeovers are shifting control of Canadian firms abroad, survey shows

By Catherine McIntyre

In-depth, agenda-setting reporting

Great journalism delivered straight to your inbox.

Commentary

Carmichael: Canada’s biggest companies aren’t wired for growth. That’s a problem for us all

By Kevin Carmichael

Briefing

Stellantis considering selling Ontario factory, union says

By Anita Balakrishnan   |   Aug 14, 2026

Intellectual property from failed New Brunswick nuclear developer sold to Ontario’s Nuclea Energy

By David Reevely   |   Aug 14, 2026

Drone maker Volatus reports revenue dip as it struggles with its supply chains

By David Reevely   |   Aug 14, 2026

Best business newsletter in Canada

Get up to speed in minutes with insights and analysis on the most important stories of the day, every weekday.

Exclusive events

See the bigger picture with reporters and industry experts in subscriber-exclusive events.

Membership in The Logic Council

Membership provides access to our popular Slack channel, participation in subscriber surveys and invitations to exclusive events with our journalists and special guests.

Recent Popular Stories

News

U.S. private equity is buying Canada’s biggest payments processor. Some people are worried about sovereignty

By Claire Brownell   |   Aug 12, 2026
In this photo illustration the Moneris logo is seen displayed on a smartphone.
News

Canada’s oil majors eye the next production boom

By Meghan Potkins   |   Aug 7, 2026
Storage tanks in the primary extraction plant at the Suncor Fort Hills facility in Fort McMurray Alta, on Monday September 10, 2018.
Analysis

These AI startups are making millions with tiny teams

By Catherine McIntyre   |   Aug 5, 2026
Shivam Mahajan and Zaaheda Islam pose in front of their company offices.
News

Brookfield and Cohere execs among high-profile guests at CVCA summit

By Catherine McIntyre   |   Aug 13, 2026
An image of a man wearing a dark suit jacket and tie. He is wearing a mic and looking slightly away from the camera.
News

Ottawa backs ArcelorMittal’s Quebec expansion with $125M

By Laura Osman   |   Aug 6, 2026
Four people stand in orange safety jackets and helmets stand in a factory, including Prime Minister Mark Carney, second right, speaking into microphone. They are in a plant with yellow scaffolding and a Canadian flag in the background.
Commentary

Carmichael: The rise of AI-powered solopreneurs could upend how the economy works

By Kevin Carmichael   |   Aug 8, 2026
Shopify president Harley Finkelstein smiling as he sits on stage at an event, his arms crossed. He holds a microphone in his hand and wears another microphone on a headset.

Canada's most influential executives and policymakers are reading The Logic

  • CPP Investments
  • Sun Life Financial
  • C100
  • Amazon
  • Telus
  • Mastercard
  • bdc
  • Shopify
  • Rogers
  • RBC
  • General Motors
  • MaRS
  • Government of Canada
  • Uber
  • Loblaw Companies Limited
logic-logo

Canada's Business and Tech Newsroom

100% human-crafted journalism

Newsroom

  • News Tips
  • AI Policy
  • Editorial Disclosures
  • Story Pitches

Company

  • About Us
  • Terms of Service
  • Privacy Statement
  • Corporate Information

Contact

  • Contact Us
  • Advertise
  • FAQs
  • Work at The Logic

© 2026 The Logic Inc. All Rights Reserved.

Trusted by leaders

Error

Account creation failed.

Please email us at [email protected].

Create Account

[wppb-register form_name=”cozmo-registration-form-for-modal”]

I do have an account
Login
or

[wppb-login]

I don’t have an account