2020 Impact

It's been a big year at Upside, here's an overview of the donations catalyzed and how we supported our Members

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Donations Catalyzed


Three Liquidity Events

In 2020, three Upside Members experienced liquidity events resulting in a total of $1,008,482 in charitable donations. One donor chose to remain anonymous, because the event was part of a secondary buyout.

SalesRight, co-founded by Taylor Bond, has been acquired by FastSpring, leading to Upside's eighth exit. Taylor will be donating the proceeds of his exit to Eva's Initiatives for Homeless Youth. Read more about Taylor's liquidity event here.

A liquidity event for Grantbook resulted from a shift towards employee ownership. Grantbook's co-founder, Peter Deitz, and his partner, Samantha Green, are directing the proceeds to Food Share, Building Roots, Centre for Social Innovation, and Canadian Physicians for the Environment.


The Home Front

At the beginning of the pandemic, The Upside Foundation spearheaded the formation of The Home Front, a volunteer organization dedicated to supporting frontline healthcare workers on the frontlines of the fight against COVID-19.

Through The Home Front's campaigns, $34,165 has been raised from 119 individual donors and supported four organizations: Anishnawbe Health Toronto, Markhaven Home for Seniors, HomesFirst Shelter’s Willowdale Welcome Centre, the Ontario Health Coalition, camh's COVID-19 Mental health Resiliency & Coping Fund, North Bay AIDS Committee Tech Lending Library.

Read more about The Home Front and donate here.


Barry Gekiere Memorial Fund

Barry Gekiere, former Managing Director of MaRS IAF and a legend in Canadian venture capital, passed away this March. To honour Barry's legacy and extend his impact, Upside launched The Barry Gekiere Memorial Fund.

This charitable fund supports The Leukemia & Lymphoma Society of Canada, the largest voluntary health organization dedicated to funding research, finding cures and ensuring access to treatments for blood cancer patients.

See here to read Barry's tribute or to contribute.

Ocean Research and Conservation AssociationEast York Learning Experience
Tech4SickKidsWorld Wildlife FundPEI Literary Alliance
Tech4SickKidsWorld Wildlife FundPEI Literary Alliance

Supporting Our Members


This year we facilitated 34 gatherings with current or prospective Upside Members, Upside's Partners, investors, and other leaders in the startup community. We hosted a lot more events than usual this year, especially early on in the pandemic when our Members were looking to connect with other founders to hear how they were adapting to the ever-changing conditions. From peer to peer roundtables and feedback forums, to a Q&A about government financial supports, to an anti-racism workshop, here's a snapshot of our programming this year.
In-person events before all our programming became remote
New Member Celebrations
Online discussions for the Upside Member community
Small group, industry-specific roundtables for founders

Our Commitment to Diversity, Equity & Inclusion

This year has been an opportunity for internal reflection and analysis around our commitment to diversity, equity and inclusion (DEI). At Upside, we are committed to better understanding the role we play in broader social and economic systems that are lacking in diversity, and do not provide equitable opportunities for all. We continuously strive to improve the diversity of our team, and ensure that founders from diverse backgrounds have an opportunity to benefit from the Upside community.

We want to ensure that our programming is inclusive, and to leverage our position in the industry to advance thinking about how we can be anti-racist and anti-oppressive, both in how we build companies and how we invest in our communities through philanthropy. In 2020, in partnership with Upside Member MESH Diversity, we hosted two Anti-Racism Workshops, and an online discussion for our Members around their evolving DEI strategies and how they are making a social impact now in addition to their future Upside donation.

In the new year we will publicly share our comprehensive anti-racism strategy, including the content we have planned for our Upside Member community.


Huge thank you to our partners for making  all of the above possible. See the Partners page on our website to learn more about each generous supporter.

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