Diversity, Equity & Inclusion at Upside

Our reflection and analysis around our commitment to diversity, equity and inclusion and how we build an organization that is actively anti-oppressive.

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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 want to leverage our position in the industry to advance thinking about how to be anti-racist and anti-oppressive, both in how we build companies and how we invest in our communities through philanthropy.

Our Areas of Focus

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Increase diversity in our Member community
Ensure underrepresented founders feel welcome
Ensure diversity, inclusion & belonging within Upside’s team
Use our position to advance thinking in the industry

Table of Contents


When the Black Lives Matter movement rapidly gained momentum around the world in the summer of 2020, we affirmed our commitment to standing with and for the Black community.
Since this initial reflection, we have broadened our perspective and approach to include all forms of racism, as well as other forms of oppression against all equity-seeking groups.

We have taken the last year to reflect, learn, ask questions, engage with experts, and begin this work. Our work so far has enabled us to better understand:
  • racism and systemic oppression against Black people, Indigenous people, Asian people, people of colour, and anti-Semitism
  • the barriers that prevent groups of people from enjoying equitable access to opportunities, resources  and support
  • white supremacy and white fragility
  • how silence and fear of speaking up or a lack of willingness to engage in difficult conversations upholds existing systems of oppression
  • social oppression in philanthropy
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Many of these concepts, and terminology, was, and still is, new to us.

Since originally engaging in this work, we have expanded our approach from a diversity lens to a broader anti-oppression framework, which focuses at a higher level on addressing the systemic inequalities that are operating simultaneously at the individual, group and institutional level. We have developed an initial understanding of the role we can play in making progress to build a more equitable society.

We are very grateful for the generosity of those who have been focused on this work for decades supporting us in our learning journey, directly and indirectly: in particular to Dr. Leeno Karumanchery, Co-Founder and Head of Behavioural Sciences at MESH/diversity, who has spent hours of his time supporting our efforts, patiently educating, coaching and providing feedback, in both public and private settings.

Much of our learning has come from others sharing candidly where they are at, what their journey has been, and the lessons they’ve learned along the way. We felt that part of our contribution to making progress on this could be to share publicly, vulnerably, how we are thinking about this, in hopes that we can all support each other in our efforts to do better. Sharing this Anti-Oppression framework is one step we are taking to contribute to this conversation.
Why It Matters

Our Members are, or will one day be, in a position to make significant charitable contributions.

One of our most important roles in combating systemic oppression in Canada is to support our Members to develop a comprehensive understanding of systemic oppression as a lens to inform their charitable giving.

It’s important that we help our Members:
  • understand equity
  • develop awareness around the pitfalls of white-saviourism models of philanthropy
  • expand their views of the work being done by the Canadian charitable sector and its context in society
Casting a wider net
Within Upside today, it is important that our Members, team and Board represent a wide variety of communities and perspectives. This helps us to ensure that the net we have cast for those who may be able to give is wide enough, that a diverse array of charities are supported, that a diverse array of founders have an opportunity to take part in our network and reap the benefits of being a socially responsible company.

There is a long history in philanthropy of under-engaging BIPOC based on an assumption that they have a lower capacity to give. There is an under-representation in tech, venture capital, and leadership of organizations in all spheres of women and BIPOC; it’s important that we do our part to make progress here, by elevating, supporting, profiling, and opening up our network.
Diversity in Philanthropy
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Over the past several months, philanthropy has faced rising criticism for its lack of transparency or accountability, perpetuation of wealth inequality, and preservation of a system of exploitation... Decades ago, Martin Luther King Jr. warned philanthropists not to “overlook the circumstances of economic injustice which make philanthropy necessary”.

- Three Ways to Improve Diversity, Equity, and Inclusion in Philanthropy, Stanford Social Innovation Review
Philanthropy is itself a complex concept, one that inherently implies inequality in society, and frequently comes under fire as being an insufficient mechanism through which people and businesses leverage philanthropy for positive PR, tax breaks, and in exchange for regulators or the public 'looking the other way' on harmful business practices. Philanthropy should be seen as one important tool, effective only when applied in consortium with many other mechanisms, for building a society in which all people have an equal opportunity to thrive.

When individuals who control funds are not diverse, they are less likely to donate to diverse causes and communities (source).
Charitable Donations Call Out

Lesser known, small to medium size charities make up the vast majority of charitable organizations and often impact our local communities the most, but lack the brand recognition and ability to fundraise to the same extent as larger charities. These smaller grassroots organizations hold a great amount of social capital and “serve our most vulnerable [populations], those living in poverty and whose disadvantages keep them from enjoying the same quality of life that we sometimes take for granted.” There is evidence that bias and racism play a role in the risk calculation that prevents people from donating to grassroots organizations, which is reinforced by the metrics often cited for impact, such as overhead. 

The uniformity of individuals with decision-making authority in this sector makes inequitable funding outcomes more likely. A recent survey by Philanthropic Foundations Canada reported that 62% of foundations reported having a greater proportion of males to females on their Board and a majority of foundations reported that board diversity could be attributed to gender, age, or lived experiences and not to equity-seeking groups such as racialized individuals, people who identify as LGBTQ2S, and Indigenous persons. This is systemic and an issue that can only be solved by diversifying the group of individuals who are giving and participating in philanthropy.

It's important that we think critically about the appropriate role for philanthropy, the givers and the recipients, in the greater context of society

Our current development model is a form of white-moderation designed to help white people feel good about themselves and thus maintain the status quo

- It’s time we fundraise in a way that doesn’t uphold white moderation and white supremacy

...White-moderate disdain of funding advocacy and systems change work has let the fires spread unchecked.

...Nonprofits often become a fig leaf, a hobby for the rich,
 a self-reinforcing cycle of pity-and-heroism that prevents the actualization of true justice. 

- Have nonprofit and philanthropy become the  “white moderate” that Dr. King warned us about?

Charity positions the wealthy as generous changemakers and the poor as passive recipients. Charity never examines how philanthropists acquired their wealth – or at whose expense – and reinforces the harmful divides in our society...I encourage [leaders] to critically examine how their organizations reinforce a culture of white benevolence and steer towards a culture of solidarity instead.

- For the sake of the communities they serve, non-profits need to step up in combatting internal inequities
Some of the opportunities for Upside to make a difference here include: 


Since our Members are the ones deciding which charities are supported, our role lies less in selecting diverse charities and more in helping to educate our founders about their options and “[encourage donors to think about anti-racism, systemic oppression, equity, wealth disparity, intersectionality, and other areas important to social justice, and their roles and privileges within these areas]"


Ensure there is diversity among Upside Members, as this representation alone will increase the likelihood that the charity recipients are more likely to be diverse


Ensure there is diversity among our team and Board, and that we proactively invest in learning that challenges us, to ensure that our policies and approaches are well informed, progressive and address long standing equity issues

Our strategy stems from these 3 core opportunities.
Diversity Within Upside

To achieve anti-oppressive outcomes, organizations like The Upside Foundation must be be intentional about the individuals who are giving and making decisions about where funds are allocated, and progressive in how we think about philanthropy. In order to reflect on our organization’s diversity, we have gathered data on our Members, Board, and team. 

Board of Directors and Founders

Current Board of Directors Makeup

Through intentional recruiting, our Board of Directors has become more diverse over time. As we seek to recruit new Board Directors, we are being more intentional and seeking out new sources of prospective Directors to ensure that a wide variety of demographics and perspectives are represented. 


Internally, we are a small team with only 2 full-time employees, along with a variety of part-time / short-term team members (volunteers, contractors and interns) who have worked with us over the years. All of these team members have thus far been women, with a mix of white and PoC. With such a small team, measuring the diversity of the team hasn’t been a top priority, rather our focus has been on ensuring that when we are recruiting, the structure of the roles and the pipeline of candidates, are inclusive and diverse.

We’ve taken great care to ensure that our job description and overall recruitment process is transparent, inclusive, minimizes opportunities for bias, and does not discriminate against individuals from different backgrounds (for example, excluding educational requirements, posting salaries, equating foreign experience with local, offering flexible work hours and locations, conducting first round interviews over the phone, etc.).

Upside Members

Why It Matters that our Members are diverse: 

  • Ensure we are casting a wide net and not missing any opportunities to facilitate community impact
  • Ensure charities representing a wide variety of communities are supported
  • Ensure diverse founders have an opportunity to experience the benefits of being part of The Upside Foundation community, including:
  • Access to a network of successful Canadian founders, industry experts, prominent Venture Capital (VC) firms, law firms, conferences
  • Private events with programming geared towards information sharing and thought leadership
  •  The unique opportunities afforded to Members to navigate the industry, build their profile, access exclusive spaces, etc.
  • The business benefits of being a socially responsible company

Upside Member Composition

Board Members by Gender
Board Members by Race

Upside Member Composition in Context

These numbers in isolation were hard to understand.  We therefore contextualized our numbers by assessing different datasets: see Diversity in the Industry for more details on the datasets we consulted and built. Here's how we saw Upside's makeup comparing to the industry as a whole:

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  • Our proportion of women founders (28%) is significantly higher than industry average (15% at incubators & accelerators / 4% of venture funding), but still a smaller proportion when compared to 47% of SMEs being owned by women
  • 65% of our Members are white- a lower number than any other comparison group (71-77%)  except for Toronto’s population
  • 4% of our Members are Black - double the proportion of those in industry groups, quadruple that of those receiving VC funding, greater than the proportion of Canadian population, but only about half of the Toronto population
  • We have no Indigenous Members. Unfortunately it looks like this is fairly consistent across the industry
Diversity in the Industry

To contextualize our diversity, we compared our numbers to the following datasets:

1. The Canadian population Race Statistics | Gender Statistics
2. The Greater Toronto Area population  Race Statistics | Gender Statistics
3. The industry in which we operate tends to be tech startups, however, that group is not clearly defined, nor does demographic information exist for that group. We looked at a few different datasets in an attempt to answer this question:

  • We first looked at ownership of Canadian Small & Medium Enterprises (SMEs) (Race Statistics 1 | Race Statistics 2 | Gender Statistics). However, many SMEs are not planning to sell or IPO one day, so they’re not exactly our target market. 
  • We then studied the distribution of VC funding (we could only find American Race Statistics, but we did find Canadian Gender Statistics). This more closely aligns with our target market, as these companies are on track to sell or IPO one day.
  • The most accurate group to represent the tech startup ecosystem is likely participants in Canadian accelerators & incubators. With the exception of some statistics from individual organizations, there is no comprehensive data set for this group.

    So we built our own.

    We were already doing outreach to every current participant in Canadian accelerators and incubators in Q3 2020, so we collected the associated demographic data from the participants in current cohorts at MaRS, NEXT Canada, C100, Ryerson DMZ, Creative Destruction Lab, Launch Academy, Propel ICT, L-Spark, etc. From this pool of over 1000 founders across Canada, we built our own industry dataset.

Gender Composition

Demographics Chart Men
Demographics Chart

Racial Composition

Demographics Chart White
Demographics Chart  POC
Demographics Chart Black
Demographics Chart Gender

An Industry Problem

This data speaks to the greater problem of gender and racial diversity that is pervasive across the tech startup ecosystem. At every step in the journey of becoming a founder, the diversity of individuals in the industry decreases. 

WOMEN Representation
across Founder Journey 

Representation Chart Female

BIPOC Representation
Across Founder Journey

Representation Chart BIPOC
Chart Legend Bipoc

Generally, we found the core Canadian incubators and accelerators are still predominantly populated by white men. Even when we intentionally expanded our search to include programs/awards specifically focused on BIPOC and women founders, the diversity statistics improved only slightly.

Demographics Chart Canada

This lack of representation in the Canadian tech industry and consequently of founders building businesses heading for a liquidity event (potential Upside Members) identified an opportunity for Upside, along with the industry as a whole, to improve our practices.

Our Areas of Opportunity

1. Increase diversity in our Member community

The lack of diversity in the Canadian startup community directly impacts the diversity of our Member community. 

What we’re doing:

  • Work with other industry groups, incubators and accelerators to share best practices in our collective attempt to work with more diverse founders
  • Seek out new partners beyond the traditional core incubators and accelerators, at which the representation of BIPOC and women founders are higher
  • Track the demographic information of not only our existing Members, but also the founders in our recruiting pipeline
  • Work with our BIPOC and women Members to build bridges into their networks

2. Ensure underrepresented founders feel welcome in our community

We've audited our external messaging, ensuring our messaging uses inclusive language, pictures portray founders of numerous ethnicities and genders, and explicitly states our values.

While our speakers represent diverse demographics, we were surprised to learn that our BIPOC Members participate in our events at a lower rate than do our white Members, and that women participate more than men do. We’re not sure what is driving this difference in participation. We have interviewed Members across all demographics and genders to learn more about their perspectives on our programming, and while we have learned a lot about what founders value, haven’t yet seen anything to indicate that our programming isn’t inclusive.

Demographics Chart Participation
  • Track the demographics of speakers at our events and include this lens in our ongoing programming planning
  • Track the Members we are highlighting and celebrating on social media, to ensure that we are providing coverage of founders from various demographics
  • Increased intentionality regarding moderation of our events, including actively monitoring for any interactions that may make someone feel uncomfortable, and being prepared to step in to redirect the conversation where necessary

3. Ensure diversity, inclusion & belonging within Upside's team

As we recruit for open positions on our Board of Directors or our team, we take active steps to ensure that our approach aligns with best practices to create an inclusive process that leads to a diverse pipeline. At all steps in our process, we have seen our candidate pool reflecting a wide variety of demographics and backgrounds.

What we’re doing:

  • Create a skills and demographics matrix to identify the attributes that would make candidates an ideal fit for our Board of Directors
  • Ensure that our candidate pools are diverse by pursuing multiple sources of referrals
  • Continue to seek out and implement best practices for inclusive team member role design and job postings, including continuing our practice to remove educational and experience requirements not essential to the role, posting job salaries, and designing flexible working environments

4. Using our position to advance thinking in the industry

We consider this to be the most important opportunity we have to make an impact. In the Canadian startup community, Upside is a trusted organization for founders, accelerators/incubators, charities, and VCs. Upside can leverage this position to help founders understand the nuances of philanthropic giving from an equity, diversity and inclusion (EDI) perspective help our founders to think about how to make their organizations equitable and inclusive. 

What we’re doing:

  • Hosting workshops, educational events and conversations focused on learning, decision-making and action regarding anti-racism, taking a stance on controversial political & social issues, and making progressive socially responsible choices. This lens will continue to be embedded in our programming, much of which we have opened up to a broader audience.
  • Continue to profile ways that  those in our community can become more actively anti-racist through our social media channels, including amplifying the voices of those who understand these issues better than us
  • Profile best practices and highlight specific opportunities for how founders and companies can shift from awareness to learning to action, implementing processes and metricizing for consistent monitoring and results
  • Continue to partner with, support and amplify communities of under-represented founders, including BIPOC, women, and LGBTQ+ entrepreneurs
  • Offer educational opportunities for our community to consider social justice and equity perspectives in their philanthropic choices

We understand that we are but a small player when it comes to solving the challenges of racism and systemic under-representation of minoritized leaders. However, we believe it is important that we understand the ways in which we can be an active part of the collective effort to make our world a more inclusive, equitable and just place. These reflections are a starting point: we’re sure that we’ve gotten some things wrong, and we commit to continuing to learn and improve. We welcome feedback and opportunities for collaboration so that we can all do better: please email jennifer@upsidefoundation.ca if you have any thoughts you'd like to share.

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