Celebrating International Charity Day with the Upside Foundation

In celebration of International Charity Day, we sat down with the Upside Foundation to understand why it is important for entrepreneurs to build social impact and charitable giving directly into their business models. We learned about their journey to starting Upside and how they make it easy for founders to give back through their equity pledge model.

Why did you start the Upside Foundation? 

Founded 8 years ago, the mission and vision behind The Upside Foundation is one of a thriving tech community who’s success powers opportunity for all Canadians. The foundation was co-founded by Robert Antoniades, General Partner of Information Venture Partners; Mark Skapinker, Managing Partner at Brightspark Ventures; and consultant Janie Goldstein. The founders were searching for a way to encourage their portfolio companies to give back, noting that this generation of entrepreneurs strives to make an impact. Drawing on the experience of similar organizations, such as Israel’s Tmura and Silicon Valley’s Entrepreneurs Foundation (subsequently Pledge 1%), the trio designed a model built by Canadians for Canadians to enable successful entrepreneurs to give back to their communities. 

Why do you believe it is important for founders to build social responsibility into their businesses? 

As inflation prices continue to rise, almost 50% of Canadians are doing worse financially than they were this time last year. As the cost of living becomes less affordable – food insecurity becomes even more prevalent in vulnerable populations as 63% of households relying on social assistance were food-insecure. Simultaneously, the Canadian tech ecosystem continues to boom after a record year of $13.58B venture capital disbursements and the first quarter of 2022 remained at a similar pace. 

These divergent experiences of Canadians during the recovery of COVID have served to underscore the need for community-led support. Upside makes it easy for members to give back to the communities they care about at an early stage. Equity pledging allows founders to build a strong culture around a common mission, grounded in a cause that gives their success as a business a greater meaning. 

How does your model work? 

Company founders donate stock options, warrants, or personal proceeds (typically 1%) to The Upside Foundation. When the company has a liquidity event, such as an IPO or acquisition, the cash proceeds from the sale of the equity are donated to the charity of the founder’s choice. 

What have been some of your successes to date? 

As of August 2022, we’ve onboarded 369 Members. We have experienced seven liquidity events within the last 18 months alone, totalling 17 overall. Some of our most recent success stories include:

Wattpadwas acquired by Naver in early 2021. Catalyzed by their Upside donation, the company is formalizing its Corporate Giving Program supporting charities that align with diversity in entertainment. 

Level Jump founded by David Bloom and James Tam, and acquired by Salesforce in October 2021. Throughout the acquisition process, Salesforce was impressed by how LevelJump embodied their 1-1-1- model of philanthropy through an Upside pledge. They donated their Upside to the SickKids Foundation in support of #Tech4SickKids. 

Inkbox– founded in 2015 by brothers Tyler and Braden Handley, was acquired by BIC, resulting in Upside’s first exit of 2022. Inkbox also donated their Upside to the SickKids Foundation in support of Tech4SickKids. The initiative is one that unites Canada’s technology and innovation community with a goal of raising $25M. Their donation will help drive big-data solutions and a modern new hospital to support artificial intelligence’s limitless possibilities. Since their pledge, the team has worked with SickKids on several other projects both personally and as part of Inkbox, like the BE BOLD campaign. 

Is there anything else you’d like to share with our community? 

We recently launched an initiative called Charity Champions. It’s a content series highlighting the incredible partnerships our members are doing with charities long before their liquidity event. It’s been incredible to research the work they’re doing to support their communities. 

Our #1 goal is helping our Members connect with a community of like-minded entrepreneurs. It is our passion at Upside, which is why we host biweekly breakfast events in Toronto. If you are an early-stage founder looking to add some impact driven founders to your network, get in touch with us (maria@upsidefoundation.ca) to attend the next event!


It was great to speak with the Upside Foundation team to understand how they’re enabling founders to build social responsibility directly into their business models. To learn more about the Upside Foundation, visit their website here.