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The Upside Foundation

The Upside Foundation of Canada lets startups and founders make a legally binding pledge of part of their exit proceeds to charity. Investors Robert Antoniades and Mark Skapinker founded it with consultant Janie Goldstein. Jennifer Couldrey was its first employee and long-time executive director.

NonprofitTorontoupsidefoundation.ca

The people

Jennifer CouldreyExecutive Director, The Upside Foundation (2015–2022) · 1 TechTO talk
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Robert AntoniadesCo-founderprofile coming
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Mark SkapinkerCo-founderprofile coming
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Janie GoldsteinCo-founderprofile coming

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Working at The Upside Foundation

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About

The Upside Foundation of Canada is a charitable foundation that enables high-growth startups and their founders to commit a portion of their eventual exit proceeds to charity through a legally binding pledge — an equity pledge model used internationally since the early 2000s. Beyond running the pledge process, it hosts networking events and connects founders with investors and other ecosystem opportunities, then facilitates the donations when an exit happens. It was founded by Robert Antoniades, general partner at Information Venture Partners, Mark Skapinker, managing partner at Brightspark Ventures, and consultant Janie Goldstein, on the view that this generation of entrepreneurs wants to make an impact. Jennifer Couldrey joined as its first-ever employee when roughly 50 companies had signed on, served as executive director, and departed in September 2022. She spoke at TechTO in May 2019 on building a culture employees love — specifically, on social responsibility as a way to attract and keep talent.

Backers

A registered charitable foundation rather than a venture-backed company; it is supported by the pledging companies and the investor community that founded it.

Quick answers

What is The Upside Foundation?

A Canadian charitable foundation that lets startups and founders pledge a portion of their exit proceeds to charity through a legally binding commitment, then facilitates the donation when an exit occurs.

Who founded The Upside Foundation?

Robert Antoniades of Information Venture Partners, Mark Skapinker of Brightspark Ventures, and consultant Janie Goldstein.

Who was Jennifer Couldrey?

The foundation's first employee and its executive director. She joined when about 50 companies had pledged and left in September 2022 to work as a certified EOS implementer.

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Maintained by TechTO · facts sourced and dated · last reviewed Jul 23, 2026