Fintech Impact

In this 158th episode of Fintech Impact, Jason Pereira, award-winning financial planner, university lecturer, writer, and host interviews Jennifer Couldrey, the Executive Director of The Upside Foundation of Canada, an organization that enables equity donations by Canadian business founders who wish to make a positive impact on the future of their communities!

Episode Highlights:

  • 1:20 – Jennifer Couldrey introduces The Upside Foundation.
  • 2:14 – How did Jennifer get into this business and how did The Upside Foundation get its start?
  • 3:52 – Jennifer breaks down The Upside model.
  • 5:56 – Why are these Canadian founders interested in donating equity?
  • 8:05 – Jason and Jennifer talk about how The Upside Foundation thrives in the long-game.
  • 9:07 – What does a typical deal look like and what factors play into these parameters?
  • 10:59 – Where are the donations being directed?
  • 13:01 – Is this a one-time donation or a continuously-managed fund?
  • 14:59 – Jason and Jennifer discuss how people view different charities.
  • 21:12 – What is the feedback that The Upside Foundation is receiving both before and after their clients’ exit events?
  • 25:57 – If Jennifer could change one thing in her industry, what would it be?
  • 29:12 – What has been the biggest challenge of getting The Upside Foundation to where it is today?
  • 30:25 – What motivates Jennifer to get up every day and push forward with The Upside Foundation’s mission?

3 Key Points

  1. Canadian founders use The Upside Foundation as a way to make a palpable impact in their communities.
  2. Companies are presented with the option of donating via stock options or personal proceeds to the cause of their choice.
  3. 90% of charitable donations are donated to elite donations such as universities, hospitals, and larger organizations that decide where the money should be allocated.


Tweetable Quotes:

  • “It’s a way of embedding this charitable impact into your business from day one.” – Jennifer Couldrey
  • “Part of the reason we have the flexibility to give through stock options or to give through personal proceeds is just to make that decision really easy for people.” – Jennifer Couldrey
  • “Having the ability to course correct is a valuable luxury that I think that is afforded through having these endowments paying out small amounts over large amounts.” – Jason Pereira
  • “When people think about charity, they usually think about helping the poor...but if you actually look at where charitable dollars go, 90% of charitable dollars are going to help elite institutions.” – Jennifer Couldrey
  • “When you have something, it’s hard to give it up. The bigger that number is, the harder it is to cut that check.” – Jason Pereira


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Fintech Impact is an exploration of the fintech world where we interview different fintech entrepreneurs about what they do, their story, and what their impact is on consumers, incumbents, and the industry is as a whole.

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