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Simon Pickup has extensive experience in the business world, beginning in 2004 when they founded Youth Hydrogen. In 2007 they joined The Promoters as Operations Manager, where they staffed and executed experiential marketing campaigns for corporate clients. In 2010 they Co-Founded Ace Marketing, a promotions company providing staff for experiential campaigns and events in western Canada. That same year they also became Sustainability and Special Projects Manager for SPUD.ca - Sustainable Produce Urban Delivery, where they were primarily responsible for developing and executing SPUD's sustainability strategy. In 2014 they joined GridGear Solutions as Director, and in 2021 they became an On Deck Miami Fellow. Currently, they are the Chief Executive Officer of both Hydra Energy and Stealth Company.

Simon Pickup attended Harvard Extension School from 2009 to 2010. In 2013, they attended Draper University. Simon also holds a Certificate in Project Management from The University of British Columbia, which they began in 2007.