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Samuel Bail has a diverse work experience. Samuel started their career in 2008 as the Director and Manager of Private Medical Services at MCI Medical Clinics Inc. Samuel then moved on to become an Analyst at Lazard in 2010. In 2011, they co-founded Troubadour Goods.

Samuel Bail began their educational journey at Upper Canada College from 2000 to 2004. Samuel then attended McGill University from 2004 to 2008, where they earned a BA in Honours Economics with a first-class degree. In 2009 and 2010, they attended Saïd Business School at the University of Oxford, where they earned an MSc in Financial Economics.