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Joseph Leonard started their work experience in 2010 as a Clerk at the Chicago Board of Trade. Joseph then worked as a Marketing Supervisor/Membership Team Lead at Sam's Club from 2012 to 2013. In 2013, they became a Lumber Trader at Greenleaf Trading, LLC. and later transitioned to become a Project Manager at BNG Fuel Corporation from 2013 to 2015. In 2015, they joined Ozinga as a Sales Representative, and finally, in 2019, they briefly owned Awesome CBD LLC.

Joseph Leonard attended Lewis University from 2008 to 2012, where they earned a Bachelor of Science degree in Business Administration and Management, with a focus on General Management.