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Milo Dubak has extensive experience in executive roles within various companies. Milo started their career as the Chief Brand Officer at C5 Beer Pong in 2012 and held that position until 2020. In 2013, they became the Chief Operating Officer at Pure Freight Lines, Ltd. and later transitioned to the role of Chief Executive Officer in 2022. Milo also served as the Vice President of the nonprofit organization 28. Jun from 2011 to 2020. Additionally, they took on the role of International Operations Specialist at Dubak Electrical Group in 2020. Currently, they are the Chief Executive Officer at both Pure Freight Lines, Ltd. and Pure Freight Management LTD.

Milo Dubak graduated with a degree in Political Science, with a focus on International Relations, from the University of Illinois Chicago in 2012. Prior to that, they attended Lyons Township High School from 2004 to 2008. In addition to their education, they obtained a Department of Transportation Safety Training certification in 2014.