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Joshua Diller has over 15 years of legal experience, with expertise in various areas of law. Joshua is currently the Vice President & General Counsel at Windy City Motorcycle Company, where they provide strategic guidance in legal matters such as mergers and acquisitions, corporate governance, regulatory compliance, contract drafting and review, labor and employment, and litigation. Joshua also manages the company's real estate portfolio, including acquisitions, dispositions, and leasing. Prior to this, Joshua worked as a Partner at Katten & Temple LLP for over 12 years, specializing in legal advisory services. Joshua started their legal career as an Associate Attorney at O'Rourke Katten & Moody.

Joshua Diller completed their education with a Bachelor's Degree from DePauw University in 2001. Joshua then pursued further education at Chicago-Kent College of Law, Illinois Institute of Technology, where they obtained a Juris Doctor (J.D.) degree in 2006. No specific field of study was mentioned for either of their degrees.