John Cunningham

Partner & Co-Founder at CollegeWeekends.com

John Cunningham has over 20 years of experience in the corporate and entrepreneurial worlds. John began their career in 2001 as the Director of New Ventures at Landmark Communications. In 2002, they joined Monument Capital as a Senior Associate and focused on sourcing new investment opportunities for a venture capital fund. In 2003, they founded EXCELerate Management Company, LLC and acquired a sports performance training franchise. John opened two locations in the Hampton Roads market and was profiled over 30 times on the local ABC and NBC affiliates. In 2009, they served as a Senior Advisor and Consultant for RaceIt, a leader in online registration solutions for events. In 2010, they became a Partner at BragStats. From 2013 to 2016, they worked at the World Economic Forum as an Entrepreneurship Program Leader. During this time, they supported global entrepreneurship initiatives in partnership with Stanford University, Ernst & Young, Endeavor.org and Purpose.com. In 2016, they became a Mentor at the i.Lab@UVA. In 2018, they co-founded CollegeWeekends.com (CW LLC), an online short-term rental platform. Since 2011, they have been at EY, where they have held various roles including Corporate Development, Digital Platforms Leader, and Global Digital & Emerging Technologies COO. In 2022, they joined the Board of Directors of the Hampton Roads Youth Foundation.

John Cunningham attended Skyline High School from 1988 to 1989, Hampton Roads Academy from 1989 to 1991, the University of Virginia from 1991 to 1995, where they earned a Commerce degree in Finance & Marketing, and the University of Virginia - Darden Graduate School of Business Administration from 1999 to 2001, where they earned an MBA.

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