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Robert Flynn has a wealth of work experience, seamlessly transitioning between various roles within the technology and media industries. Robert began their career as a General Partner at Entertainment-Media Ventures Partners in 1987, where they worked until 1994. Following this, they co-founded Liquid Audio in 1994 and served as the SVP of Business Development until 2003. Moving on, Flynn served as the CEO of Zetools, Inc. from 2003 to 2006, before co-founding Modern Feed & Supply, Inc. and serving as its CEO until 2008. Robert then became a partner at One World Media from 2008 to 2010, before eventually co-founding Aggregage in 2010, where they currently hold the position of CEO and Co-Founder. Additionally, Flynn served as an advisor at Crosswater Digital Media starting in 2004.

Robert Flynn attended the Webb School of California from 1967 to 1971. After completing high school, they enrolled at Stanford University from 1971 to 1975, where they obtained a Bachelor's degree in English. Later, from 1981 to 1983, Robert pursued higher education at UCLA Anderson School of Management, acquiring their MBA with a focus on Entrepreneurial Studies.