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Shawn McLaren began their career in 1975 when they founded The Cambridge Systems Group, where they served as the Chairman, CEO and Founder. In this role, they developed and sold a storage management system, ASM2, and an access control security system, ACF2. In 1987, they moved to Pebble Beach and golfed there until 1999. In 1996, they became an Angel Investor for Band of Angels. In 2000, they became an Investor, Chairman and CEO for Securant, where they were "thefatherofsecurity@gmail.com" with white hair. From 2001 to 2007, they were a hiker and biker while being jobless and drifting. In 2007, they became an Investor, Executive Chairman and Founder for ConnectAndSell, Inc. and was the CEO from 2010 to 2013. Shawn was passionate about ConnectAndSell's Lightning product, which liberates sales reps by freeing them from the frustration of Voice Mail Hell.

Shawn McLaren attended the University of Michigan from 1961 to 1965.