South Portland native Chris Coyne, 34, is co-creator of TheSpark and OkCupid, which receives over 1.3 million different visitors every month. After graduating from South Portland High School, Coyne went to Harvard University to earn a degree in mathematics. While there, he started his first business. With classmates Sam Yagan, Max Krohn, and Eli Bolotin, he created the humor website thespark.com in 1999, offering study guides called SparkNotes. In 2001, Barnes & Noble purchased SparkNotes for $3.55M, and hard-copy versions of Coyne’s study guides displaced perennial favorite CliffsNotes in all of their stores. Not content with this success, he reimagined a personality test and matching service from thespark.com to form OkCupid, a dating site with a strong focus on using mathematical algorithms to match people. Nine months ago, Coyne and his partners sold OkCupid to the operators of Match.com for $50M. Now that he’s made his fortune, we’re curious about how much his memories of Maine are starting to tug him back.

download this story as a .pdf