While attending Homewood-Flossmoor High School, Heiferman sold coupon books for a nearby town, earning enough to pay for his first year of college.

[1][3] Scott Heiferman's first job out of college was in Montvale, New Jersey working for Sony as an 'Interactive Marketing Frontiersman.

[7] Heiferman was influenced by the book Bowling Alone, which is about creating connections between strangers[1] and the deterioration of community in American culture.

[10] Around the same time, Heiferman also started a photo-sharing service called Fotolog, which he sold five years later for $90 million.

[4] In 2004, Meetup reached one million users and Heiferman was named "Innovator of the Year" by MIT Technology Review.

[4] Subsequently, then Presidential hopeful Barack Obama promised to attend any Meetup event of supporters that can get at least 100 attendees.

[4][6] In 2005, Heiferman made the unexpected decision of charging users a fee to start and run Meetup groups, rather than using an advertising-based business model.