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Here we go: #20 — Chatroulette By the time Chatroulette exploded, it was already a tale of “what could have been.” Launched in late 2009 by a Russian teenager, the site operated out of a Moscow bedroom.

Its explosive growth was second only to its remarkable media attention.

Ning’s incredible PR and huge fundraising were probably instrumental in its initial user surge.

And its privately-held data means that we will never know exactly how much was smoke and mirrors.

Ever since the dawn of the Web 2.0 era, founders and investors have been mesmerized by the concept of “going viral” — the tantalizing prospect of sudden riches, hewn seemingly out of thin air.