The site initially had 20 users, and then it doubled daily for a period, according to Ternovskiy in 2010. Ternovskiy built the site on an old computer he had in his bedroom. Ternovskiy chose the name 'Chatroulette' after watching The Deer Hunter, a 1978 film set in the Vietnam War in which prisoners of war are forced to play Russian roulette. Ternovskiy says the concept arose from video chats he used to have with friends on Skype, and that he wrote the first version of Chatroulette in 'two days and two nights'. The Chatroulette website was created by Andrey Ternovskiy, a 17-year-old high-school student in Moscow, Russia. Following product changes in spring 2020, and enhanced by the COVID-19 pandemic, Chatroulette's user numbers have more than doubled between 20.

Done previously founded IT consultancy Simple Machines in Sydney, Australia, and before Chatroulette was CTO for rental platform Goodlord in London. In spring 2020, Ternovskiy appointed Andrew William Done, Australian tech entrepreneur, as the CEO of Chatroulette. Parody shows such as The Daily Show and South Park have lampooned this aspect of the service, and nudity has become an established part of the site's notoriety. According to a survey carried out by RJMetrics, about one in eight spins on Chatroulette yielded ' R-rated' content. Around the beginning of March, creator Andrey Ternovskiy estimated the site to have around 1.5 million users. In February 2010, a few months after the website was created, about 35,000 people were on Chatroulette at any given time.

At any point, either user may leave the current chat by initiating another random connection.

Visitors to the website begin an online chat (audio, and video) with another visitor. Chatroulette is an online chat website that pairs random users with a choice between two other users for webcam-based conversations.

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