Samay came from what he described as a conservative Kashmiri Pandit family. He enrolled in a print engineering course in Pune, which he said was a waste of time, and started doing open mic events and eventually became a regular in the local comedy scene.
After performing at multiple open mics since 27 August 2017, Samay began opening act for well known comedians like Anirban Dasgupta and Abhishek Upmanyu in Pune. As he gained recognition, he moved to Mumbai to pursue a career in stand-up comedy and gave several successful shows in Mumbai and in several cities across the nation.
During the COVID-19 pandemic, all outdoor events were canceled and thus, Raina could no longer perform stand-up comedy. He then began streaming games of chess on his YouTube channel at fellow comedian, Tanmay Bhat‘s suggestion. His viewership got a boost when he invited YouTuber, Antonio Radić, popularly known as Agadmator, to his channel. In response to this, Indian GM Vidit Gujrathi tweeted that he too would like to join Raina on his channel. Eventually, Gujrathi made an appearance on Raina’s channel, giving another boost to Raina’s viewership. Since then, the two have fostered a strong relationship and frequently feature on each other’s channels. Gujrathi attributes his moving from Twitchto YouTube to Raina’s suggestion.
According to many proponents of chess, including GMs Viswanathan Anand, Vidit Gujrathi, Anish Giri, Teimour Radjabov, Baskaran Adhiban, Emil Sutovsky and IMs Tania Sachdevand Sagar Shah, Raina has been instrumental in popularising chess in India through his channel.
Raina tries to make the game of chess more appealing to the masses through his humour which according to many have helped him reach a larger audience.
In addition to the chess players mentioned above, several well-known chess personalities like Pentala Harikrishna; Judit Polgár; former world chess champions Vladimir Kramnik and Viswanathan Anand; and the current world chess champion, Magnus Carlsen have appeared on Raina’s channel. He also organised chess tournaments featuring Indian celebrities such as cricketer Yuzvendra Chahal.
On 1 November 2020, Samay Raina released a mock diss track about Sagar Shah on YouTube.
Chess and Comedians on Board (COB)
As of 12 May 2021, Raina has an ELO rating of 1695 at rapid chess on Chess.com. On 5 May 2021, Raina won the $10,000 Botez Bullet Invitational, a one-hour amateur bullet arena tournament sponsored by Chess.com and hosted by the Botez sisters. He was the only Indian streamer competing among some of the top international Twitch streamers, and earned a prize of $4000.
To attract online audience to chess, he started organizing Online Chess Tournaments on his channel, called Comedians on Board (COB).
During the COVID-19 pandemic, he began streaming games of chess along with various comedians and chess masters. Through his YouTube channel, he has raised substantial amounts of money for various causes including help for waste pickers, and relief for West Bengal and Assam flood victims.