Stand-up

After performing at multiple open mics since 27 August 2017, Raina began opening 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 several cities across the nation.^{[citation needed]}

Comicstaan 2

Eventually, he joined Comicstaan 2 from a suggestion from his co-winner Aakash Gupta. Later, he became the joint winner of Comicstaan 2 with Aakash Gupta, aired on Amazon Prime Video.^[7][8]

YouTube

During the COVID-19 pandemic, the government cancelled all outdoor events, and thus, Raina could no longer perform stand-up comedy. He then began streaming chess games on his YouTube channel at the fellow comedian Tanmay Bhat's suggestion.^[9] His viewership boosted when he invited YouTuber Antonio Radić, popularly known as Agadmator, to his channel. In response to this, Indian GM Vidit Gujrathi tweeted that he would like to join Raina on his track. Eventually, Gujrathi appeared 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 Twitch to YouTube to Raina's suggestion.^{[citation needed]}

According to many chess proponents, including GMs Viswanathan Anand, Vidit Gujrathi, Anish Giri, Teimour Radjabov, Baskaran Adhiban, Emil Sutovsky and IMs Tania Sachdev and Sagar Shah, Raina has been instrumental in popularising chess in India through his channel.^[10] Raina tries to make the game of chess more appealing to the masses through his humour which, according to many, has helped him reach a larger audience.^[9]

Several well-known chess personalities like Pentala Harikrishna, Judit Polgár, former world chess champions Vladimir Kramnik, Viswanathan Anand and Magnus Carlsen have appeared on Raina's channel.^[11][12] He also organised chess tournaments featuring Indian celebrities such as cricketer Yuzvendra Chahal.^[13][14]

In addition to chess, he also live streams many other games on his YouTube channel.

Chess

As of 22 June 2022^[update], Raina has a rating of 1660 at rapid chess on chess.com, while the highest recorded rating was 1942.^[15] 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 $4000.^[16]