He enrolled in a print engineering course at PVG's COET in Pune, Maharashtra which he said was a waste of time, and started doing open mic events and eventually became a regular in the local comedy scene.

[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.

He has raised substantial amounts of money for various causes through his YouTube channel, including help for waste pickers,[21] and relief for West Bengal and Assam flood victims.

[22][23] In June 2024, Samay Raina launched India's Got Latent, a reality show focused on uncovering hidden talents.

Hosted on Raina's YouTube channel, the show quickly garnered attention and positive reception, particularly among younger audiences, for its distinctive, humour-driven approach to talent discovery.

[24][25][26] The show marks Raina's continued efforts to explore creative formats that merge comedy with interactive entertainment, following his previous successful ventures in stand-up and online content creation.

The app, inspired by his YouTube show, offers unfiltered and uncensored content, paving the way for creators to explore their talents without restrictions.

He aims to eventually transition the platform into a full-fledged OTT service, featuring shows across genres such as poetry, rap, and reality TV.

[27] Assam's chief minister Himanta Biswa Sarma, posts a tweet on Twitter on 10 February 2025, by stating that Guwahati Police has registered an FIR against YouTubers Ashish Chanchlani, Jaspreet Singh, Apoorva Makhija, Ranveer Allahbadia, Samay Raina and others for promoting obscenity and engaging in sexually explicit and vulgar discussion in India's Got Latent.