In his final year, Gupta was the president of Natuve- The theatre society of Shaheed Bhagat Singh College.

After graduation Gupta worked as an audit associate with KPMG for one year, while doing theatre on weekends with different groups in Delhi.

[citation needed] Gupta eventually chose to quit his corporate job and to focus on learning different forms of theatre, while keeping up his work in comedy and improv.

His unique sketch comedic style landed him in the grand finale of the show and he ended up being the co-winner of Season 2 along with Samay Raina.

After his new found fame from Comicstaan, Aakash started doing multiple shows across India and filled up auditoriums and college gigs.

Gupta was a part of a comedy reality show on Amazon Prime video titled LOL: Hasse Toh Phasse[7][8] along with Sunil Grover, Gaurav Gera, Kusha Kapila, Mallika Dua, Cyrus Broacha and more.

Gupta teamed up with Kenny Sebastian, Kaneez Surka, Prashasti Singh and they called themselves The Gharelu Gilehris (Homely Squirrels).

In 2022, Gupta played a lead role in the web series Couple Goals S3 which premiered on Amazon Mini TV.