He served as member Rajya Sabha Select Committees for the GST[4] and Real Estate bills.

[10] In 1991, after returning to India, Chandrasekhar married and joined his father-in-law's company, BPL Group.

[11] In April 2013, Chandrasekhar was awarded an Honorary degree by Visvesvaraya Technological University, Belgaum, for his work as an entrepreneur.

[13] He also held equity shares in six unlisted companies: Vectra Consultancy Services, SPL Infotech PTE, Jupiter Global Infrastructure, Minsk Developers, RC Stocks & Securities and Sanguine New Media.

In addition to this he indirectly has stakes in Axiscade Engineering Technologies, Jupiter Capital Private Limited, Mistral Solutions, Assystem Axiscades, Tayana Digital, Hindustan Infrastructure Projects & Engineering Pvt Ltd.[11][14] In late 2006, Chandrasekhar entered into a media foray due to investments made in Asianet Communications through his firm Jupiter Capital Private Limited.

[15] In late 2008, he entered into a joint venture with Rupert Murdoch's News Corp as Asianet Star Communications.

In 2016, through ANOPL, he invested nearly 60 crores in ARG Outlier Media, the holding company of Republic TV.

[25] Rajeev is married to Anju Chandrasekhar (m. 1991), the daughter of T. P. G. Nambiar, the founder of BPL Group and resides in Koramangala, Bengaluru.