Security footage from Lai's residence show a private vehicle pull up outside his house at 1:30 a.m. In the footage
, a masked man emerges from the car seconds after, ignites an object and hurls it at the front gates before driving away.
Minutes later, similar devices were thrown at Next Media's headquarters in another part of the city.
Police told CNN that both cases are currently undergoing investigation, and no arrests have been made.
Two vehicles suspected to have been used in the attacks were found torched, with license plates removed, reported the South China Morning Post
Lai's assistant said that this was not the first time the media mogul's private residences had been targeted.
"We're not shocked. Unfortunately, violence has become a regular feature of Hong Kong now in the political discourse. That's just a simple fact," Mark Simon, Lai's assistant, told CNN.
Next Media and its founder, who retains a majority -- 73% -- stake in the company, are known to be critical of the Hong Kong and Chinese governments, and have been targeted in several attacks.
In 2013, a stolen car crashed into the front gates of Lai's residence, and a machete and an ax were left in his driveway. A week after the attack, two masked men set fire to bundles of the
Apple Daily newspaper, a Next Media publication, in an intercepted delivery van, according to the Guardian
, a British newspaper.
For several days in mid-October, a group of protestors blocked the entrance of a printing plant that published Apple Daily, in attempt to prevent the pro-democracy newspaper from reaching newsstands.
Lai, a fervent China critic and staunch supporter of the Hong Kong pro-democracy protests, resigned as chairman of Next Media shortly after the protests sites were cleared in December.