Diller's bid exceeds that of rival information site Answers.com, which had reportedly offered $270 million for About.com. Demand Media Inc. (NYSE: DMD), owner of eHow, could also be a potential bidder.
IAC would leverage About.com's 900 topic sites and use them as content for Ask.com's question-and-answer format, according to Reuters.
IAC bought Ask.com, formerly Ask Jeeves, for $1.85 billlion in 2005, with plans to build it into a search engine to rival Google Inc. (Nasdaq: GOOG) and Yahoo Inc. (Nasdaq: YHOO). But Diller soon abandoned those plans.
"We've realized over the last years that you can't compete head-on with Google. It's just pointless," Diller told Bloomberg around the same time.
Ask.com shifted to provide targeted information for users. "It will be answers that will be informed by community. That, we think, is a way we could compete," Diller told Bloomberg.
The Times initially bought About.com for $410 million in 2005, but it began losing traffic after Google changed its search algorithm. Last month, it wrote down the site's value by $194.7 million.
Diller's latest bid is reminiscent of his 2010 takeover of Newsweek magazine and subsequent merger with the Daily Beast. Newsweek was a fiscally troubled asset with a strong brand name, and while About.com doesn't have nearly the same strength, IAC views its $300 million price tag as a bargain, according to Reuters. With around $1 billion in cash, IAC can also raise its bid.
Shares of IAC were down 41 cents to $51.90 at Tuesday's close, while the New York Times gained seven cents to $9.33 in after hours trading.