But as a recent Times article points out, sometimes being lean and hungry can be a company's greatest asset.
Started in 1999, the site's previous incarnation 'Ask Jeeves' made a big impact with its focus on answering natural language questions, such as "Where can I find organic vegetables?".
However the dot com crash and rise of Google saw the company become the world's third most used search engine.
A change of management is seeking to change this situation by focusing on non-tech savvy markets like school children with homework queries and mothers looking for household advice.
The new look ask.com also aims to offer a more human approach by making its trademark cartoon butler the focus of its brand strategy.
Can ask.com win this epic battle? The search engine itself isn't so sure. The search query: "Can ask.com beat Google?" was unable to provide an answer.
