In 2011, reports circulated that Levie was offered hundreds of millions of dollars for Box. Specifically, Levie reportedly turned down more than $550 million from an unnamed company. At the time, Levie was 26 years old.
Ultimately, Levie decided to hold on to his startup. The following two weeks, Levie says, were "gut-wrenching." He wondered if he had made the right decision. He explained his logic to New York Times' Quentin Hardy:
"The mind-set was: Is this a once-in-a-lifetime opportunity to build something really new, create products and services that no one has had before? Are you better off doing that on your own, or can you do it better with the resources of a big company?" he said.
Levie's decision didn't come down to the hope of getting a larger offer later.
"You think more about the company and the mission than whether you should hang in there so you can someday afford two really big yachts, instead of one."