Last week, he shared another fun story during his podcast called Founder Calls.
He had Yahoo cofounder Jerry Yang as a guest and asked to name an area he would avoid if he was starting a new business today.
"I probably wouldn't want to do a storage, file system in the cloud, unless they can sell it to you," Yang joked.
But Levie was quick to point out that Yang had actually been in the cloud file storage business in the past. In fact, Yahoo was one of the first in the business when it launched a service called Briefcase back in 1999.
"Do you know who our first-ever competitor was? Yahoo's Briefcase," Levie told Yang. "But it had some issues. It may or may not have left some openings in the market for startups to emerge - we thank you for that."
Before Box took off and became a public company, it had a meeting with Yahoo's Briefcase team in 2006. Levie said Briefcase didn't have the same speed and cost advantage as Box did, and the meeting was to pitch Yahoo on a potential partnership - and possibly hear acquisition offers.
"I think there was a chance they were maybe sussing us out to do an acquisition offer or whatever, but they never called us back," Levie said.
Briefcase didn't last long after that meeting. It only offered 30MB of online storage and never became part of Yahoo's core product line, ultimately shutting down in 2009. Even Yang, who was Yahoo's CEO at the time, admits he wasn't all that impressed by Briefcase.
"I did [use it] and it didn't last very long. It wasn't a very good product," Yang told Levie.