Box’s CEO just compared Donald Trump to old, dying technology

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Box CEO Aaron Levie Business Insider/Eugene Kim

Box CEO Aaron Levie is one of the funniest CEOs in tech. He’s also one of the 
most outspoken critics of Republican presidential nominee Donald Trump.
So at BoxWorks, his company’s big annual conference taking place this week, Levie made sure to throw in a joke about Trump during his opening keynote speech — comparing him to old, dying technology. He said:

“[Trump] is like your legacy content management and collaboration technology. Lots of vague promises that don’t seem to be fulfilled…Really it’s about building walls to make it hard to share the best ideas and to collaborate. And he seems to be successful even though he has a crazy user interface. I don’t understand how this works.”

His point: old software that needs to be installed in your computer and servers, and not offered over the web, are a dying breed, and blocks faster collaboration, as seen in the recent shift to cloud software. Box is a file storage and work collaboration software offered over the internet, or the cloud.

Levie also cracked a few jokes about Bernie Sanders and Hillary Clinton during his speech. He compared Sanders to “freemium” software, which is offered for free in the hopes of eventually turning users into paying customers, while taking a dig at Clinton’s email gaffe, as well.

“Bernie is sort of like freemium enterprise software. Millennials want him, he’s really going up against the establishment, the traditional old guard, but nobody can really figure out who’s going to pay for everything,” Levie said.

“Hillary Clinton on the other hand is like your traditional IT stack, very stable, reliable, pragmatic, but can’t quite seem to get email right ever.”

Given Levie’s public swipes at Trump, it’s not too hard to see him make these comments. A quick look through his Twitter feed shows jokes like this:

In fact, he was so motivated by Trump jokes that he’s making this Trump-inspired hat available at BoxWorks as well:

BoxWorks is the biggest stage of the year for Box so it made a number of important announcements as well. It rolled out a completely revamped version of Box called “All New Box,” including a Box Relay, a new workflow product that’s co-developed by IBM for the first time.

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