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Aaron Levie
Box CEO Aaron Levie.

You can be suitably entertained by following Aaron Levie’s 140-character musings on Twitter — almost 700,000 followers have figured that out. But for a longer-form version of entertaining banter, let us point you toward the Box CEO’s podcast discussion with Zillow’s Spencer Rascoff.

On a new episode of Rascoff’s “Office Hours,” Levie lives up to his reputation as an “outspoken CEO” and talks at length about why he is that way, why he does it on Twitter and how politics figures into the mix.

Levie, who, along with friends from high school in Seattle, started his popular cloud storage and collaboration platform 11 years ago at age 20, also talks about why it made more sense to run Box out of Silicon Valley than his hometown.

Check out some of the highlights, below, and listen to the entire podcast on Zillow’s site.

On what he posts to Twitter

“On Twitter, generally there are three categories of things that I will Tweet about. The first is — the tech industry has so many just fun, random things going on in it and it’s sometimes fun to comment about them and sometimes it’s a funny thing that happens and you can kind of make light of an event. Sometimes it’s super-serious stuff that — like, encryption, where you want to talk about kind of the global encryption issues and privacy issues. The second topic is if we have major things going on at Box. I have no shame in promoting those to people on the internet, so that’s the second topic.

“And then the third is when something really strikes me as an important maybe political issue or social issue that is worth throwing in a little bit of support for or spotlight around, you know, pass some threshold of importance or significance. And the past year has produced no shortage of those kind of topics, so unfortunately, if you were like a random person on the internet to follow me on Twitter, I don’t think you would really know what’s going on in my mind, because it would basically just be like Trump — like, he must be thinking about Trump 40 percent of the time, new Box features 20 percent of the time, and like self-driving cars, you know, the remainder. So, it’s an interesting kind of mix of issues.”

On sharing his opinions about politics

“The only issue I’ve run into with employees are employees wondering if we will have issues, so not where they disagree with the opinions, but where they equally wonder, ‘Should I have a point of view on these things so publicly?’ And my general answer is that we’re at a point as a country, and as a globe, realistically, where innovation, technology, openness are all going to run into an intersect with politics and government. It’s almost impossible to divorce your political views and your opinions about the future and politics from your business, especially if your business is in technology.

“I could imagine a political environment this year where it wasn’t as profound of an issue. Where you sort of had two good choices on both sides where like in general we’re gonna end up with a fairly positive outcome, or at least a neutral outcome, regardless of the choice, and then maybe I might be less vocal, because then I’ll let sort of the world decide kind of what outcome they prefer. In this case, it’s sort of like you have one outcome which is neutral to positive, just ’cause we don’t know what it could look like. And then you have another outcome where almost unequivocally, categorically it’s gonna be a negative outcome, because – whether that’s because of being able to recruit people from around the world, whether it’s partnerships with other countries, whether it’s internet policy and understanding of technology. So, unfortunately, this election happens to intersect directly with business and with – especially, if you’re in a technology business. So, even moral issues aside, it is a business issue, which is why I’m very active and involved in it.

“And then, even if it weren’t a business issue, Donald Trump has certainly crossed the threshold for me personally of caring about it as a moral issue, where you want to make sure that you do whatever you can to try and stop him from being elected.”

On why he packed up Box and left Seattle

“For us, it was probably partly the time period. It was 2005. You basically had — the bubble had burst four or five years prior. Seattle did well in some areas, didn’t do well in other areas from that, from a venture model standpoint. So, in general, VCs had sort of reeled in and weren’t doing — in the time period that we were raising, I don’t think there was a single venture deal in Seattle at that time or whatever.

“And then we were like 19 and 20, showing up at your door asking for a couple hundred thousand dollars with this idea that frankly, as also you know, like most of Silicon Valley — I’m sorry, most of Seattle venture community is like ex-Microsoft people anyway. They just think Microsoft is gonna own this space, ’cause it — “I don’t know, it looks like something Microsoft would do. They’ll probably just control it at some point.” And that’s — I actually think that’s a bigger problem than we recognize.”

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