clock menu more-arrow no yes mobile

Filed under:

Full transcript: Box CEO Aaron Levie on Recode Decode

Levie started Box 13 years ago as a reaction to having to trundle paper contracts around the Paramount Studios lot.

If you buy something from a Vox link, Vox Media may earn a commission. See our ethics statement.

Box CEO Aaron Levie Recode

On this episode of Recode Decode, hosted by Kara Swisher, Aaron Levie, the CEO of enterprise security and file-sharing service Box, talks about why the next big opportunities in tech won’t look like Facebook or Uber, but rather will grow more slowly into fields like health care, education and manufacturing.

You can read a write-up of the interview here or listen to the whole thing in the audio player above. Below, we’ve also provided a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Recode Decode on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

Kara Swisher: Hi, I’m Kara Swisher, editor at large of Recode. You may know me as someone whose interest in the enterprise only extends to Star Trek, but in my spare time I talk tech, and you’re listening to Recode Decode from the Vox Media podcast network. I made Aaron Levie laugh. That’s an unusual thing. Today in the red chair is Aaron Levie, the CEO of the enterprise file-sharing company Box. He’s also a hilarious Twitter comedian in his spare time.

Aaron Levie: Oh boy.

Honestly, that should be his full-time job. He’s been on the show before back in 2015 when he started this.

Wow. Did we kick off this show?

Yes, we did. I think we did. Back then he called himself older and wiser than some of the kids who were starting startups. Now he’s just older. I can’t wait to hear what new wisdom he’s gained in the past few years. Aaron, welcome to Recode Decode.

Thank you.

So much to discuss. I don’t know where to begin.

I’m glad that you re-professed your love for B2B.

Yes I do. I always love ... who doesn’t love B2B? First, let’s go over where you’ve been since three years ago. You went public, you did all kinds of stuff.

Yeah, it’s been a good few years. Obviously a lot of craziness in our space.

Three years ago, when did you go public?

We probably just had gone public, so three years later being public. I think we’ve done something along the order of 13 earnings calls, and so that’s been a pretty good experience. A little over $500 million in revenue last year.

Now you have to say, right?

Now we have to talk about it and a lot more scrutiny. We’re aiming for and guided to a little over $600 million in revenue this year, on about a path to about $1 billion in revenue in the next few years. All the fun and joys of being a public company.


We are cashflow positive. There’s like nine forms of profitability in the Valley. We’re in the middle tier.

You’re not raining cash?

We don’t have an AdWords yet, but we’re working on it.

All right. Talk about that experience. You did say that you were — how old are you? — older and wiser.


Oh man. God, please.

Much wiser.

Yeah, whatever. Oh my god, that’s real young.

I look like 45.

You do, at least. At least. Pushing 50.

At certain angles. If you just get the gray patch, I look a lot older.

What’s the experience been like? You went public. It was somewhat of a rougher ride for a couple companies like yours. Talk about that experience and what you learned from it.

Thank you for saying a couple companies. It felt like it was just us.

No, there were a couple.

I’m glad that you included others in that. It was a rough ride because we got really unlucky that the moment we filed to go public there was a very brief correction in SaaS valuations and we got that right at the center of our IPO process. Plus, we were known for burning a lot of cash, and the reason for that was we were building out a pretty significant enterprise sales force and doing a lot of deep engineering on the scale of our platform with the intent of making sure that any Fortune 500 company, a bank, a hospital, a life sciences company would be able to actually deploy Box across the entire organization. You have to have a certain amount of that enterprise scale to be able to get there, and that was where we were spending our money, on the singular bet that we were going to go empower the Fortune 500 and how they work and share and collaborate.

Fortunately, a number of years later from that, we now have about 69 percent of the Fortune 500 companies, so customers like Eli Lilly and Pfizer and Amgen and Coca-Cola and General Electric all use Box to be able to manage and secure their data and content. We’re going through a little bit of an evolution where we started out by selling end user file sharing and collaboration, and now we’ve been building a much broader platform.

Right, which you have to.

Which you have to. You have to have a platform, obviously, these days. The whole idea is can we be an end-to-end platform that helps companies manage and secure and govern their most important information.

Their filing sharing, at the heart.

Yeah, the heart, but really being able to secure and manage that content, which is obviously a space that you know and love deeply.

I know more than you think.

You have things like GDPR and you have very specific industry regulations, and then you have data residence and then you have cybersecurity challenges. Companies are dealing with this just massive nightmare of how do I both modernize the way that my organization works and the way we collaborate, the way that we accomplish our daily tasks with all of the new challenges that ...

Which they shouldn’t really do themselves. Which most people do, homegrown.

Yeah. You have decades and decades of legacy technology that companies had to manage in their data centers. In our particular category, there’s probably $30 billion to $40 billion or $50 billion being spent every year on all of this technology, but in this customer’s data center. Well, we’re trying to go to companies in the Fortune 500 and say, “Listen, we can deliver a much simpler way to manage your information. You’re going to be able to collaborate and work in a much more modern way, and you’re going to be able to stay secure, you’re going to be able to stay compliant, you’re going to be able to handle all the privacy requirements of any large multinational company.”

Which they’ve gotten used to from AWS and others.

Yeah, Salesforce, Workday. We’re a part of obviously a much bigger movement, and so a lot of that sales work is being done for us. I think the crux of the moment we’re in right now as both a company and in the space is the Fortune 500 — which is basically a proxy for any large business around the world — is dealing with this challenge of, okay, we have a bunch of practices, we have a bunch of behaviors, we have a bunch of ways that our culture and work styles have evolved for 20, 30, 50, 100 years, if you’re a company that’s been around for 100 years.

All of a sudden, this whole digital thing happens and now you have Airbnb attacking your industry. You have Netflix attacking your industry. You have Lyft and Uber that are attacking your industry, depending on which space you’re in, and all of a sudden you have to modernize the way that you serve your customers. You have to modernize your internal work styles, you have to modernize the way you do product development. You have to modernize the ways that you collaborate. If you’re in the Fortune 500, you’re looking for partners that can help you through this journey. This is how we see our role in the environment.

One of the things that you have to sell them on because one, obviously, was you were a small company, security. The areas you deal with are not small. Your company hadn’t been particularly plagued by that, but many others in this space have, this idea of security in general. Then also that you’re ... Like today Slack went down. Slack went down.

I saw that earlier.

Then it was like, “Ha ha.” There was a whole trending Twitter thing, but it’s like, “Whoa, I use this for my business. No thank you.” It’s not a joke.

Did you take some time off today?

No, I didn’t, but I was annoyed. I’d be very annoyed if my power went off or my water went off or whatever I use. It was interesting to me that everyone was looking at a consumer product, like, “Oh ha ha,” but it really is something I use for my business. It was interesting. I was more irritated.

The mission criticality of these types of services is only growing by the day. We’re used in hospitals. We’re used in medical procedures. We’re used in disaster relief. We’re used in movie companies that have to be able to collaborate in real time on a script. If you go down or you’re not secure, you don’t have the right compliance, you have no ability to go serve your customers. That is a big issue. The foundation of everything we do is security, robustness, reliability, all of the things that ensure that a large, regulated company can have a safe place for their content.

I think people look at these in terms of consumer products. That’s how they first got introduced to a lot of stuff that in the workplace lagged for a long time and now isn’t. You mention it, and you think of it like a Facebook Work in that case, or anything else that you’re using. It’s also a mentality I think a lot of Silicon Valley companies have. I’m like, “Oh well, you got billions of dollars of investment. Screw you.” You work or not is my choice as a customer.

You certainly had a consumer movement that impacted how technology worked in the enterprise, and we were a part of that movement. When we founded the company 13 years ago, we didn’t really think about consumers or enterprises. We just said, hey, people, they want to be able to share and collaborate. Whether you use us in a business environment or a consumer environment ...

You always focus on a business environment. Dropbox was the consumer.

Folklore is always good.

Tell me about it.

We started the company focused on people, basically, independent of the market.

Who cares, right?

We were 19 and 20. We didn’t think about whether you were a business or a consumer. We just focused on people. What happened was, our business model changed within about a year and a half of launching, where we said we don’t think there’s a viable business in the consumer market.

Yes, and then you bought that blazer there.

Then I started buying suits and started looking more serious, started dying my hair gray and now I have way too much of it.

You started off ... I’m sorry, I did get that wrong.

No, no.

You were focused on business very early.

Within a year and a half. For the past 12 years, we’ve basically been 100 percent.

Then they shifted.

The market realized, like, “Oh shit, the money is going to be in the enterprise.” We fortunately had over a decade headstart on that. The trend of consumerization of enterprise technology or this idea that ...

Which we talked about before.

Yeah, why in the workplace are you using worse technology than in our personal lives when we actually spend way more money on technology in the workplace. There’s a variety of reasons, just like the legacy enterprise software vendors never cared about user experience and all of these factors, but now finally ...

They haven’t locked in.

They haven’t locked in yet, monopoly control of data. It didn’t really matter. The buyer was an IT buyer, not the end user. The end user really had no power to affect the kinds of decisions that were being made in the software development process. That’s all changed in the past couple of years.

Since you’ve been going public, how is your competition? With not just Dropbox but the big companies really were the ones that were coming at both of you.

I think it’s important. Obviously the Silicon Valley dynamic is it feels like it’s a Box versus Dropbox environment. I think that both of us would recognize that the market is obviously far bigger than us.

They have gone public since, right?

They have gone public. We probably wish it was just a head-to-head battle, but the reality is you have Microsoft, you have Google, you have more traditional companies like EMC and others. This is where actual spend is going for how companies manage their information and their data. Our job as a startup but a public startup is to make sure that we are out-innovating the much larger incumbents in this market and delivering a much better user experience, being fundamentally more open and integrated with the rest of the technology ecosystem, which is not something that Microsoft is particularly suited for. Then make sure that we can constantly out-innovate the bigger competition.

Our competitive advantage fundamentally as a startup is that we can move faster. We can get closer to customers and better serve them and be much more open and interoperable with the rest of their technology landscape.

That’s what you say, but it’s hard. Obviously they can replicate. Look at Snapchat and Facebook. That’s the equivalent.

I’d say there’s some differences between Facebook and Microsoft just in terms of ...

No, Facebook’s doing it really well, coping beautifully. They’re doing a great job at it. How do you then think about, what are the features that people want now? What are they looking for?

It’s helpful if you don’t break down my talking point so significantly. It’s better if you just believe all of my corporate marketing message.

They’re also smarter at Microsoft than they used to be.

They are very good, and Satya’s a really great leader and he’s got a great set of team below him and it’s been incredible to see how he’s in just a matter of years completely transformed ...

Not quite as feckless, but not the other part. I like that word.

Yeah. Very different than bomber style and in terms of the organization. We kind of see a juncture that the enterprise market is facing right now. We’re either going to repeat the, I think, mistakes of the ’90s and 2000s, which is you give all of the power to two or three or four companies — and we know the names of those companies, the Oracles of the world and Microsofts of the world — or we, as the enterprise industry and big companies say, I’d actually rather have innovation coming from a multitude of vendors, Slack and Workplace by Facebook and ServiceNow and Workday and Salesforce, and I want those technology companies to be really, really deeply integrated with one another.

The benefit that I’m going to get as an enterprise IT buyer is I’m going to get constant innovation in each swing lane.

Each sector.

In each sector.

Rather than mashing them together.

Mashing them together.

Did you ever think about mashing you all together?

Do I think about ...

Like a cabal. You’re like the Dirty Dozen. But go ahead.

I’m sure Morgan Stanley and Frank Quattrone really think about mashing these things together.

Yeah. All of them. Which one of you would ... Benioff would kill you all and throw you all — from Salesforce — to hell one at a time as he took over. Correct?

This is certainly fan fiction for the enterprise software industry.

He’d be meditating with you and suddenly you’d be falling 50 stories. You’d be like, “Oh.”

It might be a trap.

Have you meditated with him?

I have not yet done full zen experiences.

You been invited?

No. Is there some kind of ...

He has some meditation thing.

Yeah, I’m not a meditator.

No. In any case, each of them work together, so you have the Workday element, the Salesforce, because you all are in similar lanes, but different ... You’re in the same pool but different lanes.

I think that’s a good pool analogy. We are all swimming in the same direction in a giant pool and basically there’s another pool next to us which has no lanes and it’s just one giant shark-infested water.

Microsoft cannonballs in, Ellison, they all cannonball in.

That’s just really a yacht, I think. They’re not even in a pool. We basically see that the future of IT is going to come down to do customers want innovation from best-of-breed vendors and us all to work together, which means even working with Microsoft and Google and these incumbents. It doesn’t mean that it’s going to be Microsoft all of a sudden disappears. I think this is where we on the startup side get it wrong. Microsoft is going to be a dominant force in technology, effectively in perpetuity. The question is will there also be a space for best-of-breed technologies that can deliver innovation around that.

Right. There’s a choice though. I notice you didn’t mention Google that much. They have made a big push into this.

Google’s made a huge push. I think we’re seeing more success from Google on the computing side, so really on the infrastructure space.

Sure. Meaning cloud?

Yeah, just cloud computing, sorry, what Diane [Greene] has been driving. I think on Google Suite, like Google Docs, Gmail, etc. ...

It’s more consumer.

It’s more consumer.

It’s because of my kids. It’s my kids.

It could be your kids. I think that they also work for adults.

I know, but I’m just saying.

We use them at Box. We have a couple thousand employees. Certainly there’s nothing about Google Suite or Gmail that doesn’t scale to large enterprises. I think that there’s just a traditional approach that corporate IT has, which is, okay, we’re going to be using Microsoft Exchange in Outlook and we’re going to use that in the cloud from Microsoft. There’s a new set of technologies Google has, some enterprises have it, but a lot of SMBs is really where the focus is.

Sometimes I feel like they never have taken it super seriously.

It’s hard when they have such ...

They have other things to do.

They have such an incredible business model and things like search and Android and YouTube.

The invisibility cloak that they’re building.

I don’t even know about that one.

Yeah, whatever, lifting cars. They have a lot of focus.

Certainly flying cars probably is a little bit more exciting than doing corporate security. Yeah.

Apparently it works.

I saw a video, it seems like it floats above water.

That’s what they say. They keep telling me to come over and see it.

Why haven’t you done a test flight?

I don’t know. I just don’t want to.

Are you too neurotic for a test flight?

No, I did a VR thing yesterday. No, I’ll do the ...

Oh okay. This is actually dangerous. This is not VR.

It’s not that dangerous.

Okay, if you crash into the water and you’ve got to swim ...

If Larry Page is in it, it’s not that dangerous. Whoever. I don’t know. He’s floating around with the invisibility cloak and the hover car.

Yeah, you’re right, I’ve seen the hover ...

You haven’t seen him.

Okay, right. That’s my point. It’s still buggy.

You don’t understand, he has to have a time machine.

It’s still buggy though. You can see his arm pop out of the cloak.

Can you imagine Larry Page floating around?

I can, actually. He’s one of the few people I can.

I can.

Him and Sergey just floating around.

I don’t even want to get into ...

That’s the future.

Let’s not get into Sergey. Let’s not go down Sergey Avenue.

This idea is a cabal. You’re thinking of like a cabal of you, a bunch of you. Neil, Mark, a bunch of ...

I think that’s what we’re seeing from customers. If you look at a Coca-Cola or an Eli Lilly or a Pfizer or a GE, their IT stack looks very different than it would have 10 or 15 years ago. It has Workday in it. It has ServiceNow in it. It has Salesforce in it.

These things work.

It has Box in it. We work together.

Slack, yeah.

Not necessarily perfectly at all times, but we got to drive more interoperability. I think the thing that our more insurgent ecosystem is going to face is can we all work together to deliver an incredible experience jointly that is as integrated as what a Microsoft or Oracle is going to be able to provide with one ...

It used to be you didn’t get fired for using Microsoft, but now I think people do demand more.

They demand way more. Consumer expectations have dramatically changed. They’ve polled those expectations in the workplace, and they’re saying, “No, I’m not going to fill out an expense report in some software that’s 20 years old. That’s just too painful.” Or, “I’m not going to share files inside of that legacy system.” What they do is they bring in their own tool, creating a massive security vulnerability for the company, and then that’s where we come in and we say, “Okay, we can hopefully solve this whole problem.”

What are the big topics? Would it be cybersecurity? What’s the big thing going? What occupies most of your time?

This will sound obtuse or amorphous but it’s really this idea of what does the future of work look like? You’re a company that has 100,000 employees. You have a bunch of practices. You have a bunch of behaviors, you have a bunch of business processes that have been codified after decades and decades of being successful. You’re a retailer, you’re a car manufacturer, you’re a life sciences company. How do you begin to change the pace of innovation? How do you begin to change the speed at which you make decisions and you drive new products into market? How do you get closer to your customers?

This whole idea of the digital age is like, really all it means is business is moving a lot faster, customers have way higher expectations, so if you don’t respond you’re going to get disrupted. I think where enterprise software is going to have to go and where customers are demanding us to go is to say how do I begin to work in the digital age? How do I begin to ...

I’m enjoying this talking point.

Oh cool.

I want a specific.


I am enjoying this talking point. It’s a good one.

I appreciate that.

Times they are a-changin, essentially.

That’s the synopsis of the talking point.


You obviously know this idea of Amazon, two-pizza teams, much more modular innovation where small teams are able to work against a much broader technology stack and deliver customer innovation local to the customer. That is not how 98 percent of the world works.

Yeah, they do it.

That is not how any large company that was built in ...

No, it’s a slow-moving ...

Very slow, three-year business processes to get a new product to market. A customer has a request or a new expectation, and then the entire giant ship has to turn just a little bit to ...

Mark Mullenweg was just talking about that. Facebook, they’re using his WordPress platform because inside of Facebook, they have a few technologists there that can put up a website, but actually it’s faster to use a more innovative [tool].

It’s faster just to use a new tool for that. Then the question is, how do these large companies get to a point where they can have smaller teams that are much more agile, that are much closer to customers? One part it’s culture. If you’re the CHRO of a large Fortune 500 enterprise, you’re saying, “I have to change my culture and my organization to get there.” If you’re the CIO on the IT side, you also have to have a modern technology stack that is things like Slack that are going to let you have team collaboration ...

On a smaller level.

... at a smaller level that is much more local and around one specific business problem or one specific product.

It is interesting when you think about it. It’s a topic I’ve been thinking about as a business. I feel like I want to Marie Kondo everything. Do you know who that is?


The one who brings you joy, the lady who, she cleans out your closet but it’s all about life.


You should read it. It’s a small book.

This is way more zen than the stuff I read. I’ve heard the name. I don’t read those kind of ...

You take everything out of your closet, and if it doesn’t give you joy, you throw it out.

Yes, that’s right. You’re always removing things.

Removing a lot.

That’s exactly what ...

Or changing or moving them into a smaller ...

That principle is exactly what most IT organizations need to be able to have within their environment. Then the question is, okay, I’m a Fortune 500 company. I’m a CPG company, and all of a sudden I have the tools that make it easier to share in real time, make my organization much more open, much more transparent. That’s fucking up the culture, because I’m used to an environment where information is power.

It’s moving up and down.

I have a very extreme hierarchy in terms of how we make decisions in the organization, and all of a sudden a 21 year old that just came out of college might have a better idea for a new product. How does the culture of the organization begin to adapt to the fact that if you have a flatter environment where the best ideas can come from anywhere, where people need a lot more transparency so they have the information to make those types of decisions faster, what does that mean to the traditional corporate structure? What does that mean to how these companies are run and operate, and that’s the exciting set of changes that are to come.

I want to get back to enterprise in a minute and Silicon Valley.

Thank you.


Okay. It’s a company.

How did you get to be so good at Twitter? What is the deal? You’re really deeply funny.

I think people just have incredibly low expectations for what they expect on Twitter.




I don’t think it’s me, I think it’s everybody else.

There’s a lot of very funny people on Twitter. You’re one of the funniest.

I appreciate that.

Deeply funny.

Oh thank you.

Deeply funny. How does it change? Did you just start? A lot of CEOs try to do it and it sucks. They are terrible. They’re either earnest or stupid or just bad. How did you think about it? I want to hear about your process.

This is like “Inside the Actor’s Studio” or something?

Yes, exactly.

It feels like that in this room.

I have to have a beard and go, “So,” vaguely menacing.

I would say that there’s probably ... Unfortunately there’s not that much thought or ...

I thought so. Yeah.

... process to it other than try and say what’s on my mind. And if you can kind of word it in a way that people like, then you feel better when you get “Likes” on it.

Did you think about it as a CEO, of not doing ...? Would you start just doing it when you were a startup and just, it amused you as a 22 year old or ...?

I think Twitter’s a fascinating outlet for being able to get out your thoughts and I grew up with a very ... I mean, the internet was core to my being growing up and so to me it was just like another chat forum. But with more of a ... it’s more of a broadcast chat forum. But yeah, I mean, unfortunately not a lot of methodology behind it.

You just do it.

Just tweet.

You just ... And you’re not ever very mean.

Thank you.

That’s an interesting thing. You’re cutting ...

Sometimes I’m mean to airlines. That’s about it.

But they’re funny-mean. It’s never ... Do you worry about how it’s put out, because you’re the CEO when you say things? Or do you just not? You just do it?

In general I try not to be too mean, just as a way of life.

But when you’re doing stuff. Because you do political stuff. You do all kinds of things.

I do. I think during the election cycle I got a little bit more casual in nature on some of the Trump stuff. But in general I think that I have to have ... We try and focus on policy as opposed to the politician, I think.

Hard not to. He’s a fetid gift that keeps on giving.

It’s hard to maintain that sort of policy-oriented structure just given the amount of ... The climate that we’re in, but that’s my general approach. And then again, just try not to overthink it too much and I delete tweets sometimes that are just stupid.

Like what?

I’ll type something and then my mom will text me and she’ll be like, “That was really stupid.” And I’ll be like, “You’re right, Mom.” And then I delete it.

Really? Your mom calls you?

Yeah. She’ll call me if a tweet ...

What does she ... Give me one she ...

She’ll just be like, “That tweet wasn’t funny.”

It just wasn’t funny.

It wasn’t funny, or it didn’t make any sense. I’ll be like, “Yeah, you’re right.” Or, she’ll be like, “You misspelled something.” And I’ll be like, “Fuck.” So, I have to go delete it. I get a lot of real-time texts from my mom on Twitter.

Oh really?

On issues. Yeah, yeah.

Wow. Damn. She DMs you?

I have a good editor. No just, iMessage.

She iMessages you?


I wish she would just go on Twitter.

If she did DM, she would accidentally tweet and then it would be sort of awkward, so.



What does your mom do?

She’s a speech language pathologist.

So she knows some words.

She likes words, and she likes to have them pronounced accurately, so.

Wow. Where is she from?

She’s up in Seattle. She works with 3 year olds, so that’s the level of help that she tends to give me.

I see. Okay, good. Well, that’s perfect.

I need it.

So when you think about Twitter, one of the things I ... the cesspool nature of it has gotten worse and worse. Do you still like the medium as a communicator, of someone who needs to communicate stuff?

Well, I think, me aside for a second, I think that the ... Twitter is on one hand, it’s an amazing platform because it’s given anybody a voice anywhere around the world. That’s awesome. I don’t think anybody would say, “Okay, forget the Arab Spring,” or just underrepresented communities that now have a much broader voice. That’s awesome.

At the same time, you also can see that it’s a cause of harassment, and it’s a cause of a lot more anger and negativity in some areas. I don’t know how you solve that. I don’t know how you ...

Shut it down.

I don’t ... Well, and then now you don’t have this medium.

Fine. I might do that. I might just do that.

Really? I don’t know that shareholders are really ...

I know. If it was private, I’d be, “Shut it down.”

You’re ... Okay, this is benevolent.

I was just thinking about this the other day. What would I do?

That’s certainly one approach to private equity, is you just buy things and you shut them down. You just pray that ...

Mm-hmm. You’re just so rich.

But, you get returns from that.

No, nobody gets any.

There’s no returns.

I would like to be that rich. Just shut things down.

You know, call up Bill, Bill [Gates], and see if he can help you out on that endeavor.

He could probably do that, couldn’t he?

He could. He could.

That would be close to a lot of his money, though.

I think if he was dealing with a lot of harassment, he would just buy Twitter and shut it down.

He doesn’t have ... a lot of his fortune.

I don’t know what you do if you’re Jack [Dorsey] and you have this incredible democratizing force that can and has brought a lot of good around the world. At the same you have all these other challenges that ... Maybe magically machine learning helps with this. Maybe you just have to hire 10,000 editors.

Ten? Ten million.

You know, 10 million editors that can do all the different controls and abuse kinda claims. But I think something needs to change. I don’t think we’re in a good spot and I think it needs to continue to evolve.

And, how do you assess Trump’s use of it? Watch and wait.

How do I assess it? I mean, I think it’s ... you kinda wish he had never discovered Twitter, so.

Yeah, he’s pretty good at it though.

He is ... I mean, at some measurements, in a bad way, yeah.

In a bad way, he’s good. Yeah. He’s not funny.

I don’t follow him like that.

Today, he did all-caps.

I don’t even follow ... I don’t know what he does.

All-caps today. He’s just crazy.

Probably just like “Supreme Court,” exclamation points.

You use all-caps ever?

I have not done that many caps.

Do you know what it was on? What was it on? He always caps on ...

Yeah, and I try and like spell things better than he does, and that kinda stuff.

Yeah. So, when you think about where Silicon Valley is ... I do wanna talk about this issue, I’ve talked about it with lots of people. How do you assess sort of the mood of Silicon Valley right now? You know everybody. Everybody likes you.

Oh, thank you. I’m sure that Drew [Houston] doesn’t like me that much but ...

He does. He does.

Well, that’s good. Well, I like him. But, I think that the situation we’re in right now I think is an awakening of how much responsibility the Valley has and basically the role of these technology platforms kind of have an impact on our democracy, and on, you know, how the world literally functions. And I think companies like Facebook and Google and others are waking up to their role in society in a much more extreme way, and less intellectual way, because I think it’s always intellectually people have known it but now it’s like emotional, like you can feel it.

Yes, you can feel it emotionally. Why didn’t they before? Because everyone’s saying, “Now we know.” Like Mark [Zuckerberg] said, “Now we take a broader responsibility.” Like why didn’t they have a broader responsibility before? What’s in the thinking? Because usually he’s pretty thoughtful about people here. And the sense is like, “We didn’t know.” I think that’s bullshit.

So, actually, I’m down with that being bullshit.

Maybe I’m just not ...

I think the problem is these things are not binary.

Right. Okay.

It’s this increasing boiling frog issue of like, okay, if Zuckerberg knew the impact of Facebook when they did that one thing where like nine years ago ...


Beacon, thank you. So yeah, like he knew the impact. Like, “Wow, I could actually hurt people’s personal lives if we publish things that people didn’t know we were publishing.” But I don’t know if they ever did like a whiteboard scenario saying, “Okay, let’s imagine that you have a nation-state that’s trying to impact our election, what are the 100 ways that you could manipulate an election in the U.S.? And how many degrees could that become away from that nation state, so you wouldn’t even know that it was coming from them and it could be actually routed through somebody else?”


These are fun conversations to have in a completely hypothetical way but then to see it happen for real, you start to realize, “Oh shit. What have we created here?” And so, I’m sure to some extent it’s bullshit to say, “We’re all of a sudden surprised by this impact.” But I think what we’re seeing is all these sort of new compounding layers of ways that these platforms are impacting the world.

Whether it’s addiction, whether it’s the Russians, whether it’s just does one thing ...

I mean, being a founder and at least knowing some of the origin process for how companies get created, like you’re generally only thinking of the positive things when you’re starting up.

So, why is that? I wanna get to that.

Because you’re 20 years old and you’re like, “I’m gonna build a cool startup that can like solve how people socially network with each other.” You’re not thinking about, “Well what if Russia hacked this thing?” And so then it’s in the core ethos of the company. You didn’t have the deep paranoia and skepticism thinking through every possible way that this could break. You’re really thinking through ...

How it would work.

More of the optimistic scenarios of like, “Well, what if family members were more connected all around the world? And what if you could stay in touch with somebody you went to college with 30 years ago?” And so ... and then you’re like, “Oh shit, but the real world is way more serious than that. There are way more apocalyptic ways to use those things.”

Yeah, it’s interesting. I had a lot of discussions with him years ago about this and they were very brush-offy. Like, “Oh, you are so negative.” Or ... no, he said that to me at one point when I complained about ... I was like, “Aren’t you anticipating this?” And they were like ...

You know what you should do? I have a career job for you. Chief risk officer.

Kind of chief nag.

Chief paranoia officer. Chief nag, CNO? Okay.

Yeah, “This is gonna blow up in your face.”

This would be great, or you could probably do it for a bunch of companies.

At one point, I was like, “People are gonna kill each other on this.” They were like, “What?”

That’s depressing. Yeah.

And they’re like, “How could you think about that?” And I’m like, “Have you met most of humanity? Humanity’s an awful group of people who are someday gonna be blowing up this planet.” I’m sorry. Was that negative?

It might be accurate and it might be pessimistic, but yeah.

One could only hope the sun will blow up and take care of everything. It depends.

And then, that will solve it way faster.

Then everybody melts.

You and Elon Musk are probably very aligned on that one.

It doesn’t even matter if he’s on Mars if that happens. I’m sorry, Elon.

He’s out too.

Everybody’s out.

Well sure, if we’re talking about full universe.

If the sun implodes, yes.

Yeah, that’s too bad.

Like that [finger snap]. You’re not even gonna feel it.

No AI’s gonna work, don’t have to worry about AI at that point.

No, no. Do you wanna go to Mars?

Not personally, no.

A lot of these guys wanna go to Mars.

I’d go if there were no consequences, like I could get back in a week.

There are consequences, what do you mean there are no consequences?

Right, that’s my point.

Listen, Christopher Columbus, there are consequences.

If it’s like a week-long kind of endeavor, absolutely, I’d love to go to Mars, but not ...

It’s not a week-long endeavor.

I can’t do a life-changing sort of thing, I can’t be uprooted right now.

We like Earth.

I just have too many priorities right now, and I have a job, and you can’t take time off for Mars at the moment.

Okay, a lot of these guys would like to go to Mars.

Totally. And maybe one day I would be in a position where I could think about Mars.

Yeah you don’t want to go to Mars. You and I could stay here and hold down the fort.

I’m just trying to store files right now.

Yeah, exactly.

Mars is just so much ...

So what happens in this reckoning? What happens in this reckoning?

I think that what happens in the reckoning ...

Because there’s also diversity issues.

So I was gonna say, you have this sort of multinational challenge which is like, “The democracy at risk.”

Right, at risk, and there’s nation-states attacking you.

And nation-states and cybersecurity. And then you have very local issues, like housing and what are we doing for our local community. And then diversity and inclusion, like why are these companies so hard to get into and so closed off and why are we not able to impact the leadership ranks of these companies from a diversity inclusion standpoint.

So I think there’s a lot of stuff where we’ve gotta get our houses in order, and that is taking on a variety of different work streams. Some are cultural, some are policy, some are technological, some are broader community things. I think what we just need is a consistent push back on our companies, and we need to continue to see a path for remediating or improving on these tensions.

What has to help people in the diversity area? Matt was on before, he was talking about that, and he has distributed companies so he can pull from all over the world. And you’re all fishing in the same pool here. Are most of your employees here?

The majority of, I don’t know, yeah, probably 1,200 or so are in Silicon Valley, and then the rest are distributed throughout the U.S. and other countries.

But mostly here?

Mostly here, yeah.

So what’s the problem in the diversity area?

I think the problem has been a lack of focus and prioritizing of this issue by leadership teams, CEOs, etc. I think that we could definitely blame the pipeline. I don’t know if you’ve fully read “Brotopia” but it was actually real interesting. Like, today, we’re blaming the pipeline, but we caused the pipeline problem that was created decades ago.

Yeah, yes.

So it’s like, yeah we created the very problem that we’re now facing, and we’re blaming it on “the pipeline.” For those that didn’t see that on the podcast. So I think it fundamentally has to be at the focus of the CEO, the leadership team and the organization. Which means you have to evolve your hiring practices, you have to evolve your recruiting programs, you have to think about internal promotion, and equitability in ...

And keeping people there. A lot of people bring people in and then lose them, I’ve seen that happen.

Yep, so you’ve gotta make sure that you don’t have very small pockets of underrepresented groups that are sort of not fully integrated within the rest of the culture and the organization. Which obviously also means you have to get to critical mass, and your organization has to look a lot more like the broader population. So I don’t think there’s a silver bullet, other than it being a focus and priority of ...

What’s changed you? We reminisced and said you’re what, you’re now a famous person in this area.

Joelle [Emerson] is deeply focused on these issues, and she was a lawyer by training and did a lot of public interest law, and kind of employee lawsuits and whatnot, and kind of realized that there’s a legal dimension to this which is like, “Let’s sue when the harassment has gotten so bad.” But also, there’s a cultural dimension which is like, “Why don’t we just fix the underlying practices that cause harassment and cause these diversity issues?”

So a lot of my own evolution, personally, when thinking through this, has obviously kind of been influenced by her in this. But, again, it’s sort of how you hire, how you would track talent, how you retain talent, and then the culture that you’re driving from an inclusion standpoint, every one of those dimensions matters.

What do you think you’ve done well in this area and what do you think not well?

I’d say a few things that we’ve done well, I think that we’ve implemented the Rooney Rule, basically. Which is for any leadership hire director and above — so not just our executive staff, but the population of a few hundred leaders within Box — we make sure we have a couple underrepresented candidates before we’re able to hire anybody. And that’s dramatically changed the mix of candidate pool that we look at, and it’s changed and impacted the direction of hiring, which then goes on to change the hiring that they will then do in their own team, because you now have a leader that might be a woman or person of color. So that’s one area.

We’ve tried to put a huge focus on internal inclusion, so focusing on our employee research groups, and organizations internally that are meant to drive much more community within the company, but then us be able to hear the lessons and issues that different groups are facing. And how do we better support immigrants, how do we better support our Latinx population, and how do we make sure that that is a ... You know, these things are much more tied to the culture and the company. I think it’s making sure that we hold teams accountable to the diversity within the ranks of their organization. We look at metrics every single quarter, as to the population of each individual function within Box’s sales, marketing, engineering, etc., to ensure that we think it’s trending in a much better direction, where we can get to 50/50 from a gender standpoint at least in the next few years.

And then additional programs on the recruiting side. We created a fellowship program called Box Business Fellows, where we go to HBCUs and try and have people come to Box for a week and learn about all the roles in our company. Not just the engineering side, but all the business roles, sales, finance, recruiting. And then we use that as a way of hopefully creating a little bit more of an opening in the Valley for individuals who would not have thought that ...

They would do it. Yeah

That they’d have a career in Silicon Valley. They’re in school in Atlanta or D.C. and their logical opportunity is to go to Coca-Cola or go to a consulting firm. And we’re saying, “Hey, actually, Silicon Valley has a lot more jobs than just the crazy AI engineers that you read about when you see us in the news.” So it’s a bunch of these kind of programs, and just making it a priority of the leadership team to be able to drive.

And what about around immigration? Have your staff been pressuring you? To be more outspoken?

Probably not pressuring me to be more outspoken, it’s more ...

There’s been a lot of pressure of a lot of CEOs.

Yeah, I think it’s just maybe my nature to maybe already be outspoken on these types of topics. We obviously are very focused on trying to drive a much better dialogue on the immigration front, and hopefully, ultimately policy change. I don’t think we’re gonna see anything the next couple of years.

You don’t have an ICE contract, do you?

We don’t.

What would you do if you did?

I think that, A) it wouldn’t matter what the use cases are, and that would be pretty horrid, but we’re definitely getting into an arena where you’re having these really interesting, difficult questions that these companies are facing.


I think maybe we’re just fortunate that our government operation is so nascent.

You don’t have to find a new one, yeah.

We haven’t had to deal with ...

Oracle’s all over it.

We haven’t had to deal with the issue of like, “Is our AI being used for drones?” You know?

That’s Google, yeah.

We kinda dodged a bullet on that, being too early from a scale standpoint.

What would you do?

I think this is where you have to listen to the pulse of the organization and where it’s definitely not a space for unilateral decisions, but I think employees have to be passionate about the company that they work for.


And they have to be passionate that the technology that they come in to work every day to go build is being used in ways that are aligned to their purpose now. The problem is, there’s not a homogenous purpose within the company, but generally speaking, there’s some shared ethics and shared beliefs ...

Facial recognition, all kinds of issues.

By how these companies work, so I think if we felt like our technology was being used to either harm other people or make America a worse place for, again, the kinds of employees or communities that we work with, I think we would decline that kind of contract.

All right. Let’s talk about the future. Where are things going in tech, and especially in enterprise? Also with Box, are you gonna sell your company?


The answer to that is, “No comment.” No, no, not, “No comment,” because that could be a yes.

Yeah, officially, the official answer is ...

“There is no outstanding offer.”

Something like that. Here’s the deal. We did about 500 million last year.


We’re in path and guided to do over 600 million this year. We’re in a market that is, we think ...


$30 billion to $40 billion to $50 billion spend every year, so we’re so early in this space. So, my goal is to make sure that we can capture as much of that as possible, and the company’s goal is to make sure that we capture as much of that as possible. And so, that generally leads us to being — and wanting to be — independent. Although, as a public company, that is ...

Yeah. “I’m open to everything.”

We have to listen to ...

Did you ever think of selling the company before? There were a couple times, right?

We thought about it, we definitely went through the entire process to think that through and ask ourselves, “What are we really trying to build?”

When offers came around?

As offers came. And I think we’ve used the same framework for the past 13 years, which is: Do we believe that there is a way brighter future ahead of us as an independent company, or do we think that we need to pair up with somebody bigger to be able to accomplish what we’re trying to do? And so far we’ve always landed on there’s a brighter future ahead of us an an independent company, and we can actually go and take as much of that opportunity on as an independent organization, without needing to pair up with somebody bigger.

The real reason I ask, actually, is I just had a really interesting conversation with someone about how the big companies are dominating everything and the startup culture is really smaller.


And I was just thinking, there hasn’t been a Snap or an Airbnb or a Box or a Dropbox in a long time. Like the last ones that came out were the class of, whatever, Uber class is.

Yeah, class of 2009 or whatever.

Yeah, something. There hasn’t been that many.

Yeah, it’s actually really interesting.

I can’t think of one, can you?

Well ...

Who? Pinterest was back then.

We work as I think a little newer, but that depends on how you classify that. I think that it’s totally right, and I think in part it’s because there’s not a lot of opportunity if you’re just ... If you’re just solving for a slight gap that an incumbent has, the incumbent’s just gonna mow you over. So if you’re building like a tweak to search engines, or a tweak to social networks, it’s so easy to be a fast follower, if you’re a Facebook, or you’re a Google, in a market that you ...

Remember Peach?

I remember that for about a week and a half.

Week and a half. On a Friday.

You’re right, it was like a long weekend that it was cool for, and I think that’s what happens in so many spaces. So if you’re trying to build the next photo-sharing app, it’s not gonna work. So, just, sorry to break that news to you. So I think then, the question is, where are the next opportunities for technology companies?

And frankly, they’re in markets that take a lot longer to build into, so it’s gonna be in health care, it’s gonna be in life sciences, maybe we’ll continue to see some more innovation to education, it’s gonna be in manufacturing. These are not the markets that — Facebook became a $20 billion dollar company in five years — they’re not particularly viral. They don’t just spread overnight between people.


I think this is the reality in the era that we’re in right now, which is that the next Airbnb, the next Uber, the next Lyft ...


The next Box, they’re gonna be not just solving for deficiencies in the existing technology industry, they’re gonna go out and solve very different kinds of problems, using technology to enable ...

What would you go in if you were now? You were 19, I can’t believe you started a file-sharing company.

You like bringing it back to that.

No, you did.

It’s an enterprise cloud content management platform.

That’s not what you call it then. What do you call it then?

Online cloud storage.

Okay. We need that.

It’s really lame.

That’s needed.

And that’s why our evaluation was very low at the beginning. Our first funding round was at a $240,000 post money valuation.

Oh wow, who is that? Is that mom again?

No, it was basically mom. It was some neighbors of mom and some local folks in Seattle. So those were the days when you did an angel round.

What was another big investor of yours? Cuban or something?

Cuban was an investor for about 18 months and then he got tired of us. I think we were too annoying for him. Fortunately I haven’t been asking myself, “What else would I do?” I think it would be going out into a market.

Into a bigger area.

It would have to be a non ... You’re not, again, solving some problem that Google or Microsoft or Oracle is trying to solve.

Do they have too much power when you think about? You were a famous startup, does the startup environment feel ... It feels desiccated in a lot of ways.

I don’t know that it’s ...

That’s a big word.

Yeah, it is.

Try that.

No. I don’t know that .... I think that ...

It’s a lot of money.

It is a lot of money. I think what’s happening is ... So there’s a difference between, does Google and Microsoft have too much power on the dimension of society. That is a really interesting conversation. Do they control too much about how we live our daily lives?


Without answering that for a second — and I’ll let you be the person to answer that one — the next question is, do they control too much power in Silicon Valley as it relates to startup survival? It’s hard because I don’t know that Facebook shouldn’t be able to copy a little app that ...

No, I agree. What’s interesting, it used to be, if you think about it, the term Microsoft-related, it used to be just Microsoft. There was one boss. AT&T, or Microsoft, or blank. And then they got broken up, or they got hit by a monopoly, and then everything flowered again. If you think about it, so much came out of the Microsoft mess that was good. Not good for Microsoft, but they did just fine eventually, but it was a lot more innovation came out of it.

So you’re saying government regulatory pressure on ...

Well yeah, that’s what I thought. I want to ask you about the last part.

Well, the challenge is, I don’t know where you break up the company.

Well you don’t, that’s the issue, is you can’t really break them because they’re all in their own lanes.

Yeah, like, “We’re gonna give the Facebook News Feed, that’s gonna be now a different independent company.”

But you can’t look at them and say they’re competitors either. Are they competitors? No.

They’re all these mini conglomerates. Not mini, massive conglomerates of semi overlapping ...

Semi overlapping so you can’t really point to any of them. And I would challenge them to call any of ... Facebook. “Mark, who’s your competitor?” I don’t think he could ... Who? Who? Or Apple, or any of them. And so it really doesn’t ... It’s really hard to break down.

So talk about regulation. How do you look at it? Because you’re in a space that probably companies already need assurance. So you’re more careful comparatively.

More careful?

Meaning your business people want everything locked down. You know what I mean? So you’re not quite as loose with the way you run things.

We’re almost the aggregate of all of our customers.

I wonder if there are Russians running around your platform.

What’s that?

Russians. I don’t see there are Russians running around your platform.

They’re certainly not running around, no. Not exactly how you use our product.

You know what I mean.

Yeah. I totally agree. I think we’re actually probably blocked in most of these countries. But I would ... that this is a dilemma that the government faces, which is what should regulation look like as it relates to Silicon Valley. There’s not a single regulation you could have, there’s probably campaign advertising regulations. There’s probably how should medical devices use AI in the future? How should our transportation, the future of transportation and infrastructure work once we have self-driving cars? So there’s probably no wholesale regulation you could apply because of the vast ...


Just the fierce nature of these companies, and the differences of the spaces they occupy. What you need, though, is probably in every major regulatory body or agency, super, super savvy regulators that are looking at these industries through the lens of in a world of AI, in a world of machine learning. When a utility is actually no longer an objective utility, but instead making decisions on behalf of their consumers, what news are you gonna see in the News Feed? Unfortunately, which person maybe has to be harmed in a self-driving car accident? Those are fundamental decisions, which means you need regulators to actually weigh in on as a society, what are the outcomes that we want?

Are willing.

And do we find acceptable. And these are the questions that we are so early in ...

And not capable of answering.

And incapable of answering as both an industry as well as a government.

They sure can arm you about restaurants.

That is the focus. So we know how to regulate Red Hen, but we don’t know ...

I’m gonna go to Red Hen.

I don’t know why you haven’t been there. Why haven’t you done a podcast from there?

I’m going to. I’m going to. That’s a really good idea.

Yeah, thank you.

It’s a great little town. So what are you worried about in regulation? Because someone who is not ... With all the focus on Facebook and others, they were like, “It’s like a contagion here, because we didn’t do anything and here we are with ...” If the Democrats get back in power, the ones that I’ve been interviewing are pretty pissed at Silicon Valley in general.

They would love to stop the News Feed.

Or lots of things. They look like they couldn’t do anything. What are you worried about from your business point of view?

I think what I’m worried about would be ...

Because you don’t want a lot of regulation, right?

Because of the customers we serve, we serve probably seven of the top 10 life sciences companies in the U.S. Many of the leading banks. Many of the leading hospitals. We are almost by proxy regulated because we build software and technology for those regulated customers. So we have a pretty large compliance, legal, etc., function at Box that already is more or less regulated.

Right. Because you have to.

Because of our customer base. So I think the worst-case scenario for us is that Silicon Valley gets so far behind on these issues that we just can’t be trusted as an industry. And then you start to have either companies from other countries, or you have just completely different approaches in architecture to technology.

We rely on the Fortune 500 trusting Silicon Valley’s technology to some extent for our success, and when you see that these tools can be manipulated, or they’re being used in more harmful ways, or regulators are stamping them down, then that, I think, impacts anybody, whether you’re a consumer enterprise. So we actually have an extremely strong vested interest in ensuring that Silicon Valley and D.C. are operating effectively. And so I don’t know if it will be Box specifically being regulated is the outcome, but we care that we get through this mess, and that Facebook resolves their issues, and Google resolves their issues, and so on.

Right. That you don’t get pulled into it. Because it is a contagion for you.

It’s a contagion because it’s gonna reduce trust in these types of platforms.

Yeah, because it used to be Silicon Valley, you’re all loved, and now you’re not so loved.

Yeah, I don’t know how loved ... I don’t know the love quotient at the moment.

The love isn’t good.

Okay, I’ll take your word for that.

Low love. It is. You can feel it.

Yeah, I think we’re in a lower love state right now.

Yeah, and then it gets pulled when Trump ... The Amazon thing, you don’t think it impacts, but it does. Because people do understand that technology could be very malevolent to them.

Yeah. 100 percent.


The jobs thing, I think that we as an industry, again, perfectly similar to the Cambridge Analytica and Facebook thing, way too ...


Cavalier and lacking empathy on how are people gonna perceive as this technology rolls through an industry. Are people gonna be able to learn how to use it, to be competitive in their job? Are they gonna be able to be retrained in some area? Now at the same time I’d say that we’re still very early in that process, and so the rhetoric probably exceeds the actual job disruption that’s actually occurring, and it is coming, which means that it’s time to get ahead of it now and start to have these conversations.

Do you think about that with your technologies? You could replace a lot of people. There used to be file cabinets.

There used to be file cabinets. So the person administering the file cabinet ...

How dare you.

Yeah, we’ve probably at least got rid of 30 file cabinet jobs globally.

Right, easily, yeah. I had a file cabinet.

You would not be employed if that was your only job.

I still have those files.

You do? They should be in the cloud.

Yeah, I know. I’m like Herbert. Not like Herbert Hoover, but J Edgar. I have some files.

Who kept all his files?


Yep. Is that just leverage in the future if you need it?

Oh yeah. I got a lot of files.

Do you print out this podcast later or something?

I have files. Let’s just say.

I have files.

Let’s just say that. Just like that, in that voice.

Yep. I’d be like, “Okay.”

I have files.

I’m not gonna mess with you.

I have documents.

You’ve got documents?


Okay. I’ve got PDFs. Okay.

I’m saying, do you worry about it? Because you do ... Is it something you think about?

It is. And I think that, again, maybe this is the naïve optimism like #Naive optimism of Silicon Valley. In general, when we look at our technology, when we look at Salesforce or Workday or these kinda tools, I think actually what we’re seeing is that as companies can be more efficient in particular areas — whether it’s collaboration or in HR or in a sales process — it’s not that they hire fewer people, it’s that their business is able to better serve their customers.

So what they’re creatively making is more important than the process.

And actually they often will create more jobs. And the more ...

That’s a good talking point.

Everything’s a talking point.

You actually believe it.

It’s just words.

No, I understand. I think you actually believe this one.

Let me give you a really bad example. And a very local example.

Why would you say that?

Because I don’t want you to judge me.

“Let me give you a bad example?”

I don’t want you to judge my example.

Why would you say that? You know when someone does ... They put a fork in front of your face, “Taste this, it tastes funny.” That’s that sort of saying. “Let me give you a bad example.” Go ahead, give me a bad example.

But what if my example’s not good and you’re like, “That was the stupidest fucking example I ever heard of?”

Just give me an example and I will judge it afterwards.

Okay. So we at Box, we have a data science team, and their job is to make our business processes more efficient, and they have a process which is to try and identify the leads that are most likely to close so our sales reps are able to better serve our customers. And they invented a better algorithm that could do that in a much better way so that we can better sell to our customers. It didn’t result in hiring fewer sales reps, it meant that we could actually hire more people because our sales process was more efficient. And so now something that was inefficient previously in some particular area got more efficient, which meant we could actually fund it more because it was now economically a viable way to go and serve that particular customer base.

So I think that what we have to remember is that we have not reached the exact perfect symmetry of supply and demand globally. What we’ve reached is the perfect symmetry of supply and demand with today’s level of efficiency. And so if you could make transportation a tenth of the price, could you dramatically increase the number of people that are consuming that service? Same with health care. Same with consumer products.

It’s dramatically inefficient. You’re right.

We have inefficiency everywhere. And so if technology can make a particular job or a particular process more efficient, potentially you’ll actually hire more people to do that task because now it’s not actually ... You’re able to better serve customers to be able to do that. And then you’ve got all the indirect ads on jobs that nobody’s really tracking. So yes, the truck driver ...

I hate that example.

Okay. That’s why I began by saying these are bad examples.

All right. But go ahead, do it.

No, I’m not gonna go that direction.

It’s not a bad thing. A well-used one. But go ahead.

Okay. I don’t wanna even use it now.

Use the example.

No. All I was gonna say ...

They may have something else for them to do.

Not even that. Well, sure. But also just think, all the surrounding industries that grow when you can go make logistics more efficient.

I agree.

So we have to be thoughtful about the fact that yes, there might be specific tasks that change, but that doesn’t necessarily mean entire jobs change. And even when entire jobs change, then what we have to do is find a way to route that labor to a different part of the market.

Let me get back to the truck driver. People use the truck driver analogy a lot of the time because it’s an easy analogy to make.

I didn’t mean to fall in that trap. I’m sorry.

You know what I’m saying. But here’s what I think. I’ll go down the negative side. Not just truck drivers, mechanics, gas stations, parking lots, shopping malls, insurance companies, if you don’t have a car you don’t need to buy insurance. And all those impact ... There’s an iteration and a cascading effect that I think people here don’t think about. And it is what it is.

And my only talking point to that would just be when ATMs first came out.

Bank tellers.

We thought that was gonna destroy the bank teller job, and we’ve probably reached peak bank teller in the past couple of years.

We have?

There’s a stat that’s like 10X more retail branches since the moment that the ATM was invented.

Interesting. Yes, you’re right.

Don’t take that specific number.

You just don’t know.

But banking grew because now it was more accessible for people and thus the growth of banks exploded.

But I do think Silicon Valley has to have a sense of what they’re inventing. Especially around transportation.

100 percent.

Because to me that’s the one that’s really ...

And this is why, again, I wanna make sure ...

And AI. Automation.

I’m not giving an out for anybody that is not thinking these through. I’m just saying that there will be commensurate ... Maybe not commensurate like quantitative, but there will be ... For everything that we make more efficient, there will likely be job growth either in that direct area or in surrounding functions. So what we have to do in Silicon Valley is be way more thoughtful about identifying those areas of growth, making sure that if there are impacted jobs, how do you ensure that more people can discover those new opportunities.

How you train.

Yeah, how you train them. I think that is more of a responsibility for Silicon Valley. I don’t think that somehow we should be fully exempt from thinking about that. And so that doesn’t change.

It’s hard because is it the government’s job? Is it ... It’s hard to know whose job it really is, and then it ends up being nobody’s.

I think it’s the market’s job. So that’s gonna be colleges, that’s gonna be community colleges, that’s gonna be online education, that’s gonna be companies doing retraining, and then that’s gonna be the government hopefully getting ahead of this just a tad so you can tilt where do we want K-12 education to go? Where do we want public schools to be moving toward? Etc.

Yeah, not this government today.

We might have to wait a couple more years.

A couple more years or so. All right, last question, Aaron, for you. Where is the workplace enterprise? You’re aiming, what is the puck, whatever the puck example is, where the puck is going.

Yeah, that’s hockey, right?

Right? Or whatever. As a business thing, what do you — not giving me all your big secrets — what do you think about? What do you think your business is in five years? Or where enterprise is? What is the next trend in enterprise?

Unfortunately, it’s gonna sound a little bit similar to what we were talking about a couple of advertisement breaks ago. But this idea that business is getting faster. Every company, no matter what industry you’re in, has to serve customers in a much more digitally driven way.

Again, if you’re a hospital, how do you provide a 24/7 experience to patients? If you’re a life sciences company, how do you learn from what 23andMe is doing, and have more precise experiences, and personalized medicine? If you’re in transportation, we know that’s gonna be moving to be more on-demand, more rental based, probably less ownership of cars. So every company’s gonna be digitized. Every industry is gonna be digitized.

So our job at Box, and probably the job largely of the enterprise software space, is to provide the tools, and to provide the weaponry that helps these companies modernize both their work places and their business processes, so where we’re gonna be going is literally that entire spectrum. We wanna power how a company works and shares and collaborates, and just the data that they’re able to move through their organization.

And we wanna be the platform beneath the applications that they’re building, if those applications relate to content that we manage. So if I’m a bank, how do I have a better experience with my customers where I can exchange documents seamlessly, so you don’t have to fax in documents and you don’t have to FedEx data information anymore.

I’m arguing with people about that all the time.

You are?

I have some lawyers, they just keep sending me papers.

So there you go.

Literally, I said, “Are you paper people still?” They’re like, “We’re still paper people.”

They are paper people.

I said, “I don’t like paper people.”

I love paper people because that means we still have a market.

I’m not sure I wanna work with paper people. Do you? Well, you can go take their paper away.

As long as there are paper people, we have customers.

There are paper people. I can’t even get them to sign online documents like DocuSign or Adobe.

Now you see our opportunity.

They give me lame excuses of which I don’t believe them.

Yeah, there’s the law, or there’s a security ...

There isn’t, I checked.

Yeah, exactly.

They don’t like that.

Most people are usually 10 years behind in terms of actually the state of the compliance and regulatory parameters.

Astonishing. You can use my paper people thing. That’s what I call them.

You call them paper people?

I’m like, “What are you, crazy?”

Are these the people that also have filing cabinets?

I have paper right here. Yes.

They probably do, right?

Yes. I don’t mind some paper.

My first internship was at Paramount Pictures.

Oh really.

That was where we got the idea for Box. Or not the first internship, but ...

There could’ve been a whole new history for you. For your future.

I could’ve been filing in movie studios. But we got the idea of Box ... I was literally faxing out information.

What did you do at Paramount?

I literally was a paper person. That’s what you do as an intern. So I put documents in filing cabinets, and then faxed them out, and FedEx’d them back. And I was like, “Holy shit, this is crazy.”

Was it scripts?

No. It was contracts for “I Love Lucy” to rural America. And literally the contract would be $500 for rerun residuals to “I Love Lucy,” and I was literally just faxing those back and forth. So nothing glamorous whatsoever. I think I may have seen Lisa Kudrow once as I was driving by in a golf cart.

She was in a golf cart or you?

I was in the golf cart. Yeah, they let you use the golf cart as an intern because I had to move all the paper around.

Oh my God. I had a friend who worked for one of those, and she would drop off scripts every day to the show, everyone at the studio. None of which they read. And I was like, “Why don’t you just email them?” And she was like ...

“I can’t do that.”

That’s what she said. And I said, “Why not? Then we can go out to dinner.” It was amazing.

I would have loved to move scripts around, but these are just $500 contracts.

All right. How was your Lisa Kudrow experience?

Again, I think it was from a distance. It’s not even clear it was her.

You’ve met celebrities since.

At the time you had to imagine that it was a celebrity.

Who’s the best celebrity you’ve met as an internet executive? Come on.

The best celebrity that I’ve met.

Yeah. Oprah for me, but go ahead.

Oh really, was Oprah yours?

Mm-hmm. Several times.

One time I ran into Harrison Ford and tried to explain cloud computing to him, so that was a good moment in my life. It was really a brief conversation.

“Kid. Hey kid.”

It didn’t go very far.

Oh my God, that would’ve been so good to see. I wish I had been standing next to you.

I think he was like, “Why are you in front of me?”

I had to explain Twitter to DeNiro once.

Wow, okay, that’s pretty cool.

Yeah. “Do I need to be on Twitter?” And I go, “No, you do not.” And that was it.

Is he on now?

He better not be now.

But he should be. He would love it now. And he could just respond to every tweet from DT.

Oh no he can’t. He needs to stay away from the Twitter. He should never be on Twitter. Anyway, Aaron, as usual, it was great talking to you.

Good chatting.

Thanks for coming to the show.

This article originally appeared on

Sign up for the newsletter Sign up for Vox Recommends

Get curated picks of the best Vox journalism to read, watch, and listen to every week, from our editors.