Liz Gannes

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Q&A With Mailbox CEO Gentry Underwood on the Launch of His Much-Hyped App

It’s a rare thing for a basically unknown startup to put out a trailer video about their new app and get 1.2 million views and more than 250,000 signups. But that’s the status of Mailbox, which today will start letting those people use its iPhone email app.

Mailbox CEO Gentry Underwood

Mailbox CEO Gentry Underwood

Mailbox aims be a smarter email product that helps its users deal with their mail on the go. The core difference between it and other mail apps is a set of gestures where users swipe left and right to archive, trash, snooze and categorize email.

We’d gotten to know Mailbox CEO Gentry Underwood a bit from his company’s previous project, a smart to-do-list app called Orchestra. Orchestra launched for iPhone in the fall of 2011. In part based on the strength of the team’s background at companies like Ideo and Apple, it has raised more than $5 million from investors including Charles River Ventures, SV Angel and Kapor Capital.

In a conversation yesterday, Underwood said that tackling task management via a separate app ultimately seemed like a bad strategy, because the whole system was still so dependent on email. Here’s an edited version of our chat:

Liz Gannes: So, how did you get from Orchestra to Mailbox?

Gentry Underwood: We started Orchestra because we thought people used email as a to-do list pretty terribly. But then later we were looking across Orchestra at how to make it easier to use, and we thought the easiest way would be plug in your email credentials and suck in all your email. But that’s a crazy idea. First of all, nobody wants all their emails in their to-do list, and second, no startup in their right mind builds an email client. But we decided to defer judgment and ask what if, and the more we pushed, we realized there was something there.

So you’re crazy, by your own definition, but why are you good?

To use the poker metaphor, the ante is really high. One is, it’s a really difficult design challenge. You gotta create something everyone has so many expectations around but, generally speaking, has a lot of bad habits around. You have to build something that’s familiar enough, but different enough that it actually pushes people to have better experiences. So you need a world-class design team.

On the technology side, you have this 30-year-old medium, these are protocols that were designed for computers chained to desks. They’re slow, they’re clunky and they don’t do well on mobile networks. To get around that, you’ve got to build an app that has one foot in the cloud and one on the device. So you need great mobile engineers and a really capable back-end stack team. The fail whale’s no good. You have to build robust infrastructure.

And then, most businesses over the last decade that have tried to improve on email have, in one form or another, died — so it’s hard to raise money around that problem. And without money, it’s hard to put a team together that can do these things.

MailboxOkay, but someone like Google has all those three types of talent, and lots of money, and their own email system they want to take mobile.

But they have 300 million established users. A lot of our design here has a strong point of view. We kind of force people into new behaviors. We can do that because if you don’t like our product, that’s okay. If an established player tries to turn the ship, there’s screaming.

So what is innovative about what you’ve been able to build so far?

Our key innovation is that we are working on the “why” of mobile email. What people want to do on their phones around mail is really different than what they want to do on their computer. The No. 1 use of email is triage. It’s, “I don’t care about those two,” “That one I need to deal with when I get back to my desk,” “I should respond to this one now and be done with it.”

I do feel like there’s this magical cabinet in my brain where when I see something on mobile email, and I can’t deal with it in the moment, and it disappears to some place where I never remember to deal with it again.

Yeah, what do people do? They use “mark as unread,” they use stars, or they hope to remember. So a lot of balls get dropped, and a lot of people feel guilty and crappy. Your experience of email becomes this “uhh” thing. So what we did is create an experience around, “This I’ll do quickly,” “This I’ll defer,” “This I’m done with.”

But in looking at your app, it’s not dramatically different. It’s just some gestures on top of an inbox.

We’ve tried to create something that’s familiar. But then when you start using it, it seems obvious. We’ve put in all the things that as [Apple designer] Jony Ive would say are “naively obvious.” You get to that place where it’s beyond “It just works” to “Well, of course it should be this way.”

It seems like one of the most interesting current challenges is creating mobile apps that replace the default apps. But it’s hard because those defaults are made by the same companies — Apple and Google — that make the operating system. How do you break through?

You have to build a product that’s 10 times better. The obvious example is Google Maps. The other thing you can do is leverage network effects. If also being on Mailbox makes my experience better, you might pressure me into use it.

What’s your ambition-to-rationality ratio? Is your goal to affect the most people, so you’d be okay being bought? Is it your goal to be the challenger?

We’re in this business because we want to build tools that take the friction out of working together. In theory, you could do that a lot of ways. I don’t know that acquisitions work. You want to be the one where the company thinks that service is so central going forward, like Instagram to Facebook, but a lot of acquisitions don’t work that way. But I think there really is a lot of opportunity for an app like this at scale, because mail is ubiquitous, we all use it, but there’s so many ways that the information being delivered in email could be better delivered. For example, a shipping confirmation you get via email.

But it seems like all the smart apps want to do that for you — the smart calendar, the smart assistant, the smart email. Google Now does shipping invoices. Some of the smart calendar apps I’ve tried tell you when your package is arriving that day. And, yeah, smartphones were probably too appified and siloed before, but now it seems like everyone’s approaching the same topics from different angles.

For me what’s exciting about email is email is the front door for so much of that information. And in a mobile world, these apps are so sandboxed that this has to be really thoughtfully done. We can be the port city of the mobile world. So a third-party email client can create a really good relationship with Evernote, or Dropbox, or Pocket, or you name it, and can route all sorts of very interesting information to those places. That may not be something that Google or Apple is interested in doing.

A subtext of what you’re saying is that, in a way, it’s great that these companies are having these platform wars, because it makes opportunities for startups.

All the third-party guys can work together and have amazing relationships with each other, while these guys are stuck in the OS wars.


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