When Mailbox sold itself to Dropbox for a reported $100 million or so this March, the month-old iPhone app wasn’t even available to the public. People could download the email organizer, but using it required joining a mailing list that stretched to nearly 800,000 names at one point.
Mailbox was popular because it provided innovative new ways to organize and clear an inbox. Users can swipe a message to the left to “snooze” it, a command that instructs Mailbox to resurface the email after a set period of time. Other swipes — hard left, right, or hard right — archive, delete, or file messages.
Today, Mailbox is releasing its first new product from within Dropbox, an iPad version of its flagship iPhone app. Future releases will bring Mailbox to Android and enable support for Yahoo mail and other services beyond Gmail.
We sat down with Mailbox CEO and co-founder Gentry Underwood to ask about his app’s incredibly rapid success and its future within Dropbox.
Wired: Why don’t you think anyone had addressed the pain points around email — it is a painful thing. Why do you think there was such a big opportunity for Mailbox? You did a very cool thing, but in some ways a very simple thing. Why hadn’t anyone tried more of this before?
Gentry Underwood: Why was there this strange gap in the market that we were able to move into? The gap was created by mobile devices themselves. It’s very natural when a new platform comes along to expect behavior to work as it did in the old platform, which means, for a smartphone, take a desktop email client and jam it down into the mobile device, because that’s all you know. You don’t know how people’s behavior is going to be different; you’ve never seen it before. Well, turns out we use our mobile phones really differently than we use our laptops. It’s taken us a while to figure that out and understand it, and that creates a design opportunity for a different kind of tool. Fundamentally, Mailbox is not an email client so much as it in an inbox, oriented around delightful processing.
Another reason that tool hadn’t appeared is third-party mail apps are really hard to build well. They require a massive technical investment. Mail itself is this very old protocol that generally is very slow. To deliver mail quickly when you open your device, we actually took a lot of infrastructure that historically has lived directly on the mail client and we moved it into the cloud. When you set up a mailbox account, Mailbox begins checking your mail from the cloud, reformatting it, sending you push messages when there are new messages, and having this tiny little snapshot ready for you when you open up the phone that, as soon as you hit the network, we just hand it to you as quickly as possible. That allows us to create a fast experience even though we’re only accessing the radio for a brief amount of time. But it’s a massive technological challenge to pull that off. For every person using mailbox there needs to be a bit of dedicated infrastructure that’s acting like a mail client on behalf of the cloud.
That must be fairly resource intensive.
It is. It’s why we needed a waiting list.
I’m guessing the Dropbox resources are partly why the waiting list is now gone.
Turns out they’re not. The Dropbox resources have been useful to us around having a roof over our head — we were about to outgrow our space in Palo Alto and were in the process of looking for a new one — and getting a lot of the basics of keeping a business up and running taken care of.
What we’ve really leaned into is the recruiting resources. Now that we’re integrated into that and are beginning to interview candidates from engineering and design pipelines, we’re seeing faster traction on new hiring.
What’s the hiring environment like?
This is the hardest it’s ever been. The supply /demand ratio is just completely out of whack, particularly in the Bay Area, for engineering — mobile engineering, in particular — and product design, mobile product design in particular.
So being able to attract talent was an impetus for selling to Dropbox?
We felt like we had stumbled into this really large market, this very big opportunity. We felt like we could raise money but we still would have the problem of scaling a good team, and obviously it’s not just engineering and design; there’s also customer service and all the details of actually building an office and growing a team and building a culture.
What were your initial conversations with Dropbox’s CEO Drew Houston like?
What eventually became discussions of acquisition actually began as discussions about integrating Dropbox into Mailbox. If you think about mail as attachments, there’s a relationship between those things, and there’s no good mobile mail client that let you attach things easily from Dropbox, and that was an interesting conversation to start down.
What we found as we kept talking was that there was a lot of overlap in the “why,” the underlying mission of the organization, the reason people show up at work every day. I left my job at IDEO, my cofounder left his job at Apple. They were both good jobs, but we felt building tools that reduce friction around work was a valuable place to put one’s time and energy. You’re kind of greasing the skids on human progress, and that’s a worthwhile endeavor.
I remember watching a talk by Drew at Stanford where he talked about the reasons behind Dropbox, he used almost the same language; he talked about how much pain Dropbox takes out of people’s lives. The pain that actually moved him to start Dropbox was not having a thumb drive on a four-hour bus drive where he intended to get all this work done and just being furious with himself about this one little moment of forgetfulness ruining so much productivity. And he talked about when you take that and multiply it across hundreds of millions of users, it has a big impact on the world. And for me, that resonated; that was like, well, that was the same way we saw the world.
What other kinds of things did you talk about with Drew?
We just talked about what “good” looks like. Why do these startup things? Why build a company? What’s the goal?
And, I think we shared a vision for building great tools. One of the nice things about Dropbox’s business model is it’s asking the user who uses the tools to pay for them. You can imagine Mailbox going to some company that monetizes through advertising, where over time we’re going to have to find ways to put more and more ads into Mailbox — things that might actually decrease the overall experience or invade a user’s privacy. Whereas here we just have to build a product that people really like and want to use so much that some of them are willing to pay for it. That’s a much easier design challenge. It’s something that we thought about quite a bit as we were trying to figure out where to take the company.
There have been great products that fail once they are subsumed into a large organization, like Dennis Crowley and Dodgeball — I’m sure you know the whole laundry list. What convinced you that wouldn’t happen at Dropbox?
We’re still worried about it. It’s an ongoing challenge. What’s going to make this work is a diligence that begins with choosing the right partner, but continues on both sides in an ongoing way. The integration, the leveraging of the services that are here, is a non-trivial challenge. Even if you have 30 engineers waiting in the wings, you can’t add them all to a team on the same day. It’ll crush the culture. You have to integrate these things slowly and carefully. Same thing with design. Same thing with customer service.
What made us want to take that leap was having that overlap of the “why.” Most of the acquisitions that failed, failed because the agendas at the most fundamental level of the two organizations aren’t the same.
One of the reasons you’re able to build something cool like Mailbox is that e-mail is an open system. Other ways people share, like Tweets and Facebook posts, are much more controlled, and there’s been a trend toward that kind of control. Do you ever worry that companies like Google will make it harder to get at e-mail, thus undermining Mailbox?
Mailbox talks to Gmail the same way that the native mail client does on your iPad, the same way that Mail app does on OS X. We’re IMAP. And I suppose it’s possible that Gmail could decide to shut off IMAP. It’s hard to imagine a world without it that makes sense. So it’s not a very high concern on our list.
Are you at “inbox zero?”
Yes, I wasn’t before Mailbox but I am now. In fact, 40 percent of our users get to inbox zero at least once a week which is kind of crazy.
That is a little crazy. Do you use the “GTD,” Getting Things Done, system?
I’ve read the book. The challenge that we struggle with a little bit that led to Mailbox was that things like GTD are great if you have all this discipline, if you build in place all these practices that you religiously follow, but most people don’t have the throughput to do that, the discipline.
The goal was to take practices that previously required that discipline building and to replace them with services that are automated and take care of that for you. It’s an every-man’s GTD.
When I heard about the Mailbox acquisition, not having used the app, I thought, “How insane is it that this guy invented four email gestures — swipes, in iOS jargon — and sold his company for $100 million?” Do you ever get crap from people about stuff like that? Do you ever think to yourself, “this is crazy?”
We actually were two-and-a-half years old when we sold. But still, without commenting on the specific numbers of the deal, I will say that this is a very unusual market and the potential impact of these devices, I think, is what’s driving it. Mobile is ripping the world wide open. The companies that respond to that stand to be quite relevant in the future, so that’s what creates these seemingly crazy numbers.
[Wired]