An interview with Mailbox founder Gentry Underwood

With 2013 now in full effect, many techies will be looking forward seeing the latest gadgets from the likes of Apple, Samsung, and Microsoft. However, for some (including us), one thing we’re really excited about is a new email app developed by the team behind Orchestra, dubbed Mailbox. Founder and CEO, Gentry Underwood, took a few minutes to answer some questions about himself, the company’s app, and his thoughts on solving problems. Enjoy!

Mr. Underwood, you began your career as a software designer, but then left to study psychology, anthropology, and community development. Why the change?

My first professional stint as a software designer was during the dot-com “boom” of the late nineties and early 2000′s. At the time a company could raise Series A financing on a PowerPoint deck and Series B on a working prototype. I worked at a firm that spent much of its time helping freshly-Series-A-funded companies build that prototype.

For a designer it was very strange work: even though your product was ostensibly for some kind of end-user need, at that stage you really only had one customer: the VCs who might fund your Series B. As a result, CEOs tended to shift their vision often and make priority decisions based on the fickle, ever-changing interests of VCs. I didn’t know why at the time, but I found I didn’t like the work very much. I knew I enjoyed the understanding-people part of design, and that was what seemed to be most missing from the work I was doing. So I decided to look for other fields where I could focus on people and try to understand them.

In the end, though, I discovered I’m a designer at heart. I’m too problem-solving-oriented to be very good at therapy or academia. IDEO helped me re-ignite a love for design, even in the context of software, by insisting on the centrality of the user and his or her needs.

mailbox app An interview with Mailbox founder Gentry Underwood

What led you to the idea of Mailbox? Was it a lack of innovation by Apple and its Mail app?

Actually what led us to Mailbox was Orchestra. We started the company on the realization that people use email as a terrible to-do list. We thought that maybe if we created a to-do list with built-in communication we could side-step this problem. After launching and looking at what was working (and what wasn’t) we discovered that even our most hard-core users still had inboxes filled with tasks. We were trying to figure out how best to solve this problem when we realized the opportunity lied in swapping our ‘solution’ on its head: rather than build a to-do list with email-like communication, why not transform the inbox in which that communication already lived into something more organized and easily manageable?

You say that email is here to stay. Some would disagree, but I’m curious as to why you feel that way.

No technology ever dies completely, so in some senses it’s easy to promise that email will stick around. But more to the point, email is a “we” technology. You or I don’t decide to use it  – “we” do. You may attempt to quit checking email, but you’ll still be receiving them. Sooner or later you’ll likely cave in and start checking it again (perhaps after one-too-many missed invitations, etc.). If we’re going to stop using email we’re going to have to all decide to do that at the same time, and that’s a big, big thing to ask.


We wanted an interface that made such processing as fast and delightful as possible.


malbox app inbox An interview with Mailbox founder Gentry Underwood

You’ve incorporated a lot of gestures into the app. Did you find that gestures are a lot better at completing tasks then tapping?

We studied how people used email on their phone, and perhaps the most important use case was triage: scanning your mail when you had a few moments to see what was important what wasn’t. We wanted an interface that made such processing as fast and delightful as possible. On the phone, that means gestures: the small-format, multi-touch nature of the interface cries out for them.

You seem to highlight the fact that Mailbox is super fast and light. How challenging was it to incorporate all these features, yet keep the app robust?

To make Mailbox light and fast we’ve faced two significant challenges:

First, from a UX perspective, we have to re-think the interfaces through which people consume and process mail on the go while not overwhelming the user with something too foreign to easily adopt. This is a huge design challenge.

Secondly, from a technology perspective, we have to re-think how email is sent and received. IMAP, POP3, and SMTP are old, heavy protocols, and since third-party apps on the iPhone generally don’t get access to the network when not open, this slowness is felt in significant ways. To solve this we ended up creating an intermediate service between email and the app which checks mail from the cloud and reformats it for fast-as-possible delivery as soon as the device is opened. This also lets us send push messages, speeds message sending (especially with large attachments), and improves device battery life.

Are there specific areas where you feel iOS needs to evolve?

At some point I think Apple will need to let users specify a default app to, say, open a URL from (e.g. Chrome instead of Safari), view an address in (Google Maps instead of Apple Maps), or compose an email from. This is something that has been driving lots of users crazy (mostly because of the maps issue) and will need to be addressed eventually.

Any plans for an Android app?

Definitely. Startups focus or die, so we picked one device (iPhone) and one platform (Gmail) to start, but we’ve designed our infrastructure from the beginning to support scaling to other devices and platforms as quickly and easily as possible once we feel Mailbox is “working” on the first set.

What is the best advice that you’d give to app developers who are looking to solve a problem like you are with Mailbox?

The best advice I can give anyone is to iterate, paying close, sober attention to what’s working and what’s not with each attempt at a product/solution. It might look like we just decided one day to go tackle email but the truth is much more incremental. From day one at Orchestra we set out to help free people from the tyranny of disorganized inboxes full of balls waiting to get dropped. Today we’re still trying to solve that problem. In hindsight it might seem like rethinking the (email) inbox was the best way to do that, but it’s taken a ton of trial and error to get here.

Thanks for your time, Gentry.

Thanks for asking these questions!

Leave a Reply

Your email address will not be published. Required fields are marked *