Founder Stories: Mailbox’s Gentry Underwood on Steering the Ship

Last week at Disrupt NY, I took the stage with Gentry Underwood, Founder and CEO of Mailbox, to talk about the challenges of being a first time founder. I first met Gentry a month after he started Orchestra which became Mailbox, recently acquired by Dropbox. Mailbox is a mobile inbox where you can easily scan and quickly swipe to organize emails. Available for iPhone and Gmail, Mailbox also has a “snooze” feature that lets you put off less timely messages until later.

For me personally, I really wanted to build a product that got traction. Just to have the experience of building something that took off. And to have that experience of your sail catching wind and the ship being carried. But it wasn’t clear we were going to get there and we were running out of time.”

In our conversation, we discussed transparency in the funding process and how to keep employees in the loop without sharing more info than is necessary. Gentry explained how rallying his company around a shared vision allowed him take charge of the business side while the team focused on building a solid product.

Part of your job as a founder is effectively to be like the front end of a ship and deflect as many of the waves as possible to create as steady a state as you can through something that is inherently turbulent.”

Gentry also shares insight on how Orchestra was version one of Mailbox, why iterative design applies to engineers and investors, and the value in joining Dropbox who also puts their users first.

On the Dropbox acquisition:
“There was that moment that you have the rigging this thing a thousand different ways and you hoist it up and all of a sudden the ship just goes flying and you are holding on for dear life.”

Editor’s Note: Michael Abbott is a general partner at Kleiner Perkins Caufield & Byers, previously Twitter’s VP of Engineering, and a founder himself. Mike also writes a blog called uncapitalized. You can follow him on Twitter @mabb0tt.