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Gentry Underwood closes Big Omaha with the story of Mailbox

Gentry Underwood is a designer and entrepreneur who has a passion for creating simple products that help people work together. He’s the co-founder of Mailbox, a startup acquired by Dropbox less than a month after it launched. Post-acquisition, he continues to build the mobile inbox that “puts email in its place.”

Gentry Underwood is trying to redefine the way smartphone users interact with their email.

“We want to build the best email experience in the world for as many people as we can,” he said.

Since the Mailbox founder spoke at Thinc Iowa last October, he says the last seven months have been “an absolute whirlwind.” On Friday, he closed out Big Omaha with a “fireside chat” with emcee Antonio Neves.

Underwood spoke about the development of Mailbox and how he and his team are working to redefine how mobile email functions.

“We never let go of the why,” he said. “We never let go of the problem we were trying to solve.”

But the solution didn’t come immediately. Underwood explained that Mailbox is the second iteration of his first app, Orchestra, a social-centric to-do application.

Though after the release of a promotional video for Mailbox, Underwood’s team had to establish a wait list to manage the public demand.

“If we had done all this work and it just crashed all the time or it didn’t deliver your mail it would all be for naught,” he said.

Following the company’s acquisition by cloud-storage giant Dropbox in March, Underwood says his team will continue to pursue a more user-friendly mail system on a larger scale.

“Even though we might be able to raise a bunch of money, we might not be able to put together a big enough team fast enough,” said Underwood about the decision to sell the company. “Mailbox fits in Dropbox’s mission.” 


Big Omaha is a two-and-a-half-day event that aims to inspire, educate and celebrate the entrepreneurial ecosystem in the heart of the Midwest. Produced by Silicon Prairie News, it’s part of the Big Series, the nation’s most ambitious events on innovation and entrepreneurship.

The Big Omaha Video Series is presented by the Ewing Marion Kauffman Foundation

Based in Kansas City, Mo., the Kauffman Foundation is among the largest foundations in the U.S. with a mission to foster a society of economically independent individuals who are engaged citizens, continuing the improvement of their communities.

Credits: Video by Quadrant5. Snippet photo by Malone & Company.

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