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Reply all: Some of the first e-mails were sent between the two machines shown here, at a company called Bolt, Beranek and Newman, which later became Raytheon BBN Technologies.

In 1971, Ray Tomlinson sat down at a terminal, typed a bunch of characters on a keyboard, and sent a message to another machine several feet away via a fledgling computer network called ARPANET. More than 40 years later, the rest of us depend on the same basic process—and the same dated technology—used to send that first e-mail.

Most of the innovation since then has happened on top of that old technology. There hasn’t been a big shakeup since the release of Gmail in 2004, which brought threaded messages and a gigabyte of free message storage (an eye-popping amount at the time). By now, many of us are encountering so-called e-mail overload on PCs, smartphones, and tablets. And e-mail shows no sign of disappearing. According to data from the Radicati Group, a technology market research firm, there were more than 2.1 billion e-mail users worldwide this year—and the firm expects the figure to climb to 2.7 billion by 2016.

It’s unlikely that we’ll see another large, independent e-mail service emerge anytime soon—we’re just too used to our existing e-mail accounts, experts and entrepreneurs say, toting our Hotmail, Yahoo, and Gmail addresses around with us like cell-phone numbers. But plenty of small startups are looking for specific ways to improve the way we send, receive, and sort our messages.

Several startups and experts say one of the biggest problems with e-mail is that we’re trying to use it in ways that were never intended—as an organizer, for example, or to facilitate collaboration on group projects. For that reason, many of them have introduced innovations that treat the in-box more as a to-do list than a list of messages. That’s the idea behind Mailbox, an e-mail app for smartphones built by Orchestra, the group behind a to-do app of the same name.

Gentry Underwood, CEO of the Palo Alto–based company, knows the unofficial methods some of us already use: marking read e-mails as unread so we’ll remember to respond to them, or sending ourselves e-mails as reminders. He says Mailbox is trying to reimagine the in-box as a workflow tool that’s more useful than these little tricks.

Because of the massive growth of e-mail on smartphones—and what Underwood perceives as a lack of good options for using e-mail on the go—Mailbox is focused on mobile users. The app, which is slated to launch early next year and will first interface just with Gmail, lets users “snooze” messages for a day or so by swiping. A deferral feature makes it possible to put off a message until specific conditions are met—say, when you’re in a certain location. Mailbox plans to charge for its app.

One of the main reasons e-mail innovation has stagnated, Underwood and others feel, has to do with the technology behind it. E-mail is based on two protocols, IMAP and POP, which are decades old and have never changed much. But the way we use e-mail—and the devices on which we use it—has changed tremendously.

“It’s this very old, cumbersome protocol that was designed in the early days of the Internet,” Underwood says, referring to IMAP specifically. “And obviously the amount we’ve used it has gotten crazy, and it wasn’t really designed with mobile in mind.”

Beyond the technical difficulties, several founders of e-mail startups cite the complexity of trying to improve on something that is extremely important to so many of us, but used so differently by all of us.

“There are so many different reasons why people receive and send e-mail, and even just one single person—just you—you use e-mail for a number of different uses,” says Alex Obenauer, a founder of Mail Pilot, a startup based in Blacksburg, Virginia. “So it’s tough to really home in on how to solve the problems that we face with e-mail without disenfranchising a lot of use cases.”

Mail Pilot also uses an interface modeled on a to-do list, with messages marked as “complete” or “incomplete” instead of “read” or “unread.” The company ran a successful Kickstarter campaign to raise funds for its software: Obenauer and cofounder Josh Milas collected $54,000 earlier this year, $19,000 more than their goal. Mail Pilot, which charges users a subscription fee, is currently in a public beta with a Web-based service; apps are in the offing.

In hopes of satisfying lots of users at once, a San Francisco startup called Tray is taking a different tack: it’s making e-mail more like an automated assistant. Tray cofounder Rich Waldron says his service aims to bring context to communication—telling you what’s happening around you, who’s e-mailing you, how you’re connected, why they’re important.

“We actually learn from your e-mail,” he says.

Tray lets users set up conditional tasks, much like the website IFTT (“if this, then that”), such as sending a preset reply to specific people if they e-mail you after a certain time of day. Tray can pay attention to the conversations, Waldron says, so if you get an e-mail from an important client and your calendar says you’re in a meeting, it can automatically send that person a note saying you’ll respond later. It’s currently in a private beta test, and Waldron expects that it will eventually use a freemium model, meaning a basic version will be free to use but paid versions will come with additional features.

Gaining a critical mass of users will be an uphill battle for most e-mail startups. Paul Buchheit, who led the creation of Gmail and now works as a partner at the startup accelerator Y Combinator, says that when Gmail was under development it was much easier to innovate, because the alternatives were not good.

“E-mail had been stagnant for so long—since the ’90s—that there were a lot of opportunities for us to come in and fix some really basic problems,” he says. Those problems included small in-boxes, poor search, and a preponderance of spam.

In the years since, Gmail (and others) have continued to innovate—this month, both Gmail and Yahoo Mail released revamped mobile apps, for example. The problems with e-mail are getting smaller, and most are related to social norms, Buchheit says. He doesn’t think outside services that promise to reprioritize or sort e-mail by importance can really solve them. The biggest problem he sees? Flow control: e-mail is always coming in, and we’re expected to be checking and responding to it at all times.

“Unfortunately, that’s not something you can fix with technology,” he says.

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Credit: Daniel L. Murphy

Tagged: Communications, Web

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