Xoopit continues to supercharge Gmail with new media search as Zenbe flies solo. Who’s gonna win?

Two young web-mail startups, Zenbe and Xoopit, have set out to rewrite the rules of web-mail. They see today’s leading web-mail services as dinosaurs, mired in the bureaucratic inertia of the sluggish internet titans that control them.

And they might be right. Sure, in major overhauls last year, Microsoft, Yahoo and AOL added some horsepower and storage and pulled off some elegant face-lifts. Sure, the new Gmail runs faster, supports IMAP, and offers a contact manager that no longer sucks. But what happened to that “ah ha!” feeling that accompanies an encounter with real innovation — the one many of us felt after discovering Gmail for the first time? Well, in case you’ve lost track, the last “ah ha” happened four years ago.

Recently, though, I’ve had two. One was last night, talking to Xoopit’s Bijan Marashi as he demoed a new feature that his company releases today (more on that below). The other was in late May, while speaking with Zenbe CEO, Alan Chung. Both men share the belief that the web-mail experience is loaded with potential energy and that this energy will be tapped by making web-mail more “social.” However, when it comes to specific strategies on getting there, and actually defining what “social” actually means in this context, the two companies are way apart.

The Xoopit approach: Integrate, innovate, make it fun

Xoopit, which launched into private beta at the end of March, (coverage) is a service that makes it easier to find, navigate, and use the photos, videos and files buried in your Gmail inbox. Today, it releases a keyword search function to make the process even easier. Xoopit’s core technology works by digging into your emails, grabbing attachments, following links to video and photo sharing sites, and indexing everything it finds.

Its original version, launched into private beta at the end of March, used a FireFox plugin to layer an interface for browsing and sharing photo, video and attachments seamlessly into Gmail itself. The new search feature is as seamless: You search as you normally would, and Xoopit simply directs the query to its engine, bringing results to a sidebar on the right side of Gmail’s standard results page (see screen shot below). From this sidebar, you can sort the results, filtering, for example, for Word documents or photos from Flickr. It’s generally quite cool, but the interface is not efficient enough. Marashi’s query produced over 700 results spread across hundreds of photos, documents and videos, and the sidebar could only display a handful of each. Maneuvering around involved too many clicks.

But the simplicity of Xoopit’s implementation belies its potential: Xoopit has built a completely integrated search engine for email that adds real value to Google’s own, and the company has every intention of spreading beyond Gmail onto the other major web-mail services and social networks. Marashi stresses that utilities are only one part of the picture and that “fun” will play a large role in Xoopit’s strategy. Asked to define “fun,” he remains cagey, but says we can expect to see the inbox and the media within combine to evolve into rich, engaging social experiences. For Xoopit, then, fun and interactivity are central to the idea of “social” email. Its strategy revolves around creating a compelling application, blending effortlessly into existing platforms, shoving open the door and changing the game from the inside. Ah ha! (Click to join Xoopit’s beta.)

Zenbe’s Strategy: Take ’em all head on!

Zenbe, on the other hand, wants to change the game from the ground up. It is a standalone web-mail application, and yes, it really intends to compete directly with Google, Microsoft, Yahoo and AOL. The hope is that, with clever design and rapid innovation, Zenbe will be able to convert users fed up with the non-progress coming from the giants and attract a respectable percentage of the hundreds of millions of people worldwide coming into web-mail for the first time.

Zenbe, which was created by AJAX pioneers with serious interface experience, is certainly cleverly designed. Unlike Google, which has separated email and calendar into two sites, Zenbe has them integrated into one (see screen shot below). Instead of searching for that one email with that file you need, Zenbe has a tab for attachments and makes them easy to navigate. It’s also far easier to tag an email in Zenbe than it is to add a label in Gmail, and tags arguably work better than Yahoo’s system of folders as a way of recovering the emails you want. Zenbe’s coolest early feature is the “ZenPages,” which let you select emails to share with the public or friends, mash up the emails with photos, videos, Google maps, and IM conversations, all in an easily navigable interface. (Click to join Zenbe’s beta.)

Zenbe’s more significant innovation has yet to become visible. According to Chung, Zenbe is a fully extensible platform, soon to be open to any third-party developer with an innovative way to exploit your email, contacts, calendar, to-do list, or all four. Zenbe’s interface includes an elegantly constructed, tabbed sidebar that has room for plenty of tabs, which will house the third-party applications. Zenbe has created tabs for Twitter updates and the Facebook news feed, but Chung’s vision is more grand.

Chung observes that in the current paradigm, “email is a one-way street,” in which you “collect tons of knowledge and then it’s dead.” ZenPages provide a way to repurpose the information collected in your inbox, combine it with theoretically any web-based form of data, and share it in multiple forms. He pictures an application that uses semantic analysis to determine the themes of your ZenPages and then queries an index of all publicly shared ZenPages to offer relevant information. (Imagine putting together a ZenPage surrounding your efforts to buy a house in Florence, Italy, and suddenly, pertinent email or IM exchanges from helpful strangers start to populate the sidebar, followed by real estate listings, photos and maps from the neighborhoods you’re considering, any of it added with a quick drag-and-drop.) In Chung’s take on “social” mail, the inbox is not an environment meant for fun forms of communication. If you want fun, you can go to Facebook to play some Warbook, tell your most recent hook-up that “u 4got ur undrwr @ my hse lol” and then hit her with a sheep. An inbox is the place you go to exchange important documents, deal with important contacts, receive your invoices and travel information and swap missives with Grandma. It becomes more “social” as it transforms from a data silo into an increasingly inclusive, dynamic and ultimately functional medium for the aggregation and rapid exchange of useful information between connected people.

And the winner will be…

First, the facts: Windows Live Mail and Yahoo Mail have somewhere between 250-260 million users each. Gmail has around 90 million. Unlike, say, search engines, web-mail is one of those services that has relatively steep switching costs: The effort involved in changing the application you use is high, and the reward — except when Gmail came along all those years ago — is not usually worth it. You typically have a huge body of messages you don’t want to lose, all of your contacts are familiar with your current address, and you’re accustomed to the interface. Making the change is not simply a matter of navigating to a new URL.

This fact alone puts Zenbe at a marked disadvantage against Xoopit, a product whose major obstacles to adoption are the installation of a browser extension and a willingness to share your log-in credentials with a new startup (not everyone is game). But Zenbe’s problems don’t end there. First, it faces a classic chicken-and-egg problem that might be impossible to overcome. Before it has a stable of terrific applications, the incentives to adopt it are not particularly strong and it’s hard to see users flocking en masse. Yet to convince developers to create those terrific applications, Zenbe needs a mass of users.

It gets worse. While Xoopit gets to exploit all of Gmail’s in-demand qualities (like threaded conversations and a great load time) at zero cost, Zenbe must build them from scratch when what it needs to do is put out some apps that flex its fancy new platform.

All of that being said, though, Zenbe is not doomed. One of its founders has sold companies to Sun and AOL. The other founded Datek Online, an online brokerage company that came out of nowhere to take a dominant position in a market packed with deeply-entrenched competition with multi-billion dollar market caps. If Compete data is worth anything, Zenbe has seen steady growth since it launched an invite-only beta at the end of April.

Finally, as Chung argues, there is still a huge, rapidly expanding piece of unclaimed territory in the web-mail market. It’s called mobile. Hundreds of millions of people around the world will have their first web-mail experience on a mobile phone, and none of them are devoted to Google. How in the world an unknown American startup will capture mind-share in Latin America and Africa is anybody’s guess.

But hey, the cutting edge is sometimes anybody’s game.