Get a Room—er, Internet Drop!

Sam Lessin is preoccupied with digital privacy. And for good reason: It’s more than a little scary how much you

Sam Lessin is preoccupied with digital privacy. And for good reason: It’s more than a little scary how much you can find out about him with a simple Google search of his name. More than 41,800 results scrounge up articles about his Internet start-up company, Drop.io, where he serves as CEO. You can find his LinkedIn profile and Facebook account (Harvard ’05!). There’s his blog at drop.io/swl and his Twitter.com account. (A recent tweet: “downloading gossip girl on our work WiMAX to watch later – the cable at home is unacceptable – not proud of it, but am doing it.”) Most of these sites include Mr. Lessin’s public information, tidbits that he volunteered to share. But there are some things Mr. Lessin, like the rest of us, would prefer not to communicate to 10 million other Internet users.

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“Look, if my entire life is going to be searchable and findable, I’m going to change how I live my life, or at least how I live it online,” said Mr. Lessin, a fit, bespectacled 25-year-old sitting in the coffee shop at the basement of Drop.io’s office (literary magazine n+1 is in the same building). He lives in Tribeca and commutes to Brooklyn, walking over the Brooklyn Bridge each day to his office on Jay Street. “I’m going to change the power of the Internet as a tool for communication.”

And Mr. Lessin plans to do just that with Drop.io. In a Web world increasingly deluged with public information, Mr. Lessin’s company endeavors to provide an alternative: simple, private spaces where individuals and businesses can share files—documents, pictures, music, love notes, whatever!—via the Web, but without fear of attracting millions of other eyes.

Launched in November 2007, Drop.io does not require users to submit their e-mail addresses, or to register in any way. The sharing spaces, called “drops,” are not searchable on Google or any other engine. They’re also not “networked” like Facebook or MySpace accounts. Users simply come up with a location name for their space (like drop.io/myspacehere), and “drop” in some files with a couple of clicks. They can protect the page with a password, and set how long they want the drop to exist (if you only want it to last for a day, Drop.io will automatically delete it after 24 hours).

In other words, Drop.io is the anti-network.

“We are learning from and borrowing from some of the best Web 2.0 tools out there for media sharing, and re-factoring them to allow people to share what they want, with whom they want, how they want, on the fly,” Mr. Lessin explained.

For instance: Moms can upload pictures of their kids and send the Drop.io URL and password to a close group of friends, instead of uploading them to another online service like Flickr or Facebook, where most pictures are searchable. (And who knows where your kid’s face could end up!) Co-workers can share business documents and presentations in secret. An e-mail address is automatically created for the drop, and any messages sent to the address will appear on the site’s page. You can fax documents to the space. Each drop also includes a phone number and extension. Call the number and your voice mail will automatically be converted to an MP3 and posted on the site. You can listen to it on the site, or send it out via e-mail to a few friends.

Mr. Lessin maintains and updates several “drops” with his service. One of them is a private blog with his girlfriend, a Wall Street Journal reporter. In it, they share cute stories and pictures; occasionally they each stop by to coo pet names at each other. Only he and his girlfriend know the URL and password for the blog. It’s unsearchable on the Internet and will never be “cached” by a search engine to be preserved in the seemingly bottomless Internet archive. If they decide to delete their drop, it will be gone forever.

Drop.io recently launched some new advanced services, too. During the past couple of weeks, they’ve been offering a “Paywall” to their clients, so other users have to pay a price to see their drop page. High-profile celebrities could charge fans to view their blog posts or new MP3s. Authors can ask for money to access the latest chapter in their next book. Businesses with exclusive consulting documents can charge clients.

Drop.io’s developers are also working on expanding their location service. Users can currently see where drops were made on a map. Soon they’ll be able to enable a setting so their page can only be viewed at a specific address location. For example, co-workers could look at a drop only at the office, and wouldn’t be able to access it at home or anywhere else.

So how does the money work? So far, all of these services are free as long as users take up only 100MB of space in a drop. Drop.io offers premium upgrades, allowing clients to increase the size of their sharing spaces at $10 per gigabyte per year. An upgrade to 1GB of space would be $10. If you want to keep the drop for another year, it’ll cost $20.

Get a Room—er, Internet Drop!