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.

“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.

Twenty bucks seems like a small price to pay for a little privacy. Many other online companies offer similar file-sharing services for free, but they are using an advertising business model. They want as many people as possible to see your vacation pictures or blog posts or online documents because advertising revenue increases with higher page stats. Drop.io has no ads. They are a pay service, which some would consider a death sentence for a Web start-up. But people are willing to pay, especially small to medium-size businesses who want to share information with employees over the Internet simply and privately. At this point, said Mr. Lessin, thousands of people have paid for upgrades.

Mr. Lessin said he is fascinated by an increasingly indiscreet public who want to blog and Twitter and Facebook and Flickr their every move and allow companies to make money off their content. “The whole Web has evolved into search or social,” he said. “But that’s not all that’s out there.”

 

MR. LESSIN WATCHED social networking evolve from its budding stages. He grew up in Englewood, a plushy New Jersey suburb, and his father, Bob Lessin, was a well-known Wall Street mogul as vice chairman of Salomon Smith Barney. Bob Lessin was an angel investor to dozens of Web start-ups during New York’s technological heyday in the ’90s. In 1997, he invested in the Web’s first social networking site: Andrew Weinreich’s Sixdegrees.com. The site was the template for Facebook and MySpace, which would eventually become the most profitable social-networking services on the Web.

Mr. Lessin was buddies with Mark Zuckerberg and was studying social studies at Harvard when Mr. Zuckerberg launched the first versions of Facebook in 2004. Mr. Lessin kicked off several of his own Web projects while in school, including CrimsonXchange.com, an online auction platform for students to sell textbooks, tutoring services and other personal items, and Kinjunction.com, a Web site for privately connecting with family members, which launched right after he graduated.

Mr. Lessin said setting up a social-networking site like Kinjunction was difficult because he couldn’t find the perfect formula for creating a trusted social network. Creating an algorithm that automatically defines a person’s “family” seemed impossible. Many people consider their best friend part of their “family,” even more so than their distant cousin, step-sibling or even their own mother. “Networks to me are temporal,” Mr. Lessin said. “They’re always changing, the nature of the relationship is changing, it’s always in flux.” Who can say that most of their Facebook friends are true “friends”?

With Drop.io, Mr. Lessin decided to take out the guesswork. “Let’s not focus on trying to map that because we’re not going to get it right,” he explained. “Let’s let people make whatever kind of network they want. If you want to use it with your Twitter group, your Facebook, your mom,” then you can do that.

“One thing that the Internet and technology has done is that it has made it very, very simple to connect with the people that you want to. If I want my mom, I have 15 ways of getting to her,” Mr. Lessin continued. “The key is no longer where do I look or what is the information I want to send to someone; it’s how do you actually move the information effectively?” And privately.

According to a recent survey conducted by research firm iTracks (financed by Internet security and care provider Radialpoint), more than half of Americans are concerned about security threats when using social-networking sites such as Facebook, Twitter and LinkedIn, yet 64 percent say viruses or unlawful access to personal information do not cause them to avoid using these services. We’re addicted!

DROP.IO HAD RAISED $3.9 million in financing from RRE Ventures and DFJ Gotham, two well-respected venture capital firms. There are over a million active “drops” on the site at any time. The company has 11 staff members, most of whom are developers. Without much press beyond tech blogs and word-of-mouth, the company is already getting cold calls from small and medium-size businesses asking Drop.io to set up online space for sharing private files with employees.

But Mr. Lessin worries about the future. He summons French philosopher and sociologist Michel Foucault’s ideas about Jeremy Bentham’s Panopticon as a metaphor for our online world. “We’re gonna be in trouble,” Mr. Lessin warned. “I would make the argument that the ability to have asymmetrical information to experiment or to kind of push the envelope and discover new things, is fundamentally based on the ability for people not to be public all the time.

“Technology doesn’t just empower total information,” he continued. “It can also empower quality, private information and can kind of get away from that very scary Panopticon future. I think what [Drop.io] is doing is a very important piece of how I’d like to see the world evolve, where the Internet and communication can actually be used for high-quality, private communication that’s valuable rather than public drivel.”