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Leadership Remaining Anonymous

Sam Lessin, founder of file-sharing service, opines on the benefits of being contrarian and the importance of privacy in a share-all world.

Like the Swiss bankers responsible for their country’s legendary numbered bank accounts, Sam Lessin realizes that the highest levels of security and privacy are achieved through anonymity. That’s why, the online file sharing service he developed in November of 2007 doesn’t require users to submit their names or email addresses when completing the one-click registration process for their “drops,” the sharing spaces assigned to users.

Accessible by URLs only their users know, drops are not detectable by Google or other search engines, are not networked in a Facebook-like way, and can be further protected by passwords and user-generated expiration dates. Lessin says, “While most people address privacy as a function of heavy identity, complex privacy settings, and lockdown, we take a more organic approach which allows privacy and simplicity to go hand in hand rather than to oppose one another.”

Lessin realizes that the share-all world of Twitter and Facebook has made it easy to forget the importance of private communication. He explains, “For all of human history, it has been relatively cheap and easy to privately share information and communicate and exceedingly expensive to broadcast your message to the whole world.  The internet and wonderful ad-supported search and social networking companies have turned this on its head.  It is now, for the first time, less costly and easier to share your message with everyone than with just a few collaborators.  This is a seismic change, with very deep social implications, but the fact will remain that the most vibrant and valuable communication and collaboration isn’t necessarily meant for public consumption.”

The privacy features may be a stand-out characteristic of, but the company’s success doesn’t ride on that alone.  The service is able to identify the type of file being uploaded and presents it in an attractive, user-friendly format. Backgrounds and graphics are customizable, and users can even assign the URLs of drops, providing they’ve not already been taken.  Also each drop is assigned a unique set of contact information enabling it to receive faxes, emails, real-time chats, and MP3 voicemail messages.

Thanks to these functions, not to mention conference call capability and the option for users to charge for access to their drops, has millions of users ranging from photographers, to video gaming companies, to architects.Billed as “easier and more flexible than FTP and more powerful than email,” was after all created when Lessin, a 25-year-old Harvard grad, became frustrated with the limitations of the FTP site he maintained.   Today is backed by a cool $3.9 million from venture capital firms RRE Ventures and DFJ Gotham.  And thanks to Lessin’s good idea and his eloquent, philosophical way of approaching it, it’s not surprising.

I think the most important thing to getting a project off the ground is to get comfortable with ambiguity.

First off, Lessin is a big believer in finding against-the-current opportunities. He explains, “I do think that while we live in a time of increasing volatility and compounded periods of tendency towards disequilibrium, ultimately there is a balance to the force.  What this basically means is that the world isn’t black and white – it is somewhere in between, so if everyone is going black, it is probably worth exploring white.  Being contrarian for the sake of being contrarian is just foolish, but it often makes sense to explore the inverse of current trends, because in the long run there are always shades of grey.  So, when we work on one click simple privacy with no-search, no-social network, no-identity, we are walking away from conventional wisdom about web applications… but only because we think that there is long-term value there.”

Having explored the inverse side of things and discovered the need for, Lessin had to make some first steps. He says, “I think the most important thing to getting a project off the ground is to get comfortable with ambiguity that will necessarily surround the path and the results.  It is impossible to forecast or control a new process or venture, and so you have to be confident enough in your own ability (and that of your team) to learn what needs to be learned and to meet unknown challenges. ”

Lessin sees “thinking globally and acting locally” as one method of navigating through an early venture’s murky path. He explains, “ is built on a very big thesis about how to best enable private communication on a thirty-year horizon, but we are very focused on small solve-able issues on a day to day basis, like how to effectively share big files with teammates.  I think you need both.  If you don’t structure your project to have immediately achievable goals, you have no path, and if you don’t have a ultimate larger picture against which you are working, you have no purpose.”

Focusing on a casual work environment is yet another tactic that has helped along the way. He says, “we avoid formal meetings like the plague.” Instead, “everyone on the team leaves a realtime drop open all day in their browser (or on mobile when they are out of the office). We promote constant chatter about the projects people are working on, sharing mocs and relevant files realtime, etc.  That fosters a lot of creativity and cross pollination.”

So, no stranger to creativity, Lessin is well-equipped to offer advice to creative professionals looking to make their ideas concrete. He says, “Regardless of what you are doing, make sure you really, deeply believe in it. If you can’t identify exactly why you are building/creating what you are creating, it is impossible to apply the dedication necessary to make it successful.”

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