Wickr CEO Nico Sell: behind the glasses

Nico Sell’s PR wrangler is trying to convince me to spend my entire Wednesday on a boat off the coast of Northern California with the sunglasses-clad CEO as she kicks off a three-day women’s big wave surf competition at Mavericks.

I’ve been trying to get together with Sell, cofounder of the self-destructing-messaging app Wickr, for weeks and as luck would have it I’m in San Francisco that day. And though there is nothing more I would love than to do this article oceanside, I had a full day of news ahead of me.

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So we settle for a phone call.

“I only surf little waves at this point,” Sell says. “I do have a very unrealistic goal to surf Mavericks some day.”

Cruising 20 foot waves is not the only lofty aim she seems bent on achieving. Sell also wants to replace email — with Wickr, naturally — in the not-too-distant future. And she thinks her product will one day “secure all the world’s financial transactions” — a favorite tagline she uses to describe the future she believes Wickr is destined for.

So, Sell wants to replace trillions of emails and trillions of dollars in global financial transactions?

Gnarly, as the surfers would say.

Thanks to her company’s last investment, Sell may already be on the path to manifesting her dreams. In June of last year Sell raised a $30 million round led by Jim Breyer along with a contribution from the Chicago Mercantile Exchange (known best for commodity trades). In addition to funding, the CME told Sell it would be interested in using her technology to secure trades and communications related to transactions. While Sell is currently pushing her free, self-destructing-messaging app with “cool” stickers, filters, and kid-friendly features, the real power of Wickr’s technology could be much more potent in the hands of banks and traders.

But Sell is shrewd to position her product as a popular messaging app rather than a security tool. While security companies draw large rounds of funding, they don’t come close to the raises of popular messaging services. Case in point: Snapchat dropped an SEC filing late last year noting that, since April, the company has raised $485 million. And let’s not forget Facebook’s over $20 billion (by some estimates) acquisition of WhatsApp.

Popularity contest

Sell has personal experience understanding the power of branding and the “cool factor.” During her late teens she scored a spot on a professional snowboarding team. Being one of few female snowboarders, she quickly learned the pains of being under public scrutiny and the necessity of personal branding. Her experience later translated into a career in marketing.

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Just after graduating from Dartmouth, where she studied government with a focus on nuclear strategy, Sell landed a gig with Palm Computing. She worked on the Palm Pilot campaign, which in its time was a very beloved product — one of a handful of personal digital assistants that, for a while at least, transcended the cell phone market.

Sell also worked for a popular Internet website called Real.com, which — like Palm — didn’t offer her stock as part of her compensation package. Eventually she figured that she was getting the raw end of the deal, so in 1999, she started her own company, Montara Mountain, through which she advised startups in exchange for equity. Since then Sell has advised over 20 startups, including mobile security startup Lookout. Through her work with security companies she got involved with Defcon, an annual hacker conference. She’s helped organize the event for roughly 15 years, giving her access to a slew of security specialists and hackers.

Her fellow hackers helped her set up her first nonprofit project (inspired by her daughter), called R00tz Asylum, which teaches kids to pick locks, eavesdrop on cell phone conversations, and generally hack any system — computerized or not. Here again she hooked into information security’s “cool factor” to help sell an important skill set to kids.

“With hacking, you don’t go to the kids and say ‘Okay, who wants to be a cyber ace? Who wants to learn how to secure networks? That’s exciting, right? Yeah! Let’s go do that!’’’ she says. “No. You say, ‘Okay who wants to learn how to eavesdrop on cell phone calls, or turn a roller coaster off with your iPhone.”

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About the sunglasses

If you talk to Sell repeatedly you will come to know some of the pre-packaged phrases she uses, like “properly paranoid” or her favorite analogy about how she thinks Wickr will take off similarly to how snowboarding became popular: “Because the cool kids did it, it was empowering, and their parents couldn’t do it.”

When I first met Sell in November of last year, I heard many of these lines for the first time. She recited them, unbeknownst to me, most naturally. Her easy laughter masked any hint of canned speech. Since then I’ve seen her in television interviews and articles performing the same lines, as easily as she did with me in a small cafe.

In recorded interviews she’s alway prominently featured wearing that oversized pair of black sunglasses. Sell says most people wouldn’t recognize her without them (though she wasn’t wearing them the first time I met her).

“The good thing is that, even when I’m at an event and I talk to people, they don’t realize that it’s me, that I was the person up on stage, because they’re looking for the sunglasses.”

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There are many theories about why Sell is rarely seen without the glasses, a cliched celebrity disguise that she’s appropriated as a sort of personal signature. Some say she’s afraid of facial recognition software, while others have mused that she’s just overly paranoid — a tin foil hat. But Sell’s says she’s just trying to minimize her digital footprint.

“We have a saying in Tahoe: How do you protect yourself from a bear? You just gotta run faster than your friend,” she says. On the Internet that translates to having less information on the Internet than your friend — don’t be the lowest-hanging fruit. For the time being Sell can boast that there are no pictures of her eyes on the Internet, but she has no illusions that that will always be the case, especially as her company continues to draw public attention.

Sell is Wickr’s sacrificial lamb to a certain extent. She tells me that her cofounders are as concerned with having their images and personal information out in the wilderness as she is. Being the public face of Wickr means media attention and people digging into your personal background, all of which equals a greater risk of being hacked or attacked. But in order to get Wickr the popularity Sell was after, someone had to go out there.

“I took the bullet for the team, and as CEO that’s part of my responsibility,” says Sell. It started out with just print interviews, until Wickr’s PR team convinced her to contribute to the discussion around NSA whistleblower Edward Snowden. Now Sell regularly appears in the media, talking about the evils of data mining companies and how users can and should protect themselves.

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The sunglasses and Sell’s unabashed criticism of Facebook’s and Google’s use of personal data sometimes makes her seem like the poster child for Internet safety. But, according to her, the steps she takes to secure her own identity is not part of some elaborate awareness campaign — she’s doing this for her own benefit.

More than just a messaging app

Sell noted that the app has over 4 million downloads, which says nothing of monthly active users. Compared to WhatsApp’s 600 million or even Snapchat’s 100 million monthly active users, that’s a drop in the bucket. However, the path to monetization with both of these companies is still unclear. Earlier this year, WhatsApp reported lackluster revenues of $10.2 million and Facebook has said it doesn’t expect the product to pull in big profits for a while. Meanwhile, Snapchat is playing with in-app purchases and advertising, though the company has yet to turn a profit.

As for Wickr, it currently doesn’t bring in any revenue either, although it plans to ultimately operate on a freemium model with special pay-to-play features. She only expects four percent of power users to use premium features. But Wickr isn’t just another messaging app.

What sets it apart from the competition is its technology. Wickr uses Perfect Forward Secrecy, a cryptographic protocol where each piece of data is linked to its own tokenized key. What that means is that if a Wickr message were somehow hacked in transit, the hacker would only be able to access the single hacked message (as opposed to your entire account). However, Perfect Forward Secrecy is very difficult to hack. Additionally, Wickr doesn’t store data about its users or messages on its servers. Plus, its application is easy to use.

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In many ways Wickr is a great marketing campaign for some very serious software that otherwise would remain stuck in the shadows like most other security products. It is incredibly difficult to make security sexy. You’ll notice that most people don’t have mobile antivirus or any other sort of security software downloaded onto their cell phones. This is a major struggle for consumer security products — one that Sell has more or less bounded over.

And that means that Wickr might eventually have a much easier time monetizing its product. If Sell licenses out the technology to financial companies for securing digital money transactions, trades, and general communications, I bet Wickr could whip up some pretty nice revenue. Plus, with all the major data breaches of 2013 and 2014, it’s likely banks are looking for just such a technology.

For now, Wickr does have a lot of competition in the messaging space. Earlier this year, WhatsApp decided to partner with open source organization Whisper Open Systems, founded by well-known cryptographer Moxie Marlinspike. Marlinspike worked on Twitter’s security team for a spell and is also an outspoken member of the crypto community. Together Open Whisper Systems and WhatsApp plan to incorporate end-to-end encryption into WhatsApp’s messages. That gives WhatsApp’s 600 million users fewer reasons to defect to Wickr, if they care about security.

Wickr also has some competition in the enterprise and financial sphere. Confide offers end-to-end encrypted disappearing messages aimed at professionals. It’s finger swiping interface also prevents screen captures. And for the especially paranoid there’s Silent Circle, which sells the Black Phone, its own mobile phone hardware and software that encrypts both messages and voice calls.

These competitors hardly put Sell out of the game. Even if Wickr doesn’t become the top messenger or even a top messenger, it may not matter. While messaging is the product of the moment, Sell’s technology stands to offer something lasting. And if her ultimate bid is for the financial industry, her company and technology are positioned to stay around a lot longer than some of her revenue-less contemporaries.

Which brings us back to Mavericks. Sell’s been surfing longer than some of the girls in the competition, so there’s hope for her yet.

“That’s the point of the whole evolution. If people can see role models of what’s possible than it makes it more possible for them too,” says Sell.

Her role models have been the hackers, Defcon, and the startups she’s advised. Now it’s Sell’s turn to compete.