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Skiff Mail is taking on Gmail by betting on privacy — and crypto

Skiff has spent the last couple of years developing a privacy-focused, collaborative document editing platform that you could most succinctly describe as “encrypted Google Docs.” Now, it’s coming for Gmail. The company is launching an email service called Skiff Mail that aims to be, well, encrypted Gmail — and eventually much more than that.

Ultimately, Skiff co-founder and CEO Andrew Milich says Skiff wants to build a complete workspace, something as sweeping and broad as Microsoft 365 or Google Workspace. But the only way to do that is to solve email, which is, in so many ways, the core of both platforms. “It’s the most private corpus of our lives, you know?” Milich says. In an effort to keep people’s most important information safe — which includes doctors’ notes, confirmation numbers, work emails, family chats, and everything else — he says email felt like a “logical and critical next step.”

Email’s also a potential growth hack for Skiff. “It’s really, really hard to move off of a service you’re using today when your main identity,” Milich says, “your main communication layer, the way you’re actually living on the internet, is outside of that.” In other words, for every user going to Skiff Mail instead of Gmail, that’s another person for whom Skiff’s other products are just a click away. Right now, Skiff is free for personal use and makes money through business subscriptions; Milich didn’t say what Skiff’s plans are for email but said that advanced features will likely be paid ones down the road.

Rather than reinvent the wheel and come up with some Hey-level new paradigm for how email works, Skiff is starting fairly simple. The app right now, which works on web, Android, and iOS, looks like Gmail minus all the color and UI cruft. It’s almost all text, with folders on the left and a reading view for your current message on the right. In other words, it’s an email app — a pretty barebones one at that. Right now, there’s no support for custom domains. You can’t check your Gmail in Skiff, and there’s not even much in the way of automation or organization tools. Milich says the simplicity is mostly by design: “We didn’t go super-ambitious and say, like, ‘We’re going to reinvent email with a new set of inboxes, a new set of filter rules, a new set of templates.’” The goal instead was to make all the important stuff — text editing, search, managing attachments — work really well.

Skiff’s email client is pretty basic for now, but that’s by design.
Image: Skiff

That’s not to say there’s no ambition to Skiff Mail. It’s just that Milich’s whole theory is that this “privacy-first app” strategy only works if people actually like using the apps. So many apps and services focused on privacy and security practically scream their values at you. The apps are harder to use, force you to manage more systems or click through a thousand warning messages, or just look like they were built by cryptographers rather than designers. (Because usually, they were!) One Skiff advisor told me many of these products look more like advocacy campaigns than competitive products. Skiff’s trying to live all those same values: the company often publishes its research, and much of its code is open source — but in a much more user-friendly package.

Get Milich talking long enough, though, and he’ll start to veer into much funkier territory. One of Skiff’s recent projects has been to integrate its document platform with the IPFS protocol, a decentralized networking layer that users can now choose to use to store their data. Milich also has ideas about bringing Skiff Mail to the Web3 community. He imagines users with .ETH domain names using those addresses for totally encrypted and decentralized messaging, for instance, or maybe enabling wallet-to-wallet communication via MetaMask integration. “Encryption and public key/private keys are so much about what identity means at Skiff,” Milich says, “and it’s also what we’re seeing identity become in web3.”

There’s increasing evidence that “Gmail but private” is a compelling offer for many. Proton, the maker of ProtonMail, said last year that it has more than 50 million users, while platforms like Fastmail and Librem Mail continue to grow as well. Gmail remains the behemoth in the market, effectively the only company that actually matters in email, but those looking for something different have more choices than ever.

Still, even if Skiff could figure out how to build the greatest and most private email system ever conceived, getting people to switch email providers is a nearly impossible task. The inertia is enormous. Switching email accounts is like changing phone or credit card numbers, the kind of thing you only do when absolutely necessary. That’s why most companies don’t even try to take on Gmail. Even the majority of email apps that do exist are mostly front-ends on Gmail, not wholesale rethinks of the system. Milich says Skiff has some ideas about how to ease the transition but acknowledged that it’s a huge hurdle.

One of the tricky things about the idea of “private email” is that, by design, nobody can actually control email. It would be easy enough for Skiff to build an encrypted email platform if it was just Skiff users emailing other Skiff users, but… that’s not how email works. Instead, the team has tried to build a tool that scales up and down the security spectrum. When Skiff users do email other Skiff users, everything is encrypted by default and easy for senders to revoke or verify, but when you’re emailing outside the ecosystem, the SMTP protocols still work.

Milich hopes that as more providers embrace privacy, they’ll build tools to match and, by extension, improve the whole ecosystem. But he figures that, even for now, if the least Skiff can do is say “we’ll keep your most important communication safe, even from us,” that counts for something.

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