“It just works!” — welcoming Tailscale to the Uncork portfolio

Andy McLoughlin
Apr 9, 2020 · 3 min read

Every so often you witness a product launch that captures the imagination of its intended audience, and very, very occasionally you have the good fortune to be involved in some small way. Last week we were excited to announce our investment in Tailscale as they pushed their product into general availability.

For the uninitiated, Tailscale is a new mesh network security product that uses the “zero trust” principles popularized by Google’s BeyondCorp project to secure each node in a network versus just the perimeter. But what does that mean in practice? Tailscale makes it drop-dead simple to create a secure private network between your mobile devices, servers, computers, and cloud instances, enabling fuss-free always-on remote access to all of your infrastructure.

Traditionally this would have involved all manner of network jiggery-pokery — futzing with firewalls, configuring VPNs, and dealing with pesky subnets. But with Tailscale, devices connect directly wherever they are. This is terrific for hobbyists and small businesses, but the team has also built all manner of enterprise-grade features that are essential to enterprises — integration with single sign-on providers, enforcing multi-factor authentication (even for legacy applications that can’t natively support it), and easily revoking access for employees who have moved on. Their incremental deployment model is also a boon for businesses who can roll the product out bit-by-bit, versus the traditional risky all-or-nothing approach of legacy connectivity providers.

With Tailscale, devices connect directly — minimal latency, fewer moving parts, and everything is encrypted.

Network security and connectivity are notoriously difficult spaces to win affections (literally every engineer and network admin has extremely strong opinions) but Tailscale has slowly been building a movement over the last few months, with the founders and early team sharing updates and answering questions on Twitter and Hacker News. On the day of launch, the response was almost (almost…) universally positive with users talking about the incredible ease of setup, the almost magical network traversal, and — most importantly — the fact that it just works. Taking advantage of the popular open-source WireGuard VPN core, the team has built a beautiful, scalable product with the right balance of geek credibility and business-readiness.

Of course, there are always the nay-sayers, including the classic “I could build this myself from open-source components” crew, the “cool I guess but your pricing is crazy” crowd, and one man who was just really incredibly upset about the current lack of IPv6 support. And, maybe a first in my experience, the person who continually complained that every single damn story about Tailscale hits the Hacker News front page (“why?! how?!”), causing their launch release to be temporarily removed from the site before reinstatement from the administrator (who concluded that people just really, really like what they’re building). Very few companies can claim to have been “too hot for Hacker News” and lived to tell the tale!

Truly great products can lead to great businesses, but sometimes timing can accelerate adoption and (hopefully) success. We invested in Q4 2019 — pre-COVID and the global “new normal” — as we saw how people and infrastructures were becoming more and more distributed, and we’ve certainly witnessed this need only accelerating in the last few weeks.

Tailscale’s product enables and secures this new means of working and we’re excited to see how the business evolves over the coming years. We’re also thrilled to welcome Tailscale’s founders Avery (Pennarun), (David) Crawshaw, and (David) Carney to the Uncork family, and look forward to working closely with them and our co-investor Heavybit as Team Tailscale builds the next great infrastructure company.

WireGuard is a registered trademark of Jason A. Donenfeld

Uncork Capital

Uncork Capital (formerly SoftTech VC) is a seed-stage…

Uncork Capital

Uncork Capital (formerly SoftTech VC) is a seed-stage venture firm that commits early, helps with the hard stuff, and sticks around. Really.

Andy McLoughlin

Written by

Partner at Uncork Capital (formerly SoftTech VC). Previously founder of Huddle and angel investor. Brit in SF. Probably taller than you. Tech. Whiskey. Music.

Uncork Capital

Uncork Capital (formerly SoftTech VC) is a seed-stage venture firm that commits early, helps with the hard stuff, and sticks around. Really.