Team CRV
Published in

Team CRV

#PowerToTheSecurityConscious — Tailscale’s Commitment to Fix the Internet and CRV’s Investment in the Team’s $100 Million Series B

By Reid Christian, General Partner

Avery Pennarun, David Crawshaw and David Carney came together in 2019, to build Tailscale and exemplify the term founder-market fit. This team of repeat founders combined spent nearly 16 years working on “Google scale” problems and now are back at it tackling “startup scale” problems, in building Tailscale! (Fun Fact: The term Google scale refers to the notion that there are certain problems that only Google bumps into because of its size and scale. The name Tailscale was born out of the idea that this founding team is building for the long “tail” of problems to be solved outside of Google for the mass market).

After spending two years as a paying Tailscale customer, and more importantly getting to know the founders and their vision to fix the internet, I’m proud to finally partner with Tailscale and to lead its $100M Series B.

Naturally, the pandemic got in the way of us meeting in person over the past two years, so it was only recently that I got to meet the founders (and co-investors like Amit Kumar — hi Amit!) in person in Montreal. We unknowingly received a tricked out Uber en route to our board dinner.

With the explosion of the web, this team is convinced (and I am now too!) that the layer below the web, the internet, must be fixed.

Thinking being, the internet has become increasingly complex, brittle, and inherently less secure. The internet is as defined, a network of networks and Tailscale is connecting devices and managing these networks, in as fine-grained, secure manner as you can imagine. They are calling this a “Mesh VPN’’ because it enables every device to be connected to every other device in a peer-to-peer approach (and you can read a much more thorough description of why that’s important in this terrific post from Avery, “How Tailscale works.”)

Why is this concept securing millions of dollars from an early stage, enterprise tech focused firm like CRV? Because we all want to live and work in a world where simple, secure networks rule. Whether you’re an enterprise level CIO or maintaining your home lab, we all want secure networks that require just a few minutes to set up and just work. For me personally this concept harkens back to the glory days of my youth: Starcraft LAN parties. A simpler time, when lugging your computer to a friend’s house was the challenge, not the connectivity and security of the network. David Crawshaw describes this phenomenon in his post, “Remember the LAN”. I can’t think of a bigger, hairier problem to tackle with a strong team that is razor focused on making the user experience simultaneously seamless and secure.

Developers love Tailscale, people rave about it on Twitter and enterprises are adopting it, but my bet is that Tailscale will become a household name quickly with the virality of the product. Mark my words, Tailscale will quickly go from being an IT product to mass mainstream adoption in no time.

We look forward to being a part of Tailscale’s rapid adoption in the coming years. Our investment team enjoys working with companies, like Tailscale, that are already seeing product validation in the market. If you’re reading this post, building a product that’s eliminating frustrations and on the hunt for a partner who can get you and your team to the next level, we’d love for you to get to know the CRV team. We strive to work with early stage founders who are tackling thorny, gnarly problems (like a broken internet) that simply have to get fixed.



CRV is a venture capital firm that invests in early-stage enterprise and consumer startups. Since 1970, the firm has invested in more than 400 companies at their most crucial stages, including DoorDash, Airtable, Patreon, Drift and Iterable.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store

CRV is a VC firm that invests in early-stage enterprise, consumer and biotech startups. We’ve invested in +400 startups like DoorDash, Airtable and Iterable.