Tailscale
Company History
Tailscale History: Founding, Growth & Key Milestones
Founded 2019 in Toronto, Ontario, Canada
When was Tailscale founded?
Tailscale was founded in 2019 in Toronto, Ontario, Canada by Avery Pennarun, David Crawshaw, David Carney and Brad Fitzpatrick, making it 7 years old.
- Founded
- 2019
- Founding place
- Toronto, Ontario, Canada
- Founders
- Avery Pennarun, David Crawshaw, David Carney and Brad Fitzpatrick
- Headquarters today
- Toronto, Ontario, Canada (remote-first)
- Milestones documented
- 7 (2019–2026)
- Current CEO
- Avery Pennarun
- Acquisitions
- 1
| Year | Event |
|---|---|
| 2019 | Tailscale founded |
| 2020 | Brad Fitzpatrick joins; public launch with $3M seed |
| 2020 | $12M Series A led by Accel |
| 2022 | $100M Series B |
| 2024 | 5,000 paying teams |
| 2025 | $160M Series C at ~$1.5B valuation |
| 2026 | Border0 acquisition and nearly 40,000 paid customers |
- Where was Tailscale founded?
- Tailscale was founded in Toronto, Ontario, Canada in 2019.
- Who founded Tailscale?
- Tailscale was founded by Avery Pennarun, David Crawshaw, David Carney and Brad Fitzpatrick.
- When did Tailscale start?
- Tailscale was founded in 2019.
- How old is Tailscale?
- Tailscale is 7 years old as of 2026.
Founding Story
Avery Pennarun, David Crawshaw and David Carney started Tailscale in 2019 after working together at Google, where Pennarun and Carney held engineering management roles on Google Fiber and the team had worked on networking in Fuchsia. Their founding idea, described in the Series B announcement, was that most software teams build internal tools that never need to scale, yet still struggle with networking and access. WireGuard gave them a fast, simple encrypted tunnel, but it needed a control plane to handle keys, identity and NAT traversal. Tailscale built that layer. Brad Fitzpatrick joined in January 2020, days after leaving Google, and the company launched with a $3 million seed round in April 2020 as remote work surged.
Founders
Avery Pennarun
Avery Pennarun is co-founder and CEO of Tailscale. Before Tailscale he worked at Google, including on Google Fiber, and earlier built open-source tools and wrote widely read essays on engineering and product management. He co-founded Tailscale in 2019 and has led it through four funding rounds, most recently the $160 million Series C in April 2025. Avery Pennarun was born in 1975.
David Crawshaw
David Crawshaw co-founded Tailscale in 2019 and served as its chief technology officer, building much of the early coordination server and client in Go. He previously worked at Google, including on the Go programming language. (Exact birth year remains publicly undisclosed).
David Carney
David Carney co-founded Tailscale in 2019. Serving as the absolutely critical initial backend architect, he helped design the highly robust, incredibly scalable control plane that allows millions of distributed devices to instantly discover and connect to each other securely without a centralized bottleneck. (Exact birth year remains publicly undisclosed).
Brad Fitzpatrick
Brad Fitzpatrick created LiveJournal and the Memcached caching system, then spent years at Google working on the Go language. He left Google in January 2020 and joined Tailscale days later as a late-stage co-founder, working on the open-source Go client. Brad Fitzpatrick was born in 1980 in Iowa. Education: Aloha High School. Bradley Joseph Fitzpatrick was born on February 5, 1980. He created LiveJournal and wrote free software projects including memcached, OpenID and Perkeep.
Key Milestones
Tailscale founded
Avery Pennarun, David Crawshaw and David Carney start Tailscale after working together at Google.
Source: tailscale.comBrad Fitzpatrick joins; public launch with $3M seed
Fitzpatrick joins in January; Tailscale announces its launch and $3 million seed round in April.
Source: businesswire.com$12M Series A led by Accel
Series A of US$12 million (C$14.5 million) announced in November 2020.
Source: betakit.com$100M Series B
Series B led by CRV and Insight Partners, at a reported valuation of about $780 million.
Source: tailscale.com$160M Series C at ~$1.5B valuation
Accel leads the round with CRV, Insight Partners, Heavybit and Uncork Capital; more than 10,000 organizations use Tailscale.
Source: tailscale.comBorder0 acquisition and nearly 40,000 paid customers
Border0 joins Tailscale in March; by July Tailscale has about 300 staff and is nearing 40,000 paying business customers.
Source: betakit.comMajor Acquisitions
Border0
2026Add audited, identity-based access to production systems such as databases and Kubernetes.
Keep researching Tailscale
Tailscale Company History FAQ
When, where, and by whom was Tailscale founded?
Tailscale was founded in March 2019 in Toronto, Ontario, Canada, as a remote-first zero-trust networking company by Avery Pennarun (CEO), David Crawshaw (CTO), David Carney, and Brad Fitzpatrick. The founding team comprised veteran systems programmers and former senior Google engineers.
What foundational problem did Tailscale set out to solve?
Traditional corporate VPNs (like Cisco AnyConnect and OpenVPN) rely on centralized hub-and-spoke architectures that route all traffic through slow corporate firewalls. Tailscale set out to make modern, end-to-end encrypted WireGuard networking effortless by building a peer-to-peer mesh that connects devices directly without manual firewall port forwarding.
What is WireGuard and why did Tailscale build on top of it?
WireGuard is a modern cryptographic network tunnel protocol created by Jason Donenfeld that runs on state-of-the-art cryptography (Noise protocol, Curve25519, ChaCha20-Poly1305). WireGuard is vastly faster, more secure, and contains fewer lines of code (~4,000 lines) than legacy OpenVPN or IPsec.
How did Tailscale achieve viral developer traction upon launch?
In March 2020, Tailscale published its public launch post on Hacker News right as global COVID-19 lockdowns forced millions of engineers to work from home. Developers were amazed that Tailscale installed in seconds, bypassed complex home routers, and connected laptops, servers, and Raspberry Pis with zero configuration.
What is Tailscale's breakthrough NAT traversal architecture?
In a famous engineering blog post by CEO Avery Pennarun ("How NAT Traversal Works"), Tailscale detailed how it uses STUN, ICE, UPnP, and packet-probing tricks to establish direct, peer-to-peer UDP connections between devices behind strict NATs and corporate firewalls, utilizing lightweight DERP relay servers only as a fallback.
What was Tailscale's $110 million Series B financing round in 2022?
In May 2022, Tailscale raised $110 million in Series B funding led by CRV and Insight Partners, with participation from Accel, Heavybit, and Uncork Capital, valuing the remote-first cybersecurity startup at over $1 billion.
What is Tailscale SSH and how did it eliminate SSH keys?
Launched in June 2022, Tailscale SSH replaced traditional, cumbersome SSH public/private key pairs with cryptographic identity. Tailscale authenticates and authorizes SSH terminal sessions directly through the user's corporate identity provider (Okta, Google Workspace, Microsoft Entra ID) using device-level WireGuard encryption.
What is MagicDNS and how does it simplify private networking?
MagicDNS is Tailscale's automated private split-DNS system. It assigns clean, memorable machine names (such as "laptop" or "backup-nas") to devices on a private Tailscale network ("tailnet"), automatically resolving them to internal 100.x.y.z IPv6/IPv4 addresses without requiring complex local DNS servers.
What is Tailscale Funnel and how does it share local servers publicly?
Introduced in late 2022, Tailscale Funnel allows developers to route traffic from the public internet directly to a web service running on their private local machine or development server, securely exposing internal webhooks, demos, and APIs without port forwarding.
What was the partnership with Mullvad VPN in 2023?
In 2023, Tailscale partnered with privacy-focused Swedish VPN provider Mullvad, allowing Tailscale users to route all public internet outbound traffic through Mullvad's global privacy exit nodes directly from the Tailscale client application for a simple add-on subscription.
What is Headscale and how does Tailscale interact with it?
Headscale is an independent, open-source, self-hosted implementation of the Tailscale control coordination server developed by the open-source community. Rather than fighting Headscale, Tailscale embraces it, ensuring that official Tailscale open-source client applications remain compatible with self-hosted control planes.
How has Tailscale scaled its enterprise customer base?
Tailscale has expanded from an individual developer favorite into a core enterprise cybersecurity utility, adopted by thousands of organizations—including Fortune 500 banks, technology unicorns, and healthcare systems—to implement Zero Trust Network Access (ZTNA).
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