Tailscale - Series C, $160M

When a company pulls $160M in a Series C with a $1.5B valuation in a market that’s allergic to easy money, you don't call that luck; you call it performance. And when that check is signed by Accel, with CRV, Insight Partners, Heavybit, Uncork Capital, and a cameo from CrowdStrike CEO George Kurtz and Squarespace’s Anthony Casalena? That’s not a round; it’s a syndicate that smells blood in the water and knows exactly where the current’s going.

Let’s talk about why this matters. Because Tailscale isn’t another VPN-for-your-cat startup. Founded in 2019 by ex-Google engineers Avery Pennarun (CEO), Brad Fitzpatrick, David Crawshaw, and David Carney, Tailscale didn’t just walk into the software-defined networking scene; they tunneled straight through it. What they’ve built isn’t a product, it’s a philosophy: simple, secure, zero-config connectivity that just works. No central servers. No infrastructure ballet. Just your devices, talking like they’ve known each other since dial-up.

Inspired by Google’s The Tail at Scale, the crew took decentralization and made it human. What WireGuard gave them in raw encryption, they turned into a mesh platform with the elegance of a command-line haiku. They’ve built tailnets that skip the data center drama and lean into peer-to-peer performance, used by over 10,000 paying business customers including Cohere, Mistral AI, Perplexity, Instacart, and SAP. AI powerhouses are riding this wave, and it’s no accident. This is the plumbing for the age of distributed intelligence.

And the numbers? Let’s say it loud for the folks in the back: over $18.5M in 2023 revenue, doubling YoY. 500,000+ weekly active users. Users in 100+ countries. And it’s not a spray-and-pray strategy; it’s product-led growth, sharpened to a razor’s edge. They’re playing both sides of the house: a free-tier that pulls in indie hackers and small teams, and an enterprise suite that makes the suits at Fortune 500s sleep better at night. SSH session recording, identity provider integrations, audit logs, it’s a CTO’s dream and a CISO’s sigh of relief.

Now, with fresh capital, they’re scaling engineering, tightening integrations for AI/ML teams, and hiring globally like a team that knows velocity isn’t just a metric; it’s a mindset. Grace Lin, ex-Cloudflare, is now SVP of Ops. This isn’t a company chasing relevance. It’s a company building it.

Tailscale didn’t just connect devices; they connected the dots between simplicity, security, and scale. And now they’ve got $160M to double down.