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Chronicles

The story behind the story

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Tailscale, which provides an enterprise mesh VPN service built on the open source WireGuard protocol, raises a $100M Series B at a $1B+ valuation

Zero trust security is an emerging paradigm in enterprise IT.  It means that no one is trusted by default from inside or outside a network …

TechCrunch Kyle Wiggers

Context & Ripple Effects

Tailscale's $1B+ Series B is the anchor of a funding cluster in zero-trust remote access: weeks earlier, Twingate raised a $42M Series B led by Bond Capital, Banyan Security took a $30M Series B after 300% user growth in 2021, and ThreatLocker closed a $100M Series C claiming 23,000 enterprise clients. Tailscale's differentiator in that pack is its foundation on the open source WireGuard protocol, which is slated for integration into the Linux kernel — open-source distribution underneath a commercial mesh VPN.

First-order effects

  • Tailscale gains the capital to scale its enterprise mesh VPN sales against direct zero-trust rivals Twingate and Banyan, all of which are raising in the same window and competing for the same remote-access budgets.

Second-order effects

  • The cluster of raises forces differentiation on protocol and architecture rather than features alone: Tailscale bets on WireGuard's open-source base, SecureW2 on certificate-based authentication tied to identity providers, ThreatLocker on endpoint control — pushing buyers to choose a zero-trust stack rather than a single VPN product.

Third-order effects

  • If the funding pattern holds, enterprise remote access consolidates around identity-based mesh networking built on open protocols, displacing the traditional perimeter VPN as the default corporate access layer.

The trend: Enterprise security capital is consolidating around zero-trust mesh access, with open-source protocols like WireGuard becoming the commercial substrate.