In this fireside chat, CEO Avery Pennarun and CSO David Carney join Alex from the Tailscale team to reflect on the company’s journey so far, our recent Series C raise, and what comes next as we scale; without losing sight of what makes Tailscale, Tailscale.
Tailscale’s first funding round in 2019 happened more or less by accident. While seeking advice, not capital, the team ended up with both. That pattern continued: over time, investors started pitching Tailscale, not the other way around. With each round, the team became more intentional, choosing investors who understand the product and want to build for the long term.
The $160 million Series C isn’t about runway, it’s about opportunity. This new raise lets us move faster on ideas we’ve already validated, things our customers are asking for that have clear returns. Most of the investment goes toward engineering and quality improvements, refining the core product rather than chasing something new (though Avery admits there might be a Tailscale billboard in our future!).
Naturally, the conversation turns toward the risks of success — namely, the dreaded enshittification that creeps into too many VC-backed products. Avery doesn’t mince his words here: he hates it too and has seen it happen for many other companies. But Tailscale’s word-of-mouth growth model depends on love, not lock-in. Making the product worse is bad business for us. “We don’t win by extracting more,” he says. “We win when people tell their friends.”
Avery will be sharing more on this topic in the next few weeks, so keep an eye on the blog for an update.
As well as growing interest from big customers, Tailscale’s team continues to obsess over how individuals and small teams can do more with less; whether that’s running a homelab, building a personal SaaS project, or managing secure access at work. Features like identity-first networking, tsidp, and golink help extend what’s possible, while keeping it simple. Turns out what is needed in the homelab, also works in the enterprise and so making Tailscale better for everyone means just that.
If you’re curious how a company can grow without compromising, or how a bunch of engineers accidentally ended up reinventing the internet — this fireside chat is worth a watch.
Watch the video embedded above, or directly on Youtube here
Alex Kretzschmar
