Corporate VPN startup Tailscale secures $230 million CAD Series C on back of “surprising” growth
Pennarun confirmed the company had been approached by potential acquirers, but told BetaKit that the company intends to grow as a private company and work towards an initial public offering (IPO).
“Tailscale intends to remain independent and we are on a likely IPO track, although any IPO is several years out,” Pennarun said. “Meanwhile, we have an extremely efficient business model, rapid revenue acceleration, and a long runway that allows us to become profitable when needed, which means we can weather all kinds of economic storms.”
Keep that in mind as you ponder whether and when to switch to self-hosting Headscale.
What’s the benefit over just WG?
You dont need to manually handle the WG config files. This isn’t really an issue when it’s just you and your two devices, but once you start supporting more people, like non-technical family members, this gets really annoying really quickly.
Tailscale (and headscale) just require you to log in, which even those family members can manage and then does the rest for you. They also support SSO in which case you wouldn’t even have to create new accounts.
No need to port forward, almost 0 config.
https://tailscale.com/blog/how-tailscale-works
Your tech illiterate grandma can set it up. It’s that easy.
WG is worthless in a CGNAT environment… And as we are in 2025 and time doesn’t stop it will be irrelevant for everyone someday, unless they fully support IPv6 (which I don’t know if they do, if you can use WG in a CGNATED network with IPv6 I’d like to know though, I am very rusty setting it up, but it might worth checking it out).
CGNAT is for IPv4, the IPv6 network is separate. But if you have IPv6 connectivity on both ends setting up WG is the same as with IPv4.
Easier/zero configuration compared to manual WG setup. Takes care of ports and providing transparent relay when no direct connection works.
Personally, my ISP (T-Mobile 5G) has CGNAT and blocks all incoming traffic. I can’t simply Wireguard into my network. Tailscale has been my intermediary to get remote access.
I guess it’s time to figure how how to host an alternative on a VPS (I see Headscale mentioned in these comments).
Tailscale uses WG though, so it’s fundamentally the same thing. Like you said - just do Headscale on a VPS.
Or Wireguard on a VPS