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.
become profitable when needed
By what, laying off all QA and support staff and half your developers the moment a single quarterly earnings report isn’t spotlessly gilded?
Ok and?
Nerds stop recommending corporate crap: challenge: impossible
is this some kind of furry porn CDN
And here I am, still using OpenVPN in 2025 lol
Used to run OpenVPN. Tried Wireguard and the performance was much better, although lacking some of the features some might need/want fit credential-based logins etc
Yeah, OpenVPN definitely doesn’t have light spec requirements 😅 thankfully hardware is unfathomably powerful these days.
Sure but wireguards connection is just faster.
I didn’t really get the allure of it TBH. For most home-based nerds a simple Wireguard host (or OpnSense, OpenWRT etc running such) should be fine, and there are better options for commercial from better-known vendors in the network security space
The “well known vendors” tend to be crap especially on a security level
I think I’ll just keep using tailscale until they start enshittifying, and then set up a Headscale instance on a VPS - no need to take this step ahead of time, right?
I mean, all the people saying they can avoid any issues by doing the above - what’s to stop Tailscale dropping support for Headscale in future if they’re serious about enshitification? Their Linux & Android clients are open source, but not IOS or Windows so they could easily block access for them.
My point being - I’ll worry when there is something substantial to worry about, til then they can know I’m using like 3 devices and a github account to authenticate. MagicDNS and the reliability of the clients is just too good for me to switch over mild funding concerns.
Yeah, as I said, it’s a friendly reminder. I’m personally probably doing it this year. It’s entirely possible that enshittification could come even years from now. It all depends on how their enterprise adoption goes I think. The more money they make there, the longer the individual users are gonna be left unsqueezed.
I just replaced my entire setup with base wireguard as a challenge, easier than I expected it to be, and not hard to mimic tailscale.
If you just have to talk from many devices to the one server sure, but Tailscale sure makes it easy for many to many. Also if a direct connection is impossible (e.g. firewall of china, CGNAT etc) tailscale puts a relay server in the middle for you.
My entire setup might not be your entire setup, I have the basic functionality of connecting multiple systems into one mesh network. That’s all I needed so it’s all I did.
Can you elaborate how?
Pihole and pivpn get along like peas and carrots.
Make the “available ips” your pivpn subnet and ta-da, the mesh functionality of tailscale without the entire connection.
Want to exit node from the server? Just change the value back to 0.0.0.0/0.
Any helpful guids or links you feel like sharing for interested parties?
I did this was well awhile ago. Felt nice to completely control everything.
I’m unsure if it has been mentioned, but a similar tool which is open source (you can run the backend unlike tailscale), netbird
We’ve implemented netbird at my company, we’re pretty happy with it overall.
The main drawback is that it has no way of handling multiple different accounts on the same machine, and they don’t seem to have any plans for ever really solving that. As long as you can live with that, it’s a good solution.
Support is a mixed bag. Mostly just a slack server, kind of lacking in what I’d call enterprise level support. But development seems to be moving at a rapid pace, and they’re definitely in that “Small but eager” stage where everything happens quickly. I’ve reported bugs and had them fixed the same day.
Everything is open source. Backend, clients, the whole bag. So if they ever try to enshittify, you can just take your ball and leave.
Also, the security tools are really cool. Instead of writing out firewall rules by hand like Tailscale, they have a really nice, really simple GUI for setting up all your ACLs. I found it very intuitive.
Thank you for your insight, I’m assuming the only public part is the UI and coturn (the bit that enables two clients between firewalls to hole-punch)?
Friendly reminder that Tailscale is VC-funded and driving towards IPO
You know what’s to come.
The answer to the question is immediately. Or switch to OpenZiti or Pangolin even.
I’m not that worried as there are alternatives like Netbird. The underlying tech really isn’t hard to replicate since Wireguard is pretty standard.
I think it would be cool if Tailscale made it into the enterprise arena.
I think it would be cool if Tailscale made it into the enterprise arena.
I think they already have started. Telus is on their list of clients.
Tailscale is great. The principle concern to me is that your super easy mesh network depends on Tailscale so if they want it they have control, and if they change their pricing or options you depend on them, and though they can’t see the data you send they can see the topology of your network and where all your computers/devices are.
I use Nebula, which is more work to set up and doesn’t have some of the features, not But if you slap the ‘lighthouse’ (administrating node) on a cheap VPS it works great. And it has some advantages. But Nebula also troubles me: though it’s fully open source and fully in your control, the documentation isn’t great. Instead, you can now get “managed nebula”, which puts you in the same problem as Tailscale: the company sees and controls your network topology. I fear the company (Defined Networking) is trying to push things that way. Even their android app you can’t fully configure unless you use their ‘managed’ service.
For now, Nebula is great, and my preferred mesh network (I looked into all the main ones). And for Tailscale you can run the administration server yourself with Headscale and be fully in your control.
Actually I wish Tailscale the best as a profitable business. They’ve created a fantastic service and system. But for me, I’d rather my network be in my own hands and for my own eyes. And, as is OP’s main point, once they have enough dependent users, the service might turn much worse.
Netbird seemed to go in a similar way, though still good. I want to try zrok next, looks interesting
What do you mean by going in a similar way? Towards an IPO?
Maybe not ipo, but it seemed like it had a strong monetisation push a while ago
Netbird you can still run unlike tailscale with headscale right?
At least hope the backend can be fully ran ?
Yes, and I think it’s the full fat option as well
Nice to hear your experience with Nebula. I considered it when I went with Tailscale years ago. Now you gotta migrate off of lemm.ee as it’s shutting down soon. :D
Yep. It’s on the TODO list…
Am I totally off-base in thinking that MagicDNS and pluggable DNS nameserver overrides are a huge feature of tailscale?
I love that I can refer to my tailnet devices just via their machine name. I use it everywhere. And also that I can just slot in my NextDNS ID so that any device running tailscale now automatically uses that, and I don’t have to mess with my shared router settings or per device settings. Is all that actually really easy to set up outside of tailscale? Cuz if it is and I just somehow missed that when doing all my research, I’ll happily give plain wireguard or other mesh orchestrators like NetBird a go.
And I already know that mDNS is not the answer. That protocol is simply not reliable enough.
Nah, DNS is separate and these features are indeed pretty great. I think Headscale can also do them. I think I tested MagicDNS if I recall correctly.
I think a lot of companies view their free plan as recruiting/advertising — if you use TailScale personally and have a great experience then you’ll bring in business by advocating for it at work.
Of course it could go either way, and I don’t rely on TailScale (it’s my “backup” VPN to my home network)… we’ll see, I guess.
It also doesn’t cost them much of anything
Positive PR and little draw backs means that everyone is generally pretty happy
If I host headscale on a VPS, is that as seamless of an experience as Tailscale? And would I miss out on features, like the Tailscale dashboard? How does the experience change for me (an admin type) and my users (non-technical types)?
