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.
Just came here to say that the guy looks like a creep!
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?
is this some kind of furry porn CDN
I never really understood the point of using Tailscale over plain ol’ WireGuard. I mean I guess if youve got a dozen+ nodes but I feel like most laymens topologies won’t be complex beyond a regular old wireguard config
Same thing here, either tailscale selfhosted or Netbird selfhosted I’d the way to go for all the nice features, having the free tier or tailscale for personal data never sounded right to me.
NAT punching and proxying when a p2p connection between any 2 nodes cannot be achieved. It’s a world of difference with mobile devices when they always see each other, all the time. However, headscale does all that.
Wireguard doesn’t do NAT/Firewall traversal nor does it have SSO
Tailscale manages the underlying Wireguard for you
Simplicity?
I mean sure, but I don’t think it’s simpler than setting up a wireguard config IMO. For tailscale you gotta make an account, register devices, connect them. Feel like wireguard is about the same except you don’t have to make an account.
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
Ok and?
Nerds stop recommending corporate crap: challenge: impossible
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
I can highly recommend Netbird selfhosted, it has SSO support, logins, complex network topologies, it uses wireguard under the hood and it’s open source.
That sounds kinda cool. I’ll have to check it out. It’s kinda hard sometimes to push FOSS stuff in a largercorporate environment but this looks like something I could recommend/build for small-mid private SOHO clients.
Yeah, OpenVPN definitely doesn’t have light spec requirements 😅 thankfully hardware is unfathomably powerful these days.
Sure but wireguards connection is just faster.
Crap, I really need to switch of Tailscale but currently it is an easy way for me to access my stuff outside of home as a temporary solution while I am on a 5G modem.
Do you pay for a domain? They likely provide dynamic DNS (DNS). If you’re lucky, they have an API for it, instead of an app, and you can configure a cronjob on your home server to run every 1-5 minutes (or more often, if your IP is super unstable!).
Yeah I can always do that, but putting stuff behind something like Tailscale is (or atleast feels) more secure than making my IP known to the public. I have a DMZ setup though so it should be fine.
Your “IP address” is already public. That’s why an IPv4 address is assigned to you as a “public IP address” and you NAT to a private space. When using IPv6, everything is public.
The key is to secure everything with access restrictions.
Well yes I know, but there is a difference between using a domain bound to me as a person and a random string of numbers that changes every 5 minutes
Chances are you’ve had the same public IP for a long time. Mine hasn’t changed in 2 years.
That was the case when I lived with my parents, but now it changes every 5 minutes sadly.
So I had to shut down my Minecraft server etc for now because I am on a 5G modem which makes it really annoying to open up ports and point a domain to your IP
If your IP changed every 5 minutes, you would not be able to have a voice call or anything similar. Your IP probably changes every 24 hours
@chronicledmonocle @Vinstaal0 I used to work for a dial-up ISP. Every IP is registered to an account, if you’re going through your ISP (as opposed to, say, coffee shop or hotel wifi). Though the people who have the information are different (ICANN/registrar vs your internet provider), there’s no anonymity in your home IP address even with CGNAT.
As far as your domain, you should have privacy protection enabled so people can’t find your personal info via whois.
I can recommend to take a look at netbird.io
Much more user friendly
Json is awful for config
Crockford is a good and smart person but he really dropped the fucking ball on JSON.
Double-quotes-only and no comments kill the whole spec for me. Extremely opinionated and dumb. I fucking hate JSON.
My boss once sent me a machine generated config. He’s terminally addicted to double-quotes (like, a fatal condition). I searched and there were 27k sequences of
\".Edit: my point is - all that compute and network wasted, every single time the file is requested and parsed. Completely pointless waste
I can’t. I tried it first and installed it on my phone from f-droid. After opening it up, it connected to an already existing network with other people’s old machines from years ago on it. I was horrified.
So then I tried to delete my whole account and couldn’t due to an error. I sent them an email about it and they took like two weeks to respond.
Netbird isn’t on F-droid
Are we talking about the same thing?
It used to be
It has never been on F-droid. I’ve been following the service since it started. It didn’t even have a mobile app not that long ago.
Yeah and steam is closed source DRM platform. Great software sometimes is worth the trade off.
Steam is a private company, not publicly traded and has no VC funding.
VC funding and potential IPO normally means enshittification is inevitable, as eventually needs to make insane profits by turning the screws on its users, as their business model wasn’t self sustaining.
Enshittification is inevitable for all free services (services as in with a server component). Thankfully the functions of tailscale are open source so until enshittification actually happens I will be happy with using a a useful but VC funded project. When I am not willing to make the trade off anymore I will use headscale or some other drop in replacement.
Realistically Tailscale seems to currently be running on a model of get all of the self hosters to love running it at home so then they advocate to run it at work where all of the pricey enterprises licenses make the real money.
I’ve actually seen some real world usecases where if I had more political push, I would’ve put Tailscale onto the running as a potential solution
Hopefully they have the right people in place to push back at the VC firms about maintaining their current strategy rather than scaring away all of their best advocates before they can truly get off the ground. Having worked at a company owned by a hedgefund, part of the trick is having the right people in place in the company who can block the worst decisions by the capital-hungry owners
Enshittification is inevitable for all free services (services as in with a server component).
No, it is not that bleak. It is only inevitable when there is an active push for a short-term maximization of user base monetization (which is very much in the nature of VC). It can usually be avoided with products that are wholly under the ownership of all users (such as a cooperative or a government-provided service) or - only if one is lucky - with products of financially independent private enterprises under vaguely benevolent and unhurried leadership (such as Steam, to some extent)
Headscale requires tailscale client so it’s a no-go for me. I’m still trying to block cloudflare from my network.
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’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.
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.
Join our Discord server for a chat and community support.
Sigh…
To be fair, anything the GUI clients do can be done with the CLI which is still open source and on all desktop platforms and headscale is literally their open source control server.
Yea, but in iOS?
I mean is anything iOS really open source?
The iOS app is the exception for now but with the CLI and the core libs being open source it’s at least not off the table to make an alternate iOS client I’d say.
Huh, I actually didn’t know this because I don’t use Windows/macOS/iOS. Somehow completely missed this.
Granted this is not Headscale’s fault, they’re just using Tailscale clients. Either way I’m glad I use a roll-your-own Wireguard.
I and my partner also don’t use those OSs, but it’s more the point of using FOSS when we can.
everything is open source except half of all things.
Lol
