this post was submitted on 09 Jun 2025
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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.

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[–] lefixxx@lemmy.world 6 points 1 hour ago (1 children)

Yeah and steam is closed source DRM platform. Great software sometimes is worth the trade off.

[–] Uncut_Lemon@lemmy.world 4 points 31 minutes ago* (last edited 29 minutes ago)

Steam is a private company, not publicly traded and has no VC funding.

VC funding and potential IPO normally means enshittification is inevitable, as they will eventually need to make insane profits by turning the screws on its users, as their business model wasn't self sustaining.

[–] pulsewidth@lemmy.world 11 points 3 hours ago (1 children)

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.

[–] avidamoeba@lemmy.ca 4 points 3 hours ago

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.

[–] fmstrat@lemmy.nowsci.com 28 points 5 hours ago* (last edited 5 hours ago) (3 children)

Join our Discord server for a chat and community support.

Sigh...

And even worse:

Everything in Tailscale is Open Source, except the GUI clients for proprietary OS (Windows and macOS/iOS), and the control server.

[–] heals@discuss.tchncs.de 3 points 2 hours ago

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.

[–] drmoose@lemmy.world 22 points 5 hours ago

everything is open source except half of all things.

Lol

[–] avidamoeba@lemmy.ca 3 points 3 hours ago

Huh, I actually didn't know this because I don't use Windows/macOS/iOS. Somehow completely missed this.

[–] possiblylinux127@lemmy.zip 8 points 4 hours ago* (last edited 4 hours ago) (1 children)

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.

[–] avidamoeba@lemmy.ca 4 points 3 hours ago* (last edited 3 hours ago)

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.

[–] Vanilla_PuddinFudge@infosec.pub 18 points 5 hours ago (2 children)

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.

[–] SupremeDonut@lemmy.ml 2 points 43 minutes ago

Any helpful guids or links you feel like sharing for interested parties?

[–] natryamar@lemmy.world 2 points 4 hours ago

I did this was well awhile ago. Felt nice to completely control everything.

[–] Tillman@lemmy.world 0 points 1 hour ago

Headscale requires tailscale client so it’s a no-go for me. I’m still trying to block cloudflare from my network.

[–] qjkxbmwvz@startrek.website 11 points 7 hours ago

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.

[–] cooopsspace@infosec.pub 22 points 9 hours ago* (last edited 9 hours ago) (3 children)

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.

[–] quant@leminal.space 3 points 6 hours ago* (last edited 6 hours ago)

I spent an afternoon doing precisely that. Bought a domain, a vps, and setup pangolin. Can't believe how smooth it went.

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[–] httperror418@lemmy.world 57 points 11 hours ago (1 children)

I'm unsure if it has been mentioned, but a similar tool which is open source (you can run the backend unlike tailscale), netbird

https://netbird.io/

[–] couch1potato@lemmy.dbzer0.com 11 points 6 hours ago (1 children)

Headscale is the tailscale backend server

[–] avidamoeba@lemmy.ca 4 points 3 hours ago

Well not "the" backend server but "a" different backend server. As far as I know Headscale is a separate implementation from what Tailscale run themselves.

[–] dabe@lemmy.zip 15 points 9 hours ago* (last edited 9 hours ago) (2 children)

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.

[–] null_dot@lemmy.dbzer0.com 8 points 9 hours ago (1 children)

I use wireguard and have public DNS refer to private IPs.

For example if my server is accessible at 10.0.0.1 via wireguard then I point *.myserver.mydomain.com to that IP.

Sorry if I've misunderstood your question.

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[–] lka1988@lemmy.dbzer0.com 62 points 14 hours ago* (last edited 14 hours ago) (5 children)

Tailscale never sat right with me. The convenience was nice, but - like other VC-funded projects - it followed that ever-familiar pattern of an "easy" service popping up out of nowhere and gaining massive popularity seemingly overnight. 🚩🚩🚩

I can't say I'm surprised by any of this.

[–] Vanilla_PuddinFudge@infosec.pub 2 points 5 hours ago

I think there's room in the world for a selfhosted, foss version of their software, even if a little simplified.

[–] potustheplant@feddit.nl 10 points 9 hours ago (1 children)

Maybe this is a pet peeve but it's a vpn tool that forces you to log in with an "identity provider". Yeah, no thanks.

[–] iggy@lemmy.world 8 points 7 hours ago (1 children)

That's a basic requirement for almost any company. If you're into hard coding credentials just use wireguard directly.

[–] potustheplant@feddit.nl 2 points 4 hours ago

There are tons and tons of websites where you can create an account with just your email. I wouldn't expect a third party account to be mandatory. Specially from a product like this one.

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[–] HelloRoot@lemy.lol 122 points 16 hours ago (11 children)

a long runway that allows us to become profitable when needed

Switch to self-hosting headscale when they enshittify in an attempt to become profitable, duh

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[–] milicent_bystandr@lemm.ee 26 points 13 hours ago (7 children)

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.

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