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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[–] [email protected] 8 points 4 days ago (21 children)

Yup, I don't know if that is OP's intention, but I would agree myself with the complaint that "Tailscale is a business"

The way I see it, if it's a business it must generate revenue (either now or down the road), and that is enough to have me worried. I do have a Tailscale registration, and the way they approach email communication is already a yellow flag to me (too many ad emails)

[–] [email protected] -3 points 4 days ago (17 children)

That's not really a justifiable reason, though. The Linux Foundation provides grants and scholarships to the open source community, but they do that through private equity business. So transitively, many open source projects are funded by businesses looking to capitalize on that innovation. Do you consider that when pulling from a git repository? No, that's overbearing. Additionally Headscale is in part maintained by a Tailscale employee. That would surely create a conflict of interest given Tailscale is solely interested in generating revenue.

[–] [email protected] 8 points 4 days ago* (last edited 4 days ago) (1 children)

I get your point, though Tailscale specifically crosses a line for me in this sense:

  • Using code created/maintained by businesses: ok
  • Relying in infrastructure maintained by businesses: not ok

I am not that big of an enthusiast, but the way I see it, if a company goes rogue and you're using their open source code, it's just a matter of forking it (I'm thinking about Emby/Jellyfin as an example) If you rely on their infrastructure (such as Tailscale servers) then you are at the mercy of the companies

To that end: I'd say that OP is prettt on point by suggesting Headscale, you're still "using Tailscale" in a sense, but without chaining yourself to the business

[–] avidamoeba 3 points 4 days ago

I am not that big of an enthusiast, but the way I see it, if a company goes rogue and you’re using their open source code, it’s just a matter of forking it (I’m thinking about Emby/Jellyfin as an example) If you rely on their infrastructure (such as Tailscale servers) then you are at the mercy of the companies

🏅

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