3d ago

Friendly reminder that Tailscale is VC-funded and driving towards IPO

Corporate VPN startup Tailscale secures $230 million CAD Series C on back of “surprising” growth

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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Headscale is great if you like networking fun, but that aside I'm not understanding why VC funding is such a black mark to the poster. Tailscale doesn't generate meaningful revenue streams as its early-stage, so it has to secure funding to continue operations until they achieve high enough revenue to go public. That's pretty standard in a business life-cycle, though. It seems like the main complaint is that Tailscale is a business. And what about the Linux Foundation? They are funded through private equity. Should you consider switching away because of that?
- The problem, though, is that VC-funded projects bite off way more than they can chew from the start and have to enshittify to keep shareholders happy at that level.
  Growth for the sake of growth is a fundamentally broken concept. Tailscale provides a free service that many use. They already offer a paid support tier for companies, like other certain FOSS projects do, so why not call it good there? Grow based on actual customer needs, instead of shareholder bullshit "needs" (line must go up 🙄).
- Not that it is a business but is a specific kind of business. VC funded startups eyeing an IPO more often than not start doing things users are not happy with. Maybe tailscale won't, but might as well be aware what kind of company they are acknowledge there is a decent chance of rugpulls
- It seems like the main complaint is that Tailscale is a business. And what about the Linux Foundation?
  The Linux Foundation is not a business.
  
  The businesses that fund the Linux Foundation through private equity are though, aren't they?
  
  Sure. Do you have a point?
  
  Yeah, I think you missed that. Go back through and reread comments please. Thank you.
  
  Could you summarise for us please? It's not clear.
- 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)
  
  yellow flag to me (too many ad emails)
  Weird. I'm not saying you're lying, but besides the registration email, and onboarding welcome email, I can't think of any others I've received from Tailscale. In fact, I just did a search of my email client, and those were the only ones I've received.
  
  I do believe my experience in this regard is not representative of everyone, I probably failed to untick some checkbox (regarding communications) and the "too many ad emails" are a handful (in 3 months), which to me is a handful too much (having to untick a box should not be necessary)
  
  That's cool. I don't like spam either. You are correct in that you should have to opt in instead of opt out.
  
  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.
  
  That’s not really a justifiable reason, though.
  To you it isn't, but to some of us it is. For me the standard business cycle is not acceptable because I almost inevitably end up under the bus.
  The Linux Foundation isn't a comparable example for me since it's a non-profit. As a result it isn't subject to the same market pressures for-profit businesses do, let alone VC-funded ones.
  At this point, with everything I know and have experienced about the economy, politics and the world, I am trying to avoid depending on for-profit businesses as much as I can. I know how businesses operate, I know why they operate the way they do, I know what dynamics push them in the directions they go and I'm tired of being run over by the bus. If I ever form a business myself it would either be a non-profit, or a worker co-op, or both, as this will signal everyone who knows what I know what the direction of this business would be about.
  
  Firstly, I'm not trying to start a flame war with commenters, I genuinely just disagree on something and some people are getting a little hot under the collar by it. The Linux Foundation comment I made because ultimately VC touches more than people think. Even its something that isn't directly tied to VC, that money filters through groups like LF which is a non-profit and most would argue a quite legitimate organization. The point is there really is no separation or clear line of demarcation on what is "good" funding and what is "bad" funding.
  
  The point is there really is no separation or clear line of demarcation on what is “good” funding and what is “bad” funding.
  I understand and I disagree. A demarcation emerges from the goal of the funding and its effects. For me, one example of bad funding is funding that drives user acquisition at unsustainable prices by a firm that is also significantly controlled by the funding source. This is predominantly what VC-funding goes to. VC-funding that goes to a non-profit that the VC has no control over, where the VC can't and does not demand financial return from, is not bad funding in my books. Corporate funding doing the same thing is also not bad funding. Government funding often has the least strings attached as it does not demand direct return, and this also is not bad funding. To top that off citizens can exercise control over government funding via the democratic process, unlike corporate or VC funding, where the vast majority have zero control, and are owed no accountability by the businesses.
  
  Historically, Accel has never pushed acquisition. On the contrary, they do the opposite. Its why they VC fund over 300 companies, but you've never heard of them. That's not to say they couldn't, but they haven't ever acted in that manner previously so logically it would be safe to assume that trend continues with Tailscale. I think that's important here: its not about ability its about intent. If as a organization you give funding to another organization (even non-profits) you exercise at least some control over them as they are dependent on that money to function. This is actually a point other commenters have made in regards to Headscale. Headscale is maintained by a Tailscale employee. As they fund him personally, they can exercise some control over him as he depends on that money/employment. Again, even their comments circle back to ability vs intent. Tailscale could influence their employee, but would they? That's where a lot of the VC argument goes. Its just speculation as what a group could do, not what they would do.
  
  “The trend” is making money no matter what. That means they’re gonna screw you over eventually, the countdown has already begun, and it’s just a matter of time
  
  Is there an actual example you can provide of Accel doing that or is this more an emotionally driven statement you have?
  
  The specific company does not, in fact, matter because VCs have the same set of incentives in the end
  
  So, even if Accel doesn't do that, which they haven't done that, they are still guilty of doing that. Ok, yeah. That's some solid irrefutable logic you got going there. I think I'll go back to arguing this with commenters who are a little less emotional and more grounded in real world points about the topic.
  
  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
  
  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
  🏅
- That's pretty standard in a business life-cycle, though
  I don't know where people ever got the idea that normal = acceptable. I hear this used to justify all sorts of awful crap. It was only ever normalized because users were apathetic.
  And what about the Linux Foundation? They are funded through private equity. Should you consider switching away because of that?
  Does The Linux Foundation have complete control over Linux?
  
  So, companies should not be allowed to invest in other companies? Who is allowed to invest in companies then? Only private individuals? But those individuals are apathetic, so they have to be made to? Or if they don't want to, then since other companies aren't allowed, wealthy private individuals would need to? Its not normal because its acceptable, its normal because the alternative is fantastical and unrealistic.
  To the other point, does Tailscale have complete control over Wireguard? They don't control the technology behind that. They do for their control server tech and to some extent Headscale, but that's not what its built on anymore then what's built on Linux.
  
  companies should not be allowed to invest in other companies?
  That's not what I'm saying. I'm just saying you need to be wary of companies that do because the inevitable end of that train is enshittification. Every. Single. Time.
  does Tailscale have complete control over Wireguard?
  Who's talking about WireGuard? We were talking about Tailscale.
  
  Tailscale builds on top of the Wireguard protocol, LF builds on top of (through grants/scholarships) the Linux OS. You can't argue that it doesn't matter that LF doesn't have control over the underlying technology, but then argue that it does matter in Tailscale's cause.
  
  It doesn't matter in either case. Neither of them have control over the underlying technology.
  
  Does The Linux Foundation have complete control over Linux?
  You're the one who said it, though.
  
  Yes I did say that. I don't understand what you're trying to communicate. TLF does not control Linux, just as Tailscale does not control WireGuard. Tailscale does control Tailscale. There's nothing wrong with using Linux and there's nothing wrong with using WireGuard. There may be something wrong with using Tailscale. I don't know how to be more clear about this.
  
  Linus is fairly vocal over what is and is not allowed into the Linux Kernel. Pretty sure he has the final say on every commit.

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