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Tailscale has raised $160M

tailscale.com

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Re: Tailscale has raised $160M

#51
Depressing news, I have no hope that the countdown to Tailscale being unusable subscription trash has not started with this announcement.

I realize this is a very ironic place to make this statement, but I am utterly exhausted by VC money destroying all of the services I enjoy, like a slow disease spreading through a herd of livestock.

Re: Tailscale has raised $160M

#52
post #37

If they had taken just say $40 million would they be able to sustain their project for the foreseeable future and perhaps not yield as much future product direction and equity? I honestly don't know how this big dealmaking works but it strikes me that when you take out this big of an obligation that the obligation has a gravity that may drag you in a direction you (or consumers) do not want to go. Love Tailscale as a…

Equity investments like this don't need to be repaid, so there isn't a legal obligation to repay them. Of course, there is an obligation to maximize shareholder value — but that is totally independent of the dollar amount invested.

When founders raise this much money, it's because there's (1) a lot they want to do and hire for, or (2) they don't want to worry about monetizing the product for a significant period and focus on growth or product development.

Re: Tailscale has raised $160M

#53
Investors expect that Tailscale will extract many multiples of their contribution from users.

If you'd like to avoid this extraction, you can fork their command line client code (along with the open source headscale server) and run a mesh network across your linux machines with all the magic DNS and userspace-TCP/IP-stack goodness that you're used to. Tailscale has given away a lot of the engineering for free.

However, as soon as your fork becomes incompatible with Tailscale's stack, you lose a massive value-add: proprietary platform support. Today, you can add the sale's guy's iPhone to your tailnet in seconds. If Apple's capricious automated AppStore security pulls the Tailscale app from the AppStore, Tailscale Corp is big enough to get Apple's attention. A small FLOSS group with some forked clients on github won't be able to provide this same operational stability.

Re: Tailscale has raised $160M

#54
post #22

Off-topic, but it makes me laugh that companies will list their “investors”, “advisors”, etc. on their company page, but not the people working there. That said, Tailscale is one of the products that just works.

As someone who currently has their photo on a company's 'About Us' page, I hate it. Why does anyone care who the nth developer is? Let me just do my job without forcing me to be publicly listed for spammers and scammers to target me.

I do in fact care about the nth developer when I visit about us pages.

Maybe a slight bias on my part as I'm a developer and not an investor.

And not that funding or advising is less important, but it's a nice feeling connecting a product I like to faces who make it happen.

Re: Tailscale has raised $160M

#55
post #37

If they had taken just say $40 million would they be able to sustain their project for the foreseeable future and perhaps not yield as much future product direction and equity? I honestly don't know how this big dealmaking works but it strikes me that when you take out this big of an obligation that the obligation has a gravity that may drag you in a direction you (or consumers) do not want to go. Love Tailscale as a…

Equity investments like this don't need to be repaid, so there isn't a legal obligation to repay them. Of course, there is an obligation to maximize shareholder value — but that is totally independent of the dollar amount invested. When founders raise this much money, it's because there's (1) a lot they want to do and hire for, or (2) they don't want to worry about monetizing the product for a significant period and…

GP didn't talk about "repaying" anything. Taking 160M instead of 40M at the same valuation means giving up 4x the shares, and that's going to result in a bigger voice for those investors at the table in making decisions about the future path of the company.

Re: Tailscale has raised $160M

#56

Does anybody encounter issues with DNS after installing tailscale with it's MagicDNS enabled? It drives me nuts because my entire network just stops working. I removed tailscale but still won't be able to connect to my Ubuntu server.

The subnet routing feature can cause network issues

Re: Tailscale has raised $160M

#57
post #35

Earlier quoted context omitted.

This is not correct. Wireguard establishes a tunnel between peer A and B, and its simplicity stops there. Tailscale does tons of complex networking, filtering, nat traversal, DNS, file sharing, etc. Wireguard is a small part of the codebase today, which has grown a lot. It’s a bit like saying Dropbox is just a GUI on top of TLS.

Most of this was successfully done 20 years ago by tinc, which is a project written by a couple of European guys in their free time. It even supports routing traffic through other peers and does peer discovery just like BitTorrent (but before BitTorrent even existed) — there is no need for a central server. What tailscale has over it is hype, lots and lots of hype. Also a much more well thought out, and arguably more…

And ease of use, IMHO. That's a bit one with these kind of things. I will admit not having used tinc but I imagine it's not as polished.

Polish costs effort and money and it also really truly saves time and makes for a better product. So that matters.

Re: Tailscale has raised $160M

#58

Does anybody encounter issues with DNS after installing tailscale with it's MagicDNS enabled? It drives me nuts because my entire network just stops working. I removed tailscale but still won't be able to connect to my Ubuntu server.

I have this happen largely with Apple OS devices. Apple's DNS service can be notoriously persnickity (I've had issues with it outside of Tailscale as well), and I usually need to bounce interfaces or flush DNS cache (where I can on macOS) to resolve issues. WRT Tailscale, I also have issues with it on my phone. I currently have my phone configured to connect to my Tailnet when I leave networks I don't control so that I can maintain access to my personal cloud on the go, however after a few connections and disconnections, I have to bounce several interfaces in order to correct both DNS and routing.

Re: Tailscale has raised $160M

#59

Tailscale is a great. I think of it as a swiss army knife for easier routing and connectivity. I use it in projects to stream internet / connectivity from my phone to the NVIDIA Jetson line, making my robotics projects easily accessible / debuggable: https://github.com/burningion/bicyclist-defense-jetson?tab=r...

Off topic but rerun.io is really cool. Never heard of it until I saw your project. Do you know if it does "replay" kinda like rosplay?

Yes, rerun does replay, that was my main use case when prototyping.

They've since raised more funding recently, and have larger use cases in mind for robotics: https://rerun.io/blog/physical-ai-data

I've spoken with members of the team, and they're all great. Wouldn't hesitate to use the product / work with them anywhere.

Re: Tailscale has raised $160M

#60
post #35

Earlier quoted context omitted.

This is not correct. Wireguard establishes a tunnel between peer A and B, and its simplicity stops there. Tailscale does tons of complex networking, filtering, nat traversal, DNS, file sharing, etc. Wireguard is a small part of the codebase today, which has grown a lot. It’s a bit like saying Dropbox is just a GUI on top of TLS.

> It’s a bit like saying Dropbox is just a GUI on top of TLS. Well, it is. After all, for a Linux user, you can already build such a system yourself quite trivially...

It'll be a sad day when this reference is posted and understood for the last time.
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