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Tailscale has raised $160M

tailscale.com

71–80 of 354 posts

Re: Tailscale has raised $160M

#71

Earlier quoted context omitted.

> 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.

No it won't. The reference is universally misunderstood.

https://hn.algolia.com/?dateRange=all&page=0&prefix=false&qu...

Re: Tailscale has raised $160M

#72

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?

+1 rerun is great and they also make egui.rs, one of the best immediate mode graphics libs.

Re: Tailscale has raised $160M

#73
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…

One of the main problems with raising too much is that you stop caring about product-market fit and can go on tangents that do not make you competitive. This is quiet common afaik.

Re: Tailscale has raised $160M

#74

Earlier quoted context omitted.

> 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.

a fun thought exercise - what would have to happen to HN for this to come true? basically all the old guard have to age out and not pass on the reference?

Re: Tailscale has raised $160M

#75
post #2

When I saw the new round, I was instantly worried about change in direction that will most likely come with this, and effectively drive away regular users from a tool that seems universally loved. Similar sentiment can be seen in the discussion from three years ago [1] when they raised $100M. [1] https://news.ycombinator.com/item?id=31259950

This is mostly so that the founders can take some money off the table. The founders probably have $10 million cash after this and don't have to worry about rent ever again.

Re: Tailscale has raised $160M

#76
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…

If it's hype, it's not hype the way you're thinking. I've shown Tailscale to a lot of people (this is less salient now, when pretty much everybody uses Tailscale) and the most common reaction I've gotten is "holy shit". It is spooky simple to get working, and it's spooky simple to go from a working installation to a VPN configuration that would take many many hours to replicate with pre-existing tools.

There may be VPN nerds out there who think there's nothing special happening with Tailscale, but I submit those nerds haven't spent a lot of time dealing with the median, replacement-level VPN configuration prior to Tailscale. I'm a pentester, and so I have had that pleasure. Tailscale is revolutionary compared to what it replaced.

Re: Tailscale has raised $160M

#77
post #2

When I saw the new round, I was instantly worried about change in direction that will most likely come with this, and effectively drive away regular users from a tool that seems universally loved. Similar sentiment can be seen in the discussion from three years ago [1] when they raised $100M. [1] https://news.ycombinator.com/item?id=31259950

This is mostly so that the founders can take some money off the table. The founders probably have $10 million cash after this and don't have to worry about rent ever again.

The founders of Tailscale probably weren't too worried about rent before Tailscale.

Re: Tailscale has raised $160M

#78

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.

I think they might be operating at a scale that breaks those kinds of pages at this point? Not literally, of course, just they're past the point where the page makes sense.

Re: Tailscale has raised $160M

#79
post #74

Earlier quoted context omitted.

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

a fun thought exercise - what would have to happen to HN for this to come true? basically all the old guard have to age out and not pass on the reference?

Ea-Nasir

Us humans are kinda ok at preserving knowledge (and we're getting even better, but not in a good way).

Re: Tailscale has raised $160M

#80

Earlier quoted context omitted.

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.

That depends on the share classes. Companies with high interest from investors can sometimes get them to accept shares with reduced voting rights.
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