I just wished their server side was open source also
Tailscale has raised $160M
111–120 of 354 posts
Re: Tailscale has raised $160M
#112Earlier quoted context omitted.
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).
brb destroying some magnetic tapes because i can just put them on the cloud
Re: Tailscale has raised $160M
#113I just wished their server side was open source also
Re: Tailscale has raised $160M
#114Earlier quoted context omitted.
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.
Yes; you will burn through all the capital you raise in ~18 months. It is _extremely_ difficult to efficiently allocate large raises (100M+) in 18 months. In fact, I’m developing a pet thesis that no single human or business can efficiently allocate more than $100M. This would imply that any time a single raise is more than 100M, the investors always would have had a better return by splitting it into chunks of 100M…
The benefit for VC of lending you more than you need is (a) getting the owners hooked on spending money, then (b) taking control.
Re: Tailscale has raised $160M
#115If 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.
That's much less of a problem than not being able to raise enough in the next round because you only 1.5x'd instead of 3 or 5.
Re: Tailscale has raised $160M
#116Off-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.
It's super useful to potential hires about the kind of team you're building. Especially if there's some kind of niche you're in (product, tech, region, whatever). There are people who I would climb mountains to work with, and others within a niche whose very presence in a company is enough to steer me away. Another signal for me is the fraction of xooglers in the engineering team.
Re: Tailscale has raised $160M
#117Does 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…
Yes! I also experience this. I also had some weird interaction with another wireguard-based VPN and Tailscale, where it crashed my DNS so hard I had to reset my entire laptop.
Re: Tailscale has raised $160M
#118Off-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.
Eh. Investors/advisors don't change that frequently. And often people will go "oh? Sequoia generally invests in good companies, the invest in X? They might be worth while to buy/work for".
Putting people on the website is, very variable. Do you update the website every week or two when someone comes or leaves? Well that's awkward if someone is fired.
You get to 100 people, then 200 people. Now what do you do? Remove everyone? Only put people on above a certain level? What do you do when someone asks you not to be listed. Or when John becomes Jane, but doesn't want to be super duper public about it?
Or, when your company gets media attention and now the moment you add/remove someone from the website you get news or social media posts about it?
Re: Tailscale has raised $160M
#119If 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…
> Equity investments like this don't need to be repaid
You are saying equity is not bonds.
However investors expect to be repaid in the future with control and exhorbitant interest rates (based on risk). VC invests to make money, but that money comes from future equity rounds or IPO.
If you didn't take the VC money (and the business achieved the same growth without the money) then you'd expect you would have been better off by at least the amount invested (investors don't invest with the expectation of only getting their money back).
If the business doesn't succeed then you are on the hook to pay the debt from your equity via liquidation preferences.
VC payment is expectation statistics, but the investors know that game and invest to make money. That money comes from the current equity owners making less in the future.
Re: Tailscale has raised $160M
#120Earlier quoted context omitted.
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 V…
Because you're delegating the control plane to Tailscale. Somehow we went decades without this being a thing for security reasons, dealt with the management of VPN appliances, and now suddenly everyone is OK with Tailscale owning the control plane of their VPN for the sake of convenience.