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Tailscale raises $100M

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Re: Tailscale raises $100M

#32

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

"Fixing the internet" == you can comunicate with computers that want to comunicate with you, and not with others.

Re: Tailscale raises $100M

#33

Am I the only one that has an issue with a VPN that I can't self host? Presumably if Tailscale get's PWN'd or subpoenaed then your network is breached no?

Depends on the kind of breach. Tailscale is extremely carefully designed to minimize that risk. Notably: Tailscale doesn't get your keys. (Granted: a compromised agent would still be a problem. It's a thing I have some plans for :-))

(Disclosure: I'm a (small) investor via Latacora's sibling fund, Lagomorphic.)

Re: Tailscale raises $100M

#34
post #10

> For people who believe there’s a catch — and most still do — then I don’t know how to write a blog post or hire a marketing or sales team to change their minds. I think the catch is that (at least at the free level) one must trust an identity providers. For many companies that's probably fair enough, but for high-security companies and private individuals one absolutely cannot trust anything running outside of one'…

Yep we had it rejected w an enterprise we work with as the org needed to own the full control plane so we couldn't bring it in, and not on the schedule for the org's security team for them to bring it in. Making a smarter, easier, and less creepily managed VPN more palatable to enterprises would be awesome, so the marketing value of their fundraise is real.

Re: Tailscale raises $100M

#35

Unfortunately despite claiming that they would, they've never allowed their iOS application to allow configuration of the control server (every other client they have released does). Maybe some more funding will allow them to focus on the client quality.

also, their iOS client still has abysmal background battery usage even when not connected. It has been more than a year now, so, yes, seeing them improve in such areas would be cool.

But given the huge amount of money invested, pressure will go into other directions. I'm afraid my (aside of the iOS issues) beloved Tailscale is on a path to expensive enterprisey bloat, losing what made it so good (the JSON based ACLs, the external authentication provider reliance, etc - GitHub Auth is a killer-feature for me for example)

Re: Tailscale raises $100M

#36
I remember reading a previous HN post about Tailscale and a certain commenter said that Tailscale is ideologically driven, small-scale operation and they prefer an alternative like NetMaker which has more backing.

$100M seems more than a small-scale operation or is $100M in tech actually small scale?

Re: Tailscale raises $100M

#37
post #9

With such a huge investment comes the obligation to eventually pay it back. Is this another one of my favourite tools going the way of Dropbox, 1Password and all other companies that were formed around what should be a platform feature, which took on way too large investment sums and were eventually forced to become the everything, losing sight of their core values? I sincerely hope not, but there's so much bad prece…

I haven't really felt like 1Password's product materially strayed from the original mission. If anything, I'm even more delighted with the team functionality, shared vaults, quick keyboard access in 1Password 8, etc. I wouldn't put them in the Dropbox bucket. Also, I think the value Tailscale provides is fairly unique and far from obviously a platform feature like file storage and perhaps even password management.

Indeed, 1Password is practically a utility at this point, as far as I'm concerned. I really like the direction they're heading and they're solving some pretty tricky problems without compromising on security, predominantly in the enterprise domain. The experience is the same regardless of whether you're an enterprise user or a personal or family user. It's polished enough that my grandma can use it.

Re: Tailscale raises $100M

#38
post #10

> For people who believe there’s a catch — and most still do — then I don’t know how to write a blog post or hire a marketing or sales team to change their minds. I think the catch is that (at least at the free level) one must trust an identity providers. For many companies that's probably fair enough, but for high-security companies and private individuals one absolutely cannot trust anything running outside of one'…

Tailscale will let you use any SAML or OIDC provider you like in the Enterprise plan (presumably because of the cost of supporting the long tail of nonsense IdPs will produce).

(Disclosure: I'm a (small) investor via Latacora's sibling fund, Lagomorphic.)

Re: Tailscale raises $100M

#39

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

Tailscale is one of the ways you can restore the end-to-end connectivity principle that IP introduced and that NAT destroyed.
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