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Tailscale raises $100M

tailscale.com

321–330 of 468 posts

Re: Tailscale raises $100M

#321

Earlier quoted context omitted.

> a direct ring of trust with friends The vision you outlined is great, except it doesn't work. The trust assumptions are too high, and even a great product like Tailscale seems to rely completely on centralized identity providers (you have to choose Google, Microsoft, or Github on sign-in). Ultimately, if you want to maintain full control of your online identity and network, you'll probably need some of the decentra…

I feel like people are so concerned about infinite scaling that nobody ever tries to scale to 5 anymore. I have a big collection of movies, and I’d like my mom-technical blue collar friends to be able to watch them. I trust them, and I have trusted communication channels with them. We exchange keys somehow . With the sort of routing I’m describing, they could watch my movies and I wouldn’t have to have a public IP ad…

Definitely stealing mom-technical. Though I do disagree somewhat with the conflation with blue-collar. I would almost argue white-collar folks are less likely to understand computers.

Re: Tailscale raises $100M

#322
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.

I've seen them mention that they're looking at having the coordination server being self-hostable (and is for some client already), so I expect that to be one of the things you can get at the higher price points in the near future.

Re: Tailscale raises $100M

#323
post #97
post #81

Earlier quoted context omitted.

I thought that Tailscale was pretty interesting. Avery Pennarun, its CTO, is somebody whose judgment I am used to trusting. Then I learned that to use it, I would be dependent on authenticating using a login on one of the unaccountable internet behemoths who could take away my account for any random reason or no expressed reason at all. No, thank you.

If you use an identity provider like Okta or OneLogin, then you're not tied to any "contentful" services like GitHub or a Google account that "historically" seem to have more problems of this type. As far as threat models go, I can't really say I understand this one too much.

For enterprise, sure, using a separate IDM provider works, but last I checked, neither Okta nor OneLogin cater to individuals and their personal accounts. So as far as threat models go, I understand why people view this requirement from Tailscale as utter garbage for personal accounts.

Re: Tailscale raises $100M

#324

Earlier quoted context omitted.

I don't think Tailscale will focus on the consumer market, I'd be very surprised at least if they did. I think they built a developer-friendly product to get mindshare and early adoptors, but eventually the real market for such such products is in the B2B space, i.e. implementing the "BeyondCorp" model of zero-trust networking. There's also a market for building cloud mesh services but I'm not sure if Tailscale is we…

They already (sort of) do [0] as they have a "Personal Pro" plan that's not too obvious - personally, I hope they expand to make it more cloud-native via a la carte pricing for those users as I'd pay an extra $x/month for an additional subnet router or three. And, IMO, it's a smart approach - those who are the targeted "Prosumer" might leverage this for their homelab and carry it over with them into the enterprise. I…

I remember Astaro did this with their Astaro Security Gateway UTM solution. Provide a full featured software appliance for home users and hope the admins are so caught up that they don't want to change to another vendor at work. Astaro got acquired by Sophos in 2011 but I just checked, they still offer the Sophos UTM Gateway in a Home edition.

https://www.sophos.com/en-us/free-tools/sophos-xg-firewall-h...

Re: Tailscale raises $100M

#325

Tailscale is my favorite (product) discovery of 2022. I initially set it up to use as a VPN to get around a misbehaving corporate firewall and accidentally realized it solved a whole bunch of other problems I didn't realize I had. Usually a new product doesn't even live up to the intended use case and so TS is really anomalous IMHO in how good it is. - SSH'ing into a raspberry pi I have at home that does random IoT s…

Why use SSH? With Tailscale all you need is rsh ;)

Re: Tailscale raises $100M

#326
post #287

Earlier quoted context omitted.

But doesn't apply to my wireguard setup on my OPNSense installation at home.

This is the HN disconnect: people commenting here have completely different concerns than Tailscale's actual customers.

That is true. Sometimes we are talking about the business aspects of product-market fit, and sometimes we are talking about our own personal use of the product or domain. In this case it's both.

Re: Tailscale raises $100M

#327

Tailscale has a fantastic product, I’ve been extremely happy from day one. If you’re waiting for a weekend to have a few hours to try out Tailscale, don’t, it takes 15 minutes to get every device you own up and running and talking. This is the lowest friction personal VPN to ever exist, and once you see how easy it is for your own devices, you’ll wish you had it at work. The biggest risk that this company has is that…

> The biggest risk that this company has is that Cloudflare (in all reality) should just buy them or reimplement it. It’s the type of product cloudflare would make, that’s for sure.

The same thing is being said on HN about all kind of network software, but tell me one software that Cloudflare is really known for except its cdn ? None.

HN is really a strong echo chamber and some people believe Cloudflare and Stripe are going to be the leader in all software areas. (Even though Cloudflare is not the leading CDN and Stripe is not the leading payment processor). They are both amazing companies but they won't fix all problems of the world. I would even argue that they won't even solve more than their current core domains

Re: Tailscale raises $100M

#328
post #224

Earlier quoted context omitted.

I self host headscale as my control node of my tailscale vpn so no sign ins required, I just give keys out to anyone I want in my vpn. My problem is the client doesn't support multiple servers, so I can't have a work vpn and a home vpn, not even with an easy toggle - you have to run tailscale with different conf options for both. Changing namespaces also isn't easy, so having friends and family segregated even on one…

Thanks the main objection I have with tailscale is that you can't self-host (and you need external identity providers). I had no idea there was a self host option. I'll investigate. I assume it's an unsupported community option?

op is talking about headscale [0] "An open source, self-hosted implementation of the Tailscale control server"

[0] https://github.com/juanfont/headscale

Re: Tailscale raises $100M

#329
post #193

Funding scares me. It bring sharks onboard who do not share the same vision. They will demand revenue and ROI above all else. I like Tailscale but I hate this business model down to the core (Netlify as an example). Tailscale was doing fine as it was, capable people there already. It quickly became an "exit type of business", too quickly. These companies usually bring something really easy to use, let people onboard…

Tailscale investor here. I can assure you we share the same vision with the founders.

The problem is that vision has a pretty poor track record when going head-to-head with incentives.

Re: Tailscale raises $100M

#330
post #327

Tailscale has a fantastic product, I’ve been extremely happy from day one. If you’re waiting for a weekend to have a few hours to try out Tailscale, don’t, it takes 15 minutes to get every device you own up and running and talking. This is the lowest friction personal VPN to ever exist, and once you see how easy it is for your own devices, you’ll wish you had it at work. The biggest risk that this company has is that…

> The biggest risk that this company has is that Cloudflare (in all reality) should just buy them or reimplement it. It’s the type of product cloudflare would make, that’s for sure. The same thing is being said on HN about all kind of network software, but tell me one software that Cloudflare is really known for except its cdn ? None. HN is really a strong echo chamber and some people believe Cloudflare and Stripe ar…

We must be in different circles, because WAF (web application firewall) is what I would say they're most known for. But I agree Cloudflare isn't well known (at least yet) fort many of the other things they offer. Been a lot of buzz around workers but I haven't tried it myself yet.
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