Tailscale has raised $160M

by louis-paul • 1 year ago

659 330 1 year ago

elAhmo• 1 year ago

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

braginini• 1 year ago

Try netbird which is an open-source alternative to free yourself from worries xD https://github.com/netbirdio/netbird

650REDHAIR• 1 year ago

Thank you for sharing this link!

I was about to slog through AI search results looking for an alternative.

arcanemachiner• 1 year ago

I've always been on the outside looking in, so I've never used Tailscale or its open-source brethren.

Would this service be comparable to Headscale[0]?

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

resiros• 1 year ago

I use personally for my home network. Very easy to use and quite mature. I'd highly recommend.

regisso• 1 year ago

I highly recommend netbird, after using it for two years. The whole stack can be self hosted is open source develop by an european based company.

Valord• 1 year ago

I share your concerns.

pomatic2• 1 year ago

When they raised the 100M three years ago, I'm pretty sure they said they didn't need it and were saving it for a rainy day (or words to that effect), always seemed very odd at the time. Two q's for anyone who cares to speculate: have they burnt the original investment already? And if not, why would they need more funding? AFAICS there's no real competition in the market place for their product today, the only thing I can conceive is that they have a secret 'tailscale 2' project in the wings which is massively developer or capital intensive. Let's hope it is nothing related to AI band wagoning :-)

chubot• 1 year ago

Hm OK well thinking out loud, $100M / 3 is $33M / year?

I don't know much about Tailscale, nor about how much it costs to run a company, but I thought it was mostly a software company?

I would imagine that salaries are the main cost, and revenue could cover salaries? (seems like they have a solid model - https://tailscale.com/pricing)

I'm sure they have some cloud fees, but I thought it was mostly "control plane" and not data plane, so it should be cheap?

I could be massively misunderstanding what Tailscale is ...

Did the product change a lot in the last 3 years?

fragmede3• 1 year ago

There might be other things going on in the US that you could maybe possibly have heard about, and investors are looking for different places other than the US stock market to invest their money, and Tailscale is looking to have a war chest because of the exceedingly possible case that we're headed into a global recession.

api• 1 year ago

You can't raise VC money and save it for a rainy day. If VCs wanted their money in a bank they'd just put it in a bank.

If you raise $100M you have to put $100M to work or you'll hear constant shit from your board over it.

If they raised $160M they're going to spend $160M on something. My guess would be a lot of enterprise features and product integrations.

refulgentis• 1 year ago

I still don't know what it is and I've been reading about it for N years here. On some level, it's healthy to take capital.

kortilla2• 1 year ago

AFAICS there's no real competition in the market place for their product today

What does this mean? They are competing with regular legacy VPNs for sure. Despite tailscale existing for the last 4 years, none of the large corporate clients even got closed to it. They were all on junk from Cisco, Palo Alto, to connect employees to corp net. A “cutting edge” one might use cloudflare warp.

You might be right that there isn’t much competition for pure distributed, but it turns out the market for that is actually quite small and it’s for people who can’t afford dedicated IPs or cloud instances.

Raising money here is a bad sign IMO unless it’s for a completely new product that requires servers at exchanges to eat CDNs like cloudflare’s lunch.

PLG885• 1 year ago

There is tons of competition for Tailscale. Its 'just' an easier to use VPN with a great GTM exceution. I think they need more money as they need to fundamentally re-architect their solution to sell into enterprise use cases they their valuation requires.

specialp• 1 year ago

There are plenty of enterprises that will pay them to run their services and provide better integrations while allowing open source users to continue. Now people will get upset because some of these things will be for those customers only but it is very hard to keep developing these things and give them out for free. Partially open source still allows those to extend the work they give to the community and they will probably still continue to have a free tier to get more enterprise customers in the end.

ilrwbwrkhv3• 1 year ago

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.

tptacek5• 1 year ago

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

otterley• 1 year ago

How is Tailscale going to achieve at least $1B in annual revenue? That’s the kind of promise that would have to be made to investors in order to raise funding of this magnitude.

datadrivenangel• 1 year ago

Become the provider of choice for enterprise IT networks or get bought by Azure?

SparkyMcUnicorn• 1 year ago

get bought by Azure

Please no.

john2x• 1 year ago

We’re like trading cards to these people

throw16180339• 1 year ago

My prediction is that they'll be bought by Cisco.

baq2• 1 year ago

One would hope they’d create something like Google drive except you own your stuff that people would pay for.

fidotron3• 1 year ago

So you want a file system data store that distributes the data over the nodes you own in a sort of dynamic P2P way?

raggi2• 1 year ago

https://tailscale.com/kb/1369/taildrive

borski• 1 year ago

I imagine this was, at least in part, part of the pitch deck.

runako• 1 year ago

$1B annual revenue is ~4m business users. This is considerably smaller than e.g. Zscaler or Okta. It's a big goal, but achieving it does not require them to sign a majority of businesses or build a monopoly.

mountainriver• 1 year ago

Easily, tailscale solves on of the hardest problems in software

mrweasel• 1 year ago

Naming things?

PLG885• 1 year ago

Do they? What does it do that nothing else does?

sshine2• 1 year ago

so tailscale is selling out

that was disappointing

at least the current software is open source, so others can fork it before it closes down on itself and enshittifies.

kube-system• 1 year ago

Tailscale is a software company founded in 2019 that raised their series A in 2020, not a grassroots community project

sshine2• 1 year ago

so either you do it out of the goodness of your heart, or you maximize shareholder value at no expense

I'd sell out at $160M, too. I'm happy for them, and sad for everyone else.

brunoqc• 1 year ago

at least the current software is open source

Not the server.

headscale is nice, but it's not an official project.

4k93n2• 1 year ago

netbird looks like it would be a better option if open source is what youre after. theres a handful of others too, nebula, zerotier, netmaker just to name a few

cadamsdotcom• 1 year ago

Good. This lets them receive some of the value they’ve created (they should get paid!) and gives certainty they won’t go out of business. Which means more Tailscale now and in future!

If they turn evil (unlikely with the current folks there) they’ve written up / open sourced plenty of what got them to this point.

Don’t capture all the value you create. But you should try to capture some.

briffle• 1 year ago

The same thing has been said about many other companies taking on VC Money. Someday, those investors are going to want to see a return on that investment. Its going to take focus and determination to not just ship enshittification as a feature..

bananapub• 1 year ago

it is a nice that they're a bit embarrassed about it and spend much of the post explaining why they took more money.

overall, they still seem to have their heads screwed on straight and have an actual business model, that is also pretty fair - charge enterprises per seat to solve their network identity problems.

anyway, keep up the good work, Avery and co.

burningion2• 1 year ago

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...

syntaxing3• 1 year ago

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?

burningion2• 1 year ago

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.

ilrwbwrkhv3• 1 year ago

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

tonyarkles• 1 year ago

That was our initial use case for Tailscale as well. May 2020 we started growing a team and needed a really smooth remote access solution for a bunch of Xaviers... and we weren't allowed to be in the same room together :)

joemazerino• 1 year ago

Tailscale was invaluable for connecting my remote offices together. Long gone are the days of openvpn configs

srameshc• 1 year ago

I don't probably use Tailscale to it's full potential but I love this tool. We have our small servers at our offices across the world and it has give us so much flexibility to access some of the files via shared drives or try out installing / testing stuff. Me and my wife also drop each other pictures of our kids using tailscale now.

codethief4• 1 year ago

Me and my wife also drop each other pictures of our kids using tailscale now.

What application are you using for that (on top of Tailscale, that is)?

renerick• 1 year ago

Tailscale has Taildrop - built-in peer-to-peer file sharing feature

https://tailscale.com/kb/1106/taildrop

dharmab• 1 year ago

I'm using it for friends and family file sharing, it's fantastic.

suralind• 1 year ago

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.

Carrok• 1 year ago

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.

pestaa• 1 year ago

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.

duped2• 1 year ago

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.

guappa2• 1 year ago

Because it's so cool when I go "oh hey I know that guy!"

tptacek5• 1 year ago

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.

Valien• 1 year ago

You can always find a lot of us on LinkedIn :D {I work at Tailscale}

jedberg• 1 year ago

Cloudflare still has their about page with thousands of people:

https://www.cloudflare.com/people/

freedomben2• 1 year ago

I agree it's silly, but worth noting is that the target audience for those pages are usually:

1. Potential customers

2. Potential investors

Both groups are a lot more swayable by social proof from seeing the "investors" than the devs as they infer a lot of credibility based on who has funded you. Similarly that's why you often see big company logos on marketing pages because it makes other customers more likely to buy. "<xyz> is too big to be wrong about this product"

ShakataGaNai• 1 year ago

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?

Hamuko• 1 year ago

I think my employer decided to remove all non-executives at some point to ward off headhunters. Not sure how much it helps considering everyone's on LinkedIn.

xyst3• 1 year ago

This is a press release targeted by rapacious capitalists. By mentioning other big named investors, you keep the grift going and continue securing future funding until IPO.

groby_b3• 1 year ago

TBF, the folks who get actual value out of knowing who works at Tailscale already know who works there :)

They're not exactly secretive, there's just little value to have it on the main company page. (And if you just want pictures, https://tailscale.com/careers has that too.)

ErigmolCt3• 1 year ago

Feels like tech companies treat engineers like implementation details until they need to hire more of them.

PeterStuer2• 1 year ago

Companies hide their employees, especialy the real value adding ones, for fear of them getting poached.

apitman• 1 year ago

Even if it could mean Tailscale enshittifies eventually, this is probably a good thing for the ecosystem. As one example, the bigger they get, the more likely operating systems will build better APIs to support what they do (for example maybe Apple will provide a way to do mDNS over Tailscale), and those APIs can be used by all.

There are plenty of open source alternatives cropping up[0]. I'm curious to see what Tailscale can do with a lot of resources.

[0] https://github.com/anderspitman/awesome-tunneling?tab=readme...

LeoPanthera• 1 year ago

Apple had a Tailscale-style feature called "Back to my Mac" that was part of MobileMe. They killed it off with the rest of MobileMe, presumably because they just wanted you to store everything in iCloud.

mrbonner• 1 year ago

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.

baq2• 1 year ago

Yeah, you need to be conscious about your tailscale domain, your .home (or whatever your router or dhcp server advertises) and your .local hostnames. Even if you’re aware, things are sometimes wonky, IME primarily on macOS.

saurik• 1 year ago

I am on Arch and often end up with DNS broken in a way that requires me to restart tailscaled.

nickzelei• 1 year ago

I've had issues with tailscale dns for a while where I'll wake my mac up and the dns will just not work until I disable tailscale. I can then re-enable it and everything continues to work.

I logged a bug about it and the latest versions this seems to have gone away. I also moved away from the mac store variant and into the standalone. Not sure if that helped either.

fidotron3• 1 year ago

Yeah, I honestly couldn't get Tailscale to work reliably at all. DNS, routing, firewalls etc. My overall impression was it will work if either you go for it on your entire local subnet, or you have a very simple local network topology. Having local nodes inexplicably talking to each other via a cloud relay basically all the time just isn't acceptable. (And webrtc could always find the local candidates when doing ICE, so it's not that).

It's interesting because they have clearly demonstrated a demand for such a thing, but the "just works" pitch is a fantasy, at least today.

evanjrowley• 1 year ago

Sometimes I have issues like this. It's related to my ISP not supporting IPv6. I don't have time to explain this in detail, but at least that's one angle of it that you might want to explore further.

nickthegreek• 1 year ago

Same. When my cell has an ip6 ip, I can’t get dns to resolve on my systems at home. I can still access everything by ip4 ip though. I haven’t had time to find a solution yet. I’m still trying to figure out if it’s nginx, pi-hole, router, or Tailscale config related… probably a combination.

theglocksaint• 1 year ago

The subnet routing feature can cause network issues

belthesar2• 1 year ago

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.

selfmodruntime• 1 year ago

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.

briHass2• 1 year ago

I don't know how it works on Linux, but for Windows, the 'MagicDNS' just automatically adds a bunch of static entries to your hosts file to resolve the TS FQDNs and simple/machine names.

geenat• 1 year ago

IMHO they should be a good steward and toss the Wireguard guy a mil considering Tailscale is pretty much Wireguard with a GUI on top.

belthesar2• 1 year ago

Tailscale is definitely more than "Wireguard with a GUI", but I don't think that diminishes your point that Tailscale, if they're not already, would be great stewards if they were contributing more than code back to the Wireguard project.

aborsy2• 1 year ago

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.

homebrewer• 1 year ago

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 secure VPN protocol underneath, which is why GP's comment is on point.

aqfamnzc• 1 year ago

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...

agentdrek• 1 year ago

Probably closer to say that Dropbox is a GUI on top of WebDAV

ignoramous2• 1 year ago

they should be a good steward

Tailscale did make a donation to WireGuard. They have regularly contributed to wireguard-go, including the complicated GRO/GSO bits.

  "Tailscale made a donation during September 2022, as part of their business centered around WireGuard." https://www.wireguard.com/donations/ / https://archive.vn/MMAXO

> Tailscale is pretty much Wireguard with a GUI on top.

Well, isn't PUBG a GUI on top of Unreal?

johnbellone2• 1 year ago

PUBG pays licensing fees to Epic Games (Unreal).

jdoss• 1 year ago

Jason Donenfeld is listed as a Technical Advisor on https://tailscale.com/company. Most companies pay their advisors something, so I assume something monetary is going on here for him.

ignoramous2• 1 year ago

  When we started Tailscale in 2019, we weren't even sure we wanted to be a venture-backed company. We just wanted to fix networking. Or, more specifically, make networking disappear — reduce the number of times anyone had to think about NAT traversal or VPN configurations ever again.

Isn't logtail what got Avery et al started?

https://github.com/tailscale/tailscale/tree/main/logtail

https://apenwarr.ca/log/20190216 / https://archive.vn/xlsA1

everfrustrated• 1 year ago

That's quite insightful actually. Perhaps might explain the tailscale name a little better in that context also.

tmpz22• 1 year ago

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 product (as does everyone I talk to) but genuinely want to learn more about the trade-offs as usually when we see big dollar signs all we do is celebrate.

lazzlazzlazz• 1 year ago

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.

mitthrowaway2• 1 year ago

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.

cj• 1 year ago

(3) investors offer the option for founders (and earlier investors) to take money off the table by buying up a percentage of their stake, essentially creating a mini-exit for the founder and earlier investors

robocat2• 1 year ago

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.

vvpan• 1 year ago

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.

peterlk2• 1 year ago

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 or less. It’s not a _good_ thesis yet, just one I’m performing thought experiments with

duped2• 1 year ago

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.

IncreasePosts• 1 year ago

No one is going to answer you because no one has seen their books.

alecco• 1 year ago

obligatory "Raising too much money" (Silicon Valley) https://www.youtube.com/watch?v=8ZgfTarNxdY

pc863• 1 year ago

I'd be curious how much of this $160 million is immediately allocated to bonuses, founders taking money off the table, increased salaries, employee option pools, etc.

alabastervlog• 1 year ago

Yeah I take this as bad news, as a user. I dread the inevitable enshittification. Hopefully open source UX over Wireguard is close-enough to as good by the time they drive me away that losing them isn't too painful.

Took a project I'd been putting off and putting off because I knew it'd eat half a Saturday, and made it a 20-minute affair from signup to having everything done, including adding some devices to the network that I wouldn't even have bothered to try adding on my own.

aborsy2• 1 year ago

Tailscale deserves it. They have produced excellent software.

devmor3• 1 year ago

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.

slig• 1 year ago

They have raised before, so that money helped shape the service you enjoy.

devmor3• 1 year ago

Yes, but when they raised before they did not give up a bunch of control in return.

elevation• 1 year ago

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.

th0ma5• 1 year ago

What are the failure points of hosted solutions like Tail scale versus self hosted options?

chgs• 1 year ago

Tailscale has a single management engine. My understanding is that if the goes your existing traffic will still flow, but new connections won’t be made.

codethief4• 1 year ago

Everyone is commenting on the HN headline, no one on the actual post:

Building the New Internet

(Insert mandatory reference to Silicon Valley here :))

We think there’s a better way forward. We're calling it identity-first networking.

I would love to see this. Every day I have to stare at YAML files with IP addresses in them is a day I will never get back. I wish cjdns[0] had succeeded already but oh well, now I hope the Tailscale guys will!

[0] https://github.com/cjdelisle/cjdns/

transpute2• 1 year ago

Operant has something similar in IIoT, https://operantnetworks.com/sie-sbd-part2/

  1. Immutable Content Naming: In a data-centric system, content is addressed by its name, transcending geographical considerations. This circumvents the vulnerabilities associated with IP addresses, which can be spoofed or manipulated. By employing cryptographic techniques to validate the authenticity of content names, NDN establishes a robust layer of security that underpins the entire architecture.

  2. Built-In Data Integrity: NDN employs built-in mechanisms to ensure the integrity of data. Content is signed by publishers and verified by consumers, preventing tampering or unauthorized alterations. This approach effectively mitigates data breaches, as any unauthorized modification is detected and rejected.

codethief4• 1 year ago

This is about data, though, not about addresses, is it?

jncfhnb• 1 year ago

Fingers crossed they’ll finally enable sending files to people

mrdoornbos• 1 year ago

This sort of thing tends to trend bad for users.

segmondy• 1 year ago

woot, woot, happy for the team. I love tailscale and can't stop singing praises.

nottorp• 1 year ago

Entshittification incoming?

nextworddev• 1 year ago

You know it

finnjohnsen2• 1 year ago

I just wished their server side was open source also

flkenosad• 1 year ago

https://github.com/juanfont/headscale

rounce• 1 year ago

It’s pretty hobbled compared with OG Tailscale, so much so that I moved completely to self-hosted NetBird and haven’t looked back.

beng-nl• 1 year ago

There is a open source clone for the Tailscale server named headscale fwiw.

amriksohata• 1 year ago

What's the difference between this and say azure vent and configuring that with private endpoints

breakingcups• 1 year ago

Oh no. That's really too bad. Fingers crossed they'll beat the VC curse because it is so close to perfect as it is right now.

tonymet• 1 year ago

anyone care to share how they are spending money? labor, operations (training, transfer fees), marketing & business development. It's different than industries I'm more familiar with.

maxclark• 1 year ago

$33m/year burn accelerating to $50m+/year

Profitability and exit math just got harder

I love the service and am rooting for them - I just don’t get this cash outlay

I can’t wait to learn what I’m missing here

xyst3• 1 year ago

Hope this means headscale involvement doesn’t get 86’d.

As I recall, a few tailscale folks contribute to this open source implementation of the “coordination server”. Apparently tailscale management approved it. So this means management at any time can revoke it, and possibly kill off self hosting of the coordination server as the open source clients become incompatible.

robinhood• 1 year ago

Enshittification will start in 3... 2... 1....

Uzmanali2• 1 year ago

Tailscale just got a lot of money to keep growing. But what they are doing is more important than the money. They are helping computers talk to each other in an easy and safe way.

Before, the internet was built to connect places, not people. That made things messy. People had to set up tricky stuff like VPNs and firewalls. Tailscale makes this much easier by using your name or account, not just numbers like IP addresses.

Now, big companies and people at home use Tailscale to keep their computers and apps connected. It works without a lot of setup, and it’s safe. Even people building smart robots and AI are using it.

What’s really good is that Tailscale still helps small users for free, and they try hard not to break anything when they update their tools. If they keep doing that, they can become a very important part of how the internet works in the future.

jychang• 1 year ago

This comment reads like simple.wikipedia.org

Uzmanali2• 1 year ago

Haha, fair point! I guess i was going for simple Wikipedia rather than deep academic journal. Maybe next time i'll throw in some fancy words just to spice things up.

briHass2• 1 year ago

I'm a fan of TS and have been a paying customer for work infra for almost a year now. It really is well put together and easy to use, but I do run up against some issues/complaints when diving deep that I hope they can work out:

* The pricing tiers and included features by tier penalizes you in frustrating ways. The base plan is a reasonable $6/user/m, but if you want to use ACLs to control anything in a workable way, it jumps 3x to $18/u/m. Better solutions are available for that kind of money, and I shudder to imagine what the next tier ('call us') costs.

* Subnet routing broke on Ubuntu (maybe other distros) recently, and there were no alerts, communication from TS, or TS tools to pinpoint/figure out what was going on. I stumbled on a solution (install subnet router on a Windows box), and from there I searched and found others with that issue. Lost half a day in emergency mode over that!

* Better tooling to determine why it's falling back to DERP instead of direct for remote clients. DERP relays should be an absolute last resort to provide connectivity for Business-plan-level customers (very slow), and the way TS works just assumes any connectivity is fine.

Overall, the simplicity and abstraction of complex VPN networking is wonderful, but if you have issues or advanced needs, you are immediately thrust into the low-level UDP/NAT/STUN world you were trying to avoid. At that point, you're better off using a traditional VPN (WG, OpenVPN, or heaven forbid, IPSec), because it ends up being more straightforward (not easier) without the abstractions and easy-button stuff.

smashed• 1 year ago

* Better tooling to determine why it's falling back to DERP instead of direct for remote clients. DERP relays should be an absolute last resort to provide connectivity for Business-plan-level customers (very slow), and the way TS works just assumes any connectivity is fine.

Tailscale touts all the perf benefits of the wireguard protocol but in practice between the userland wireguard that seems to be used all the time on all platform (even linux) and the over reliance on DERP, it has none of the performance benefits of the real thing.

miki123211• 1 year ago

They also seem to be needlessly doing DERP over TCP in some cases where UDP would actually work.

diegs• 1 year ago

I thought they vastly improved user-space wireguard performance?

https://tailscale.com/blog/more-throughput

Not sure if the kernel implementation pulled ahead again, I don't really follow these things.

Also not defending tailscale, I respect them but I agree they are a one size fits some solution.

atomicnumber3• 1 year ago

$6/user/m, but if you want to use ACLs to control anything in a workable way, it jumps 3x to $18/u/m.

It's market segmentation, needing ACLs is a sign you're at least an SMB, and to a business of nearly any actual size, the difference between $6/user and $18/user is 0.

dexterdog• 1 year ago

Um, it's 3x the cost to get one feature. By your logic they should be charging $100/user/mo for the feature since that must also be the same. This is typical "enterprise" nonsense pricing and it will absolutely drive some adopters to look elsewhere.

wkat42423• 1 year ago

Uh I work for an enterprise of tens of thousands of users and $18 a month is not nothing for us. In fact considering the discounts we get at our size that would be so high we'd never consider it.

We don't even use windows enterprise for the same reason, we have legacy office 365 plans and lifetime windows licenses without the M365 addons because it saves is a few bucks per head. At our size, a few bucks a head quickly add up to millions per year. Microsoft keeps trying to dissuade us and they even pretend office 365 plans don't exist anymore ("office 365 is now microsoft 365") but they do: https://www.microsoft.com/en-us/microsoft-365/enterprise/off... . The same with their Copilot stuff. 30$ is a non starter. Our users want it but nope (and we did a trial in one big team and only 10% actually bothered to use it after the first month so I think it's more the idea of it that want rather than the actual product)

We don't use Tailscale but $6 would be feasible where $18 would be a complete nonstarter.

In fact our company is a lot more cost conscious than I am as a consumer.

TorKlingberg• 1 year ago

difference between $6/user and $18/user is 0

I wouldn't go that far. Big companies put a lot of effort into saving $12/seat.

But, if you can convince them they get >$18 of value from it they're usually happy to pay. With hobbyists it's more emotional. $6 is "just a coffee" and can be justified just to try it out. At $18/m is one of your household bills, and many will decide they enjoy watching Netflix more than messing around with Tailscale.

imtringued• 1 year ago

It's zero for small businesses with a dozen employees. The moment you have a large business you run into an obvious problem: only a subset of your employees actually use the software, but if even a single user needs a higher tier you have to upgrade all users.

snapplebobapple2• 1 year ago

My 100ish person company the differnnce was using and not using between those prices. 18 a month for acls is insane

ErigmolCt3• 1 year ago

I really hope with this funding they can improve observability and give more love to power users who occasionally need to dig deeper without going full bare metal

rjgray• 1 year ago

Do you mind sharing the better solutions you'd consider at the higher price point?

cbzbc• 1 year ago

zerotier maybe?

fakebizprez• 1 year ago

exactly. there is none.

lkuty• 1 year ago

"Subnet routing broke on Ubuntu (maybe other distros) recently"

Do you have more infos on this one? I use Debian and that would be a major problem for me.

johnmoberg• 1 year ago

possibly referring to https://github.com/tailscale/tailscale/issues/13863 which broke subnet routing for us

fidotron3• 1 year ago

Overall, the simplicity and abstraction of complex VPN networking is wonderful, but if you have issues or advanced needs, you are immediately thrust into the low-level UDP/NAT/STUN world you were trying to avoid.

This is my experience too.

I actually came to believe the TS dream of device based VPN as opposed to AP or router based is the wrong thing because it gets confused by subnets and subnet routing so often, but also that the big security problem on networks is bad devices which it's not going to help you with unless you can wrap them up anyway.

That's one of the reasons I started playing with AP to AP real time video like https://github.com/atomirex/umbrella which is a nightmare case from the TS pov. The intention is to eventually wrap clients up on separate networks so they can only see each other via the (locally run) relay.

PLG885• 1 year ago

Agreed. This is why imho Tailscale does not scale very well. Awesome for home labs and small orgs as a VPN replacement, but not enterprise scale with abstrations that actually remove complexity. I wrote about it in this blog - https://netfoundry.io/vpns/tailscale-and-wireguard-versus-ne...

lo0dot011• 1 year ago

NAT/STUN world you were trying to avoid

The clean way to build this is with firewall configuration, opening ports, and static IPs. NAT/STUN and dynamic IPs are just a hack and I don't understand why people pretend this is an acceptable solution for professional networking. Working around an infrastructure that isn't a natural law but can be changed at our will seems like a big waste of time.

supermatt7• 1 year ago

I don't understand why people pretend this is an acceptable solution for professional networking

Because it IS acceptable for many cases.

Many businesses don't operate in such a way as to have centralised infrastructure solely for providing internal networking, nor would they want to add the additional administrative or unnecessary routing overhead.

Even locations that would traditionally be considered highly centralised often have some form of dynamic network fabric as an overlay. Pretty much the entirety of cloud infrastructure runs on such systems, and they seem to do OK.

udev40965• 1 year ago

Who said you can't do both? NAT makes things easier and you can still properly configure your firewall to keep track of all the NAT traversal rules

hashworks• 1 year ago

I shudder to imagine what the next tier (cal us') costs.

There is no enterprise tier, instead you pay for any additional features you need. I.e. log streaming is 2$/month/user and SSH recording is 3$/month/user.

snapplebobapple2• 1 year ago

I switched to netburd and havent looked back. Jetbird android cliwnt is pretty usable

karaterobot• 1 year ago

Funny how, as soon as I hear about a big new funding round, my reaction is sadness because I assume the product is going to start being bad and user-hostile in about 6 months. It shouldn't be that way, but it's just a reflex after seeing it happen so often.

jayloofah• 1 year ago

As an alternative there's https://github.com/tonarino/innernet

ErigmolCt3• 1 year ago

The shift toward identity-first networking is also super interesting. Feels like we're finally moving past the idea that IPs = trust, and into a world where access control actually maps to human (or service) intent

wg03• 1 year ago

Start looking for alternatives already. Nothing good came out of VC rounds and private equity for the end consumers ever.

sidcool2• 1 year ago

I understand the cynicism. But this is counter productive. Any venture has to have a finance angle. They are not missionaries.

LunaSea• 1 year ago

Sure, but amounts matter.

wg03• 1 year ago

All in for profitability and financial activity. That's the very foundation of innovation.

But VC funding works very differently.

BiteCode_dev• 1 year ago

Steam does fine financially and without having to answer investors, which is why it's been able to stay mostly good to its user base for so long.

This is not an "xor" statement.

afroboy• 1 year ago

What's wrong with Steam (Valve) business model?

mbs159• 1 year ago

VC funding is on a whole other level, though

sidcool2• 1 year ago

Congrats TS. You deserve this.

LWIRVoltage• 1 year ago

I just this past weekend was looking into setting up a personal networking solution- and looked hard at TailScale and their competitors. I do not like- that Tailscale has chosen to only allow SSO sign-in - as that forces one to have a Microsoft,Github[MS], Google, or Apple account- and I presume that leaves one at the mercy of those companies for the free option.

I will probably eventually cave and use my main account from one of those companies since creating true secondary accounts can be difficult(they end up tied back to your main account on the backend usually, So if something happens to one or the company does something- it'll affect everything and building separation is not easy.) - But I dislike that sort of design.

moontear• 1 year ago

This is not true. You can run Tailscale with a custom self hosted OIDC provider such as Authelia.

https://tailscale.com/kb/1240/sso-custom-oidc

lloeki2• 1 year ago

Interesting. I didn't know that you could also use e.g codeberg this way.

cab11150904• 1 year ago

t weekend was looking into setting up a personal networking solution- and looked hard at TailScale and their competitors. I do not like- that Tailscale has chosen to only allow SSO sign-in - as that forces one to have a Microsoft,Github[MS], Google, or Apple account- and I presume that leaves one at the mercy of those companies for the free option.

What is going on with your sentences man.

globular-toast• 1 year ago

What is their use case in an IPv6 internet? Or is this another company with a vested interest in stopping IPv6 from happening?

pmb• 1 year ago

They are a zero-trust networking solution that also traverses IPv4 NATs. Zero-trust networking is a layer above the IP layer. In an IPv6 Internet their capital costs go down, and their product remains valuable for their paying customers. (Free accounts mostly use it for NAT traversal, businesses for the zero-trust encryption.)

Their CEO has been working with (and supporting) v6 for decades both at the executive level (now) and also as an extremely capable software engineer that I personally met with a few times while we were both engineers at Google doing network measurement.

werrett• 1 year ago

I've got conflicted feels about Tailscale. I love their product and a bunch of the people I know use their free tier, including myself.

But their enterprise strategy destroys their good will. I can only assume it's focused on killing old school VPN products. The free tier that we love is a marketing expense. And it’s not even a conversion play.

People are complaining about ~10/user/month -- add basic things that you'd need to manage more than 10 peeps (SAML/SCIM support) and you're talking ~20/user/month. For us, a small sub 200 person company, they immediately lost their chance. We have lots of problems in the security space, some we're willing to spend more than 20/user/month to solve. Legacy network access is not one of them.

jackhalford• 1 year ago

If 20$/user/month is too much, maybe you could apin up headscale and plug in your OIDC provider?

Never tried it myself, I only manage small tailnets so the free tier is fine

socksy• 1 year ago

Assuming they wouldn't want to take on server maintenance workload, wouldn't something like NetBird be a better fit? The free version has ACL already, the $5/user/month has OIDC integration, and the business version (MDM integration and auditing) is $12. Then the server is still open source so if they wanted to transition to doing it themselves they still would have that option down the road.

jen203• 1 year ago

I can only assume it's focused on killing old school VPN products.

Given how goddamn terrible Cisco anyconnect is, I hope they succeed.

littlecranky674• 1 year ago

Still can't wrap my head around that TS does not allow to signup with your custom email/password combination but forces you to use bigtech (GitHub, Apple, Meta etc.) to login. Running your custom OIDC provider as a small, private person does not make any sense either.

dijit7• 1 year ago

I think that's quite smart, and OIDC is an open standard at least.

Securing usernames/passwords and handling second factors etc; is already done so well and it's hard to do.

Having a clear 'this is where we can be secure' stances is what makes me want to trust them more.

littlecranky674• 1 year ago

and OIDC is an open standard at least

But what kind of argument is that, if you are a single individual who wants to signup, I am not going to setup my OIDC servers. That is like saying it is a good idea to run a dedicated linux server in a datacenter under your own management, when all you want is a small static website for your mom+pop store. Sure, you can run your own server and it is all open source, but just overkill.

already done so well and it's hard to do.

So hard that literally all other websites in the world with a login have implemented it. And tailscale is a VPN-like technology company - if they can't manage to implement a login because it is hard, then I would definitely not accept their offerings.

guappa2• 1 year ago

It's an open standard, but would they allow me to use my OIDC?

lo0dot011• 1 year ago

Why is that smart? I signed up for a Microsoft Account with my email and I can use Microsoft Account to log in to Tail scale but I can't use the email directly? How does the middle man bring anything to the table?

depr• 1 year ago

For a single user, email signup is easy. But if they were to offer it they would also need to offer it to business customers. That means they have to build a role system and link that to AD etc. That is why they don't have it. (Their CEO discusses this in a recent interview).

00deadbeef• 1 year ago

I like Tailscale and we pay for it at work but it has a number of serious bugs that affect our work that they seem to lack the resources to fix. Hopefully this helps.

udev40965• 1 year ago

Maybe try out promising alternatives such as netbird, teleport, zerotier, etc

asim• 1 year ago

Congrats to the tailscale guys. I remember when tailscale was not a networking company. Amazing to see where it's ended up and obviously having bradfitz onboard is useful too. I'm always curious to know what the internals of a company looks like with a lot of ex-googlers running it. Does it look like a mini Google or something else? Not sure if apenwarr is here but always interested to learn more.

PeterStuer2• 1 year ago

Glass half full customer: great, the service I rely on is going to persist!

Glass half empty customer: OMFG, this is the minimal amount they are going to bleed from us over the next 5 years!

Based customer: this is just a half filled glass, full or empty is just your projection.

teleforce• 1 year ago

Connecting GPUs across clouds, securing workloads across continents, migrating between cloud providers — it’s messy, it’s hard, and it breaks all the time.

Is the new fund raise to enable Tailscale perform these complex tasks or for scaling it?

I've once read few years back that seamless and secure cloud independent computing or cross-cloud system is the next frontier, and it seems it's a legit problem and a business opportunity for security company like Tailscale and Crowdstrike (investor). The record breaking acquisition of Wiz kind of cemented this problem space and the pain points, and it seems that Tailscale is riding on the opportunity [1].

[1]Google to buy Wiz for $32B (845 comments):

https://news.ycombinator.com/item?id=43398518

debarshri• 1 year ago

It is commendable that TS has created a market in an already crowded marketplace of VPN tools. They're competing with Palo Alto, Netskope, Check Point, and Cisco, to name a few.

One key understanding from my brief market experience is that you must build a firewall or router if you really want to own the VPN market. The way the sale is done is that the vendor goes in with the firewall, router, and switch, offering office space connectivity with the infrastructure and various network locations and upselling the VPN. This often accounts for the subpar quality of VPN software. There is a trend called SASE, which includes technologies like TS; people are questioning the enterprise value of SASE. Netskope and Cato Networks are some examples.

I believe that their enterprise journey will be challenging, given the player's extensive experience in upmarket sales. Although TS appears appealing and has potential for improvement, the GTM is entirely unique for enterprise. You need to build reseller network, System integrator partners, high value customizations, etc.

If you decide to embrace the security positioning, you must have a diverse portfolio of products. If you model the org. around Palo Alto et al., you need a huge diversity of products, VPN, hardware, cloud security tools, app security tools, etc., as the ICP (CISO) is trying to optimize their allocated budget. People in enterprise are ok with good enough products as long as they meet compliance standards, fit the budget, and does not disrupt operations.

It could be that they might acquire bunch of companies with this capital.

udev40965• 1 year ago

You are still trusting the tailscale coordination server for proper key exchange. Yes, traffic is end-to-end encrypted and the private keys stay on the device but there's no way to verify that tailscale is negotiating keys for the machine you asked for

supermatt7• 1 year ago

Im pretty sure thats not correct, as you can authorise the nodes that get added, and it is only authorised nodes that can participate in the tailnet.

The problem IIRC is that it is the coordination server that decides what is authorised, so if Tailscale was hacked (or otherwise malicious), nodes could get added to your tailnet without explicit authorisation from the tailnet "owner", which is obviously not good. To prevent this, they introduced tailnet-lock, which requires other peers to participate in node authentication: https://tailscale.com/kb/1226/tailnet-lock#how-it-works

Shorel• 1 year ago

Good call, I started using it a few months ago, and now it is something I can't live without.

littlestymaar• 1 year ago

Tailscale not having reached profitability yet and having to raise more is bad news, as it increases the odds of future enshitification.

johntopia• 1 year ago

congrats to the tailscale team

Tailscale has raised $160M

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