[HN Gopher] Tailscale has raised $160M
___________________________________________________________________
Tailscale has raised $160M
Author : louis-paul
Score : 327 points
Date : 2025-04-08 10:36 UTC (12 hours ago)
(HTM) web link (tailscale.com)
(TXT) w3m dump (tailscale.com)
| elAhmo wrote:
| 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 wrote:
| Try netbird which is an open-source alternative to free
| yourself from worries xD https://github.com/netbirdio/netbird
| 650REDHAIR wrote:
| Thank you for sharing this link!
|
| I was about to slog through AI search results looking for an
| alternative.
| drcongo wrote:
| I've been tracking this space for a while just out of
| annoyance that Tailscale offers ssh on the free tier, then
| not on the "starter" paid tier. Netbird is by far the best
| of the alternatives that I've tried.
| CharlesW wrote:
| Their Personal Plus (the non-business "starter" plan)
| does offer SSH, FWIW.
| arcanemachiner wrote:
| 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
| acheong08 wrote:
| Headscale is server only. Netbird is the whole stack
| (basically does the same thing but completely different
| software/implementation)
| bjackman wrote:
| But the tailscale client is open source too
| resiros wrote:
| I use personally for my home network. Very easy to use and
| quite mature. I'd highly recommend.
| Valord wrote:
| I share your concerns.
| pomatic wrote:
| 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 wrote:
| 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?
| fragmede wrote:
| > I don't know much about Tailscale, nor about how much it
| costs to run a company
|
| $33m/year is only 33 fully loaded software developers
| including all overhead like HR and managers and office
| space, and also a cloud hosting bill.
|
| 33 really isn't that many.
| johnbellone wrote:
| I'd be surprised if the average package for SWE is
| $1M/year (fully loaded).
| YetAnotherNick wrote:
| Generally package is around half of what company spends
| per extra engineer. And $500k average for a tech heavy
| product company doesn't sound too far off.
| MrDarcy wrote:
| This is just wrong. What exactly do think companies are
| spending 500k on per engineer beyond the TC package?
| throwaway98797 wrote:
| office space of course!
| andruby wrote:
| HR, marketing, sales, management, office space, servers,
| licenses, insurance, etc.
|
| It seems on the high end, but not too unrealistic.
| hug wrote:
| It's wildly and hugely unrealistic.
|
| The rule of thumb that employees actually cost a business
| roughly twice their salary is based on two things:
|
| 1. Retention. Hiring costs are "huge", and so if you have
| a higher or lower average retention, may make up a
| disproportionate cost compared to salary. Ramp up time
| and institutional knowledge loss is no joke either.
|
| 2. A spread of average wages. 500k is not average, and a
| huge number of the costs are relatively fixed. $1,000 a
| month worth of software licensing isn't an uncommon
| number and is fully 1/3 of the salary of a $3k a month or
| $36k/year junior clerk. It's _peanuts_ when you look at
| it next to a $500k /year salary. It may be that the clerk
| is, all in, costing the company 3x their salary after
| indemnity insurance and so on. The dev will never reach
| 10%.
| nialv7 wrote:
| Holy hell I need to ask for a raise.
| kenrose wrote:
| You're not wrong to think Tailscale is primarily a software
| company, and yes, salaries are a big part of any software
| company's costs. But it's definitely more complex than just
| payroll.
|
| A few other things:
|
| 1. Go-to-market costs
|
| Even with Tailscale's amazing product-led growth, you
| eventually hit a ceiling. Scaling into enterprise means
| real sales and marketing spend--think field sales, events,
| paid acquisition, content, partnerships, etc. These aren't
| trivial line items.
|
| 2. Enterprise sales motion
|
| Selling to large orgs is a different beast. Longer cycles,
| custom security reviews, procurement bureaucracy... it all
| requires dedicated teams. Those teams cost money and take
| time to ramp.
|
| 3. Product and infra
|
| Though Tailscale uses a control-plane-only model (which
| helps with infra cost), there's still significant R&D
| investment. As the product footprint grows (ACLs, policy
| routing, audit logging, device management), you need more
| engineers, PMs, designers, QA, support. Growth adds
| complexity.
|
| 4. Strategic bets
|
| Companies at this stage often use capital to fund moonshots
| (like rethinking what secure networking looks like when
| identity is the core primitive instead of IP addresses). I
| don't know how they're thinking about it, but it may mean
| building new standards on top of the duct-taped 1980s-era
| networking stack the modern Internet still runs on. It's
| not just product evolution, it's protocol-level
| reinvention. That kind of standardization and stewardship
| takes a lot of time and a lot of dollars.
|
| $160M _is_ a big number. But scaling a category-defining
| infrastructure company isn 't cheap and it's about more
| than just paying engineers.
| croemer wrote:
| At least tailscale funnel isn't control-plane-only,
| unless I'm totally misunderstanding something
| lukeholder wrote:
| This is an AI comment
| dblohm7 wrote:
| I can confirm that kenrose is an actual human being :-)
| fragmede wrote:
| 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.
| 9dev wrote:
| Aren't they Canadian though?
| palata wrote:
| Apparently, yeah:
| https://en.wikipedia.org/wiki/Tailscale. Based in
| Toronto, Canada.
|
| Go Canada!
| api wrote:
| 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.
| groby_b wrote:
| That depends entirely on how you raise the funds. Yes, you
| can say "Here's the growth rate we'd get without your money
| - based on that, this investment gets you an ROI of x%."
|
| With x% high enough, sure, you can get VC money without too
| many strings. (Also, reading the Series B post, they were
| planning to invest - just in organic growth instead of the
| usual growth hacking)
|
| And if you read the Series C post, you'd know what they're
| spending on - GPU (and general) cloud interconnectivity.
|
| There's really not much need to guess, Tailscale's
| financing announcements are about as open as you can get.
| specialp wrote:
| 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.
| ilrwbwrkhv wrote:
| 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.
| tptacek wrote:
| The founders of Tailscale probably weren't too worried about
| rent before Tailscale.
| ilrwbwrkhv wrote:
| Why? Did they have a previous exit?
| vvillena wrote:
| IIRC they were senior engineers from Google.
| otterley wrote:
| 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 wrote:
| Become the provider of choice for enterprise IT networks or get
| bought by Azure?
| SparkyMcUnicorn wrote:
| [delayed]
| baq wrote:
| One would hope they'd create something like Google drive except
| you own your stuff that people would pay for.
| fidotron wrote:
| So you want a file system data store that distributes the
| data over the nodes you own in a sort of dynamic P2P way?
| sebastiennight wrote:
| Sounds like Pied Piper to me.
| raggi wrote:
| you should see what happened to the rodents in the lab
| raggi wrote:
| https://tailscale.com/kb/1369/taildrive
| borski wrote:
| I imagine this was, at least in part, part of the pitch deck.
| runako wrote:
| $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.
| sshine wrote:
| 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 wrote:
| Tailscale is a software company founded in 2019 that raised
| their series A in 2020, not a grassroots community project
| sshine wrote:
| 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.
| hobofan wrote:
| As GP said, they have raised money before. So why are you
| now disappointed and think they "are selling out", when
| nothing has changed, and Tailscale has been a clear-cut
| for-profit startup from the start?
| brunoqc wrote:
| > at least the current software is open source
|
| Not the server.
|
| headscale is nice, but it's not an official project.
| 4k93n2 wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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.
| burningion wrote:
| 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...
| syntaxing wrote:
| 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?
| burningion wrote:
| 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.
| syntaxing wrote:
| I can't seem to find the replay function. As in replaying
| the sensor data as if it was "live". Would you happen to
| have a link to this feature?
| nikonp wrote:
| Rerun co-founder here. Rerun doesn't have replay in the
| sense of you send messages in and can play back the same
| messages in the same order later. We have playback in the
| sense that you can play it back in the viewer. We also
| have apis for reading back data but its more focused on
| dataframe use cases rather than sending you back messages
| ilrwbwrkhv wrote:
| +1 rerun is great and they also make egui.rs, one of the best
| immediate mode graphics libs.
| tonyarkles wrote:
| 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 wrote:
| Tailscale was invaluable for connecting my remote offices
| together. Long gone are the days of openvpn configs
| srameshc wrote:
| 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.
| codethief wrote:
| > 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 wrote:
| Tailscale has Taildrop - built-in peer-to-peer file sharing
| feature
|
| https://tailscale.com/kb/1106/taildrop
| dharmab wrote:
| I'm using it for friends and family file sharing, it's
| fantastic.
| suralind wrote:
| 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 wrote:
| 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 wrote:
| 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.
| duped wrote:
| 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.
| tptacek wrote:
| 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 wrote:
| You can always find a lot of us on LinkedIn :D {I work at
| Tailscale}
| jedberg wrote:
| Cloudflare still has their about page with thousands of
| people:
|
| https://www.cloudflare.com/people/
| xyst wrote:
| lol - wonder if HR or whoever maintains this site just
| scrapes the internal directory to generate the is page.
|
| Names/photos are not even clickable. Just first names and a
| photo.
|
| Thats so cloudflare.
| freedomben wrote:
| 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 wrote:
| 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 wrote:
| 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.
| xyst wrote:
| 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_b wrote:
| 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.)
| apitman wrote:
| 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...
| mrbonner wrote:
| 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.
| baq wrote:
| 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 wrote:
| I am on Arch and often end up with DNS broken in a way that
| requires me to restart tailscaled.
| nickzelei wrote:
| 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.
| fidotron wrote:
| 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 wrote:
| 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 wrote:
| 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.
| kccqzy wrote:
| I encountered a similar issue when I first started using
| Tailscale. My fix is simple: disable IPv4 inside Tailscale.
| Just use the v6 ULA address that begins with fd7a
| exclusively. This works even if your ISP doesn't support
| IPv6: the inner IPv6 packets can be encapsulated inside v4
| packets. There's unfortunately no GUI to do this; you'll
| have to change the Tailscale ACL to disable IPv4.
| theglocksaint wrote:
| The subnet routing feature can cause network issues
| belthesar wrote:
| 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.
| j-krieger wrote:
| 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.
| geenat wrote:
| 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.
| belthesar wrote:
| 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.
| aborsy wrote:
| 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 wrote:
| 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.
| RealityVoid wrote:
| And ease of use, IMHO. That's a bit one with these kind of
| things. I will admit not having used tinc but I imagine
| it's not as polished.
|
| Polish costs effort and money and it also really truly
| saves time and makes for a better product. So that matters.
| mikepurvis wrote:
| It definitely matters. I used tinc extensively at a prior
| gig, and it not having a story for its own key
| distribution was exceedingly painful.
| tptacek wrote:
| 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.
| formerly_proven wrote:
| My only technical complaint with Tailscale is that its
| hole punching doesn't seem to work with some common
| CGNATs/double NATs when both endpoints are using them,
| and then traffic ends up trickling through their public
| proxy servers, while running your own is kinda annoying
| and not recommended or documented.
| password4321 wrote:
| > _running your own [proxy servers] is kinda annoying and
| not recommended or documented_
|
| ?? https://tailscale.com/kb/1118/custom-derp-servers
| candiddevmike wrote:
| 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.
| aqfamnzc wrote:
| > 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...
| eddieroger wrote:
| It'll be a sad day when this reference is posted and
| understood for the last time.
| tptacek wrote:
| No it won't. The reference is universally misunderstood.
|
| https://hn.algolia.com/?dateRange=all&page=0&prefix=false
| &qu...
| johnmaguire wrote:
| I think the parent commenter used "understood" to mean
| "recognized."
|
| That said, I don't really understand the supposed
| misunderstanding you point out. It seems that dang argues
| that "the exchange was pleasant and successful." I've
| never seen someone claim otherwise.
|
| Rather, I've seen it used as an example of how technical
| users can fail to recognize the complexity inherent in
| their workflows, and therefore may also fail to see the
| real-world business value in creating (and selling)
| simpler interfaces. See also a SMOP:
| https://en.wikipedia.org/wiki/Small_matter_of_programming
| tptacek wrote:
| No, it's not that simple. This is an instance of context
| collapse; people dunk on that exchange because they
| believe it's an HN person belittling Dropbox as a
| product, when in fact it was an HN person helpfully
| offering notes on a YC application.
| johnmaguire wrote:
| Whether the poster was "belittling Dropbox as a product"
| or "helpfully offering notes" seems like a judgment one
| can make about the exchange, regardless of poster's
| intent. I never understood this to be the reason it was
| referenced, more the SMOP thing. But I hear what you're
| saying about the details getting warped over time. (edit:
| And I do think people sometimes use it as a case of "if
| you listen to everyone's feedback..." but I think that
| still rings true: regardless of the judgment you place on
| it, it could have been demoralizing to Dropbox's
| founders.)
| fngjdflmdflg wrote:
| They dunk on it because the author didn't see the the
| benefit of the product over using FTP. And it's hard to
| say the usage of "quite trivially" isn't "belittling" in
| some form, although I don't think using a loaded word is
| useful here. Even the followup response shows the same
| issue with the commenter's thinking:
|
| >You are correct that this presents a very good, easy-to-
| install piece of functionality _for Windows users_. The
| _Windows shortcomings_ that you point out are certainly
| problems, and I think that your software does a good job
| of overcoming that. (emphasis added.)
|
| They still fail to understand that this is not a Windows
| or Linux issue but a reliability and ease of use issue.
| Not to mention the fact that the desktop Linux
| marketshare was probably less than 1% and therefore
| irrelevant in this context to begin with.
| swyx wrote:
| 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?
| dmit wrote:
| Ea-Nasir
|
| Us humans are kinda ok at preserving knowledge (and we're
| getting even better, but not in a good way).
| swyx wrote:
| brb destroying some magnetic tapes because i can just put
| them on the cloud
| scarface_74 wrote:
| How many people on HN today would get the structure -
| "less $x than $y. No $z. Lame"?
| romanhn wrote:
| Here's the source for those not familiar with the
| classic: https://slashdot.org/story/21026. Can't believe
| it's turning 25 next year.
| dmit wrote:
| A weekend project _tops_
| freedomben wrote:
| Isn't Dropbox just a GUI on top of rsync? I've also seen
| people say "FTP"
| incanus77 wrote:
| Yeah, the same way a car is just a GUI on top of two
| bikes.
| agentdrek wrote:
| Probably closer to say that Dropbox is a GUI on top of WebDAV
| ignoramous wrote:
| > _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?
| johnbellone wrote:
| PUBG pays licensing fees to Epic Games (Unreal).
| jdoss wrote:
| 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.
| ignoramous wrote:
| 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 wrote:
| That's quite insightful actually. Perhaps might explain the
| tailscale name a little better in that context also.
| tmpz22 wrote:
| 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 wrote:
| 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 wrote:
| 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.
| firloop wrote:
| What if they were offered $160mm and Tailscale countered
| with 4X the valuation, lowering the number of shares by
| 75%? Similarly, what if they wanted $40mm but the only deal
| on the table was $160mm due to ownership targets of funds
| that can actually write $40mm+ checks? It's hard to play
| these armchair games, even less so when the terms aren't
| known.
| santoshalper wrote:
| You're right that we don't know all the terms, but $160M
| raised is not small and it is very reasonable to worry
| about what level of control will be given up long term
| because of it.
| MrDarcy wrote:
| 409a valuations are made up by independent appraisals,
| but it'd be quite strange for an investor to agree a
| share is worth 4 times the appraised value.
| nradov wrote:
| That depends on the share classes. Companies with high
| interest from investors can sometimes get them to accept
| shares with reduced voting rights.
| cj wrote:
| (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
| robocat wrote:
| > 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.
| pc86 wrote:
| Not only the "expectation" but lots of VCs have preference
| built in that guarantees them huge returns on basically any
| liquidity event. It's probably not as likely in a Series C
| like this but 2-3x preference is not unheard of. There are
| few investment vehicles where for every $1 you put in
| you're guaranteed to get the first $3 made back first.
| vvpan wrote:
| 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.
| peterlk wrote:
| 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
| freeone3000 wrote:
| Why would you not just have the same amount of income, but
| spend less money?
| tikhonj wrote:
| Some business can certainly allocate more than $100M, but I
| could see that thesis for VC-backed tech-style product
| companies.
|
| A few examples come to mind immediately: trading
| firms/hedge funds often have more capacity than that in
| their existing strategies; hardware businesses can have
| substantial up-front costs; companies with high COGS might
| need that much to just scale at the rate they're already
| moving, since each unit locks up a bunch of capital until
| it's sold.
| robocat wrote:
| The benefit for VC of lending you more than you need is (a)
| getting the owners hooked on spending money, then (b)
| taking control.
| mmx1 wrote:
| You can't be serious. Lots of businesses easily have that
| much just in cost of goods or marketing spend. $100M is not
| such a crazy amount especially considering the cost of
| hiring technical people.
|
| Also note that the benchmark of "efficiency" should be a
| function of growth, not some absolute standard.
| mindwork wrote:
| Now I'm waiting for all AI billboards in San Francisco to
| be replaced with Tailscale ads
| duped wrote:
| 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.
| pc86 wrote:
| Isn't it better to 1.5x in 6 months on 40 million than 3x
| in 2 years on 160?
|
| By definition focusing on things that don't grow your
| business because you have way too much money in the bank is
| going to be worse for your business than being forced to
| focus because you've only got a year of runway.
| IncreasePosts wrote:
| No one is going to answer you because no one has seen their
| books.
| alecco wrote:
| obligatory "Raising too much money" (Silicon Valley)
| https://www.youtube.com/watch?v=8ZgfTarNxdY
| pc86 wrote:
| 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 wrote:
| 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.
| aborsy wrote:
| Tailscale deserves it. They have produced excellent software.
| devmor wrote:
| 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 wrote:
| They have raised before, so that money helped shape the service
| you enjoy.
| devmor wrote:
| Yes, but when they raised before they did not give up a bunch
| of control in return.
| elevation wrote:
| 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 wrote:
| What are the failure points of hosted solutions like Tail scale
| versus self hosted options?
| chgs wrote:
| 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.
| codethief wrote:
| 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/
| transpute wrote:
| 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.
| codethief wrote:
| This is about data, though, not about addresses, is it?
| transpute wrote:
| It's both,
| https://en.wikipedia.org/wiki/Named_data_networking
|
| _> NDN has its roots in an earlier project, Content-
| Centric Networking (CCN), which Van Jacobson first publicly
| presented in 2006.. NDN applications name data and data
| names will directly be used in network packet forwarding..
| Its premise is that the Internet is primarily used as an
| information distribution network, which is not a good match
| for IP, and that the future Internet 's "thin waist" should
| be based on named data rather than numerically addressed
| hosts._
|
| NDN talk by Van Jacobson at Google (2006):
| https://www.youtube.com/watch?v=oCZMoY3q2uM
| jncfhnb wrote:
| Fingers crossed they'll finally enable sending files to people
| mrdoornbos wrote:
| This sort of thing tends to trend bad for users.
| segmondy wrote:
| woot, woot, happy for the team. I love tailscale and can't stop
| singing praises.
| nottorp wrote:
| Entshittification incoming?
| nextworddev wrote:
| You know it
| finnjohnsen2 wrote:
| I just wished their server side was open source also
| flkenosad wrote:
| https://github.com/juanfont/headscale
| amriksohata wrote:
| What's the difference between this and say azure vent and
| configuring that with private endpoints
| breakingcups wrote:
| 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 wrote:
| 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 wrote:
| $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
| xyst wrote:
| 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 wrote:
| Enshittification will start in 3... 2... 1....
| Uzmanali wrote:
| 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 wrote:
| This comment reads like simple.wikipedia.org
| Uzmanali wrote:
| 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.
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