Live data from Hacker News

Tailscale has raised $160M

tailscale.com

191–200 of 354 posts

Re: Tailscale has raised $160M

#192
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.

Re: Tailscale has raised $160M

#193

Earlier quoted context omitted.

I'd be surprised if the average package for SWE is $1M/year (fully loaded).

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.

> $500k average for a tech heavy product company doesn't sound too far off.

Tailscale puts salary ranges on their job postings. The salaries aren’t bad, but no, they aren’t $500k.

Re: Tailscale has raised $160M

#194
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.

Re: Tailscale has raised $160M

#195
post #10

Earlier quoted context omitted.

Thank you for sharing this link! I was about to slog through AI search results looking for an alternative.

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.

Have you tried ZeroTier? Their free plan's been working well for me. I haven't tried NetBird.

Re: Tailscale has raised $160M

#196
post #6

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.

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

We’re like trading cards to these people

Re: Tailscale has raised $160M

#197
post #151
post #85

Earlier quoted context omitted.

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…

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.

I think we are saying slightly different things. COGS are composed of many smaller capital allocations. According to this untested, pet thesis, putting on a report that $250M was spent on capex is just fine; but if you go to a single vendor and sign a $250M contract, you have wasted money by not being more careful about how that capital is allocated. $100M is _a lot_ of capital, and I think it’s easy to lose sight of how much stuff you can do with that much money when applied to industries that don’t pay tech salaries for speculative growth. As examples: how many pounds of food could you grow for 100M? How many doctors could we train for 100M?

I think the thesis is thought provoking. Not sure yet if it’s worth anything, but it also doesn’t preclude businesses from having massive cashflow.

Re: Tailscale has raised $160M

#198
post #116
post #22

Earlier quoted context omitted.

As someone who currently has their photo on a company's 'About Us' page, I hate it. Why does anyone care who the nth developer is? Let me just do my job without forcing me to be publicly listed for spammers and scammers to target me.

It's super useful to potential hires about the kind of team you're building. Especially if there's some kind of niche you're in (product, tech, region, whatever). There are people who I would climb mountains to work with, and others within a niche whose very presence in a company is enough to steer me away. Another signal for me is the fraction of xooglers in the engineering team.

> Another signal for me is the fraction of xooglers in the engineering team.

In which direction?

Re: Tailscale has raised $160M

#199
post #151

Earlier quoted context omitted.

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.

I think we are saying slightly different things. COGS are composed of many smaller capital allocations. According to this untested, pet thesis, putting on a report that $250M was spent on capex is just fine; but if you go to a single vendor and sign a $250M contract, you have wasted money by not being more careful about how that capital is allocated. $100M is _a lot_ of capital, and I think it’s easy to lose sight of…

Maybe 200 doctors at prevailing medical school rates? That’s not an obscene amount.

Re: Tailscale has raised $160M

#200
post #136
post #27

Earlier quoted context omitted.

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…

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.

Not necessarily. You hear plenty of stories of companies who raised money they never ended up needing to touch.

What matters is why. Is it because growth is so bonkers that your burn stays minimal/zero despite increasing costs? Or is it because you don't spend anything and thus can get by with stable revenue. VCs are very happy with the first, less so with the second.

VCs would always prefer you get to megascale with less money - the less you raise, the less they get diluted.

Post reply on HN