131–140 of 354 posts
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> 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...
Isn't Dropbox just a GUI on top of rsync? I've also seen people say "FTP"
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…
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…
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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.
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.
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
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…
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.
What are the failure points of hosted solutions like Tail scale versus self hosted options?
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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.
The founders of Tailscale probably weren't too worried about rent before Tailscale.
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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.
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.
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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.
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…