Tailscale has raised $160M

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 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 :-)

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.