Tailscale raises $100M

With such a huge investment comes the obligation to eventually pay it back. Is this another one of my favourite tools going the way of Dropbox, 1Password and all other companies that were formed around what should be a platform feature, which took on way too large investment sums and were eventually forced to become the everything, losing sight of their core values?

I sincerely hope not, but there's so much bad precedent.

I haven't really felt like 1Password's product materially strayed from the original mission. If anything, I'm even more delighted with the team functionality, shared vaults, quick keyboard access in 1Password 8, etc.

I wouldn't put them in the Dropbox bucket.

Also, I think the value Tailscale provides is fairly unique and far from obviously a platform feature like file storage and perhaps even password management.

1Password went from being buy once upgrade forever to SaaS. A lot of folks bought back when that was the package (and business model) so it's viewed relatively negatively here from some folks. I don't blame them, but also, I think 1Password is a success. I just don't think they'd have been viable under their original business model.

But is "buy once, upgrade forever" really a viable long term business model?

I dunno, but you ought to figure it out (for your business) before you make that offer!