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And they had Paper, which was an excellent product (I was at Dropbox a decade ago; we all used Paper constantly and it was great) very close to what Notion later became. They never got it over the hump to wider PMF — like you say, a failure of product and of enterprise execution.

(Given that it was so close to Notion, I think Paper is one area where the product vision was on to something good; but they didn't succeed at product execution, connecting customer feedback to iterating correctly on product improvements.)

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Never worked at Dropbox, but I absolutely loved Paper.

The problem at Dropbox seems to have been that there was no cohesiveness to all the products. Paper, Passwords, Sign, all seem to have never been truly integrated into a single experience. Each one felt like it was trying to have its own identity.

Yeah, when signing into Paper it always felt pretty silly how the auth flow was all like "are you sure you want to share your Dropbox account info with this Paper thing?" as if it was some third-party service.

Ironically, just within the last year Paper has gotten much more integrated into Dropbox as a single UX. And… it's significantly worse: slower, clumsier, harder to navigate. (I don't think there's any inherent reason those had to be correlated; it's just that Paper has clearly been destaffed a lot in recent years, so naturally any new changes will tend to be less polished.)

Another issue: Paper was tied to your Dropbox account.

From Dropbox's perspective, this sounds great. Accounts become more useful and valuable. The addressable market of a Dropbox account grows! Plus, everyone has a Dropbox account already, right?

Unfortunately, it turns out that business customers generally don't deploy Dropbox wall-to-wall. It's expensive. Not all employees need file sync.

A Dropbox account ends up being an obstacle to adoption.

And a distraction: a common account creates an irresistible urge to spend a lot of time finding ways to tie this new product into the old one.

I'm not sure I ultimately buy that Dropbox is expensive - for one thing, Notion now charges basically the same as Dropbox, and you don't even get file sync in the deal.

I can definitely believe that that was an objection customers had, though. I just suspect that what it really meant was another way of expressing that there wasn't PMF - if the PMF were there, they'd have willingly paid, just like they do now for Notion or Slab or what have you.

And yeah, there was definitely some energy going into trying to tie the products together more (putting Paper docs in your Dropbox folders) - and when that finally shipped it sadly made the Paper experience worse, not better.

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