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No, definitely agree. One of the great SaaS companies, strategy matters, though, and the early success distracted them from building a defensible business.

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I was at Dropbox from 2016-2020. We were certainly trying to build a sustainable business, but there was a major identity crisis. Were we consumer web? Buy Mailbox and build Carousel, then shut them both down.

Maybe we’re Notion/Evernote? Buy Hackpad, plow a ton of money into Paper (which was legitimately good), then quietly deprioritize it.

Maybe we’re actually some kind of enterprise document productivity suite? Buy HelloSign. Plow a bunch of money into a desktop app. Pull more plugs.

A lot of smart people were trying. We made a lot of bets (too many?). None of them proved to be a second act, and the competitors eventually caught up.

I intend to write a piece going deeper into the failures; I would love to chat if you're open to it. Also, not to say Dropbox sucked or anything, it is just that the broader strategy and industry structure make it hard; if anything, the success of the first product made it difficult to evolve the business.

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