What’s missing: Google Photos for Documents

What Dropbox should have built

Andreas Stegmann
hyperlinked

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This is the third installment in my series in which I publish product concepts.

Why not keep the idea for myself? I believe in the power of open communication. There’s a great chance somewhere, someone has a related thought — if so, or in case you have other feedback, let’s connect and learn from each other. Contrary to public perception, ideas on its own are worthless if not paired with the right execution (hard).

Most of those ideas had some incubation time to think things through. This particular thought is about 2 years old.

Idea

When Adam Nash took on his role as VP of Product & Growth at Dropbox, he asked on Twitter what the cloud storage provider should build next. I had my answer ready:

This was in 2018. What happened to Dropbox since then:

  • Nash moved on
  • Dropbox underperformed the NASDAQ by ~60%
Dropbox is barely in the Top 20

Why Dropbox succeeded initially

It looked very different a decade ago. Dropbox was one of the darlings of Silicon Valley. Drew Houston’s founding story is legendary:

VC: “There are a million cloud storage startups!”

Drew: “Do you use any of them?”

VC: “No”

Drew: “…”

Growth was spectacular with zero marketing — Dropbox was one of the first companies with freemium model (free tier = marketing expenses).

I wrote in 2008

The “wow-factor” after the first use was comparable with the experience I made by migrating from Thunderbird to Gmail.

and tweeted in 2010

after all my attempts in syncing it’s the only service that works as advertised.

As Paul Stama I was obsessed with living the cloud life.

What happened to Dropbox

As always, I think there a several reasons:

  • Far into the mid of the 2010s Dropbox was more or less the only reliable option. Look at this list of Microsoft failures I compiled in 2014. Well, competitors finally got their act together. They caught up while Dropbox hasn’t found a new USP. Cloud storage has become a commodity.
  • Big Tech can shoulder to cross-subsidize their respective cloud product — Dropbox can’t. Christina Warren was disappointed by having to “pay twice” to get features Microsoft’s OneDrive has for free.
  • The B2C approach hits its limits compared to the enterprise sales-driven approach used by Box and others.
  • Zack Kanter thinks Dropbox was distracted by engineering their own cloud infrastructure.
  • Marco Arment gets downright angry when he talks about how the new Dropbox client messes with Mac system conventions.
  • Jan Schultink sees a dilution in their early simple product concept.
  • Alex Danco looks at the file as a not internet-native medium:

Dropbox’s problem is the fact that it’s a great file management service — we just don’t care about files that much any more. […] Files seem woefully old-fashioned when you consider organization tools like Evernote, task management tools like Trello, and communication channels like Slack.

We will come back to that point later.

Dropbox is the Twitter of cloud storage. It stumbled into product/market-fit very early, maybe too early, and then basically stopped improving.

2018 has seen many Tech IPOs where (to paraphrase Steve Jobs) the company is only a feature (in a potential bigger company / product). What you invest in right now is the potential that these become differentiated in their own right.

Imagine Dropbox wouldn’t have burnt through their acquisition of Mailbox, but built Slack instead of Dropbox Paper. Different game.

But I guess it’s not too late for Dropbox to become differentiated. How? I say it needs to get back to its roots: To make dealing with files more simple and more pleasant.

Dropbox won the 1st round because it was easier to use, more accessible. I haven’t seen any product initiative to extend that lead.

What makes Google Photos great

Which takes us to Google Photos. It applied this lesson to a different vertical: Personal images.

Google Photos launched in a saturated market but took the crown. Because you throw photos at it and it does the rest.

I must say, concerning file management I’m a nerd. For example, here’s how my music library is sorted in folders thanks to Foobar formatting:

$if(%album%,%artist%\[‘[‘%date%’]’ ]%album%\%artist% — [%tracknumber%. ]%title%,%artist%\%artist% — %title%)

With pictures I have a similar structure. The details vary, but basically:

%location%\%year%.%month% %event%\ 

Depending on the amount of pictures it could also be sorted by people on the photo. Unlike with music, I don’t have much metadata to rely on, so I have to sort manually combined with some basic sorting by Hazel.

Hazel Sample Rule

I admired my rules strictly. Then came my first child. The amounts of pictures taken skyrocketed and I couldn’t keep up with sorting.

I resigned to let Google Photos do it for me — and it works even better than before. I search for a location, scenery or name and fitting images appear. Pure magic. Extracting metadata from images is maybe the best example of AI in action yet.

What Dropbox could offer

Consider me so spoiled by Google Photos that I want this magic for everything. Documents come to mind.

This is how the desktop of my wife and many others looks like as of today.

Looking at this Twitter thread, she’s far from the only one.

Where you see clutter, I see opportunity.

Dropbox could offer sorting and organizing files. For that, Dropbox would need to let go of files as the organizational layer and try something new. Dropbox Paper plays around with new conventions — but it’s a side project.

I imagine the default interface revamped — more or less like fyi. Instead of the hierarchical folder structure, we are presented with a big search bar, a chronological view (“What file did I work on last?”) and a people-driven view (“What’s that file called I worked on with Anna?”).

Good search is half of the equation. I noticed I rather open a new tab and search in [cloud sync provider of your choice] than opening the Finder, just because I prefer their search and get to the file I need faster.

By creating a new UI on top of the old folder structure, features are possible that weren’t before. I listed requirements for what I want from a next gen-file system (excerpt):

  • Sync all files stored on different devices instantly
  • Automatic file versioning
  • Easy sharing and collaboration
  • Option to categorize items with folders AND tags
  • Advanced search options & search within content

A different attack vector on becoming the default interface to interact with documents and information (a powerful place to be in).

Because the service analysed the contents of a given file, it can match phrases that are not in the document’s title (Google Drive does this already with Google Docs) and set automatic tags.

This intelligence screams for AI as buzzword marketing efforts and it could help, for sure. My hunch is that 80% of all useful information is already hidden inside the document’s contents and metadata, though. This is how Fileee advertises this analysis.

Unfortunately their last blog post dates back to 2016, not a good sign

Everything wrote down here applies not only to Dropbox — other cloud storage services or startups have a shot as well. Sophisticated ML algorithms favor scale, though.

On mobile Apple tried for years to obfuscate the file system. I get their reasoning. The historical cruft of 20 years of file management shouldn’t need to live on forever. But Apple didn’t offer a convincing alternative, they only took features away. Users don’t have powerful file managers at their disposal. The impact by a new view like this one would be especially huge on mobile devices.

Note, in my concept the user can always switch back to the advanced view — there are use cases where the common folder structure has its advantages.

Computers will run on files for a very long time. It’s just that the end user doesn’t need to see them.

I do think a new way of presenting files will win eventually. Regardless if Dropbox gets the memo or not.

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Andreas Stegmann
hyperlinked

👨‍💻 Product Owner ✍️ Writes mostly about the intersection of Tech, UX & Business strategy.