Simple Document Collaboration

A VC client recently asked me:

“What’s the simplest way to upload a few documents about a company or deal and have a group discussion about them?”

They want to be able to have the pitch deck, pro-forma, legal docs, miscellaneous spreadsheets, PDFs, and other documents about a deal in one place with a single conversation thread about the deal below the list of documents. Simple enough, but is it?

The Use Case

  • Low-friction high-speed communication is very important to them.
  • Documents could be anywhere (Dropbox, Google Drive, Box, attachments), so platform agnosticism is important.
  • Their team is hardly ever at a desk, so a great mobile experience is critical.
  • Some of the people they work with (investors, analysts, etc) won’t install something new just for this. They need to be able to collaborate via email, because face it, email is still a thing and it’s not going away.
  • They don’t want to learn a new system or tool. It should integrate with their existing workflow.

I’m not aware of a tool that does exactly this, so I began thinking about the tools this client already uses and how they might adapt them for this use.


No doubt Slack is the pretty girl at the dance right now. However, there are valid concerns about it being too easy to use, allowing people to be lazy and rely on the fact that they posted something to mean that everyone else saw it and understood it.

Usage: Create a new channel for each company/deal in Slack. Keep all discussion about that company/deal in that channel.


  • Easy to use
  • Great UI and usability
  • Good mobile app
  • Easy to limit participation on a per channel basis
  • Lots of integrations with 3rd party services
  • Easy to invite others to collaborate
  • Private messages with one or more people via DM
  • FREE


  • Not everyone will want to use it on mobile since they have to install the app.
  • That ‘another thing to check’ feeling.
  • No easy email integration for people who still work from their inbox.
  • No daily activity report without a 3rd party integration
  • Can be hard to keep important discussion separate from chatter

Basecamp 3 (not previous versions)

Basecamp feels excessive for such a simple task. There are lots of tools that simply aren’t needed and might be confusing to people who aren’t familiar with them. The simple threaded messaging and ease of collaboration via email might be worth the baggage.

Usage: Create a project (a.k.a. a “Basecamp”) for deals, turn off all the other ‘Tools’, then create a Message for each company/deal and keep the conversation threaded there.


  • Easy to use via email with the right notification settings.
  • Good mobile apps.
  • Easy to invite others to collaborate.
  • Daily activity reports via email.
  • Easy to assign and track tasks via To-Dos (if that’s important).
  • Private messages with one or more people via ‘Pings’.
  • Applauding‘ a message is fun.


  • UI can be a little clunky and difficult.
  • There is a lot of cruft in messages sent via email. Basecamp hasn’t figured out how to strip email signatures and such from messages, so things can get cluttered real fast.
  • Difficult to have different groups of people without creating a ‘Basecamp’ for each deal/company, which feels excessive.
  • Campfire, the realtime chat that’s built in, totally sucks compared to Slack.
  • No good 3rd party integrations, but the API just opened so that may change.
  • $79/mo (not a deal-breaker, but still).

How would you solve this problem?

I’ve not found anything that does exactly what this client needs. Maybe I didn’t look hard enough, maybe it doesn’t exist. So tell me… how would you solve this? Do you have this pain, too? Should we build an app to do solve it?

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