Every CEO’s recurring homework

A how-to for investor updates

Putting together investor updates isn’t typically a CEO’s favorite activity… but it is an unavoidable part of the job. Having investors that care enough to want updates is, on the whole, an excellent problem to have ☺

I’ve seen some great posts on what to put in investor updates (good one from Jason Calacanis here), but these have only covered the investor view of things. To balance this out here are some best practices I’ve put together over the years.

For those just getting up to speed on dealing with investors, hopefully this saves you some time on figuring out what to do. For those of you who have already figured out your system, hopefully you pick up a trick or two.


There are three goals for investor updates:

  • Succinctly give investors the updates they need to hear.
  • Spend as little of my time as possible preparing info.
  • Determine which investors are still engaged.

In terms of timing and tools used, here are some best practices I’ve arrived at:

  • Investor updates go out every 2 months (this is also how often we have board meetings).
  • Updates go to all investors, even those that don’t contractually have information rights. Investors can only be helpful if they know what’s going on.
  • At most two hours is spent putting together a deck. Metrics take the most time, but we mostly just copy/paste graphs from internal dashboards.
  • I used to use Keynote, but switched to Google Slides since it’s easier to collaborate and get feedback on before sending.
  • Updates get sent 48 hours in advance of board meetings to board members and observers. After each board meeting, I send out the deck to all other investors.
  • I always send updates using DocSend links to I can see who’s reading the info. Each investor gets a separate link so I can see who’s forwarding it.

The topics covered in the investor update doc mirror the agenda for each board meeting and cover these six topics:

  • Summary of the most important news
  • Team update
  • Product update
  • Key metrics
  • Upcoming questions to answer
  • Financials

To get a sense for the length and layout of the update deck, check out DocSend’s investor update from January (sensitive info is blurred out):

Case_Study_Image_Template_large


Because I send out our updates with DocSend links, I get some fascinating insights in aggregate. Here are a few of the highlights:

  • The average view time is over 6 minutes. This is quite a long view time relative to other types of documents (a fundraising pitch deck gets viewed on average for under 4 minutes).
  • Our investor update documents range from 11 to 18 pages long.
  • Over 87% of document visitors make it all the way through the update.
  • Over 80% of our investors (at least one person from each firm) regularly look through our updates.

A final point to make is that using DocSend essentially makes each update a bit like role-call, where I get to see if anyone doesn’t look through the material (or if they forward it places it should go).

Since our investors all know how DocSend works, it definitely increases the pressure for them to look through the material. I’m essentially invoking the social norms of an in-person meeting. Just like it’s rude to be on your cellphone in a meeting (everyone can see you aren’t paying attention), it’s rude to not go through a DocSend link (or you at least better have a good excuse).

If you put time in to making a thoughtful investor update, remember that you deserve to know who actually looks through it.

Investor update stats

With DocSend, you’ll be able to share sensitive materials with external business partners while getting real-time, actionable, feedback on document engagement, so you can be in full control of your business outcome. Say goodbye to email attachments once and for all, and click here to get started with a free trial of DocSend!