In my experience it’s nearly impossible to keep all investors and advisors involved and up to date. In fact, it’s sometimes more of a burden than it is helpful. You need to spend time building your product, company, hiring, and making sure the gears are grinding, not reporting to and hand-holding all of your investors. Big syndicates are good (and a champagne problem) in that they allow you to pick and choose who you want to keep involved.  Out of our pool of 15-20 GroupMe investors, we probably only kept 3-5 completely up to speed on a regular basis. I think 3-5 really active investors is manageable, and most productive. After that, you hit diminishing returns.

Man, most of the investors, left out in the cold.

Well, not to worry: as Andy Weissman pointed out in the comments to this post, the GroupMe syndicate kept in touch through...wait for it...GroupMe. Now that is eating your own dogfood.