I recently spoke with an entrepreneur who was asking for guidance on a rather large syndicate he was putting together (a syndicate is the pool of investors a startup assembles for a round of financing). At GroupMe we had a big syndicate: 15+ investors participated in our Series B, most of whom were individuals. Big syndicates take time to put together, and they take more time to manage. To do more financings and corporate deals you’ll need to collect signatures, circulate documents, build consensus, have people vote, etc. A lot of people think the more people they bring on board, the more help they’ll get.
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.
Some investors can help with specific problems, and most will always answer and help when called upon, but very few will be by your side every step of the way. My advice to those with big syndicates would be to not worry about managing everyone, just find the handful that really help and want to be most engaged and leverage that. The worst thing to do is to waste cycles trying to get disengaged people to help when you can extract more value from those that are willing.