Our company has attracted 14 private investors, each for relatively small stakes. They not only provide seed capital, but also diverse experience and valuable advice.
Can you recommend a process/model/template/other for keeping them in the loop with the company's progress?
Send them a monthly letter, including:
The very act of producing this letter every month, even if you didn't have investors to send it to, is remarkably valuable in keeping focused on the important things.
As an angel investor, I've seen both ends of the spectrum.
I have startups that send me relatively regular updates (though not quite to the level of detail that Joel suggested) and others that I don't hear from at all other than major updates (like a new financing) or when there's some signature required.
I personally lean towards solving for what is expedient/efficient for you (but meets any minimal contractual requirements).
I usually keep my angel investors updated via a monthly progress report and cash flow statement using Google Docs. I will also let them see the upcoming tasks on Pivotal Tracker.
One of the problems with a lot of small investors is that a lot of your time can be eaten up answering their questions about how the business is going. They have money invested and will want to be informed about how their investment is going.
If it was me, I would try to do a few things upfront:
Then update them regularly at the timeframes you have nominated. At these times be transparent with information but understand that they may not have the financial/business understanding you do.
Hope this helps