As you may know, there is tension between investors and entrepreneurs in general.  There is a long history of bad blood and poor actions on both sides that I won’t get into right now.

During my time as an investor, I have found that the easiest way for an entrepreneur who has raised money from me to build trust, is to over communicate the health/status of their company.

As a very active seed investor, we typically don’t have a lot history with the founder(s) and usually invest after a few meetings, so while there is some trust built during the investment process, you still don’t really know each other that well.   So trust (on both sides) is built over time.

If you have taken money from investors, I encourage you send monthly updates to them.  I have created an easy template to follow.  The information that I ask for (and that investors want) is something that you should be tracking and sharing within your respective organizations in any case, so it is not onerous.

The side benefit to the entrepreneur to send monthly updates is that your investors/angels will bug you less often as they already know how things are going, so it allows you more time to focus on your business and less time doing coffee meetings with all your investors.

The other benefit is that when you need to raise that bridge/extension round (which is highly likely), you have built trust with your investor(s), so you have a better shot of raising that inside round.  I have seen several situations where I don’t receive any information from an entrepreneur for six months (or more) and then they come to me saying things aren’t going well, please invest more money, that is not a good situation to be in as an entrepreneur.