James Sinclair advises startup founders to write a weekly investor-style update for themselves and to send a condensed version to actual investors monthly. He argues this habit builds transparency, accountability, and investor trust, and that even imperfect monthly updates are better than none because they create relationships that help when bad news arises.
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If you're a startup founder, with or without investors, you should be sending an investor update to yourself every single week. The only difference is that if you do have investors, they should get one once a month. There is literally no reason not to do it. If you need a template, there's one in my link thing, whatever. You can download a template. Point is, nothing bad ever happens from an investor update. You don't know who your investors know, where they know what they know, who they're talking to, where they're talking, where they're going, where they grew up, their friends from college, you have no idea. And investor updates that every month, even a shitty one, is better than no one. Just a quick high level what's happening, what's going good, what's going bad, what's moved. And what it means is when inevitably you have bad news, because you will have bad news, you will have built an army of people that trust you because you've created that relationship of transparency, of confidence that you're the right person to be leading this team. And more than that, if you do it to yourself every week, it creates extraordinary accountability. Good luck.