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One and a half year ago I was working on a product called Mbassador (a LinkedIn for best friends only). I made a list with my close (business) friends and emailed them once a month with an update. After 8 updates I figured out I was writing for them, but instead I wanted to write for myself... and give them access to my journal. That's when I povited and changed Mbassador into Mindwave.app; a journal for founders & makers.
After I figured this out I didn't send out any updates anymore. So, my monthly update was a positive experience after all. But not in the sense that I would recommend it to others, not for close friends or anyway. If you're building a startup and want to inform a business network and early-stage investors, sending out monthly updates are quite common.