Eh... I lean towards "no" on that point, unless you can do it well. I've received far too many reddit-tier fellow kids/omg so random/cringe emails, and I hate it. An example from Queal (a Soylent-style meal powder):
Winter is coming in Westeros and you must prepare by stocking up on food. Who knows if Drogon will fly by and burn your storage of snacks. Or the Night King will come to reign in the long winter. So prepare to receive a package from *REDACTED* with tracking ID: *REDACTED*
You can keep an eye on the progress of your package with this tracking link *REDACTED*.
People in the Seven Kingdoms still use carrier pigeons, so please note it could take up to a full workday for the link to become active.
Autumn will end soon enough, be prepared!
Please just fucking stop. I really like their product, but their emails make my blood boil. Don't be like Queal.
That is a perfectly valid point. Don't send fun emails if you can't write fun emails. Humor is an absolute minefield to trample through. You have to cater for your audience and if you don't have a set audience you're limited to the lowest common denominator.
This one was really important to me. Even the transactional emails were a bit fun to read. I kept them informal, as if I was talking to a friend of a friend. I certainly swore in them, too (at myself), when I was apologizing for things not working right.
Occasionally I'd get replies saying that the person looked forward to me automatically emailing them. That was a good litmus test.
Yes, do that. Also a tangent: remind me why you're sending me an email if you haven't sent one in many months.
Sometimes I see an interesting project that hasn't launched. They just have an "sign up for news updates".
Then 12 months later I get a standard news email and I have no clue what it is and ignore it.
At least start your email with something like "Hey, 12 months ago you signed up for the mega cool electron thunder splitter. We've launched!"