Does it look like you're spamming?

There are lots of terribly complicated rules in email marketing and retention. “Only send email to people who opted-in”, “Never use a pink background”[1], “Have a working unsubscription link”, “Don’t put FREE in the subject line”[1].
Another one should be “How does what you’re doing look to a typical recipient?”.
I’ve received several pieces of spam recently from senders who were ticking quite a lot of the “email best practices” checkboxes, but who completely blew it by not looking at it from the recipients point of view. The mistakes they’ve made, and the things to learn from them, and much the same, so I’ll just give one example.
“Likes Music” is not the same as “Likes Groupon Clones”
I’ve been a subscriber to our local radio station’s mailing list for years – promos KFOG is running, local gigs, that sort of thing, all in a newsletter sort of format. They recently sent out an ad for a Groupon clone called “SweetJack” – on it’s own, not as part of a newsletter. I’m not interested, and I think it’s a fairly poor pitch and won’t work well for their demographic, but fair enough. A couple of weeks later I start getting spam from SweetJack, thanking me for signing up – to the tagged email address I’d only given to KFOG. And no mention of KFOG at all.
Most recipients are just going to see this as spam out of the blue from SweetJack, and hammer on the “This is Spam” button until it goes away. That’s dreadful for SweetJack’s reputation, and is going to hurt their delivery.
Recipients paying more attention are going to notice that the first they heard of SweetJack was an out of the ordinary promo by KFOG, and then they start getting spam from SweetJack. They’re likely to assume that KFOG sold their email addresses to SweetJack – and that they’re sending their spam to an email address that only KFOG has in my case confirms that. That’s going to be dreadful for SweetJack’s reputation and going to damage the relationship between KFOG and their existing subscribers. A dreadful idea.
Digging down deeper, it seems that while KFOG being bought out by media behemoth Cumulus Media a few years back didn’t damage their on-air content, it did change the amount of respect they have for their subscribers. SweetJack is a new Groupon clone started by Cumulus Media. They did have legitimate access to the KFOG mailing lists, sorta. It’s probably not an AUP or privacy violation. It’s just the sort of thing an eager marketing guy at the corporate owners would think was a great idea, to leverage the value of their existing subscribers.
But it would have been a pretty bad idea had they carried it out perfectly, with clear messaging and transparency to the recipients. And they blew their one opportunity to do it well, and I’m betting that most of the recipients have SweetJack categorized as “spammers”, both mentally and in their mail clients.
1. Not a real email marketing rule.

Audit trails are important.
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