So if the same qualitative factors were kept for your outreach, just an increase in the quantitative equation means it's spam? One discrete instance is not spam but the combination of all of them makes the whole spam, when certain thresholds are reached? If so, how do we define those thresholds?

It's an interesting question! To me, an (or perhaps _the_) obvious threshold is once the emails become automated.

Why does that factor make it spam?

I'm quite sure you can do all sorts of mental gymnastics to avoid thinking of yourself as a spammer.

Here's my basic criteria for spam:

1. It's unsolicited.

2. It's trying to sell something / exploit people.

In my grading scale I classify you as a spammer. A "bespoke" spammer perhaps, but I still do not want to waste time reading anything you send me, or waste time even clicking "mark as spam", unless I ask for it. You would be stealing my mental CPU cycles (which are few and precious).

> 2. It's trying to sell something / exploit people.

Are these synonymous?

No. I'm drawing a distinction between “I want to sell you something” and “click this link to a website that strongly resembles, but is not, YourBank to transfer all your money to us.”

I think / is usually reserved for synonyms. Should just use the word "or" if it's this or that.

Yes / No

I remember an old boss launching a product this way - he read the spam law and while I don't remember the specifics, sending an unsolicited email to people whose emails you obtained legitimately was okay if you weren't explicitly selling something (which I think is very open to interpretation).

> was okay if you weren't explicitly selling something.

The CAN-SPAM Act does not forbid explicitly selling something. Rather it requires an opt-out mechanism and identifiers for who the sender is.

Yeah okay - obviously varies by country although I think the opt-out mechanism is pretty universal.