It reads to me like "ball's in your court, I'm happy to talk but I'm done chasing".

Being proactive and contacting people over and over is fine for a while if you're "hustling" but eventually it just becomes spam, you sound desperate, and you'll be hurting rather than helping your chances.

Also, if you feel your proposition is good enough and you don't get the response you were after, then move on and focus on getting your pitch to the right people.

First cold email - No response

1-2 weeks later - Second cold email - No response

Monthly update/touch up - No response

Move on.

Some people would consider the second or third email as spam, that is fine. If they block you, that means that was a dead end anyway.

My experience is that people are busy and we forget to reply sometimes. 3 emails in a row, in a matter of days, would be spam for me too.

The second email is spam, and I’d be sure to never do business with that person at that point. I’d be closing off a door at that point.

You're going to miss out on quite a few opportunities if you consider someone's second email as spam.

It hasn't hurt me so far.