Roy Bahat, a venture investor who led Bloomberg Beta, writes about startups, angel investing, introductions and learning to code.
HN links his post on forwardable introduction emails as a reference on how to make introductions, alongside similar posts from other writers.
I like to think of it more as being intentional, and less as desperate/too forward. You want to know what you're looking for and, just as important, what you're not looking for.
In terms of reaching out, here are some things I did when I was job hunting:
1. The classic referral
Find the job post and work backwards from there (e.g., is there somebody I know (1st connection) or somebody who knows somebody I know (2nd connection) on LinkedIn who works at the company?).
If I knew the 1st connection, I'd reach out and ask if they were comfortable referring me.
2. The forwardable email
If it was a 2nd connection, I'd reach out with a forwardable email (https://also.roybahat.com/introductions-and-the-forward-intro-email-14e2827716a1) and ask if they'd be able to forward an email and make an intro if they received a positive response.
3. Job hunting as an occasion
I made time to catch up with good friends. It felt energizing to get the moral support, with the added bonus that sometimes they knew people working at companies looking to hire. For example I would eventually get a job offer from Figma and that was because a good friend's partner worked there and was glad to refer me. I hadn't even heard of the opportunity before we talked.
4. The weak ties
I also made time to catch up with people I didn't know that well. There's some research on "weak ties" that suggest that people who you don't know well probably are exposed to a very different network to you, and will come…
Maybe "name and shame" is a lousy way to describe it. But, I think it makes sense to talk about the offer more openly with people in the same startup community.
As a successful startup, there will be future rounds of funding. Any follow-on investor will eventually find out about problems on a cap table. They will probably fight to reverse it before an investment, or worse - it will sink the deal and the company. If OP's VC is a novice, maybe they don't know about liquidation preference. If they are not new, then perhaps the community should know about such divergent investment terms.
I agree about talking to a lawyer. But, in my experience, lawyers can find a way to make things work - and they won't stop a deal because of non-standard round terms. The non-standard terms hurt the company as they try to bring on additional investors. Any experienced founder or investor can provide guidance about how trying to "reinvent the wheel" for fundraising will cause problems down the line.
To OP, I suggest reading section 3 in this article by Roy Bahat: https://also.roybahat.com/dear-first-time-angel-investor-c6af249a694b
Here are some other great posts about this:
http://also.roybahat.com/post/92544681186/introductions-and-the-forward-intro-email
https://alexiskold.net/2015/06/24/how-to-write-a-forwardable-introduction-email/
http://avc.com/2009/11/the-double-optin-introduction/