Ask HN: CTO wants me to leave

this is the point in your life where you decide to be a lion, or a lamb. the hyenas are circling and they're not going away.

Do you always assume people are full of malice based on one side of the story or...

The issue in that respect is not what you legally can do, but structuring it in a way that won't scare away investors with too much complexity.

Generally, though, nothing will "protect you from future investor rounds" if they really want to fuck you over, other than being diligent and keeping a lawyer around, and picking honest co-founders. If the investors coming in and other still employed founder(s) wants to mess things up for you, it can be tricky to protect against them diluting your share holdings to next to nothing, for example (e.g. do a round on a very low valuation; issue large amount of options to remaining founders to make up for the extra dilution they take). Of course, if investors try to do that, chances are they'll screw the remaining founders first chance they get too.

And what matters even more than loyalty, in this kind of game?

Contracts.

If this is getting ugly, and the company has a product/service that could take off and be worth serious money, your only friend is your lawyer, and your primary assets should words with some signatures underneath.

And if, heaven forbid, we're talking about a cofounder who doesn't have a rock solid contract, the time to fix that is right now, with the help of that lawyer, while leaving immediately still appears to be a significant threat to the business.

Don't sell yourself short: simply knowing your limits is a major skill, that will let you contribute where you can, grow where you can, and defer to others where you must. Also, having been involved since the start gives knowledge and perspective that can't necessarily be hired elsewhere.

Ultimately if you want to stay -- and especially if you still have the support of your biz cofounder -- you should insist on having the chance to grow with the company, learning as you go along. And the plan for the future needs to be well understood among the principals, before the fundraising, because that process will tend to firm up roles, equity, vesting, employment agreements, etc.

It's true that sometimes a member of the founding team isn't right – the commitment or skills or shared-vision isn't there, and perhaps the original title/status/equity even gets in the way of acquiring what's needed. But it sounds like you're humble and flexible enough that you should be able to retain a key role.

If you are considering leaving from, or think you might be pushed out of, a valuable position, you will likely want to consult with a lawyer, separate from the company lawyer, about how to best protect your rights. (The fundraising process itself, and getting the whole company/team into "standard" documents, could either work to your advantage, or make it very easy for you to be booted with very little, so educate yourself early, to avoid signing away anything valuable.)

If intimidated by the idea of talking to a lawyer, remember that many will give a free 30-60 minute initial consultation, so simply by the act of shopping around, always improving your 'executive summary' of your situation before each discussion, you'll learn a ton at no cost. (No two lawyers will have the exact same analysis, so the 5th or 10th you talk to may still improve your understanding.) And if you find someone you like, they may give you quite a bit of continuing good advice simply in return for the future-chance/option-value of representing you in a future dispute.