[pc86]

It's a serious contract issue but it's not criminal.

The two founders own 66%, presumably 2/3 of the board seats (but if they can't even be bothered to write a vesting schedule they probably don't have a board at all). For the sake of argument if each of them own 10k shares (30k total), there is nothing criminal about the board voting to issue 100k new shares to the two remaining founders. So now they each own ~48% and OP owns ~4%. Shitty move? Yes. Morally and ethically terrible? Absolutely. Will OP sue them? I would hope so. Illegal? Not even a little bit.

The way you prevent this is by having a contract. But again, OP was just doing this with his buds so no need for a contract, right? This is why you sign a contract for anything you're doing that involves more than $100 in assets or a few weekends of time.

[mamon]

You cannot issue 100k new shares out of thin air... If the company is worth $1.5M, split in 30k shares then each share is worth $50. Issuing 100k new shares would require those two founders to invest additional $5M (which I assume they don't have).

[valuearb]

Sure you can. You issue the remaining founders options for 100k shares at an excercize price if $50 per share. You can probably even do it at $10 or $20 per share, since investors shares are likely preferred, and don't have vesting requirements, meaning you can discount common shares for illiquidity/fewer rights.

[doctorwho]

Shareholder oppression is criminal. Whether the actions they take constitute shareholder oppression or not is a matter that usually gets settled in court or arbitration.