If he doesn't have a majority of the vote on his own, the only way it could have passed is if your other friend voted in favor of it, as the issuance of new sha

If he doesn't have a majority of the vote on his own, the only way it could have passed is if your other friend voted in favor of it, as the issuance of new shares/equity in an LLC requires a vote if the shares were not already authorized. I'm guessing that the guy probably decided to waive some of his salary in exchange for equity-based compensation (possibly by increasing his salary, which wouldn't require a vote, and then swapping the monetary increase for shares of equivalent value, which also wouldn't require a vote if the shares were already authorized)... When you talk to a lawyer about this, make sure to have a copy of your capital (/equity) table, and all resolutions about the authorized number of shares, and any documents you have related to the actual issuance of shares or capital. Don't fire him or do anything else of that nature until you talk to a lawyer, as any sort of action could be construed as retaliatory and you'll want legal advice about that to make sure you do it the kosher way.