In *I'm the Boss!* each player takes on the role of an investor trying to seal the most profitable deals. At setup, everyone gets an Investor card – alphabetical order decides the first player – and five Influence cards that will be used to sabotage or boost negotiations. A dollar marker is placed on any space of the board, each space representing a potential deal with a dividend value. On a turn, a player may either open negotiations on that space or roll a six‑sided die to move the marker clockwise. When the marker stops, the player chooses to negotiate the deal or draw three Influence cards; if the hand exceeds twelve cards, the excess must be discarded.

If the player decides to negotiate, they bargain with the investors controlling that space, splitting the amount – dividends multiplied by the share value on the deal tile. Influence cards provide tricks: Clan cards can stand in for investors, Travel cards remove investors from play, Recruitment cards (in sets of three) steal another player's investor, Boss cards grant full control of the negotiation, and Stop cards cancel the effects of Travel, Recruitment, or Boss cards. When a deal is sealed, the bank pays out, the deal tile covers the space (blocking it), and the dollar marker moves to the next open space.

The cycle repeats until nine deals have been made; thereafter, after each subsequent deal, a die is rolled to see if the game ends, with the probability increasing each time. The player with the largest bankroll at the end wins. The game blends dice rolling, hand management, set collection, and heavy negotiation, all spiced up by cards that can flip the outcome at any moment, guaranteeing chaotic, laugh‑filled sessions.