The quickest path to success often runs straight through the thickets of questionable legality. Franchises that can overcome the morally dubious aspects of certain enterprises—and can deal with the risk of being caught engaging in those enterprises—might wish to consider such time-honored practices as back-of-the-wagon discount sales, fly-by-night gambling halls, highway robbery, racketeering, and pyramid schemes. Shady business practices can also include corporate espionage against rivals and other Acq Inc franchises, including stealing goods or sabotaging commercial efforts.

***Resources.*** An intended shady business practice is detailed by the players and approved by the DM. Any shady business practice requires at least two workweeks of effort, plus 50 gp per franchise rank in expenses to set up the scheme.
***Resolution.*** A shady business practice requires three ability checks, reflecting the ongoing progress of the chosen scheme. Any of the characters or staff members involved in the shady business practice can make a check. The abilities and skills applicable for each check are determined by the DM, reflecting the selected scheme and the ongoing narrative. For example, an attempt to set up a fly-by-night casino might require an Intelligence (Investigation) check to case a town for a suitable location, a Wisdom or Charisma check making use of gaming set proficiency to run the operation, and a Dexterity (Sleight of Hand) check to get away with the profits. At the DM's determination, each check gains a +1 bonus if the character making the check has a background appropriate to the shady activity.
The DC of each check is determined randomly, reflecting the risky nature of criminal enterprises. The DM rolls 2d10 + 5 for the DC, generating a separate result for each check. The total number of successes determines the outcome of the activity, as noted on the Shady Business Practice table.
Some outcomes of shady business provide an additional benefit, chosen by the DM and relating to the characters' chosen enterprise. For example, a franchise engaged in corporate espionage might gain insight into a rival, while a franchise selling black-market goods might learn the name of a corrupt government official.
*Why would I know anything about shady business practices? Why are you asking me? I'm sure I don't know what you mean. Plausible deniability certainly is not an important business tip I'd recommend.*— **Rosie Beestinger**
##### Shady Business Practice
| Successes | Benefit |
|:---------:|---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
| 0 | All participants in the shady business practice are arrested, and the franchise is fined 250 gp per franchise rank. |
| 1 | The shady business practice is a borderline success, providing 50 gp in profits per franchise rank. |
| 2 | The shady business practice is a moderate success, providing 100 gp in profits per franchise rank. Additionally, the franchise gains a minor benefit related to the enterprise. |
| 3 | The shady business practice is a full success, providing 150 gp in profits per franchise rank. Additionally, the franchise gains a major benefit related to the enterprise. |
***Complications.*** Achieving 0 successes automatically generates a complication, but the DM might decide that any illicit enterprise runs the risk of unforeseen circumstances. The DM can choose a complication or roll on the Shady Business Practice Complications table.
##### Shady Business Practice Complications
| d6 | Complication |
|:---:|-----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
| 1 | One of the franchise's staff members is arrested in connection with the scheme—and is set to be interrogated about all the franchise's activities.* |
| 2 | Characters or staff members meet a corrupt official or noble as a result of the scheme. This brash and flamboyant individual threatens to draw attention to any future shady enterprises. |
| 3 | A rival uncovers the shady scheme and threatens to expose it.* |
| 4 | A citizens group hears rumors about the franchise's involvement in the shady scheme, and forms a watch organization to monitor the characters. |
| 5 | An NPC who participated in the scheme tries to blackmail the franchise, asking for payment or a favor to keep quiet. |
| 6 | A thieves' guild or other criminal organization takes an interest in the scheme. They order the franchise to run this activity every month, and demand a 10 percent cut. While the franchise does so, all checks for shady business practice activities are made with advantage.* |
*Might involve a rival