Story time: A relative of a former coworker had been laid-off from their bank job during the global financial crisis in 2008, but then picked up a position as a Colorado cannabis dispensary's CFO (their first).

When he arrived for his first day on the job, he discovered that employees were making cash pickups from the dispensaries using their personal automobiles. So they were having an hourly employee driving around in a Honda Civic with $50,000 or more in small unmarked bills the trunk. When they arrived back at the office, they would re-count the bills then store them in a plain steel filing cabinet. Like you'd buy at Office Depot.

The first thing he did was order some burglary-rated safes and got rid of the filing cabinets.

Then he called some of the armored car companies (cash-in-transit firms), and was surprised to find they didn't want his business! It turns out their main customers (banks and credit unions) were VERY concerned over getting his drug cash mixed up with their customer's cash through a mix-up inside the truck. Marijuana sales were (and still are) illegal at the federal level. Even though the cannabis business was legal in Colorado, banks are regulated at the federal level via the Comptroller of the Currency and they couldn't take the chance of their cash being intermingled.

To solve this problem he started a subsidiary armored car business and ordered new vehicles for it (had them painted with green leafs on them..) They would only be used to transport dispensary cash. He even called his counterparts at other dispensaries and sold them on using his new firm for their cash transport woes. This was successful and he now has competition in the transport business.

To continue on his entrepreneurial arc, he set up another subsidiary to manage their real estate transactions. They were having problems acquiring new locations for their dispensaries as real estate sales are also subject to federal scrutiny via the Department of Housing and Urban Development.