I remember working for a sketchy start-up right out of college. They were doing telecom stuff when the carriers were de-regulated in the early aughts. Even now, they were tied up with some fintech companies and some shady investors. I was a combo developer/csr/account management person at any given time depending on what was going on.

They would rarely put stuff in writing. I was always told to do stuff. Never in email, never in memo's or any other written form. It was always, "We're going need you to scrub some files from xyz database." or "I need to rewrite this contract and add these additional sections which weren't on the original document." If I needed details, they would put them on a sticky note. I remember they had someone come around and take these notes off of people's desk when the task was completed.

I remember at Christmas one of my uncle's was a stock broker and a big knocker at some financial company. He was asking what I did and where I worked. He started asking more questions and told me I needed to be very careful - what the startup was doing was either really illegal or they were operating in a very gray area. Neither of them will end well for anybody and if the SEC thinks I'm involved in any way of covering up what they were doing? Then I'm in deep shit.

I quit about three weeks later. A year or so after that, the economy collapsed. I found out they were automating robo-signatures for real estate and mortgage companies. They were changing clients contracts from fixed APR's to 3 year ARM's and a bunch of other highly illegal shit. The company went under and despite several local news reports about it, nothing happened. Pretty sure they just got lost in the myriad of other companies going under, people losing everything and the economy collapsing.

It was a good experience for me to understand and see red flags when something doesn't feel right.