I never got in trouble, but i did kind of double dipped once.

I was delivering pizza, and the owner of the franchise was looking at buying a condo bay that happened to be owned by my boss at my day job.

He was struggling to get financing in place to buy the bay and I suggested that he ask my boss for a vendor take-back mortgage for part of the financing. I know my boss wanted to sell the unit. So I guess I was discreetly working in the background to make the deal work.

In the end the deal worked out great, my main boss got rid of his commercial condo bay, and got paid back his mortgage in under 5 years, and my moonlight boss got a great deal on a piece of Real Estate.

I also once delivered to a coworker's house but my name tag said Aziz, I think he thought I was a doppelganger because I never let on that I knew him and it never came up at work.