Background: I currently run a brand with my friend. We’ve just hit two years and are doing relatively well (press coverage, multiple retailers worldwide, etc). The business only consists of us two — we design every product and run all parts of the business together.

However, over the past few months, I’ve noticed that he’s been transferring the funds from certain sales (from his friends or at pop-ups) directly to himself instead of our business bank account. The first two times, I let it slide thinking that he just forgot or something. This past weekend, we had a pop-up and sold a little over $600 in product. None of the money ever hit our bank account. He’s told me that he’s given people his personal Zelle so he could transfer it later but it’s never happened. There was also another time where he tried to take back his initial investment and lied that it was to reimburse manufacturing.

Neither of us make any personal income from our business — everything gets reinvested or used to pay off debt. He’s recently unemployed so I’m trying to be empathetic but I feel like I need to confront him about it. The amount isn’t huge, just a couple hundred dollars. We occasionally invest a couple thousand dollars from our personal accounts so maybe he thinks it’s okay?

We spend a lot of time together and are good friends so I know such a conversation could irreparably damage our relationship. The thought of parting ways really sucks because of our creative synergy and all the work we’ve put in thus far. I’m not sure what to do.