Employee hesitates to ask for a raise after paying for the company’s ads out of pocket, because their boss is also their long-time friend: ‘We were friends for a long time before any of this’

When friendship and teamwork mix, anything could happen. 

Mixing work with personal relationships is tricky. In a tale as old as time, some friendships don't survive teamwork when work-related disagreements turn into awkward conversations between friends. That said, it is not entirely impossible to start a business with your friends and not lose them in the meantime. In a way, it can also be a very important advantage to be able to rely on people you know and trust when business gets hard. It is definitely a challenge that can lead to the best or the worst outcomes. That's why there are some factors that play a huge role in whether this business endeavor actually becomes functional. How do the power dynamics work? Is there someone who has a higher hierarchy in the team? Is that an issue for the other party involved?

In this story, two friends go to work together. There is no doubt that between them there is trust and understanding, but trouble comes when the money situation of the business itself starts to decline. One of the parties takes on the responsibility of using publicity and ads to help the business, and directly invests in this process. On one hand, it works, and the company seems to be doing a lot better. On the other hand, the expenses of keeping it like that fall upon this one person. The most important part of this story is that this person does not want to put their friendship at risk over business money, but is starting to feel out of options. So, question is, how do you can you do both? Protect the friendship while also having a big disagreement on money?