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’

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• I work for a remodeling contractor here in Texas. Calling him my boss doesn’t really cover it. We were friends for a long time before any of this, we met through cars years before we ever worked together.

• When my last company let me go, he was the one who helped me get back on my feet. He brought me on, sent me to another business that ended up paying me a really good chunk of money, and for the last 18 months we’ve done well together. I want that said up front before I complain about anything, because I really do owe this man a lot.

• We work one of those wealthy communities where one lead can mean serious net profit. He’s probably the most expensive remodeler around.

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• Then this year hit. We were fully booked, and then the leads just dropped off a cliff. To stop the bl**ding I pretty much taught myself paid ads. New angles, new creatives, testing on every platform I could get my hands on. To do it right I ended up paying for three software subscriptions out of my own pocket (nothing crazy, about $70 a month).

• I never asked him to pay me back. I really felt like fixing this was my job. And it kind of worked. We also leaned harder into FB groups and tried some different approaches there... I’ve been putting in a lot of time and effort.

• Now we are about to enter in November he’s asking for more again. The subs literally kicks in in two days. More videos, more ideas, more stuff to test. The ad budget is capped at $600. I get a flat $1,000 a month that has never gone up, and out of that I cover taxes, internet, gas to the office, the days out recording, and then the editing. So that $70 is almost 10% of what this job really pays me.

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• I’ve got a 3 month old baby. Counting every client and every side gig I can get, I’m making around $3k a month on average.

• There are two things I keep coming back to. He just bought a new F-250. And he has another guy in Mexico who’s worked for him since 2019 and has never gotten a single raise (he told me that himself, like that’s just how things are).

• So with all of that in mind, what would you do? Do I just eat the $70 and treat it as part of the job? Or do I go to him and say “hey brother, can you help me out with this?”, knowing that with him, money and friendship are the same conversation?I don't want to lose the job, the friend, or both.

  u/LadyDemura

   

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• This conflict might feel quite tricky but, at the end of the day, is very simple. Someone who cares about you is always going to put your best interests at heart. A friend who sees you struggling will want to reach out with a hand and make sure you find your way back to a place of well-being, whether they are your boss or not. Power conflicts have no space in friendships, most of all in one that has been so mutually helpful, as it seems. 

• With a 3 month old at home I wouldn't eat it.

  zeddwood

• The $70 isn't really the issue to me. $1k flat for 18 months while you're basically running his whole marketing dept is.

  blinders101010

• I'd just ask him to put the subs on the company card. if a friend gets weird over $70 a month while buying a new truck, that's your answer right there.

  FrostySlabs

   

• In that way, the hard part here is to face reality. A conversation about money with a close friend is never going to be comfortable, and yes, there is a big risk that a disagreement of that sort could entirely break the relationship. However, they mustn’t be avoided. True and honest friends will find a way to help you out, while also caring about your opinion and outlook on a situation. Especially when you also share a working team with them. If these two friends decide to have this conversation and it ends up turning into a big conflict, perhaps the common interests were not entirely aligned in the first place. 

  Collaboration and empathy are skills we must all have, not only for friendships but for all sorts of scenarios. In the workplace, when we surround ourselves with a team, these characteristics are equally as important, since we should always try to seek a collective well-being in teamwork situations. So, don’t be afraid to speak up when you need help, and don’t try to solve a problem that is meant to be solved with a team on your own. 

  
   

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