it depends whats in it for you? what do you get if things go well? what do you get if things are going to shit. What are the exact numbers ? are you trying to bail out a crash and burn? what does the term bad partners entail ? are you the next bad partner? what are the risks? can you laugh off the 300k?
This is your friend. Take him for coffee ask him whats changed or whats going on for him you may be the trigger point for the behavior change be open to his answers and listen. If it doesnt have an impact and you cannot reconnect over it tell him whats going on for you show him a personal p&l let him know hes been a big help in the past and you appreciate him. Let him know if the role doesnt interest him anymore you can still be friends and that you dont want to formally document him out of the job but cant afford the negative consequences." …moving forward we have to follow the progressive discipline system to the letter,(this means write ups down the line to termination) " if we can be in this together and do it amazing"" if youd rather not thats amazing to if youve decided parting ways is a better idea at this point i get it and it makes sense" if you can sit on it for a couple days let him know that he can have a couple of days off before he makes his decision and your happy to revisit it then. Good luck this is a shit spot for you both to be in.
when everyone can freelance and everyone does … its like needles in haystacks