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Bought company I was sacked from, how to deal with ex boss as a client

47 replies

Whyintheworld · 27/12/2025 20:08

Backstory : years ago I was illegally sacked from a company; a small company with only 2 of us working/running it.
Owner was not involved in running of it, only maintained minimal back office work from abroad. Southern European company so sacking was easy as suing for unfair dismissal costs thousands and takes 3 years here. Company was on brink of bankruptcy due to owners tanking accounts (feasible to do here unlike in most functioning countries). It is the reason for the sacking added to a personal vendetta his wife had against me (two strong personalities and a friendship turned sour).

Now : I ended up turning various of the clients of that business into my own clients on my own business as they were loyal to me not the company. One of said clients of mine now, decided with me to invest in buying the previous company mentioned outright, giving me a quarter of the company shares and my previous coworker another quarter (for free) in exchange that we run the business. A fantastic opportunity, one I couldn’t be happier about and helps that I feel I got one up on the ex-owner that had illegally sacked me. The ex-owner is not aware I am part of this to this day (it happened a couple of weeks ago).

The ex owner has now asked my business partner (the investor not the coworker) if he can pay cost price for a service of ours. The service will take a few months at a cost of a few thousand.

  1. we (3 business owners) all agree cost price he will not get rather a 5 maybe 10% discount at most although I clearly don’t want to offer any discount. However business is still business and we know he’ll take his money elsewhere without some small discount. Would you be doing this if business needed the income despite personal feelings?
  2. He will of course find out I’m there involved if he becomes our client and I need to address this. I want to sound polite, professional yet powerful. One simple line of “I as a business partner at X company” will shock him to his core I’m sure, but I would like to word a very precise not emotional yet powerful “business owner to client” email to him but I don’t know exactly what to write? I want the power balance to flip on his head and make sure he has it clear. This email is to be sent the day after he makes full payment. General contents of “I’m working on this project for you and will bring about my upmost professionalism however f* you and all the rest…” without of course using any obscene language.

Many thanks for any great ideas for point 2 and opinions in general on the subject.

OP posts:
LongDarkTeatime · 28/12/2025 10:00

Don’t mix personal feelings with business. Even more important than dealing with this contract is showing your business partners you can act professionally

Imgoingtobefree · 28/12/2025 10:07

Do you think there is a chance that whatever you write and however you phrase it - he will react badly and do something in any way that could be detrimental to you or this company?

If so, then be as absolutely bland and inoffensive as possible. Perhaps imagine what you would write to a stranger?

Parsleyforme · 28/12/2025 10:13

I agree with PPs and wouldn’t say anything, it wouldn’t be professional. He will have enough of his own feelings when he finds out you are running the company. Making the announcement after he’s paid would make it seem planned and bitter. It would be better to take the high ground, be calm and confident, and let it seem as though you barely remember him/working there

LemonLeaves · 28/12/2025 10:19

As an onlooker -

Sending this type of message is unprofessional. And I'd expect a competent CEO not to engage in low-level tit for tat behaviour.

Don't do it.

SparklingCrow · 28/12/2025 10:23

I wouldn’t touch him, his ‘I want it at cost/a discount’ business, or his company, with a barge pole.

He’ll make trouble for you and your company. Your co-investor(s) and colleagues need to hear the full story.

Jellycatspyjamas · 28/12/2025 10:24

The sacking happened years ago. I assume during that time you’ve grown, taken opportunities that otherwise you might not have done and you’re obviously in a different place now. So why give this person so much thought? Enjoy running the business, take on work that will challenge you and be profitable but let this person, and your feelings about them, go.

GoodQueenWenceslaus · 28/12/2025 10:33

Whyintheworld · 27/12/2025 20:28

You make a very fair point. Exactly why I needed the public’s opinion on such an emotionally explosive matter. Just with my email header stating name and CEO of X company below might actually be all I need. Saying nothing may possibly be an even better stance and position of power in any email to this new “client” of mine.

I agree 100%, though if the work involves working with their employees you might want to ask for assurances about the stability of their employment.

oviraptor21 · 28/12/2025 10:40

I would inform your co-owners of the conflict of interest. If possible the work should be declined. If not possible, then buyer should be informed of the conflict and you should not handle any aspect of the project.

JustGotToKeepOnKeepingOn · 28/12/2025 10:46

I’d decline his business. He sounds a complete snake. He wants the service at cost?! What planet is he on? Don’t accept him as a client and definitely don’t send him any kind of email. He could do so much damage to your business and reputation by saying he had to sack you - that would be enough to get others thinking about your competence. It’s really not worth poking the bear.

MILLYmo0se · 28/12/2025 10:50

I can understand people saying not to take his business at all but as a quarter shareholder you don't have the power to do that as the other 25% and 50% shareholders can vote you down.
I just wouldnt get directly involved at all tbh. Is the company still very small, would it be usual in whatever this service he wants for him to be dealing with the 3 shareholders or CEO (is that your official title) directly? If not then let him go through the usual channels, if it is have the other person deal with him. If you go in 'CEO-ing' to make a point you are giving him the power, it ll be obvious how upset you still are. He may not even care that you are now a % shareholder of the company, he has the money from the sale, may not care who it came from, and that will make you feel worse. He ll find out anyway

Hoppinggreen · 28/12/2025 10:52

Are you desperate for the work?
I am SE and if I get asked to do something or work with somone I am not keen on I put my rates up - that way if I do it its worth the hassle for me
Thre is no way I would offer someone I didn't like a lower ratee

Charlenedickens · 28/12/2025 11:01

Focus on running the business not petty one up manship

rwalker · 28/12/2025 11:02

Revenge is for the playground be professional

treat it just as you would any other client

Tigerbalmshark · 28/12/2025 11:10

I think treating this as a business decision and assuming ex boss will of course act professionally is the way to go.

A bland email cc’ing the rest of the team saying something like “delighted to work with you on X project”, along with your “CEO” email signature, should do the trick. He can fume away when he sees it, you haven’t lowered yourself.

Cheesypasta · 28/12/2025 11:14

Hoppinggreen · 28/12/2025 10:52

Are you desperate for the work?
I am SE and if I get asked to do something or work with somone I am not keen on I put my rates up - that way if I do it its worth the hassle for me
Thre is no way I would offer someone I didn't like a lower ratee

Yes, I would reply politely but saying 'we are unable to do this at cost as you ask. We understand that you will look elsewhere and we wish you well'. It's much better for you if he does go to someone else as he'd be a nightmare client. For you the best revenge would be getting on with your business thinking 'I'm so glad I'm not having to pander to X's ridiculous demands!'

Do your co-investors know the back story? I think you need to tell them why you don't want to work with this particular client.

Whyintheworld · 28/12/2025 13:48

Co-owners are fully aware, sorry I thought it too long to explain. Investor who bought the company became client of mine personally because of the terrible behavior of the previous owners towards me. The ex-coworker now business partner is one of my best friends and became a business partner of mine in another third operation that I haven’t mentioned so I demanded he be brought into this deal as didn’t want to run it alone. He clearly is on my side for obvious reasons. Only kept working for a*hole because the salary was consistent while we were building up the third company. They are fully ok with me choosing what I want to do / whether working with him / refusing to give him service / sending any email or my liking. And yes I am the chief executive officer of the business. The ex-worker will continue his role and the investor is silent / back office IT support only.

Thank you to all. I have clear now I will simply head my email with my position and act as though its first contact, he will neither be receiving any discount so maybe he doesn’t even turn up in our books anyway!

OP posts:
m00rfarm · 28/12/2025 13:54

Of course you should not send anything. The buyer of products/services to your company can leave shitty reviews wherever he wants. That could ruin your business. And your co owners will not appreciate it. It is extraordinarily unprofessional to even consider sending an email gloating that you now own the company. If you don't make it into a big deal, then your ex boss will be allowed to process his own feelings about this. A stupid email will simply make him feel that he was correct to sack you in the first place. Alternatively, send the email, but don't take on his work. You cannot have a client with whom you have an unprofessional relationship.

GargoylesofBeelzebub · 28/12/2025 15:09

Oh god no. Why would you indicate to him that he occupies any space in your thoughts at all. Do nothing other than decline the business.

Friendlygingercat · 28/12/2025 16:35

Getting revenge on a formed boss can be very satisfactory. I was once ripped off by a boss. I paid him back in a way that made it necessary for him to resign from his job and seek another in a different part of the country. The most satisfying thing is that he can have no idea I was behind what happened.

However revenge is revenge and business is business.

Running a business you get a feelinhg for whether you want to deal with a client, or whether they would be too much trouble to make it worthwhile. In the latter case you are at liberty to decline (politely) when you are self employed. Since you are going to make little profit on the deal I would be inclined to politely decline to offer a discount and wish them well in finding another supplier.

LemonLeaves · 28/12/2025 17:04

Whyintheworld · 28/12/2025 13:48

Co-owners are fully aware, sorry I thought it too long to explain. Investor who bought the company became client of mine personally because of the terrible behavior of the previous owners towards me. The ex-coworker now business partner is one of my best friends and became a business partner of mine in another third operation that I haven’t mentioned so I demanded he be brought into this deal as didn’t want to run it alone. He clearly is on my side for obvious reasons. Only kept working for a*hole because the salary was consistent while we were building up the third company. They are fully ok with me choosing what I want to do / whether working with him / refusing to give him service / sending any email or my liking. And yes I am the chief executive officer of the business. The ex-worker will continue his role and the investor is silent / back office IT support only.

Thank you to all. I have clear now I will simply head my email with my position and act as though its first contact, he will neither be receiving any discount so maybe he doesn’t even turn up in our books anyway!

That sounds like a really sensible way forward. Keep it all totally professional - and no discounts either.

Footle · 28/12/2025 17:53

‘Upmost’ is not an English word btw. Might be useful to know it’s utmost.

Oldandgreyer · 28/12/2025 18:46

If you seek revenge, dig two graves.

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