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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:
Arlanymor · 27/12/2025 20:12

My general opinion: I wouldn't. These things have a way of backfiring. I get you are angry, I get you were hard done by, but sending an incendiary message (because let's be honest, that is what it is based on everything you have said) very often blows up in the senders face. The best revenge is living well - not rubbing other people's noses in it. You already know he will be squirming when he sees you are involved, do you need to hammer the point home? As I say. I wouldn't and believe you me there are people who have done me dirty in my career in the past. But I still wouldn't.

Whyintheworld · 27/12/2025 20:28

Arlanymor · 27/12/2025 20:12

My general opinion: I wouldn't. These things have a way of backfiring. I get you are angry, I get you were hard done by, but sending an incendiary message (because let's be honest, that is what it is based on everything you have said) very often blows up in the senders face. The best revenge is living well - not rubbing other people's noses in it. You already know he will be squirming when he sees you are involved, do you need to hammer the point home? As I say. I wouldn't and believe you me there are people who have done me dirty in my career in the past. But I still wouldn't.

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.

OP posts:
Arlanymor · 27/12/2025 21:52

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 honestly think that IS all you need - CEO is a total gut punch! And actually he will twirl round more in his head about what it all means than if you sent a direct message. Let him stress, worry, and be shocked. You don't need to see it to know that it is happening. Hold your power and know that he is now in a powerless position - but there is no need to say it, both sides know.

BastardtheCat · 28/12/2025 06:54

I’d agree with the others and say absolutely nothing at all - just do the best job and quietly live your best life.

That said, I’d hesitate before taking the job as I’d be a little concerned that he’d leave rubbish reviews/find fault with the service and try to wreck your company reputation.

sashh · 28/12/2025 07:44

Email: I am now a partner in this company. Thank you so much for sacking me, I couldn't have done this without you.

Completely luck with his head by being overly nice.

PodMom · 28/12/2025 07:53

I agree, say nothing. Let the Penny slowly drop along with the realisation that he’s of such little consequence to you that you haven’t even told him.

kotordreams · 28/12/2025 08:52

How small is your company? Would you ordinarily have direct contact with the customers of his size as the CEO ? Surely anything beyond generic emails in your name is giving him undue attention.

Livelovelaughfuckoff · 28/12/2025 08:58

Honestly I would decline the business altogether. However if you go ahead then someone should probably inform him as he may choose to take his business elsewhere because of it. Be transparent and keep your integrity.

OneOfEachPlease · 28/12/2025 09:11

All your partners and investors aware of the backstory here? Someone who was that poor at running a business might actually be quite good at ruining yours. So maybe think very carefully about whether the small amount of money that you’d take him from him is worth the stress of having him there.

I would not do anything with him that you would not, as CEO (congratulations!), do with any other client of that size. So for example, if you would not normally have contact with an account of that size then don’t have contact with it. At some point he will see your name and realise that he’s become a complete irrelevance to you and your story and that you are now incredibly successful.

Chasingsquirrels · 28/12/2025 09:17

You are giving him way too much head space.

Look at all you have achieved, you don't need to carry this hatred.

HateThese4Leggedbeasts · 28/12/2025 09:19

If you think he will strongly object to you being involved you should tell him before payment. A time consuming dispute is a distraction your business doesn't need.

burnoutbabe · 28/12/2025 09:22

Livelovelaughfuckoff · 28/12/2025 08:58

Honestly I would decline the business altogether. However if you go ahead then someone should probably inform him as he may choose to take his business elsewhere because of it. Be transparent and keep your integrity.

Yes I!d do that. Choose to decline his business.
or let him know you are involved and would he working in his account during the quotation stage so he can pull out now.

SoScarletItWas · 28/12/2025 09:28

You’re missing the point that as the client, ie the one paying, he in fact holds the power in this transaction.

When he sees you are involved, it will be another opportunity for him to make life miserable for you.

I’d stay well out of it if the company HAS to take the work. Or decline/refuse to offer the discount so that he goes elsewhere.

Move on. It’s not healthy to carry a grudge your whole life. Let your success be your revenge.

ParentingRollerCoaster · 28/12/2025 09:30

All sounds strange.

Do you definitely want the business?

Is it your decision or the decision of the 50% owner? ie is the 50% owner involved in the day to day of the business, negotiating sales and running the business?

From 50% owner: Here are our terms of business. Once the terms have been agreed upon, the service will be delivered, and your main contact will be OneofEach, who is responsible for operations at X.com

Clear roles and responsibilities might be helpful.

Or... keep it professional and polite, and allow your other business partner to take the lead on this.

It seems strange that you would have a picotal role in delivery of the service but not be part of the negotiation. There are 3 people involved, one who has significant and bitter history with the potential client.

LadyLolaRuben · 28/12/2025 09:33

I agree your former boss should be advised of your CEO role in passing and not by messaging directly. I also think he needs to know before payment/agreement is signed. You dont want to kick off trouble as it sets your new business on the wrong footing

Whyherewego · 28/12/2025 09:35

I agree with @SoScarletItWas . Just decline this business.
As a customer he can be demanding, he could make claims of poor quality, he could be unreasonable etc. He's already shown you he's capable of all of this.
Just say you're not prepared to offer a discount and he goes elsewhere.
If you insist on taking his custom, then you should really be up front about your role and prior to taking payment. You can send something along the lines of "Before we go ahead with this transaction, you should be aware that I am now CEO of the business". Then he at least enters into the transaction well aware of things

AtomHeartMotherOfGod · 28/12/2025 09:40

Arlanymor · 27/12/2025 20:12

My general opinion: I wouldn't. These things have a way of backfiring. I get you are angry, I get you were hard done by, but sending an incendiary message (because let's be honest, that is what it is based on everything you have said) very often blows up in the senders face. The best revenge is living well - not rubbing other people's noses in it. You already know he will be squirming when he sees you are involved, do you need to hammer the point home? As I say. I wouldn't and believe you me there are people who have done me dirty in my career in the past. But I still wouldn't.

Completely agree; do whatever you would for any other client.

Give him a sheer, smooth wall of service, where there are no footholds for him to exploit and attack you with.

CurlsLDN · 28/12/2025 09:40

I’m the owner of a company that provides professional services to clients.
I think, if we weren’t desperate for the work, I’d let this one go - money is not worth your mental health and it sounds like this will weigh heavy on your mind/heart.

however, I’d still let him know how well you are now doing! So I think I’d find a reason to send a brief but professional email - eg an intro to all team members

  • whyintheworld is the boss - you may remember we used to work together at X
  • sarah is finance
  • dave is the project manager

then create an out, eg ask them to send a brief but decline the brief as your company is busy and doesn’t have capacity for their project at this time.

im fully behind you relishing this moment and, in a professional, cool and confident manner having the opportunity to show your current success. For that reason i want to mention that its utmost, rather than upmost, in the sentence you’ve suggested above - not trying to be pedantic but I don’t want to give them ANY reason to think they are cleverer than you!

BDenergy · 28/12/2025 09:43

Livelovelaughfuckoff · 28/12/2025 08:58

Honestly I would decline the business altogether. However if you go ahead then someone should probably inform him as he may choose to take his business elsewhere because of it. Be transparent and keep your integrity.

This. He has the right to know who is involved I think. Telling him after he’s made payment seems deliberately provocative and intended to piss him off.

Rise above it, be honest and don’t give yourselves a reputation for pettiness.

Gliblet · 28/12/2025 09:47

SoScarletItWas · 28/12/2025 09:28

You’re missing the point that as the client, ie the one paying, he in fact holds the power in this transaction.

When he sees you are involved, it will be another opportunity for him to make life miserable for you.

I’d stay well out of it if the company HAS to take the work. Or decline/refuse to offer the discount so that he goes elsewhere.

Move on. It’s not healthy to carry a grudge your whole life. Let your success be your revenge.

This. Think about the worst client you've ever dealt with, then add the existing resentment on top of all the pickyness, quibbling, arguing, demands sent at 4.30 on Fridays marked 'Urgent: by Monday', late payments and trying to get things shaved off the bill, then tell me honestly you're going to do a job you can be proud of and that this asshat won't be able to say anything about to damage your reputation (given that the people he's talking to will only have his side of the story) afterwards.

Wreckinball · 28/12/2025 09:49

Your feelings towards him are preventing you from being professional. Don’t take this business project on. Accept he was awful to you, you sought other great opportunities and things have worked out well. Learn from it, do not try and rub his nose in it. Other PPs are right he could be a nightmare client and give your company bad PR and affect you a great deal. Steer clear of him

TheGrimSmile · 28/12/2025 09:52

Say nothing. That will infuriate him more.

C152 · 28/12/2025 09:55

I get your point about some money being better than no money but, no, I wouldn't offer any discount at all. Not because of all the previous drama, but because (i) people don't value what they consider to be 'cheap', (ii) presumably you have worked out what you feel are fair costs for your work, so you should be compensated accordingly; and (iii) people who get discounts or you do something extra for because you think it's a kindness, will end up being the worst client on earth that you will rue the day you ever took on.

ParentingRollerCoaster · 28/12/2025 09:55

Excuse typos..

One week into your role / ownership of the business, which is a 3 person business, you are deciding on a contract with the ex owner, who was doing the work before you came on board? CEO seems an odd title for a small business even if it generates large revenues. Asking for something at cost is unreasonable. If this contract so important/ significant to the business that you can not decline, then I would be questioning the viability of the business.

Charlize43 · 28/12/2025 09:59

It's evident that bitterness is already corroding you and you are not living your best life. I would sell the company and with the profits move to Bali spend your time doing lots of yoga and finding peace.

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