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Father Faces Family Breakdown After Oldest Son Demands Equal Share In Siblings’ Business

by Annie Nguyen
November 19, 2025
in Social Issues

Family dynamics can sometimes lead to unexpected rifts, especially when it comes to skills and inheritance. The original poster (OP) is grappling with the fallout after teaching his younger children a unique skill that they have turned into a successful business, while his older son feels left out.

The tension escalates when the eldest demands a stake in the business, claiming he deserves an equal share despite not having been taught the skill. In his quest to navigate this complicated situation, OP is caught between wanting to support all his children and managing the resentment brewing among them.

As he attempts to reach out to his oldest son for a heart-to-heart, the question looms: is he being fair, or has he unintentionally favored his younger kids? Scroll down to uncover the intricate details of this family dispute and the opinions from the Reddit community.

A father watches his once-harmonious family fracture as his three sons fall into conflict over a thriving business he helped fund

Father Faces Family Breakdown After Oldest Son Demands Equal Share In Siblings’ Business
Not the actual photo

AITA for not teaching a skill to my oldest son that I taught his siblings because of the custody arrangement?

This has quite literally fractured my family.

I have an older son from my first marriage who's now 24.

I have two younger kids from my current marriage who are 21 year old twins..

My divorce occurred right after my son was born..

Over the years, my visitation has been primarily summers and holidays since my ex-wife moved to a different state.

I have a particular skillset I'm was very good at.

And all three of my kids have expressed interest in it.

Unfortunately, I have only been able to meaningfuly teach it to my younger kids.

This was because to make my visitation with my older son more memorable, I would do camping/vacations etc.

I didn't have time to teach him properly.

Also, anything I did try to teach him was forgotten and not practised because he lived in an apartment with his mother.

The major issue now is that my younger kids have started a company after highschool using this skill.

I provided the initial funds and as such have a 33% stake in it.

This company has really soared this past year and it's making a lot of money.

My older son graduated from college and is doing a job he hates and is not exactly making a lot of money.

Especially compared to his siblings.

Part of this is my fault because he did ask to take a few years off after highschool

and maybe have me teach him what I knew but my wife was battling cancer at the time and I told him I couldn't..

And now, I'm not well enough to teach anymore.

He is now telling me to include him in this company as a equal partner.

That he'll do the finances.

This was not received well by his siblings who say they do basically 95% of the work.

And that he didn't struggle in the earlier years to get it running. I'm really at a loss here.

I thought of just giving my share of the company to my oldest son

but it does seem unfair to his siblings who started this company in the first place.

My oldest has become very bitter about this and has involved my parents.

They are taking his side and now my younger kids are resentful that their grandparents have been turned against them.

Our Sunday family lunches are no longer happening and I'm having to see my oldest for dinner on other days.

And everytime I see him I'm getting accused of not treating him fairly.

It kills me because I made so many compromises to have him in my life in a meaningful way.

He accused me on Saturday of pushing him out my new family and loving his siblings more.

In the intricate tapestry of family dynamics, the threads of love, resentment, and perceived injustice often intertwine in painful ways. The story of a father grappling with the emotional fallout from his decisions highlights a universal truth: the scars of favoritism and neglect can leave lasting impressions on a child’s psyche.

In this case, the father finds himself at the center of a storm, torn between his two families and the conflicting emotions that arise from his past choices.

At the heart of this situation lies a deep emotional conflict. The father’s decision to prioritize creating memories with his eldest son during limited visitation times inadvertently fostered feelings of exclusion and resentment.

While he sought to build a strong bond through camping trips, his older son yearned for something more tangible, a skill set that would affirm his place within the family.

In contrast, the younger twins, who received both the knowledge and financial backing to start a business, now embody the very success that eludes their older brother. This imbalance cultivates a fertile ground for bitterness, as the older son feels sidelined and unvalued.

Children often interpret unequal treatment through a deeply personal and emotional lens, and when they sense that affection or opportunities are distributed unfairly, it can trigger feelings of insecurity that echo throughout their relationships.

As Simply Psychology explains, insecurity frequently arises when individuals feel that their needs or place within a relationship are unstable, leading them to internalize perceived imbalances as a threat to their emotional safety.

The father’s struggle to maintain harmony within his family is commendable, yet his efforts to rectify the situation may be too little, too late. By attempting to shield his older son from the realities of his younger siblings’ success, he inadvertently reinforces the divide that has already formed.

This is why the decision to offer an apprenticeship while maintaining the financial status quo is both generous and fraught with complications. It may serve as an olive branch, but the older son’s bitterness and frustration may overshadow any goodwill.

Ultimately, this situation invites a broader reflection on the complexities of family relationships. It underscores the importance of open communication and equitable treatment among siblings, as well as the need for parents to recognize and address their children’s emotional needs.

Finding a path forward that fosters healing and connection may require difficult conversations and a willingness to confront uncomfortable truths.

As families navigate the challenges of love and loyalty, they should remember that each choice carries weight. The journey towards reconciliation may be arduous, but it is through understanding and empathy that families can rebuild their bonds and create a more inclusive narrative for all members.

Here’s what people had to say to OP:

These commenters offer context-aware, practical responses and suggest realistic fixes

SeparateCzechs − NAH with the scales kind of tipping towards your eldest on the a__hole front.

I get that he’s bitter and feels like he missed out. the grass is always greener.

Why isn’t he holding his mother responsible for moving him to another state?

He’s not holding himself responsible for not practicing what you did teach him.

I’m guessing he went to college and the twins did not?

That iniquity doesn’t seem to vex him. It’s really an a__hole move for him to involve your parents.

It’s possible that nothing would ever actually satisfy your eldest because what he wants is something you can’t give.

In my family we call it the pound of flesh(after the Merchant of Venice, pound of flesh required would be your heart.)

He wants the do-over. He wants you to pay for his notion that he is loved less.

Barnabas-of-Norwood − Your ex kept him away from the training. He needs to accept that.

He could start out at a very low non entitled role. As a bookkeeper with salary a little above the job he hates.

Obligatory “thanks for my first silver”

edit gabdmm − NTA I’m reluctant to call your older son an a__hole, but ultimately he is due to his expectation of being given an equal share.

You did what you could to provide him a loving father figure and tried to make memories with him during the limited time you had.

Why should your younger sons take a hit financially, or have to work harder for the same stake as their underqualified and underskilled brother?

It might not seem fair to your oldest, but ultimately it is.

If he is so serious about learning this skill, would it not be possible for your younger sons to teach him

as an apprentice at a lower pay until he is skilled enough to have earned his place?

jmf1488 − So what is this skill that he cant just learn from the other siblings or off the internet?

These commenters criticize the OP for inequity and urge empathy and accountability

megano998 − Wow, yes you should have done this differently.

At a basic level, your older son asked you to teach him something.

For a variety of reasons, you said no, even though I imagine there was ample time over the last 24 years.

What about all of theses lunches and dinners?

You also refer to raising him as “compromising” which I imagine would hurt his feelings greatly.

You don’t have to raise children equally, but you have to be equitable.

Your twins got to live with you, learn a valuable skills, and receive start up funds for a profitable business.

Your older son got camping trips.

I’m not sure I see equity here.

YTA ArtOfOdd − I have a question...during the time that your wife had cancer, did you ever help or teach your younger sons?

Even if it was just occasionally for an hour or two?

I'm not going to say who may or may not be the a__hole, but I will suggest you put all of your reasons

and excuses aside and look at this from your son's perspective and imagine how you would feel.

Imagine how you would interpret it as a 10 year old or a 16 year old.

You said you could only see in during the summer and holidays because his mom moved away...but you didn't move closer, either.

It would be easy for a kid to think that they just aren't important enough to be closer to. That they aren't a priority.

You said he wanted to learn during the summers, but you focused on giving him camping trips and vacations.

I assume these trips usually involved your wife and other children as well.

So there's a really good chance that what kid brain interpreted wasn't you trying to provide lots of memories of family time,

but "dad would rather go somewhere with everyone rather than spending one-on-one time with me doing something special."

You said after high school he made the effort of moving to you to learn this, but your wife was sick.

It was s__tty timing, no one's to blame, and things had to be prioritized.

But what the kid brain, that has already had a lifetime of "it's not a good time right now"

is going to register is "Someone else matters more again and it's still not my turn."

And the tough part about kid brain is it doesn't matter why, it just matters that it is.

So he goes to college for his backup plan, because evidently an apprenticeship was out of the question then, too (?),

and it turns out he hates it because it isn't what he wants to do.

And while he's in school because you didn't have time to teach him, he's watching his younger siblings

who got to learn what he had begged to be taught his entire life start a family business - with your help.

And kid brain is going to see that and interpret it as another r__ection because somehow he's not good enough,

liked enough, smart enough, valued enough, or a "real" part of the family.

And now that everyone else is settled down and the family business is going well, and the cancer is gone,

and he's done what was expected with the back up plan and hates it.

he still can't learn because you aren't physically able and his brothers don't have the time or inclination.

And he still can't learn because now, after years and years and years of asking to learn,

you compromise by asking about an apprenticeship, and it's too late because he's too old.

And kid brain (because kid brain can take a long time to wear off with our parents) reminds him that,

yet again, he's not worth the effort, not good enough, not important enough, not a priority, and so on.

Now, I wouldn't hand him any of the business or invite him in on it because that needs to be between your sons.

I doubt he'd be happy just running the books while watching his 2 brothers do what he wanted to do his whole life, anyways.

But something to consider is that he's demanding in on the business because somewhere in his head it registers

as "if I can be part of the business, I can be part of family."

Whether you intended to or not, your actions and choices have hurt your son a great deal.

And instead of being upset that he's talking to other family members who are now having opinions,

perhaps you should think about how much you really, truely want a relationship with him.

If you don't, for whatever reason, save him the misery of mental pain and just flat cut ties so he can start to heal.

If you do want a relationship with him, ask him to go to family counseling with you

and have someone trained in all of this help untangle things and translate for the two of you so you can build a better relationship than what you have now.

SaxifragetheGreen − YTA. You left your eldest out, preferring to make memories with him instead of building skills.

You could have taught him properly, but you didn't and instead chose to take him on vacations and do camping.

Then, when you could have taught him, when he did have time, when he expressed interest,

you said no and instead invested your time in the family you built without him.

Now, you physically can't teach him, having run out the clock without ever imparting those skills to him like you did to his brothers.

Your parents see this. Your parents see you investing more in your second wife than your first child, which is why they're on his side.

He accused me on Saturday of pushing him out my new family and loving his siblings more.

I haven't been able to sleep since. Sounds about right to me.

WarriorScotsInfamily − YTA He accused me on Saturday of pushing him out my new family and loving his siblings more.

I haven't been able to sleep since. From his point of view I can see how this could be the case.

You failed to teach him, you taught his siblings and now you and they are profiting while he is left to fend for himself.

My oldest has become very bitter about this and has involved my parents.

They are taking his side and now my younger kids are resentful that their grandparents have been turned against them.

Maybe you and your younger children could use this as evidence you are wrong and you should include your other child in the business?

Why can't one of these super children teach the older child this "skill" now if you are incapable?

Honestly, you and parents like you suck, you described to us how unfair you are while asking with a surprised pikachu face "am I unfair to my child?",

you know you are the a__hole, just stop being selfish and go fix this issue.

It is simple, one of you needs to teach the eldest child this skill and he needs an equal share of he company once he is skilled in it.

And he needs decent pay while he is training.

Or you can say "f__k it", keep the money and write off any chance at a decent relationship with him.

These commenters are blunt: OP neglected the eldest and must repair damage, not excuse it

posey290 − YTA - You flat out loved and put more time and energy into the twins than you did your son.

You can cry 'circumstances' all day long but at the end of the day - you alone failed your son.

You pushed him out of your family and prioritized them over him. You didn't make time for him.

Your excuses I've seen repeated all over this thread mean nothing.

Of course your parents are siding with him, I bet they've seen the favoritism

from their point of view and are equally disgusted as your oldest son is with you.

Also, your twins sound very entitled given that they leaned on you for startup money.

Just_here2020 − YTA. He got left out and tried to change that several times - and was told no.

You now have a new family that you gave the skill set to, AND capital to start a business with AND your attention.

Of course he pissed and rightly so. You treated the kids very differently.

You gave his siblings the skill set, why don’t you give him your share of the company?

This story serves as a reminder of the often absurd realities of workplace policies. Do you think the OP’s struggle was a fair representation of how companies often overlook employee well-being, or was it an overreaction? How would you handle a manager with such outdated policies? Share your thoughts below!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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