Bail My Son out of His $200K Tax Debt? 

Son doesn’t realize he’s in trouble cause they’ve never let him be in trouble

Don’t pay his debt. He isn’t going to change and will do it again. It concerns you more than it concerns him.

I am having a hard time believing that the son didn't know he was supposed to pay his own taxes in California.

Way to absolutely take advantage of great parents your entire life. Party is over son.

Why would you give your business to an incompetent child? You are not helping him. Quit bailing him out. He needs to grow up.

Jeff, you have spent your life giving him every opportunity and advantage - and then bailing him out. Stop it today. No is a complete sentence.

How can the son mention future inheritance to pay off his debt?!? Selfish! Horrible!

As a 20yr old, I believe that this grown ass baby needs to take accountability for his actions. Daddy is not going to be there to bail him out everytime

If you bail him out yet again what makes you think he won’t do it again?

The parents are the problem. Stop enabling him.

Let him lose everything. Go to jail even. He needs a harsh wake up call. If you bail him out, he will just continue to do the same things.

DONT BAIL HIM OUT

I am a former IRS Revenue Officer, and now an Enrolled Agent primarily in the tax resolution business. If I closed your IRS case with a continous wage levy, there was no negotiation. You failed and I had to take a draconian enforcement action. If you then failed to file after that - the IRS may very well be looking at a criminal referral. File and pay; file and pay. By law, the IRS can collect taxes for 10 years after the tax is assessed. The IRS lien attaches to any property the son owns today and comes to own in the future -generally that 10 years. Dad ran a responsible business and earned wealth, but has enabled his son to be a screw up. Anyone that has the audacity for their “share” of the parent’s estate before there is an estate is a screw up. Cut the umbilical cord. It’s time for the son to stand on his own. Say no. Talk over his concerns with an estate planning attorney so this 40 year old child does not squander any more. He already ruined the labor of his father’s career…

There’s literally no signs that he won’t fall into the same habits after you bail him out (again). His actions as a 40 year old father is baffling

It seems like the kid has had more breaks and financial support than most of us had during our lives. It's time to grow up kid and find your own way!

Do NOT bail your son out. No. No. No. No.

I have a buddy who’s son is just like this. My friend and his wife are the best people, but the son has been a mess his whole life. He was hooked on hard drugs and managed to get clean, but still smokes weed every day; lives in his parents “rental property” (rent free, of course); he doesn’t work, and has a teenage daughter that my buddy and his wife are basically raising. It’s so obvious that the kid needs the crutches kicked out, so he can either stand or fail on his own, but unless you’re willing to cut the cord, he’s never going to have to own his own life.

This is one of the most interesting calls I've heard in a while. It seems like the father never had the backbone to discipline his son, not one single time. He never let him deal with consequences of his actions. He shielded from receiving the much needed pain of corrective action. As a result his grown son is an entitled spoiled brat who has yet to deal with his own misbehavior. Dad knows what to do but I'm very skeptical that he has the guts to say no to his son when he has caved hundreds of times in the past.

One issue not discussed was that a $200k bailout from dad would create another taxable event, Forty years old and never learned to be an adult?? Jade is right on this one, sometimes you have to cut the umbilical cord. And no, he doesn't have a few years to wait about updating his will. He needs to get with an estate planner and get all that figured out or the IRS is going to take the house and anything else available to satisfy the tax debt. He could probably bypass Junior and set up a trust for their granddaughter - and I would make the granddaughter's mom trustee.

I love that the father is calling because he cares but his son didn’t because you could care less!

Mom and dad are part of the problem. They have been his safety net for his entire adult life multiple times. He's never learned to be responsible.

They should have gave up on this kid years ago. He’s a complete failure and wants to be bailed out. Take responsibility.

He needs to let his son grow up! Adults don't ask their parents to bail them out over & over but it sounds like they never allowed him to grow up!

This son has a long history of behavioral issues, which often suggests there was stuff going on in the home. Whether there was or not, how do you hand a business over to someone who has such a history? Sounds like the son isn't the only one with a long history of bad decisions.

He's like this because mommy and daddy always bailed him out. Leave his inheritance to his daughter and don't give him a penny. Let him deal with the results of his own actions so he can mature.

Good caller. He gets the point and gets the info out.

If he tackles it on his own, his habits will change going forward (hopefully). If you bail him out, he won't learn anything and will repeat the habits and/or choices that got him in this mess in the first place.

I didn't have tax debt, but my parents bailed me out on other debt. I regret that because I didn't learn to control my money until I went bankrupt at 40. If I had gone bankrupt at 25 I would have had a lot more time to recover.

The son didn't want dad's opinion BEFORE all this happened, but as soon as he's in trouble, he calls daddy. What a bum!

Sounds like the kid finally needs to learn a lesson...get on a payment plan with the IRS

Once I heard I heard he would blow up on us and wouldn’t talk to us about it, I said to myself he would be on his own going forward and would not get a dime from me.

Ya, I think he won't learn. Don't bail him out and let him figure things out.

Let him feel it. Stop saving him from the consequences of the mess he’s created.

Kinda funny when you owe the IRS money they add on fees and interest. When they owe you throughout the year they'll pay you to the penny and no more whenever they get around to it.

"There is nothing to learn from a second kick of the mule." The son wasn't paying attention when he got kicked the first time.

The son knows he has an inheritance coming, so he is essentially pre-inheriting his share by demanding constant bailouts. The parents may need those funds in their later years, so how can they justify continuing to fund their son's bad finances?

A resounding No!

This whole episode could've been about my family members. The business, the tax debt, etc. Gives me chills. I feel for what this dad & mom are going through.

Do whatever you want. No need to call for advice. I'm sure you know what to do. If you broke this cycle long ago, your grown son would not be messing up continuously and returning for bailout over and over.

I'm making this comment before I hear Dave's recommendation. But this is my recommendation. Don't pay off the debt, don't leave him a share of your estate to him. Redo your will to put his share of the estate in trust for the GRAND DAUGHTER, maybe providing some monthly stipend when she turns 18 or 21 until she's 35. Then pay out to her. I say this, so that her mother or father or both do not guilt her out of her inheritance.

I can help. His son should change his entity to avoid harsher late penalties. Then hire full service payroll to avoid payroll penalties. Then offer and compromise with the IRS

The day i finally grew up was the day my family cut me off due to my behavior. It was very hard for them but necessary.

No, no, and no. He knows all about taxes, he just doesn't want to pay them. Don't give him any money. He's just going to keep asking you for more. Tell him to go out in the world and grow up. It's about time. And talk to a really estate attorney. Any money you leave him, he'll lose it.

4:35 not "been" stupid... IS stupid would be a more appropriate answer... I wouldn't bail him out.

I wish he was my dad. I would call him every day and sing his praises if he were my dad.

He will bail him out then also leave him the house. When the dad said “he loves this house”. No he doesn’t. He will sell it before you are in the ground and move back to LA.

I am glad my parents were poor. I could NEVER depend on them to bail me out of anything. But, IMHO, these parents are/have always using/used MONEY as a way of tethering their children to them. I only knew my Dad had a will when he died and an attorney contacted us. Maybe if the son wasn’t so aware of what the parents were planning to gift, he would live a life that didn’t depend on it

When the IRS comes and gets his ass- then he realized what the deal is. A 40 year old man? and you are bailing him out. Hell no!

This is an excellent call for all of the young guys out there listening. This is what happens if you choose to have children and you don’t tell them no. You will be bailing them out for the rest of your life. Don’t be this guy.

Love the comment, let him take his own responsibility for not paying his taxes. He makes $75k + bonuses

Leave it to your grand daughter. He’s has to get out of his mess

NO NO NO NO NO NO NO NO. How many times do you we need to say it? This is one of those times someone needs to learn the hard way. Dad tried to help the easy way. Now it's time to learn the hard way.

$200,000 [if that turns out to be accurate] is about 10% of his parents net worth. From their perspective, it is empirically feasible to liquidate $200K and not have it be a major impact on their lives, Certainly, I would never go over 10% of net worth for such a thing. That's my personal rule. But, the flip side is he will do this again. Wash, rinse, spin. Same old same old. He'll be back, hat in hand, in a few years asking for the umpteenth bail out. I would not do it.

That's what happen when Daddy always saves the time..

Hey, dad, if you're always going to be right there bailing out your son, why should he ever be expected to pay his own way? He started this pattern of behavior more than 20 years ago when he was still in high school. You're enabling him to act irresponsibly and as long as you keep doing it, he'll keep expecting you to do it. The dad should listen to his gut and tell his son to grow up and start paying his tax bills because what he is doing right now isn't working and if it continues it is only going to get worse.

You’ve trained him to learn that you will bail him out every time, why would he think anything else? He’s been coddled all his life by the parents, he can’t succeed until he’s allowed to fail. He’ll never learn his lessons if you don’t allow him to fail and pick himself up ON HIS OWN! I did this with my children after my parents handed me everything in life, I wanted them to be given the opportunity to do what I was never able to do with my parents. The answer is “NO”.

He probably bragged about how he doesn't pay taxes. I was employed the same way in the 90s and 2000s and wasn't knowledgeable about taxes, either, so I looked it up. He blamed it on the employer when it was his lack of responsibility. Don't bail him out.

I was also thinking of Jade's suggestion!

Jade absolutely nails it at the 6:00 mark.

Dad, this is not your problem. You need to stop saying, "we have a meeting". He has a meeting. He is in tax debt, you are not.

No matter what the dad chooses, his relationship with his son is going to be strained. Either Son is mad at Dad for not helping out, or dad is mad for helping son AGAIN and Son still doesn't learn his lesson.

Not even Optima Tax Relief can save him. The answer is, Call the IRS and have them garnish his pay and freeze his accounts.

Mrs Warshaw and Mr Ramsey are so right.

Sir, his tax debt isn’t your problem…..End of story.

YOUR SON NEEDS TO TAKE FULL RESPONSIBITY FOR HIS ACTIONS I WOULDN'T LEAVE NOTHING TO HIM AT ALL BECAUSE HE LEARNS TO GROW UP

Stop enabling this adult, he will never learn if he has no consequences to his actions!

Son needs some very tough love. Has no idea what reality is, dad has always been there to get him out of trouble. Do your child a favour and let him clean up his own mess.

This dad loves his son but man, he's been bailing him out his entire life. He needs to let him figure this out. He talks about his son not being able to figure this mess out like he's 7 years old. He's a grown man and I know it's difficult but you'll be doing this until the day you die if you keep bailing him out. Some people are okay with that.

Put the son on beans and rice

In this situation, I would not bail him out. I might be willing to help him walk through it, but I would absolutely not bail him out. Also, given that he mention "his share" of the inheritance, his intentions are made clear. He does not intend to change his ways, and if you leave that property or money to him he will use it to bail himself out in the future. He doesn't respect that gift. I would change the will. I can't tell you exactly what to do, but maybe consider leaving it to the grand daughter, or possibly just keeping it in trust (if possible) with the caveat that he can take ownership IF and ONLY IF he has gotten his act together by that time. Tough love is what is needed here to steer him in the right direction towards ownership of his own life and his own mistakes.

No way. He needs to grow up and be responsible. This is terrible. At 70 years old this father should be enjoying his retirement. Go on a cruise.

Id worry that since the son is talking about inheritance Id get worried hed off his parents for the money..

I have a sister just like this, although the numbers are smaller. Can't count the number of times my folks have bailed her out of trouble. It's as much their fault as it is hers.

Time for some tough love I'd say. He made a mess of it once through ignorance - that's somewhat forgivable. I've known other folk that got messed up with being 1099'd. The second time is all on him, he's made a bigger mess and he can't play the "I didn't understand what I was getting into" card this time. Sounds like he's got a long history of messing up and getting bailed out and it's a worse mess every time. I feel for him but he's got to grow up.

I said aloud, leave it in a trust for the granddaughter. Then Dave said it👏🏾😂

Our 20 year old daughter is self employed. She started filing and paying at age 18. No excuse for this child adult

Having a kid can be VERY risky.

Jeff so sad but he’s a grown man and it’s up to him to take care of it. I can’t imagine asking my parents for my inheritance ( that’s in the Bible) Co dependency is a thing you don’t need to rescuer him, he needs to save himself it’s called tough love.

After 5 years of working endless retail and low paying jobs my Master of Divinity Student loan has $400 left.

Even if you did not know you were paid as a contractor, a salaried employee has to reconcile their taxes every year.

mom and dad are enablers.

As long as you don't file a return. Tell the IRS to kick rocks. Tell the IRS it is your money not theirs. Once you sign a return that is when you agree to their terms.

Good problem-description by this caller.

Lol the way dave cut him off

Most important thing to the father right now is maintaining his relationship with his granddaughter. Of course he doesn’t want to bail him out but granddaughter is the pawn.

Sadly, these parents are going to bail out the son again and again and again until they’re all pauperized. This kid has learned nothing the parents haven’t learned anything much either.

Dad - stop being an enabler!!! NO MORE BAILOUTS!!! Why would you give your business to a son who has never demonstrated maturity or the ability to handle money??? Baffling.

What an amazing father.

that sucks, that father sounds so understanding and well intentioned.

My net worth is about 2 million at 38 years old would never give son this kinda money.

No way would i give him any more its dospicable how he has treated his parents

Sounds like daddy has been cleaning up after his child his whole life. This is as much his fault as his son.

Sometimes you have to face the fact that the son you always dreamed of having did not turn out the way you hoped, and it becomes time to mourn and grieve, and let them go their own way. It's time to refocus resources and attention to the family members who are responsible, loving, and perhaps not male but who can preserve and grow a family legacy into the future.

Horrible!!! Shame on their son!

Wow this would no't make clients feel comfortable using his company. Because, if he does not pay his taxes how can clients be confidant he will send their payments in. They never taught him financial responsibility nor does he apoear to want to learn from his mistakes. If, they helped him it should be with the caveat that he take Dave's class.

You aren't required to give him anything when you pass away. You can skip him and give it to the granddaughter instead. Tell him up front you're not going to let him continue to waste what you intended to give to him AND her and you're taking steps to save it FOR her since he won't. Then let him deal with the IRS, even up to and including going to prison if that's what it takes. The gravy train has to stop.

Yes, No is the answer. Bailing out has not helped it is hurting him. He needs to be a grown man and stop hurting his parents because he is selfish

This shows how helping someone out of a small financial problem may become a large financial problem. I do not know what I would do if one of my kids had a $30K financial problem. Would I help him I do not know Hopefully it would not happen but you never know. I feel for this guy and his wife.

Exactly what I want in an insurance agent - inept, even corrupt in financial management. /s

I wouldn’t bail him out, and I’d go even further and consider not leaving him any money from the estate, or at least very limited amounts, and leave most of it in a trust for the grandkid