Episode 45: Confessions From An IRS Insider

Description:

Discover how the IRS approaches audits and tax conflicts. Ex IRS lawyer Scott Estill joins Tom and offers tips on how to successfully deal with the IRS during a tax conflict.

SHOW NOTES:

03:37 – When The IRS Contacts You, What Should You Be Concerned About?

05:04 – How Should Your CPA Interact With The IRS? 

09:33 – How Does Documentation Resolve Most IRS Cases?

11:00 – How Does The IRS Initially View An Audit?

14:22 – How Is Tax Court A Crapshoot?

16:41 – When Do You Need To Consult A Tax Attorney?

18:14 – Why Tax Professionals Should Always Deal With The IRS.

20:53 – Why Your CPA’s Job Is To Help The IRS Auditor.

23:11 – Which CPAs Are Best Equipped To Deal With The IRS?

Transcript

Announcer:

This is The WealthAbility® Show with Tom Wheelwright. Way more money, way less taxes.

 

Tom Wheelwright:

Welcome to The WealthAbility® Show, where we're always learning how to make way more money and pay way less taxes. Hi, this is Tom Wheelwright, your host, founder, and CEO of WealthAbility®. So just how bad is the IRS? I mean, how bad is it if you get audited, if you get into a controversial situation with the IRS? Is there a way for you to get out of it, and how do you actually deal with that?

 

This is an issue that I think really everybody thinks about. Because frankly, I think the scariest thing for most people is the IRS. It's not public speaking and it's not death, I think it's taxes. And it's particularly what happens if… is the IRS going to come get me? I'll get back to this in a second.

 

So we have a great show today because we have somebody who has been on the other side. I've always been the good guy. I've never been on the other side, the dark side as I like to call it. We have Scott Estill, who spent several years with the IRS and still does a lot of work in controversy and consulting on things like that. And he's a tax lawyer, so he's got this lawyer point of view. And Scott, it's just great to have you on the show. Really excited to hear kind of this other point of view that frankly I don't get to hear that much.

 

Scott Estill:

 

Well, thank you. Yeah, it's a pleasure to be on the show here today. And unfortunately yes, I was part of the dark side several years ago and had I guess the vision to see the light and get into private practice. And that was back, oh man, 20 something years ago. But representing the good guys since then, and like you said, have done a lot of IRS controversy work. Whether it's dealing with the IRS in an audit or going to court and fighting them in court, either way.

 

Tom Wheelwright:

So from your perspective, I mean obviously you're a professional like I am, so the IRS I'm sure doesn't scare you at all. But the typical taxpayer is somewhat afraid of the IRS and controversy, so how do you… if you were talking to a business owner or investor, what would you tell them about the IRS and what they should be concerned about, what they shouldn't be concerned about?

 

Scott Estill:

First thing I would tell them is don't fear the IRS. I mean, if you're in business in the United States today, you're kind of in partnership with the IRS. You've got to pay these taxes. I mean, you file to pay, understand the tax laws, what have you. But the fear of the IRS and the fear of an IRS audit is something that I would just get that out of your mind. I mean, just forget that and let's not worry about it. Now, that doesn't mean that we should do whatever we want on a tax return. Obviously we still need to have good records, we need to have all the information to support whatever is on the return, but definitely not fear the IRS.

 

Tom Wheelwright:

So when you go up, when you're consulting on tax controversies or you're working on some type of a case, a tax case as an attorney, you're dealing with the taxpayer represented typically, which is an accountant.

 

Scott Estill:

Yeah.

 

Tom Wheelwright:

So how do you work with them? I'm interested myself every once in a while, pretty rarely fortunately, I'm involved in a tax controversy case. But how do you deal with the… how do you involve the taxpayer representative, and what should be the role of that tax advisor or that tax repairer in handling that whole controversy?

 

Scott Estill:

Well, I think the first thing would be to look at the type of tax controversy that it is. A lot of the IRS audits today are done by mail, so they're not done quote unquote in the field. And those audits are looking for usually very specific things, like can you back up the amount of wages online, XXX, whatever it is. And those types of audits, I think you go back to your preparer. You get the information, you send it in. And in a lot of instances, those audits will resolve themselves. They won't actually go out into the field.

 

But I think getting to your point where you're looking at a difference in perspective between an accountant and an attorney. And I always like working with accountants because I'm not a CPA, I'm not an accountant. And so if we get into technical issues with the IRS during an audit, the accountant is usually much more qualified to handle that than a lawyer would be. But on a flip side of that, my training as an attorney and certainly as a former IRS senior trial attorney, I'm looking at this from a lawyer perspective. And if I go into court, what's my chances of success? What are my weak points? What are my strong points?

 

So I'm looking at the case from a different perspective than a CPA would be doing. So ideally, if it's going to be one of these correspondence audits where it's done over the mail, you go to your CPA, your accountant, whoever prepared the return. Get it in, get the information in, and if that resolves it great. You don't need to bring an attorney in.

 

But I think once you get into a field audit where you're actually sitting down face to face with an IRS agent, I think at that point I would be seeking more legal counsel than I would accounting or CPA type of counsel. So I think you have to look at the difference in perspective that we both bring to the table, and some of the stuff I bring to the table is really good. Because I can look at this from a, what's our chances of success type of thing. But I also have this weakness in that I don't know all of the accounting that may go into a particular tax return.

 

Tom Wheelwright:

Over the years, and I'm very interested in your feedback on this. Over the years, I've taken the position that through the field audit, through the audit and even the audit supervisor, reviewed by the supervisor or manager, that I'm very comfortable with that. I mean, I've had lots of experience and lots of success. And a lot of that is A, from a technical legal standpoint, I actually spend a lot of time doing that type of work.

 

But also because I know the numbers, right? I know the numbers and the documentation, and so it's really easy for me to be able to say, “Well, let's see what the auditor wants from a documentation standpoint.” Because I've found certainly in the last five years that the number one thing they're looking for is documentation. They don't even get to any kind of a controversy on a position that we've taken until they've gotten, made sure that all the documentation is exactly the way they want it. And some of them, they don't even understand the law to go beyond documentation.

 

So if I can get them the documentation, which is of course what… we actually prepare tax returns in our network of CPAs, we prepare tax returns with the assumption, even though it's pretty rare, with the assumption they're going to be audited. Because we want to make sure we have all the documentation for that. Once it gets past the audit level though, I got to tell you, I am… I think that's a point where you absolutely need to bring in an attorney.

 

And one of the questions I have for you is, it seems like in recent years that I have actually had some experience with the appeals process. And I find that IRS appeals anymore is almost a waste of time if you go straight to appeals. So what tax attorneys have told me is that they prefer going straight to tax court and then it gets to appeals, and the appeals process is much easier that way. Is that what you found too, Scott?

 

Scott Estill:

 

Yeah, I think to some extent that's true. I might take a little bit different perspective in that I normally want to take as many shots as I can at the IRS. So if you look at a quote unquote normal audit like you mentioned there, it's the IRS really looking for documentation. Do you have proof of your automobile or your rent payments? Or whatever it is they're looking at. And I think you'll find 90% of audits or so are pretty much handled right there.

 

Tom Wheelwright:

Right.

 

Scott Estill:

We don't need to do anything else, right? Give the IRS a documentation, maybe they find a mistake, maybe they don't. You owe more money, you don't, and you get it over with. But let's say the 10% of cases that we're not resolving for whatever reason, whether it's a documentation issue or whether IRS and the taxpayer here are taking different legal positions. But your next move is to go to the manager and the manager of the IRS audit department there, whatever. They almost always rubber stamp it.

So at that point, you're probably not going to get anywhere and you've got a shot at appeals at that point. And one of the thought processes here is, look, appeals right now is really not being all that independent. And so they're just basically taking the IRS position, certainly not always.

 

Tom Wheelwright:

That's my experience.

 

Scott Estill:

Yeah, certainly not always, but that seems to be the case, and so-

 

Tom Wheelwright:

It's almost like all they're looking for, Scott, is what are my chances of success? And they're applying that to determine whether there's any give on the audit. They're not looking… I've not have I'd say in the last five or six years, and again our clients rarely get audited. But I haven't seen an IRS appeals officer who actually would look at the issue as opposed to looking at the chances of winning the issue. So you're right, I mean, they don't seem to be independent in any way, shape, or form.

 

Scott Estill:

Right.

 

Tom Wheelwright:

Or at least they have not seemed that way.

 

Scott Estill:

Yeah, and I think that's right. And so what some attorneys are saying here is, “All right, let's go talk to the manager.” Maybe the manager does something, probably not. At that point then, let's just get what's called a 90 day letter.

 

Tom Wheelwright:

Right.

 

Scott Estill:

Or a notice of deficiency, and let's just go right to that. Because right from that point then, everything is being accelerated and there's also other independent people watching this. So what I mean by that is, a 90 day letter means I need to file a petition basically suing the IRS in tax court, and I have 90 days to do that.

 

Once I do that, the IRS would assign it to somebody like my old job with the IRS, and I would have to file an answer. And at that point then, we've got the court is overseeing this plus an IRS attorney, plus we get to go to appeals again or perhaps for the first time. And I think that's where the appeals officer, one, has to look at the legal issues.

 

Tom Wheelwright:

Right.

 

Scott Estill:

Or the substantiation. I mean, they have to do it because we're going to be in court. And somebody has got to tell the judge just what the problem is here. But I think then you also… appeals does look at who is likely to win this issue. And that is something that I looked at when I was with the IRS, and I still look at it today. A lot of times with my clients or whoever I'm consulting with, I'll tell them, “Look, I would rather wear the IRS hat in this litigation than the taxpayer hat because I think that the odds are better than 50/50 that the IRS would win this issue,” or the other way around.

 

And so I think you have to, when you're going through this process, you're looking at a settlement. Both sides are going to be trying to resolve this without going to court because if you go to court, anything can happen. And I've been in court enough times and you just… you're standing up there and you're just like, “I didn't see that coming,” or “I wasn't expecting that.”

 

Tom Wheelwright:

I think anybody who has ever been to court feels that way.

 

Scott Estill:

Yeah, and-

 

Tom Wheelwright:

No matter whether it's tax court or something else. I mean, at least in tax court these are tax court judges, right?

 

Scott Estill:

Yeah.

 

Tom Wheelwright:

I mean, these are people who should have good solid, and seem to have good solid foundation in the tax law as opposed to if you were to go to a district court. And then you're really just hoping that they know something about taxes other than that they have to file it by April 15th.

 

Scott Estill:

Correct, correct. With the judges, I think the judges are very competent in the tax laws, certainly in the tax court. But these are still trials.

 

Tom Wheelwright:

Right.

 

Scott Estill:

And so you still have weird stuff happening with evidence or

 

Tom Wheelwright:

That's a good point, that any time you go to court it's a bit of a crapshoot. Because you don't know how the judge is going to be leaning, because you don't know… I presume that by the time you get there, you know which judge you're going to have. But how they're going to be leaning on a particular case, a particular item, you may not know. I could see how they could come out of nowhere.

 

Scott Estill:

Yes, well you get assigned the judge real quick in the process. So we do have that in that we can look at the judge's record and see if the judge has written any opinions on issues that are what we're trying to resolve. So there are some strategy type issues there, but I think the problem again is when you get into court and you start having evidence objections. That could happen in any type of trial, criminal, civil, tax court, doesn't matter. And there's just a lot of unpredictability, and I've got enough experience that when I go into court, I kind of have a real good idea. But never is it 100% certainty, and I think that's the problem.

 

Tom Wheelwright:

Yeah.

 

Scott Estill:

And of course, both sides have that problem too though.

 

Tom Wheelwright:

Exactly, and that's why I always… I'm always telling clients, “You want to solve this at the lowest level possible. Because first of all, it's expensive to go through the tax court appeals process. And second of all, you just don't know.” Any time you get into court, I think that you might as well be in Las Vegas because you just don't know, as much due diligence as your attorney does, etcetera.

 

But I do think that you make a good point, that there is a point where accountants should… the tax preparer, who is typically an accountant, should get with an attorney, a qualified attorney. And sometimes we do that, so sometimes I'll do that before we even… just on an issue, right? Going, “Okay, how would the IRS look at this issue?” Or frequently, in fact almost always if I'm in an audit, I'm going to get some feedback from an attorney. Because I think you're right, particularly somebody like you who's had IRS experience. Just understand, okay, how might the IRS be looking at this? I think that can be really important.

 

Scott Estill:

Yeah, I think so. And even if the accountant, let's say is handling the audit, it may not hurt to buy let's say an hour of time.

 

Tom Wheelwright:

Right.

 

Scott Estill:

With an attorney, just to make sure that the strategy going forward is good. And that we're not going to do anything now to potentially harm the case down the road. But I think your other point is really well taken, and that is audits are expensive. I know it's the cost of doing business, but if the IRS says, “You owe $10,000,” and we look at this and say, “This could be a coin flip type of a case. It could go either way.” And we go back to the IRS and settle for $5000.

Obviously, those numbers can be quite a bit larger. But the point is, is that you're not paying attorney fees after that. You're getting out of this case. And I've also seen with a lot of taxpayers, a lot of my clients over the years, that they have a hard time running their business and everything with this audit in the back of their minds.

 

Tom Wheelwright:

Yeah.

 

Scott Estill:

If they can get out of the audit sooner, and yes maybe they pay little bit more money upfront to get the case solved or resolved. But they're not paying legal fees down the road to get the IRS out of their life, and now they can go about doing whatever the business is that they do.

 

Tom Wheelwright:

Yeah, I agree. An IRS audit is not productive basically.

 

Scott Estill:

No, no.

 

Tom Wheelwright:

It really creates negative energy. And this is again why, and I've said this 100 times on this show, that you always hire a professional. I mean, I'm always shocked when I see people who handled their own cases. I'm shocked when I see people prepare their own tax returns frankly.

 

Scott Estill:

Yeah.

 

Tom Wheelwright:

I just don't understand because we're always talking about, “Look, it's a team.” And I really have enjoyed the teams that I've worked with, the legal teams. Because we do come from a different perspective, I'm going to be looking at numbers and lawyers typically that's not their strong suit. They're looking at the words. They're looking at, okay, how are people… how might this be viewed? How is the judge going to react? How is the IRS auditor going to react to this?

 

And a lot of times, accountants tend to focus a little bit too much on the numbers. And so having a team approach I think can be… even though you are paying both fees, in the end I think that if you get to a point where it's not a simple matter for your CPA to handle, I think at that point, I think the CPA, I think you'd be wise to even ask your CPA, “Have you thought… is there an attorney we need to get involved here?” Because if the CPA is trying to do this, I've seen CPAs that actually will take it to tax court. I'm going, “Why would you do that? It's not your expertise. Why would you do something that you're clearly not good at?” And when there are people like you who are good at that.

 

Scott Estill:

I think your comment as far as the team approach is, I mean, that's the way I go with pretty much everything. With real estate investing for myself, it's like well I'm not an expert in that. So I bring in other people that can help me out, and I think it's the same thing here where I'm shocked at the number of people that represent themselves in an audit, especially a field audit. Correspondence, we're sending letters back and forth. Okay, that's fine. But to walk in there where you don't know what you're doing, this is not your expertise. Are you really going to challenge the IRS?

 

Are you really going to assert your taxpayer bill of rights and what you're entitled to do, and what the IRS can and can't do? I mean, it just seems to me that at a certain point there, you need to recognize that this isn't your specialty. And bring somebody else in, because a lot of people, they'll get afraid of the IRS. The fear factor sets in and everything. Really, when I go into an audit, I'm looking at ways I can help the IRS.

 

Tom Wheelwright:

Exactly.

 

Scott Estill:

I know that may not sound quite right, but…

 

Tom Wheelwright:

No, I always say, “My job is to help the IRS auditor do their job.”

 

Scott Estill:

Exactly.

 

Tom Wheelwright:

That is the job of the tax professional, for sure.

 

Scott Estill:

Yeah, I think so. And remember too that this IRS person, they've got 50 other audits or whatever. And if I come in there with a good mileage log and I have documentation on whatever expenses the IRS wants to see, and I bring bank statements in and it ties out the income I reported and everything. You can walk in there at 9:00 in the morning and go to lunch with the audit over. I mean, I've had that happen.

 

Again, we're trying to make it easy for the IRS. And as long as the IRS cooperates with us, we're certainly going to cooperate with them to try to get this resolved in an amicable way. Again, that's the way most audits go. Most IRS employees and agents are good as far as they want to get the job done, do the right thing.

 

Tom Wheelwright:

They're doing their best in a really difficult situation.

 

Scott Estill:

Well, yeah.

 

Tom Wheelwright:

As I always remind people, I mean, they're the only people on earth… really when you think about it, they're the only job where every single one of their clients can't stand the sight of them. And so nobody wants to talk to them, and it's a really tough job. So I've always taken the approach that you make the IRS comfortable and make sure that you're there, that they know that you're not there to fight them, you're there to help them. And I've always found that that actually works really well.

 

So you've run, so you've worked with… you've seen a lot of the different tax advisors on particularly accountants over the years. And at the risk of offending my CPA community, I would like to get your thoughts on… some people say, “Well, a CPA is a CPA.” And I'm always saying, “Well yeah, that's like saying a doctor is a doctor,” right? I mean, do you want a chiropractor operating on your heart? And your answer is probably not. Now, that doesn't mean they're not a great chiropractor. It just means that they should be doing what they're good at. And so I'm just dying to hear, so what kind of range of representation have you seen over the years when it comes to tax advisors and the CPAs?

 

Scott Estill:

Well, I think there's a huge range here depending on kind of what their skillset is. An analogy that I would use is that I've never represented a publicly traded company in an IRS case ever. So I've never represented Microsoft or some big company, so I think I would be pretty incompetent to represent a company there because I don't really know the law or what have you. But you bring in a small business, and that's my sweet spot.

 

So I could be a really good lawyer for a small business and a really not so good lawyer for a large corporation. And I think the CPAs are the same way in the sense of, some of the CPAs are not dealing with the IRS ever. Or they're maybe doing audits on an internal audit basis as opposed to something where the IRS or a state is auditing them.

 

And so I think you have to look at, what does this particular tax professional do for a living? And if they handle small business tax returns and they'll stand by you in an audit, then that person is going to be a lot better for a small business than some accountant who is, let's say, working for one of the big whatever. Big three or big four accounting firms, whatever there are now, where they both could be great accountants but one is very qualified for you, and the other one not so much.

 

Tom Wheelwright:

Yeah, that's a good point. I'm always telling our members of our CPA network that we really ought to be staying within what we know, right? I had an attorney once tell me, he goes, “I never get referrals from CPAs.” And I said, “You're kidding.” And he said, “No, I never get referrals because they think they can do everything.” And I'm going, “Wow, that's actually sad to me. Because I know that in this profession, the more you know, the more you realize you don't know.”

 

Scott Estill:

yeah.

 

Tom Wheelwright:

“And if you think you know everything, you're in trouble.”

Scott Estill:

Yeah, big trouble. That's a surprising comment actually, because I get a lot of referrals from CPAs. And again, not wanting me to take over the case, but just wanting to work through some strategy issues where you just, do I want to present this document? Or if I present it, is the IRS now going to want to see 20 other things, and is it going to snowball on me? And what's the likelihood that if I don't give them this, the IRS, it's going to make them angry or force them to go in a subpoena or summons of some sort?

 

So there's all these issues that can come in, and I think again you just have to know what you're good at and what you're not. And if you came to me and asked me to do a divorce case, you'd probably get malpractice out of me. Because I'll be quite blunt, I've never done one. I don't know what I'm doing, and it's the same thing. I think you have to know where your strengths are, and perhaps even more importantly to know where your weaknesses are and get out of the weaknesses.

 

And if you're a tax professional and you're really good at what you do but you really don't have much expertise or really want to develop expertise in controversy. Then do what you're good at and get rid of the stuff that you're not, or get help with it if you need it. I may get accounting help on something where I know I'm weak on, where I need to have a lot of depreciation or amortization type stuff completed. And I may not know the best way to do that or have the software that does it or whatever. There's just a whole lot of reasons why I think as professionals, we need to know what our boundaries are.

 

Tom Wheelwright:

Yeah, I think that's a really good point. So we have a relatively new IRS commissioner, Chuck Rettig, and he's well known in the tax profession. We've all heard him speak before he turned to the dark side. And do you think we're going to see positive changes, or do you think he will literally go to the dark side?

 

Scott Estill:

I think he will go to the dark side, but I think we'll see some tax reform. It always kind of makes me cringe a little bit when they start talking about tax reform, because I don't really know exactly what they're going to be trying to reform. And a lot of times they make things worse. You have to understand that this is an almost impossible job that anybody has, whether it's the commissioner all the way down. They're told, “Here, go enforce these tax laws that very few people if anyone really understand.”

 

And so now they're going to try to enforce the laws here, and they're trying to do it with quote unquote customer service to try to take away the negative stigma that the IRS has. They've got a really, really, I would say almost impossible job to be able to fully succeed. So I wish him a lot of luck, but good luck with that job.

 

Tom Wheelwright:

I feel the same way. I admire him as a tax professional and I've got some hope there. I think in my recollection, the best time to actually be working with the IRS was back with George H.W. Bush when he wanted a kinder and gentler IRS, and he got one. I actually think we saw one for several years there, and-

 

Scott Estill:

Well we did, we did. That's actually when I was working for the IRS

 

Tom Wheelwright:

Yeah, and I just thought that was a great time to be a tax advisor because we actually has a positive… the top down was very positive of, let's work with taxpayers. I'm hopeful, always skeptical, but hopeful. Because I think that again, I think commissioner Rettig is just, I think he's a good guy. And he certainly knows the tax law, and he's certainly been around it his entire career. And so like you, I wish him the best of luck. I am just… I keep my fingers crossed that we're going to see some improvements. Because we've had a pretty rough time of it, I think, for the last five to 10 years.

 

Scott Estill:

Yeah, I agree on that too is that there's got to be a different mindset. And you really do, you have very low morale at the IRS right now. And so hopefully with a more positive mindset there coming from the very top, which I think you're going to see, I just don't know if that's going to be enough to change the culture that's there right now.

 

Tom Wheelwright:

Okay, well thank you for that. And Scott, thanks so much for spending time with us. So before we finish off, just one piece of advice that… one thing that you'd like to tell our listeners that if they do this, their life will be better.

 

Scott Estill:

Well, I think they got to go out, run their business the way that they run it and make their money. Get professional assistance on the taxes and definitely keep good records, and finally, don't fear the IRS.

 

Tom Wheelwright:

I like it. Scott Estill, great to have you with us. Just remember when you're not afraid of the IRS, when you do have a team of advisors, and sometimes it's going to be your CPA. Sometimes it's going to be a tax attorney, most of the time it should be a combination of the two. And when you do that, you're always going to make way more money and pay way less taxes. We'll see you next time.

 

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