"Understanding Tax Debt Resolution with Expert Stephen A. Weisberg"

[00:00:00] I'll tell you this, I don't get into the criminal aspect, but what I do have an expertise in and I have a large portion of my clients, exactly what you're talking about is payroll tax debt. All right. Welcome back folks. This is episode 58. It's About Your Paycheck. We got an amazing guest with us today, Stephen Weisberg.

[00:00:22] So before we get into it, what we got to do, Brian? Let's make the bills. Yes, sir. So you might have some ambitious goals for 2025, right? But remember that you need a well-organized team. That is the foundation for success. So in 2025, streamline your business operations with TimeTrack Go. They have a user-friendly time tracking system software that empowers you to get organized, right?

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[00:02:26] Dot T-I-M-E-T-R-A-K-G-O dot com. Let's go. Let's go. That's right. And, all right. Our guest is a seasoned tax attorney with over a decade of experience helping individuals, businesses, and other owners, and their owners navigate IRS and state tax issues from debt resolution and audits to penalty abatements and appeals. Wow, there's a lot going on there.

[00:02:54] As the founder and lead attorney for the W Tax Group, love the name, he heads a dedicated team of professionals committed to delivering the best outcomes for clients. He also partners with CPAs, wealth advisors, realtors, and other professionals to resolve tax problems that can derail important transactions. Crucially, his approach begins with a free tax debt analysis. No scare tactics or hefty fees.

[00:03:23] Get ready to learn practical strategies for tackling tax debt head-on and protecting your financial future. Welcome, Steven Weisberg. Thank you. Thank you for having me. Appreciate it. Absolutely. Yeah. And again, thanks for kind of working with me. We've been scheduling this for a long time and we're excited to get you on because it is a great subject for our listeners. And really easily, first things off, tell us a little about your background, how you got into this. Sure. Yeah.

[00:03:51] So I'm an attorney. When I started practicing, I was actually in corporate bankruptcy. I'm here just outside of Detroit. And it was 2008 when I started. So that was an interesting time for everyone in the country and especially here in Detroit. But we were representing pretty large suppliers, auto suppliers in the industry. And at the end of the day, it just seemed, look, these auto suppliers are big, right?

[00:04:19] And then they owe a lot of people a lot of money, right? Yep. They owe Ford. They owe Chrysler. They owe GM money. But then they owe a bunch of mom and pop stores, a bunch of smaller suppliers, a bunch of small businesses throughout the community. And at the end of the day, Ford, GM, and Chrysler, they'd all get paid in full. They'd get all the money back that they were owed. But then the mom and pop businesses and the small business owners, they'd get two cents on the dollar.

[00:04:47] So, you know, we worked this case for, let's just say a year. And at the end of the day, the mom and pop businesses are getting two cents on the dollar and Ford, GM, and Chrysler are getting 100%. And listen, the car companies are very important and there's a reason they get paid in full. And that's because they had secured loans and whatnot. Still, at the end of the day, I was, I don't know if I just want to do this, you know, working and grinding for a year just so, you know, the car companies can be paid in full.

[00:05:13] And so I just felt like there had to be a better way for me or just a different way for me to connect really with the small business, the medium-sized business, the self-employed. And that's ultimately how I came to tax that defense and resolution. I didn't know where I was going to go, but I just found a way where I could fit in, where I could help everyday people, small businesses, self-employed. I could help them on a daily basis and really see the difference that I was making.

[00:05:37] Hey, this is Brent Skinner, host of Small Talk Window here at the Work Defined Podcasting Network. Have you ever wanted a short podcast to listen to during a coffee break of your work day? You've come to the right place. My guests dispense with a small talk as quickly as possible and settle into a meaningful conversation around the world of work. Awesome. Awesome.

[00:06:01] So could you elaborate a little bit more of, if you're okay with sharing, how you actually help some of your clients? Yeah, of course. Yeah. So simplistically, let's just say you have tax debt. And a lot of my clients are self-employed or small businesses. When you're self-employed, obviously you don't have money coming out of your paycheck that's paying your taxes, right? If you're a W-2 wagerer, you get your check each week or every couple of weeks and your taxes are taken out of it.

[00:06:31] And it's a pain. And you say, why is half my check gone? But no, it's taken out. They do it for you. When you're self-employed and you're just getting paid from everyday people that you are selling goods to or doing services to, the taxes aren't taken out of the pay that's sent to you. So you're supposed to be making quarterly payments. Every quarter, you're supposed to make an estimated payment so that by the end of the year, you don't owe anything to the IRS because you've paid it on a quarterly basis.

[00:07:01] And people who are self-employed, because it's not automatically coming out of their checks, they just say, okay, I'm not going to pay this quarter. I'll just figure it out at the end of the year. And then, of course, they get to the end of the year and they say, oops, I don't have the money. Right. So a lot of people are self-employed come into my space who need help because they just haven't done a good job of planning or created like an automated system so that the money comes out that is paid to the IRS. So that was kind of long-winded about who I help.

[00:07:30] But the way that I help is, let's say you owe, and just make up numbers, $25,000 to the IRS. You know, what I do is, I do, as you indicated, I do a free tax debt analysis where I look at what you owe. I find out, I pull IRS transcripts. I talk to the IRS and the state for that matter. I find out how much is owed, what years you owe, what interest you owe, what penalties.

[00:07:58] I see if there's any other years that you haven't filed a return for. Make sure I understand everything. I get my bearings. I understand what your actual situation is. And then I talk to you about your finances and I put it all together and I analyze those things. And I tell you here, this is what I think I can do. This is what I would advise you to do. And this is what, how I'm going to do it. And then I give you a number and say, this is how much it's going to cost for my services.

[00:08:23] And that's completely antithetical to how these big, maybe you've heard them on the radio, like Optima Tax and people like that, where they say, hey, we can save you. You'll pay 10 cents on the dollar or you'll pay 10% of what you owe. They've never even talked to you, but they have no, and they have no idea what they can do, what they can't do, but they're telling you right off the bat. So I'm kind of doing the opposite. I'm going to say, okay, I'm not going to tell you what I can do without having any idea of what I can do.

[00:08:50] Because what they do is they say, hey, you're going to, you're going to pay 10% of what you owe. And they say, we're going to file an offering compromise for you, which is one of the resolutions you can get into with the IRS. But you have to qualify. So they say, here, give me $10,000, whatever the number is, we'll help you resolve this tax debt. And then they do it and then it gets rejected. And they say, we tried because it is a real thing.

[00:09:13] You can resolve your tax debt potentially, but you have to qualify when you're doing an offering compromise where you're paying the 10% of what you owe. So again, back to my original point. So I do the work ahead of time. I make sure everyone knows where they are. We both know where we stand. And I tell you, this is what I advise you to do. And this is what we should do moving forward. And here's my fee. And then there's multiple different ways of resolving the tax debt from there.

[00:09:39] One of them might be an offering compromise, but the reality is most people don't qualify for an offering compromise. But the radio is telling you everyone qualifies. Oh, wow. What is that, by the way, Steve? Offering compromise. Yeah. The offering compromise, again, is what they're talking about on the radio all the time. And it's kind of like the holy grail. And so if you can get an offer and compromise accepted, yeah, you want to do it. And that's why they talk about it so much.

[00:10:06] But offering compromise is when, again, it could be 10%. Let's say you owe $25,000, though. And let's say you end up settling for $5,000. It happens. So where you can, you won't have to pay off the total amount of your debt. Oh, wow. And you only pay a portion of it. But the success rate is low because these big shops are sending out offering compromise when people don't qualify.

[00:10:34] The acceptance rate for an offering compromise where you're settling your debt for just a portion of what you owe is like 45% or something like that. When I file them, it's probably 95%. And the reason it's 45% is because people who don't qualify are getting scammed by these big companies. And people are sending in offering compromise where the person doesn't qualify. The thing I'll say about offering compromise is, yes, it's real.

[00:10:59] So when these big companies tell you on the radio, like, we've settled this tax debt, it was $100,000, and we settled it for $5,000. That's true. It does happen. It is possible. But most people don't qualify for it. Wow. So they're being a little deceptive on. Yeah. Very deceptive, to be honest. Wow. Wow.

[00:11:18] Even thank you for sharing that because I think that is good for listeners to hear and for you to show as a service provider that you have that integrity and that you're being transparent. And I like that you said you make it simple for them and easy to understand. So I think that's a big deal. One more question, and then I'll pass it over to you, Brian.

[00:11:40] Is there a minimum amount or a threshold amount that, in terms of tax debt, that person needs to have before they come to you? Yeah. It's usually around $10,000 because you obviously, you have to pay me for my services. And so if you only owe a couple thousand dollars, it's going to be a wash. You're going to be paying me to resolve a balance that is not large enough for my services to make sense just because you have to pay my fee.

[00:12:08] So it's about, it's usually around $10,000. It's kind of like the minimum or the threshold. Okay. Roger that. Thank you. That's cool. I love it because it kind of aligns with Walt and I's overall mission for this show is empowerment, right? We wanted to empower payroll folks. And so we do two shows, right? It's about payroll, excuse me. And it's about your paycheck. And now that I'm listening to Walt, it might be on both platforms really where he kind of could help businesses and folks, individuals.

[00:12:37] I really like the honesty piece of it. Look, I'm not going to rob you for $10,000, not knowing that if I can help you or not, because that's really, like, I get how people get caught up in that. But I love that kind of sentiment and it really aligns with our brand. So that's really awesome. And I honestly may need to follow up. So I have a personal case that I could, no, seriously. And you tell me, I don't know what this counts as, right?

[00:13:05] But it is a great little nugget to talk about. My daughter was like 19. She's only 21 now. It was year, what was it? 20, 23, I think it is. She did Rocket Mortgage. Not Rocket Mortgage. What is it? Turbo Tax. Turbo Tax, sorry. And I think it was like the first year that she was trying to do it on her own. I was like, look, try it. And if you get stuck, I'll help. But I wanted her to try to do it on her own. She thought she didn't do it.

[00:13:34] And fast forward last year, at the end of the year, we got a letter from the IRS saying that we owed like $90,000. And it's because she just put numbers in the wrong places. And the government thinks that she made a lot more money than she claims. And now they're like, no, you can't get this fund. So would you help out with something like that? Just kind of trying to clarify?

[00:14:01] Because it's not really a tax debt, but maybe some type of tax misunderstanding. Yeah, 100%. That's kind of what I would say is like almost a correspondence. It depends. I don't know all the details, but it's almost a correspondence audit of some sort where they're saying here, based on what you put in here, this is how much you owe. But they're assessing a certain amount against your daughter. And you're saying that's incorrect.

[00:14:24] So there needs to be a dispute opened up with them in response to that letter and say, no, this isn't correct because of X, Y, and Z. And then at some point, and I'm not necessarily saying this has to happen with you, but you go back and forth with the IRS. At some point, if you can't get it resolved after the tax has been assessed, you then take it to tax court. Oh, wow. Go to appeals and deal with chief counsel there.

[00:14:48] Now, if you have the ability to back up the things you're saying, you should be able to get it done with their collections team. The only thing is you only have a certain amount of time to do that after the tax is assessed. You have about 90 days after the tax is assessed to get it done with the collections. And I shouldn't say to get it done. I mean, you only have 90 days to file in tax court. So you don't want to give up that right.

[00:15:15] And so you want to get it resolved with collections before you go to tax court. But yeah, that's exactly where I would come in. Trying to make sure that everyone's on the same page. Make sure that they're assessing a certain amount of tax. But if that's not correct, we need to get that fixed. And in her case, it might just mean filing an amended return that has the correct numbers in it. And I thought it was as simple as that. So I did start with my CPA. We did get a letter from the IRS saying they're reviewing. But if it escalates, I may need to give you a call.

[00:15:45] You know? Yeah. So you did the right thing. Okay. You're a professional CPA, tax attorney, and you talk to them. And then, like in your case, an amended return is what makes sense there. Make sure that you're keeping up with the correspondence with the IRS and sending an amended return. And just you got to make sure you know your rights. Like I said, because you only have 90 days until you can, for it to file a tax court. So you don't want to give up that right. It might be fine.

[00:16:13] It might, you might be okay if you give up that right and you'd still be able to figure it out with collections. But you just don't want to give up that right without having to. So you'd rather figure it out with collections within that 90-day period. Hi, this is Stacey Harris. And this is Terri Zipper. And we're the hosts of the two podcasts under the HR Huddle. On Spilling the Tea on HR Tech, we uncover the latest trends, truths, and challenges from Sapien Insight Group's groundbreaking research and our analyst insights,

[00:16:40] serving up everything you need to know about HR tech with no sugarcoating. And on HR, we have a problem. We tackle the toughest workplace challenges head-on, offering you expert advice and actionable solutions to help HR leaders thrive in today's fast-changing world. Whether you want the scoop on tech or tools to solve people problems, we've got you covered. Take a listen and subscribe.

[00:17:09] If you want to become part of our community, we'd love to see you. I may need to look at the letter they sent then to make sure we're... Yeah, I'll pick to work at it for you. Oh, amazing. Thank you. Because I think they just left it off as we're reviewing and we'll get back to you. Yeah. But it's... The claim, like, it just seems so weird and they... Yeah. Yeah. Anywho. So now... So what would you tell... What advice would you give someone that has tax debt? What now? What then? Just go straight to you and Cole?

[00:17:39] Do they start the conversation with IRS first and then go to you or... Yeah. You want to go to me as early as possible. You do not want to talk to the IRS. Goals. And people get caught in that game too because... Not that the IRS is always so nice when you talk to them because a lot of times they're not nice. But sometimes they think, oh, I can do this and maybe the person I got seems nice and... The IRS is there to get money. They're the most powerful collection agency on the planet.

[00:18:05] The amount of power they have and leverage over you is just ridiculous when you look at the details. They're just trying to get the most money and they're trying to get it as quickly as possible. They're not going to tell you what's best for you, what the best way is for you to get this thing resolved. So you want to talk to an expert like myself as early as possible. You also want to do it early as possible because that's when you have the leverage or at least some leverage or more leverage than you would if you get to the point where you owe a tax

[00:18:32] that and then the IRS is garnishing your wages or taking money from your bank account. At that point, then you have no leverage basically. So you want to do it early as possible. There's a lot of people who come to me at the end of the day, but who really just kind of stick their head in the sand and they just say, this isn't happening and I'm getting these letters, but I don't want to deal with it and it's understandable. It's not to be ashamed of that. Like it's understandable. You get paralyzed when you get anxious and you get worried about things.

[00:18:59] But I just try to keep reiterating that the earlier that you come to me, the better and the better deal for you. It's so funny because my daughter procrastinated a bit. I hope she doesn't listen to this episode because she doesn't listen to the show. It's no shame. Yeah, exactly. Because the first time, I don't know, maybe a matter of months that went by. I saw one letter come in IRS. I just gave her the mail. I was like, all right, let her deal with it.

[00:19:24] And then the second letter may, but the third, the one that got my attention was like a thick packet. It was a thick letter. And I was like, oh no, this is not good. So I got, I was just like, I opened it up and, and I was like, hey, what's going on? She was like terrified. She was like, oh my God, I didn't want to tell you. I was scared. I wanted it to just go away. Like you said, it's, it happens. Yeah. You just kind of wish it away and hope that it doesn't, doesn't catch up.

[00:19:51] And you mentioned something about the quarterlies that made me think of. At one point I was a contractor early on. I used to do appliance installations, contracting work and stuff like that. And we were 1099 and we played that game. My, my CPA would tell me, hey, pay estimated taxes. Here's your amount, pay this quarterly and you'll be in better shape come year end. Man, I was young. I was like, whatever. I'll pay when I file.

[00:20:19] And then sure enough, year end came and I'm owing thousands of dollars. Thank God I was able to pay it, but I had to go through the process of penalties, interest, a payment plan and all that stuff because it was just, cause I was, I was careless. I didn't do the responsible thing and pay quarterly like they recommended. So when you said that quarterly payments or do that made me think about when I was in and it took me years.

[00:20:46] Like it's, I was so happy to get a W2 job at one point because I was like, oh my God, thank God I'm out of this rat race. Like people. Yeah. Just playing catch up every year. If you set up your, when you're getting your 1099 and you're getting that money each or throughout the year. And then you have to make quarterlies. The best way is to set up some sort of automated plan where, you know, like every dollar that I get, I'm sending 30 cents into, let's say like a separate bank account that's going to

[00:21:16] be used for quarterlies. Like the more automated you make it, the better you're going to end up. And that's why those paychecks work so well is because you don't have a choice. It's just coming right out of your, your check. And so if you can do the same thing with checks that you're getting as self-employed and just have 30% of that come out, that makes things a lot easier. So you don't have to think too much about it. Yeah. I learned that lesson the hard way, but you know what else he makes me think about is true crimes. We do a true crime every now and then.

[00:21:45] And a lot of times Walt is finding these cases where it's just business owners, tax fraud, payroll tax fraud. They don't pay their taxes and they keep the money and, and it's in the millions. These are companies and, and it's often the fact where it's, it's always a business owner on the payroll side. It's sometimes payroll folks who are not being overseen properly because if you don't have

[00:22:11] any oversight over, over your payroll person, they can easily steal. But yeah, it made me think about the business owners that just get caught up in the game and they don't want to pay the taxes. Do you get into any criminal activity, like defending or prosecute anything like that? I'll tell you this. I don't get into the criminal aspect, but what I do have an expertise in, and I have a large portion of my clients. I go along exactly what you're talking about is payroll tax debt where the business owner, or like you said, maybe a payroll personnel is taking, you're taking money out of your

[00:22:41] employees checks, right? Because you have to pay the IRS. You have to deposit with the IRS and that money that you're taking out of your employees checks that you're then depositing with the IRS. That's not your money, right? Whether it's a payroll person or the business owner. So there are, especially with business owners too, that they may have a vendor that's saying, look, you got to pay me or I'm not going to give you goods or whatever you need. And maybe cashflow is low that month or that six months or whatever.

[00:23:09] And the business owner says, okay, I'm going to take the money out of the employee's checks. And I'm just going to give the money to the vendor because I got to pay the vendor or else I can't get the goods that I need to run my business. And they figure, oh, cashflow will improve. And then I'll, again, I'll make up for it later down the line. And it doesn't happen. And the big thing with that is number one, that's in effect dealing. That's certainly what the IRS thinks you're stealing because you're taking money from your employees. That's not your money.

[00:23:39] Number two, the payroll taxes are used by the government in kind of day-to-day operations. But number three, the big thing to think about is whether it's the business owner or the payroll personnel. It's a business tax debt. It's a business payroll tax debt. But whoever is responsible and willful, and those are actually legal terms used by the IRS, whoever was responsible for depositing those taxes with the IRS and didn't do it.

[00:24:07] And if you willfully decided you weren't going to do it, you get hit with what's called trust fund recovery penalty. And that's a personal liability. So payroll tax, that's our payroll tax, that's for the business. They start out as, or they're going to end up as a personal liability for one or multiple people within the company. Wow. Right there. So I have a lot of clients. Wow. I want to ask another question here.

[00:24:36] So before I do, one of the reasons we started the podcast was to empower and educate people about their pay. And I feel like that's what you're doing when you service them too. So I have two questions for you. First, do you have any? Hey everybody. It's Libby again with fearlessness. So what's fearlessness? It's that underlying grit that empowers us to forge ahead. Even when hope seems distant, it's the courage to walk through those fires of hell, knowing that we're going to come out better and stronger on the other side.

[00:25:06] Stay tuned and learn how to get fearlessness. Any education tips to help people learn about their taxes, to be a little smarter about how they, their tax elections or how they handle their money. And then two, do you see any repeat offenders often? Like you'll help somebody and then a couple of years will pass by and then they'll be right back to you. Yeah. To answer the second question, the answer is yes. I do see repeat offenders, which is difficult.

[00:25:34] And I try to set them up so that moving forward, they're in a good spot and they've gotten through this thing and they feel relief and they know what they're doing so that they're not making the same problems. But I can't always ensure. I can't guarantee that this doesn't happen. Yeah. I try to set them up as best as possible. But I do see repeat offenders that beefs them out for sure.

[00:25:59] In terms of education, I, my personal opinion is the only education that you really should have is if you're self-employed is to make sure that you're making the quarterly payments to make sure that's automated and things of that nature, because I personally think you should go to a professional whose expertise is tax preparing for tax advisory. The tax code is huge. It's a mountain.

[00:26:27] You know, for me to even pretend like you could kind of learn what you need to be doing, really not feasible. That tax code certainly needs to be cut down and I wish it would. But certainly in this iteration of it, there's no way you're going to be able to learn what you need to learn. So if you just have a professional that you feel good about and that you trust and that you can rely on to help you with your taxes. Awesome. Thank you. Awesome. Yeah. You made me think about payroll vendors when you said the liability ultimately goes back to

[00:26:54] the responsible, I forget the phrase you use because- Unwillful. Yeah. There you go. Because I tell Lee, we're both payroll managers. So I like, we tell our leadership in the event that they don't know, most of them, thank God they know, but it's pay. The vendor does the filing of the taxes, but in the event that they miss something or because their human systems errors happen all the time, you may get a leader that's, oh, call the vendor.

[00:27:20] And I'm like, look, we can definitely do that. But at the end of the day, it's the business's responsibility. The IRS doesn't care about the vendor. IRS is coming straight to the business that is responsible for filing. They're not going to be like, oh, the vendor. Okay. No problem. You're off the hook. No, it don't work that way. So it made me think of that. And then another thing was the question is, do you partner with a CPA? Is that you have a CPA in your tax group?

[00:27:47] So we do have accountants here, but that's not what we focus on. Our focus is working with tax debt, helping people navigate that system, helping resolve tax debt issues. And we do provide it because not everyone has someone that they can go to. And our accountants are great. So don't get me wrong. They're great here, but that's not where we focus and where our nieces. So I guess the quick answer is I partner with a lot of CPAs and enrolled agents and tax preparers. And I like to

[00:28:17] be able to give that business to them, to people that I trust. So I have a lot of good relationships with CPAs where I send work to them with tax taxpayers who need tax preparation done. And then alternatively, they send people to me who have tax debt issues. And my whole thing is I'm with CPAs, and I just like to make clear the taxpayer is always going to stay your client, right? Like I'm just here

[00:28:40] to resolve the tax debt issue, to resolve the tax assessment issue for CPAs. You can be on every email if you want. The taxpayer is always your client. Like my client for tax debt purposes, but it's always going to come back to you. Like we're not trying to do tax prep or tax advisory, those things. Amazing. All right. Love it. So Steven, what information would you like to share for folks or businesses that are interested in your

[00:29:09] services? Oh, sure. So I actually give out my direct number. You can certainly call the company here, which is called the W tax group. But my direct number is 248-971-0885. That's 248-971-0885. But I'm very active on LinkedIn. So my name is Steven A. Weisberg. And then if you go to,

[00:29:33] you can go to the W tax group's website, which is wtaxattorney.com. But go to weisberg.tax. That'll go come straight to me. You'll see me directly on there. That's kind of my personal page that everything there gets to go through the W tax group of my company. But that's a good way to get to me directly. You can have more of a personal relationship with me there. Select

[00:29:57] weisberg.tax. And weisberg is W-E-I-S-B-E-R-G.tax. All right. Love it. Yeah, man. Thank you so much for joining us. Oh, you're welcome. Thanks for having me. That was a great conversation. Yes. Agreed. I really thank you guys. Yep. Absolutely. And I'm really happy about that and sharing the info. Folks, reach out. Your information will also be in our show notes so folks can look at it there.

[00:30:24] And I did see that you had a lot going. I love your page on LinkedIn and everything you're doing. Amazing. Thank you for joining us today. Send me your daughter's stuff. I'll take a look. So yes, I'm going to dig for the form over the weekend and I'll scan it in and just let me know what you can glean out of it. I appreciate that a lot. So folks, listen up and definitely reach out to Steven if you have any issues. If you're business owners out there, we warn you all the

[00:30:50] time. Don't get caught up in that temptation to not pay your payroll taxes because you got it right from a lawyer's mouth here and the warning. So we definitely want you guys to heed that. Yeah. And until the next time, folks, we love you. Thank you. Before we sign off, here are a couple of quick things. Don't forget to follow It's About Payroll on LinkedIn and it's about your paycheck on Facebook and TikTok.

[00:31:14] Thank you for being part of our payroll community and thank you for being a part of this journey with us. Until the next time, keep learning, keep growing, and most importantly, keep going.