Cited Authorities
Behind every successful legal career is a series of decisions that never made it onto a résumé. Cited Authorities features conversations with accomplished lawyers, and the leaders who shape their field, about career inflection points, professional judgment, reputation, leadership, and the real stories behind professional success.
Excellent legal careers are not accidents. Hear the stories of how they were built.
Cited Authorities
Glen Frost: Building Frost Law and Practicing Tax Controversy
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Episode 7 of Cited Authorities. A conversation with Glen Frost, Founder and Managing Partner of Frost Law.
Glen is an attorney, a CPA, and a Certified Financial Planner, with an LL.M. in Taxation. He is admitted to practice in Maryland, the District of Columbia, Virginia, Florida, Pennsylvania, and Arizona, and before the U.S. Tax Court, the U.S. Court of Federal Claims, and the Supreme Court of the United States. He started as a solo practitioner and built Frost Law into an 80-plus person multidisciplinary firm of attorneys, CPAs, enrolled agents, and Certified Fraud Examiners.
In this episode, Glen and Alex talked about how Glen built Frost Law from a one-lawyer office. The first hire. The pivot to a multidisciplinary firm. Scaling across multiple state bars. Expert-witness work in tax sentencing. IRS workforce cuts and how they land on clients waiting on audits and appeals, the Employee Retention Credit era and what it did to Frost Law's growth, penalty regime questions and circuit splits practitioners are watching, and the advice Glen gives young lawyers weighing Big Law, accounting firms, and tax boutiques.
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And to be able to come in, diagnose the issue, and then help these business owners solve these issues, it's extremely rewarding and feel like I'm making a difference every day. The law license, right? And really going back to law school, and I think it's a unique experience when you're in law school, it's a cratic method, and you're kind of exposed to an area that you've never been exposed to in your life, and you go deep in it. I was fortunate to work while in law school, working for a law firm doing tax law, and as well as I did the tax clinic at University of Baltimore School of Law. And, you know, I think building that practical and deep knowledge in the actual practice of law, I think, yeah, coupled with law school and passing the bar, I think that portion was certainly the most difficult.
SPEAKER_00And of course, we share that same you bought law connection through Fred Brown. And Fred told me that while you were there, you founded the Business and Tax Law Association while you were a JD student. What were you trying to build before you could practice?
SPEAKER_01Yeah, absolutely. So I actually co-founded that with a great friend of mine, Giovanni Albertanza. And I was extremely tax focused at that time. And I think Giovanni, as well as Fred, convinced me to go much broader. They said, hey, if you just do tax law, nobody's going to come. So you should like really broaden this business and tax law association. But but what I was trying to do is bring people together in different disciplines, business lawyers, tax lawyers. And I've always done that with also trying to bring in CPAs, financial professionals, trying to get different perspectives on unique areas.
SPEAKER_00You started solo in 2007. Did you know while you were in law school, like this is what I want to do? I want to build this firm and scale it to 80 plus attorneys, or was it more let's see how this goes? And then it just kept getting better and better.
SPEAKER_01During law school, I was fortunate to have a great law clerkship with a tax law firm in Maryland. And I was a CPA while I was in law school. So that allowed me to administratively practice before the IRS and really learned a lot of that way. And worked for the same law firm all throughout law school, pretty much, and then joined a firm, Thomas and Libowitz in Baltimore, and then practiced there for close to a year, while licensed, and then went out, founded my own firm, and didn't know the size it was going to grow to, but just knew that we were going to try to do great things with clients and assist as many clients as possible.
SPEAKER_00It's unique because of the amount of CPAs you have working at your firm. What spurred that decision?
SPEAKER_01Yeah, I think it's always having both financial background as well as the legal background. It's always the lawyers are afraid of the accounting side, the accountants are afraid of the legal side, and really having both and to be able to combine both of those disciplines into one, I think just allows us to be better advocates for clients. It allows us to have deeper understanding of issues, and clients like to come to a place that understands both and can more efficiently and more practically solve a lot of client issues.
SPEAKER_00Who doesn't like a one-stop shop?
SPEAKER_01For sure.
SPEAKER_00Yeah. At the same time, I feel like you have to have a niche, but you've carved out a niche with that combination.
SPEAKER_01Yeah, and law has been very regulated. And in the past, there's certain regulations against multidisciplinary practices, certainly doing other things while in a law firm can be very regulated. It's unique when you're in an area such as tax law, because although we operate as a law firm, we're governed certainly by the Maryland Rules of Professional Conduct as well as other states' professional conducts. You're also practicing a lot of the time for the IRS administratively. And you're governed by kind of a different set of rules, you know, Circular 230, where enrolled agents, CPAs, et cetera, can all practice. So kind of a unique area in the text controversy relevant.
SPEAKER_00Yes. And those rules are not always easy to reconcile between CPAs and attorneys. You read one rule for a CPA and then an analogous rule, a parallel rule for an attorney. And it's like, I think those are not exactly conflicting, but don't offer the same guidance.
SPEAKER_01Yeah, and lawyers, we have a duty to be zealous advocates for our clients. Accountants have generally different duties, and it's generally not that. And especially if you're acting in the capacity of a return preparer, well, then you have certain duties to the client, you have certain duties to the government. You're kind of a quasi-government agent, you're in between both. But big picture, the law, the accounting, I think what we're starting to see in places like Arizona, Utah, starting to see private equity come into the industry. You're starting to see non-lawyer ownership of law firms. Both KPMG and Apri own started law firms in Arizona. You're going to see this multidisciplinary practice evolve and develop. And in fact, in Europe, many of the firms, the large big four accounting firms, they also practice.
SPEAKER_00Glenn, in practice, what does the CPA credential let you do that a pure tax attorney can't?
SPEAKER_01Yeah, the only thing a CPA credential can allow you to do, really, that a tax lawyer can't, is more so in the context of being an accounting firm where you can provide audit and a test services and you can sign financial statements, financial reports. Now, law firms typically can't do that. You've got to be a licensed CPA firm to do that. In the context of tax and tax controversy, certainly tax lawyers, enrolled agents can do the same that a CPA can do.
SPEAKER_00Who was the first attorney you brought on after being a solo practitioner?
SPEAKER_01I think I'll start with the first employee because she's still with me today, Caitlin Lossner, who at the time she was in law school, she had an accounting background, and I said, okay, well, you're gonna do half administrative, half legal type work, and she's always been a team player, and she did a great job all throughout law school work for me. And then we hired her as a full-time associate when she graduated, but she's an attorney, CPA, LLM, and tax, and also my law partner.
SPEAKER_00So she was in law school when you hired her initially. Yes. And then she's still with you today. How many years later?
SPEAKER_01Uh, I guess that would be 15 years later.
SPEAKER_00Wow. And did she have the same vision that you had for the practice throughout?
SPEAKER_01I don't think she has the same exact vision, but I think she compliments me extremely well. It's obviously good to have people around you that compliment you, that are good at skill sets that you're not good at. And I think she was on board and always been kind of an advocate for the mission. I've had more of that visionary role where she's been more execution.
SPEAKER_00With your respective business acumen between the two of you, how do your personalities differ?
SPEAKER_01I think she's she goes deep on things. She's very thoughtful, can come at things from which I think is good, is a healthy level of skepticism where she's trying to pick things apart and she sees situations in business that might have issues or might have red flags, and she identifies, you know, those certain circumstances of when we should go down a different path.
SPEAKER_00And Glenn, you you now have offices in seven plus states. At what point during your practice did you realize this has to expand and quickly?
SPEAKER_01You set up an office in a geographic region, and you realize, hey, there's great people all over. We're very fortunate in a practice area where we can primarily practice remotely. Very few clients that actually want to meet in person. Now, meet a couple clients a month in person. So it becomes very conducive, and especially after COVID, it became very conducive to hiring talent, just looking for where are the people located that we want to hire, that we want to work with, that have the talent to service our clients. And so it's just allowed us to not be restricted geographically. And you know, we have attorneys of many different states, and we'll continue to hire. I think if we were limited to just the DC, Maryland area and hiring, our talent tool just wouldn't be what it is.
SPEAKER_00Yeah, that opens up so many possibilities as far as who you can hire when you can hire from anywhere. Yeah, for sure. You've testified, Glenn, as an expert witness on criminal tax sentencing. What does the stand teach you about how judges think about tax crimes?
SPEAKER_01You have to really sometimes explain complexities and tax losses and things that normal people just don't really know. So it's it's just a matter of calm, cool, collected, and very, very well prepared in order to show them we've adequately prepared, we've understand the government's position, and here's the taxpayer's position.
SPEAKER_00Aaron Powell People think about tax loss. They think about actual tax loss and not um anticipated, expected. So that's a major distinction.
SPEAKER_01Sophisticated means enhancements, you know, all different types of analyses that have to be done in many different areas for sure.
SPEAKER_00Yeah. I mean the sentencing guidelines, the guidelines by itself, that's a pretty complex set of provisions. Then you add the tax code on top of that. It takes a different kind of individual to be able to decipher that.
SPEAKER_01Yeah, and that's where a tax controversy lawyer, criminal tax lawyer, can really add a lot of value is knowing that well, it's where a lot of value is added in the criminal tax realm.
SPEAKER_00Of course, we know that the tax division was recently dissolved. Where do you see tax enforcement heading within the next six to twelve months on the criminal side?
SPEAKER_01Yeah, I think on the criminal side, obviously you're gonna see less of just pure tax evasion. I think you're gonna see more focus in areas like COVID abuse, pandemic fraud, so PPP loans, employee retention credit, fraudulent claims. I think you're gonna see a real emphasis on some of the government programs and preparers along with individuals that were taking advantage of some of these programs. I think we'll see more and more of that, and that'll be the primary focus.
SPEAKER_00DOJ Tax Division is now dissolved. Workforce has been cut significantly. How has that affected your controversy practice? Sure.
SPEAKER_01I think that particularly the impacts to the IRS and some of the instability. I think there were seven IRS commissioners last year in 2025. Nearly 30% of the IRS workforce is cut. A lot of the senior workforce, a lot of tenured people are gone. So you're left with a lot of junior folks. We lost a ton of legacy knowledge within the IRS. So what we've seen is just more delays, more backlogs. The IRS Office of Appeals, as an example, is just backlogged from tens of thousands of cases. And I don't know how they're gonna clear the backlog. It's gonna be years to clear the backlog. Taxpayers in certain circumstances are gonna have to get certain statute extensions signed, and it's just created more work and more difficulty getting results for taxpayers administratively.
SPEAKER_00How do you think appeals is going to handle that? I know there's an expedited program, but 10,000 plus cases that seems insurmountable. Do you anticipate a fire sale in terms of what's offered?
SPEAKER_01We hope. That would be nice. Hopefully they get more reasonable and expedite settlements. And I think it's just do more with less. You know, we're hoping some of these statute extensions that are going to need to be signed, we're hoping they're more automatic. They have to be signed by the government. Um, we're hoping that the government automatically is sending these statute extensions out. We hope that comes to fruition, but just overall, it's going to be a long, long time to get a lot of these cases resolved. And we have we have hundreds of cases um currently in appeals.
SPEAKER_00Well, I want to go back in time. You were a CPA before becoming a lawyer. At what point in time did you decide that you wanted to go to law school? And why did you choose UB?
SPEAKER_01So I started my career at a pretty large accounting firm. I was an auditor at Grantporton. And I think it was a great place to start my career learning financial statements, learning how they operate, how they work, learning businesses, learning internal controls. But what I kind of quickly learned as an associate auditor at a large accounting firm is I wasn't making a lot of difference. I was ticking in time numbers, I was writing and drafting financial reports, and it just truly didn't feel like it was making a difference. Things were immaterial, and no one really appreciates an audit. So decided to go to law school, thought I could make certainly more of a difference, and was very fortunate to find the field of tax controversy. And what's so good with tax controversy and the size client that we focus on, it's generally we're dealing directly with the business owner, directly with stakeholder. And oftentimes this is the most important issue that that business owner is dealing with in their life. And to be able to come in, understand it, diagnose the issue, and then help these business owners solve these issues, it's extremely rewarding and just do feel like I'm making a difference every day.
SPEAKER_00There's probably a certain amount of understanding from your clients that it's obviously you're in a different business, but at the same time, you own a company that has 80 plus employees. So, Glady, you now have 80 people in offices across seven states. What's the next chapter for Frost Law?
SPEAKER_01One thing that we did very heavily, and I think it was extremely good for our company and the clients we represent. What happened right around the pandemic, the IRS really shut down and announced that they were going to be taking almost no enforcement action. And when you have that many tax controversy lawyers and staff on staff, and you're like, wow, the IRS is going to pretty much eliminate what we've been doing for years, it's a scary time. Well, fortunately, the CARES Act came out, and things like PPP, restaurant revitalization fund, emergency disaster loans, along with the employee retention credit. We represented thousands of small businesses at the time. And being able to dive in and go deep on each of those issues and counsel clients through that during what was the most difficult economic times of our lives was extremely rewarding because we were seeing businesses that would have gone under on the matter of tax had they not yet gotten that relief that they were entitled to. So we went really deep on those areas. And I'd say we went extremely deep on the employee retention credit, and the government chose the tax code to administer COVID relief, right? You they chose the most complex vehicle out there to administer relief that was intended to be passed on to the taxpayer at the time of the pandemic. And now we're in a situation where many of these taxpayers still have not gotten that belief that they applied for back in 2021, 2022. And so we went extremely deep with that. We've been working with many taxpayers, both administratively as well as we have cases in the U.S. District Court, the Court of Federal Claims, to work through, compel the government to pay eligible taxpayers and get the funds that these businesses were entitled to. So we went very deep on certain areas. I think we're going to continue to do that, where we can become subject matter experts on very specific areas of the law, and then be able to represent a broad population geographically all over the country with that specific issue. Another thing we've been doing a lot recently is with certain theft losses and whether or not those theft losses are deductible. And so that depends on whether it was an investment, not an investment. We've been assisting taxpayers who are victims of scams and thefts with navigating the tax law around theft loss deduction, et cetera.
SPEAKER_00So Glenn, you mentioned the employee retention credit. During that time in COVID, you're assisting these firms in frankly a dark hour, but for your firm's help to these businesses, is that when your firm experienced the most growth?
SPEAKER_01So I think when you can really become a subject matter expert on a very specific area of the law and then disseminate that information quickly, I think that's really what did cause us to experience a lot of growth. Being able to quickly digest and explain to the market, other stakeholders, accounting firms, other lawyers, et cetera, some of the complexities, some of the nuances, both in written content, webinars, person presentations. I think that that really kind of set the stage nationally that people look to us whenever there is a new issue. They look to us to try to navigate it, to try to figure it out, and to try to explain it in real terms.
SPEAKER_00Of course, you know, there are circuit splits involving the IRS's ability to impose penalties under the Seventh Amendment, under the Eighth Amendment, the excessive fines clause, looking at F-bar claims. There's a case I recently wrote about that has been appealed to the Ninth Circuit. What's your prediction on what's going to happen to the IRS's ability to assess penalties moving forward, given what's going on around the country in circuits, and given the Supreme Court's ruling in Jarkesey, what's your prediction of what's going to happen to the penalty regime moving forward?
SPEAKER_01A lot of it's just coming back to what I'll call common sense. And there's case law that says not checking a small box on a tax return can constitute willfulness. Or we can penalize you for up to 300%, 50% per year for six years, or it's it's not $10,000 per form, it's $10,000 per account. And you had all of these accounts, even though they had $50 in them, the government has taken a little bit too zealous positions on some of these matters. And I think that it's just the courts coming back to reality and saying, okay, what's reasonable for a taxpayer in this situation? Look, if there's truly willful conducts, and I think there's many ways the government can penalize taxpayers. But most taxpayers aren't that extremely willful, haven't committed criminal tax evasion. I think the courts are going to side more with the taxpayer that look, tax code's overly complex. This taxpayer hired an advisor, or this taxpayer thought they were doing the right thing, and they're gonna apply a sense. A reasonable that's going forward to it.
SPEAKER_00Glenn, if there's a U-Bault Tax LLM student out there who wants to build something like frost law, what would you tell them that nobody told you?
SPEAKER_01Yeah, absolutely. I think first and foremost, very important to go get excellent experience wherever you get, whether it's a clerkship at a court, whether it's working for the IRS, working for private practice, get as much experience as you can, get different perspectives. I think that's going to help you tremendously. But as you expand and have your own firm, one thing that would have helped me if I had identified this a lot earlier, not everyone is like you. Like people are motivated by different things. People are better at certain things. So figure out what your zone of genius is, figure out what you're really good at, and focus on those things. And focus on finding people that can work with you that have different core competencies, zones of genius, and make sure that you have the people in the right places. And I think delegate, let go, but just make sure that you have the right folks and that you're all aligned and kind of focused and focused on the same mission.
SPEAKER_00That's great advice. Thank you for your time. I appreciate it.
SPEAKER_01Yeah, likewise, thank you very much for having me.