Interview with Guinevere M. Moore

Editor’s Note: Guinevere (Gwen) Moore is a founding partner in Johnson Moore in Chicago IL. She is a recognized tax litigator who represents taxpayers in civil and criminal tax controversies over a broad range of tax areas.

TG: I’m here with Gwen Moore from Chicago. Thanks for taking the time to talk to us at Tax Times. Can you tell us how you got into Tax?

GM: I got into tax completely by accident! I was a history major in undergrad and, as graduation approached, I debated getting my PhD in history and becoming a college professor or going to law school. I had no idea what going to law school or being a lawyer would be like. I had worked in the History Department at DePaul University when I was an undergrad so I knew what that was like. It dawned on me that I needed to get some perspective. So right out of college I took a job with Ernst & Young for a year while I was deciding what I wanted to do. Ultimately, I decided to go to law school. I was worried that if I didn’t like law school, I would be saddled with a lot of loans. So I worked full-time and went to school at night. During the day, I worked full-time for a tax resolution firm that did collections work. That’s how I got started doing tax.

Although collections work is a grind—and it is a grind—it gave me a solid foundation for anticipating how the IRS will respond to things, client communication techniques, and understanding how to deal with clients who are in crisis. I really enjoyed helping them through that crisis. When I got my first summer associate position at Katten Muchin Rosenmann in Chicago, I looked up Jenny Johnson (now Jenny Johnson Ware) because she had a great reputation and I knew that she did criminal tax work. She was running the Mock Trial Program for the summer associates. I told her the experience that I had, and I asked her if she had anything for me to work on. I was able to do some projects with her as a summer associate. My start as an associate the next fall happened to coincide with two huge events. One was the John Doe summons on UBS and the other was the collapse of Lehman Brothers. Very soon after I started, the firm laid off something like 16 to 20 lawyers. I was terrified about losing my job, as I know many people were. I was lucky, however, because I was busy working on tax controversy that came in from UBS clients. I was able to keep busy because I had background in an area that was growing and the source of a lot of work. And I really, really enjoyed it.

I wanted to work in an area of law that would give me meaningful client contact from the very beginning of my career as a lawyer, and tax was a great way to do that. The bonus is that it is incredibly interesting. Tax touches every aspect of business and finance and people’s households and jobs and companies. No matter what the tax problem is, there’s often a “people problem” behind it. And that’s the part of it that I really enjoy.

TG: It sounds like your practice was growing as your firm was shrinking. How did you manage that?

GM: Well, I think all firms were shrinking at that time. The economy was in flux, to say the least, and I asked Jenny and some other partners if they had any non-billable work for me to do. I said, “Do you have an article you’ve been meaning to write? Do you have a presentation that you need prepared for you? What can I do to help you?” I wanted to show that I was willing to do whatever was needed. That worked out well for me. The UBS John Doe summons resulted in many new clients and was lucky for me because I had a unique skill set to offer from my experience in tax resolution in law school. I had also done the non-billable work that generated those new clients by helping to write the articles and the presentations, so when the billable work came in, I was staffed on that work. I was able to keep myself really busy at a time when a lot of people just didn’t have a lot of work.

The other thing I did, when I look back on my early days as a lawyer, was to ask for every opportunity that I wanted. As a first-year associate I asked to second-chair a deposition. I knew that it would not be necessary for the client and the client wouldn’t want to be billed to have me there, but I wanted the opportunity and experience. So I asked, “Please can I come to this deposition? I’ll help you prepare for it. I’ll put the documents together. I won’t bill my time.” The next time a deposition needed to be taken or defended, I was in a much better position to get the spot of being there on a billable basis. I had the experience under my belt. I felt like it was worth it for me to offer to do things the first time on a non-billable basis and to volunteer to help with articles and other marketing projects because it put me in a better position to get the billable work when it came around. As a new attorney in the middle of a financial crisis, I needed to find a way to keep myself busy and show my worth. As a young attorney, you’re trying to show partners why you can be valuable to them and what your work product looks like. I was able to demonstrate that in a way that resulted in me getting a lot of billable work and really getting into the field as it was picking up just as I was coming up. But I also was willing to make sacrifices of my own time and just offer to do it to get the experience that I thought I needed. Looking back, I don’t know if I would have offered up so much of my free time to ask for non-billable marketing work or to come to a client deposition on a non-billable basis had it not been for the financial crisis.

TG: I’ve heard people say that you should say “yes” to every opportunity but, of course, you can’t do that. So how did you politely decline the opportunities that you did not want to take?

GM: You know, I didn’t but I should have. It’s funny. I feel like in many regards, lawyers measure their worth to each other in the number of hours that they bill. I have done that and regretted it and wished that I could take it back. I can think of certain specific times when partners who I didn’t even work for on a regular basis asked me to do something, and I said “yes” because I was afraid to say “no.” I missed important family events, and I worked until 2:00 and 3:00 in the morning. 

I think I did this for two reasons: number one, because I was afraid to say “no” and, number two, because, quite frankly, I felt like it made me somehow better, more valuable, to always be the person who said “yes.” That was a mistake. It was certainly not in my best interest to do that and, quite frankly, you don’t do your best work at 2:00 in the morning. I would recommend that people not do that. I didn’t feel like I could say “no,” especially because as a younger lawyer, when I was coming up, there were so many people being laid off because of the economy. But as I got more experience, I got a lot better at saying “no.”

The best advice that I would give is think very carefully about who you’re saying “no” to and whether you need to offer a reason or not. One thing that I’ve learned: if you don’t need to give a reason, then don’t. You can just say, “I’m not available” or “I don’t have the time for that,” of course, in a nice way. Women, especially, have a tendency to offer a reason as to why we can’t do things, and our reason might be different than what somebody else thinks is a good reason. It can be better sometimes just to say, for instance, “Wednesday at 3:00 p.m. doesn’t work for me.” You don’t need to say, “It doesn’t work for me because I’m taking my baby to the pediatrician.” You can just say, “Wednesday at 3:00 p.m. doesn’t work for me. How about Thursday at 10:00?” And people will figure out a way around it. We don’t always have to explain why we can’t do things.

TG: That’s really good advice. Let’s switch gears then and talk about how you and Jenny went about starting your own firm.

GM: Jenny and I had worked together, as I said, from the very beginning of my career as a lawyer, and we knew that we had an exceptional working relationship. We really enjoyed working together, we worked very well together, and we have different strengths and weaknesses. When we were at Holland & Knight, the firm could not have been more supportive of us and our practice. It was a wonderful place to be and build a practice, but we felt like we could do some fantastic things on our own that we could not do at a big firm.

One of the things that we have appreciated about starting our own firm is that we’re able to explore alternative fee arrangements with clients and branch out into new areas. When Congress repealed TEFRA (Tax Equity and Fiscal Responsibility Act of 1982) and gave us the BBA (Bipartisan Budget Act of 2015), we saw this as an exciting new time to be in tax controversy and tax litigation and tax in general because there’s a whole new audit regime for partnerships. It creates opportunity for people to explore new roles and figure out what BBA audits are going to look like. We decided that we would be a natural fit to serve in the role of partnership representative. It seems a natural outgrowth of what we already do, which is representing clients before the IRS. It’s what we’re good at and we really enjoy it. We’re excited to continue that as the partnership representative for various partnerships; that’s something that we would not have been able to do if we were still at a big firm. It’s nice to be able to put our heads together and be creative and try new things and figure out what other ways we can serve clients other than just by billing hours.

TG: That’s a perfect example. Speaking as someone who practices inside a very large firm, I can assure you that we have explored the idea of serving as partnership representatives but our risk management function and other people within the firm have said “no.” So you’re quite right that the autonomy that a small firm brings is special.

Another hot tax topic that I know you’ve been involved with is cryptocurrency and its taxation. Do you want to tell us a little bit about what you are doing there?

GM: This is another area where it is exciting to be able to be a part of figuring out how these cases are going to go and how people will grapple with new issues. People are still wrapping their brains around questions like “What is cryptocurrency?” and “How is this treated as property? Tax lawyers ask, “Does property treatment make sense? What are the implications of that?” It’s been fun to be on the forefront of that area. 

After I did a presentation on cryptocurrency in Las Vegas at the ABA National Institute on Criminal Tax Fraud last year, I bought one Bitcoin to see what the process was like. After buying Bitcoin, I have followed much more closely the price fluctuations and the crypto virtual currency community to see what they are saying about where this business is going. I just think it’s a fascinating area to be in.

There are a lot of interesting issues. For example, there is the question of how the cryptocurrency miners will be taxed, what their expenses are, and how those expenses will be treated. Obviously, when the IRS issues a press release saying that 10,000 soft letters are coming out, it creates a lot of distress in the community. What I’m hearing is the concern of people who haven’t filed tax returns at all though they should have reported their cryptocurrency transactions. For the most part, they are people who truly do not understand how tax works. They don’t otherwise have a filing requirement and, therefore, they are not familiar with filing thresholds or concepts of income, gain, loss. And it’s because they’re young kids, they’re in college, they’re on their parents’ tax returns. After I presented on cryptocurrency at the IRS Nationwide Tax Forum in Chicago two weeks ago, I had a line of 30 tax preparers with questions. At least half of them said, “I have a client whose kid is in college and they don’t think that they need to report it. Where does it belong on their parents’ tax returns?”

There is definitely a disconnect between crypto investors who are young people who don’t otherwise have a filing requirement and their compliance, where they need to be. We have to help them get into compliance. But those people are not the people for whom criminal prosecution is warranted. On the other hand, I understand the IRS perspective: they have to prevent cryptocurrency from becoming the next offshore haven, and so they need to make a strong showing of enforcement. I think the soft letter approach was the right approach, because in order to get people into compliance, you want to give them a chance to understand what the obligations are. The problem is that it’s so new that the parents may not even know the kids are doing it and the preparers don’t necessarily understand how to treat it. Additional guidance is needed from the IRS. [Editor’s Note: The IRS issued new guidance on the tax treatment of cryptocurrency on October 9, shortly after this interview. See Revenue Ruling 2019-24.]

TG: You’d mentioned being a working mom and going to the pediatrician without necessarily explaining that to a colleague who wants to schedule a conflicting call. Can you talk a little more about juggling your responsibilities? You’re a mom with four young kids and a very successful tax attorney. How do you do it?

GM: I do it by asking for help when I need it and accepting help when it’s offered. When I just had one child, I was aiming for perfection. I had an idea in my head of what I wanted, what perfection looked like. The perfectly present lawyer who did everything for her clients and the perfect mom. When I became pregnant with twins and my daughter was not even one, I realized that perfection is not attainable. That was the best thing that ever happened to me because perfection isn’t attainable. If you accept that as true, then you can figure out instead what’s workable and figure out what you enjoy and spend your time on that.

I particularly enjoy mornings with my kids. I feel like kids are at their best in the morning—at least, my kids are at their best in the morning. I spend my mornings with my kids and I come into the office later, which means I stay at work later. I get home just in time for bedtime, but I don’t sweat it if I miss dinner or other after-school things because I get meaningful time with them in the morning that we enjoy together. Learning what works for you and doing that without feeling like you need to be in two places at once takes practice. Certainly, for me, if I spend my time feeling guilty about something, then that’s time that I’m not spending with my kids and I’m not being productive working for a client. So you just need to move forward. 

The other most important advice I would give people is this: think creatively about what works for you and then figure out if there’s a way to make it happen. For example, in 2014 Jenny and I had two trials back-to-back set for trial in Miami. For the first Miami trial, we had to go down there and interview witnesses, prepare witnesses, try the case. We needed to be down there for about three weeks, and I had a one-year-old daughter. There was no way I was going to be away from her for three solid weeks, and it didn’t make sense for me to fly back and forth on the weekends. Jenny also had a young son at the time. So we talked about it as moms: how are we going to make this work? We decided to rent a condo, bring our kids, and bring a nanny. We were able to see the kids in the morning, and we were able to see them at night and then sit at the dining room table and work together after the kids went to bed. We were still working long hours getting ready for trial and then trying the case, but we weren’t away from our children for three solid weeks. It wound up being more cost effective for the client because paying to rent a condo for three weeks is cheaper than two hotel rooms. It worked out well for everyone and then, happily, we won the case.

After we finished the first trial, there was a debate about when the second trial was going to take place. It was a moving target because of different concerns with IRS counsel. I was pregnant with twins and was approaching my due date. I just raised my hand and said, “My doctor said I can’t travel past this day. The trial has to be by this day.” The judge got creative and said, “We’ll move the trial from Miami to Chicago.” The whole trial was moved, and it wound up working out great because both our team and the IRS Counsel team was from Chicago and most of the witnesses were traveling from different parts of the country. This is one of the great things about Tax Court being a national court: we can move a trial.

My point is that if I had not had a strong female partner as an example, I would probably have been afraid to say, “In order for me to make this work for me and my family, here’s what I need.” Or “Let’s think creatively about ways that we can make this work.” Having come up as a lawyer with Jenny, and because the two of us think alike in terms of balancing our family and our work lives, we’re able to come up with solutions that work for us, our families, and our clients. One of the reasons we have women’s networking events is because not everyone has had the benefit of working with a team who is supportive of the juggling act we have to do. We want to help other women and offer support and ideas about how they can make it work, too. ■