In this inspiring and practical episode, Eric Green sits down with tax attorney and educator Beverly Winstead to break down one of the most overwhelming challenges taxpayers face: getting out of tax debt—and staying out.
Drawing from her book Get Out of Tax Debt Now, Beverly shares not only the technical steps to deal with the IRS, but also the mindset shifts that are critical to overcoming financial struggles. From her journey as a student-athlete to running the Low Income Taxpayer Clinic at the University of Maryland, Beverly brings a unique blend of personal experience, resilience, and professional expertise to the conversation.
This episode goes beyond tax strategy—it’s about real-life challenges and real solutions. Beverly opens up about her own financial hardships, including student loan debt and facing foreclosure, and how those experiences shaped her mission to help others navigate the system with clarity and confidence.
Whether you’re a taxpayer feeling overwhelmed or a practitioner looking for a better way to guide clients, this episode delivers clear, actionable advice without the jargon.
If you’re tired of ignoring the problem and ready to take control, this conversation is your starting point.
Grab a copy of Beverly’s new book here!
Want to contact Beverly? Email her at: beverly@irshelpattorneys.com.
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Watch the episode here
Listen to the podcast here
Get Out Of Tax Debt Now With Beverly Winstead
Introduction Of Beverly Winstead And Her Book
I’m joined by my friend who’s been here before, actually, it’s been a couple of years, Beverly Winstead. Beverly is an Attorney in Maryland. She runs the low-income taxpayer clinic at the University of Maryland. I’m very excited because I just finished her book, Get Out of Tax Debt Now. I learned a lot about Beverly reading it. You always find things you don’t know. No, but I found out you’re human.
I thought you were Superwoman. What I like about this, Beverly, is you can tell that you teach students and the low-income clinic. It is very clear, broken down in a very easy format to follow. It’s always concerning because we’ve got the real thick procedure stuff and all. This is one you should be able to pick up and, probably, give it a couple of hours after dinner, should be able to have a pretty good handle on what’s going on.
That was definitely the intent behind it. I wanted it to be short, I wanted it to be not too high-level, but I wanted it to be informative.
It is, and it’s simple to read. What I learned was how I struggled starting my business and your struggles at the beginning, and there are good lessons in there. I think it helps you empathize with the folks that come in who do need help. Just as some background, we were talking about this, you played basketball in college, athletic scholarship became an academic scholarship. I went to Hofstra to play football, got injured freshman year, I reinjured my hip.
The doctor’s like, “Look, can’t force you to quit, highly recommend you seriously consider retirement,” and a very mediocre college football career came to an end and I just focused on academics. As some background, what led you to where you are now running the clinic, your own practice in IRS representation of all things?
Beverly’s Journey From College Basketball To Law School And IRS Representation
I love sharing this story. I tell everybody I was a little girl growing up in the country. I’m just a country girl, even though I’m in this big city world. I think what just led me here was just a series of events. I graduated from high school, came up here on a basketball scholarship, had a very successful basketball career at Bowie State University. Once I had completed, I actually wanted to play professional basketball.
That was like my dream. When I was a little kid, I actually dreamt that I was going to be so good that I actually would play on the men’s team, I would play in the NBA. Turns out I wasn’t that good, I wasn’t that great. After I graduated from college, I actually went to quite a few pro camps. I actually did extremely well in the pro camps, but the lesson I learned out of still not being picked up is that you still need other people to vouch for you.
I could go and I could get MVP in all these camps and all this other stuff, but if I didn’t have the backing of my college coach, no one still was going to take a risk on me. I had done some things to, I think, damage a little bit of my relationship with my coach in high school. I just think it was because I was young, that’s all. You’re still trying to learn and figure out what it is that you want to do. I think also that was God redirecting me.
I’m the type of person where I always thank God even for closed doors because He’s trying to lead me to another path. The path that I am on, or I was then pushed toward, was actually academics and figuring out my purpose relative to sports. That’s how I ended up, I feel like, becoming an attorney, going to law school after meeting a great gentleman who used to work for IRS. He used to look at me and he was like, “You’re actually really smart. You should really think about going to law school.” I’m like, “What? I’m smart?”
“You’re not as dumb as I thought.” I actually had a mentor who was very similar, former IRS trial counsel. Listen, your mentor was the former head of CI. That’s a pretty good mentor.
I’m the type of person who always thanks God for closed doors, because He’s trying to lead me to another path. Share on XYes. He said, “We definitely need a lot more representation.” When he said representation, really Black and persons of color attorneys. Now I get it. I just went to law school. University of Maryland took a chance on me. I was so thankful and now I’m back there teaching and I also have my own practice also.
What led you back to teaching? I teach a class every semester for Lisa up at the UConn clinic. I actually covered the clinic when Diana Leyden was going up on the bench. I actually taught the clinic for the summer. It’s a lot of fun. I enjoy the students. You’re out in practice, you go to law school, you go back out to practice. What led you back to running the low-income clinic and going back to academia?
You know this, Eric, because you played football. You come from a place where I think there’s some inherent part of you that wants to be a coach or wants to teach and share your knowledge and wisdom with other people. Again, when the opportunity presented itself for me to teach, I actually thought I would only be teaching for a couple of years. I enjoyed it so much and I enjoyed working with the students that I’ve been actually at the university for over ten years now.
No, it’s crazy how time flies. We met through the ABA. In fact, actually I think Caroline Ciraolo actually introduced us. I’m trying to get Caroline on the show but she’s always too busy. Anyway, but in terms of the book, what made you write the book?
Motivation For Writing The Book, Financial Struggles, And The Importance Of Mindset
The main reason is because I remember, and I tell a little bit about my financial struggles, and some of the things that helped me to navigate when I owed a lot of money for law school loans as well as I was struggling trying to keep my house. I talk about my house going into foreclosure. It was books, honestly, like Dave Ramsey and Suze Orman, that I needed at that time.
I wanted a book that combined mindset with practical, informative tips on how to deal with tax debt. Share on XAll the books that I read by them, they only had one chapter dealing with tax debt. I said, “That does not give us justice, one chapter.” I wanted something along those lines where it was more like a self-help book. The other thing that helped me was I believe a lot in mindset because mindset actually helped me when I was really going through.
I don’t know if you know I lost my brother and I actually went into a state of depression. I had to really work on my mindset to be able to get back and to really get back and be acclimated to society. I wanted a book that was a combination of mindset as well as just some basic informative tips about how to deal with tax debt.
Review Of Key Tax Topics
The mindset is big. When I wrote How to Build a Million Dollar Tax Representation Practice: A Step-by-Step Approach, I tried to be very honest and transparent about the struggles. I remember my wife Dina saying, “Are you sure you want to publish this?” I know that everyone who’s ever met me will know that it’s totally sleek exterior, everything is perfect, whatever. No, it was a crapshow, quite frankly. Building here, but grit and determination adds up for a lot. Perseverance is omnipotent, as I think Calvin Coolidge said. I actually have the quote up on my wall.
It’s the struggle. I think what comes through with the book is that people who are struggling, there is a way out of this. You can get to the other side of this. It might suck getting there, but you can get through it. That comes through loud and clear, and you do talk a lot about mindset, getting in the game because a lot of people do damage just putting their head in the sand and hoping it goes away. It won’t. I think it is great for people.
By the way, even for practitioners, if you’re a CPA saying, “It sounds like it’s really for taxpayers.” If you’re reasonably new to this, or frankly, even if you’ve been doing this a while, it’s a great way to communicate with your clients because we have a tendency sometimes to get caught up in the techno-tax geek language. Clients don’t know what the hell you’re talking about.
One of the things I really like about it is it brings it down to here’s what you need to know. Here’s how it works, here’s how an audit works. You cover audit, you cover collection, you cover penalties, which are the topics that people mostly want to know about. It’s a great read, it is a quick read. I love the taxpayer playbook for dealing with the IRS.
The Taxpayer Playbook And The Need For Short Reads
You know I had to do that because I’m a basketball player. I’m still a basketball player at heart. One of the things I also talk about in the book, and the reason why I think it’s a short read is because people, I’ve learned through teaching, they don’t like to read. Even my students. You’re in law school, and I’m just like, “Just read.”
It’s this generation. My kids are like, “Yeah, I don’t like reading.” This is a whole different topic. Tiktok and, Instagram, and YouTube, they’ve got used to digesting it in like three-minute video clips. I would urge anyone, everything you need to know is in a book. You sit down and read.
Practical Advice For Taxpayers
Not only is it in a book, but if you just, a lot of times I will have a taxpayer that’ll call me and they’re so freaked out about the notice and I’m like, “What does the notice say?” Even in the book, I just said, “Take time, take a deep breath, read the notice. That’s going to be your starting point.” That way, you will know a lot about deadlines, you’ll know what you can expect, maybe later, if you miss a deadline. That also hopefully will give you some insight as to whether or not you should reach out to someone who should be able to help you through this process.
Including Beverly, by the way. I will don’t only have a link to the book in the description, but I will actually connect you. Actually, i’ll give you Beverly’s email. Reach out to Beverly. If you’re in Maryland and want to get to the clinic, obviously, she can help you there, but you help taxpayers all over.
Yeah, just like you. Absolutely.
I refer people, especially if they’re in DC, Virginia, or Maryland. They’re like, “I’d like to talk to someone in person.” Call Beverly. Here’s her info. There you go. You’re doing a lot of good, both from the clinic and your own practice, as well as putting the information out. So, thank you.
Thank you.
It’s wonderful. I know that I caught you in the workday and you still have teaching to do, but thanks for taking even this short amount of time to help us with this. Everyone, Get Out of Tax Debt Now. Pick up that and honestly, something good you may want to give to your clients.
Thanks, Eric.
Beverly, thank you and thanks to everyone for reading and see you next time.
Important Links
- Beverly Winstead
- Get Out of Tax Debt Now
- How to Build a Million Dollar Tax Representation Practice: A Step-by-Step Approach
- Beverly Winstead Email
About Beverly Winstead
Being an attorney has given Beverly Winstead the opportunity to change so many of her clients’ lives for the better by solving their personal and business tax issues. From negotiating with the Internal Revenue Service (IRS) a settlement that is comfortable for a client to getting IRS to release a lien or levy, the favorite part of her tax practice has always been the peace she gives to her clients when she tells them that their debt has been significantly reduced or their tax issues have been resolved.
Her decision to practice law was a natural fit because of her competitive spirit. She went to college on an athletic scholarship at Bowie State University (BSU) and received numerous honors, such as being selected to All-Conference, All- Regional, and All-Tournament teams during her tenure. To date, she has been the only woman in the history of the Central Intercollegiate Athletic Association (CIAA) to win three championships.
She graduated from BSU with a degree in Business Administration with a concentration in finance. After finishing her undergraduate studies, she worked for the local government doing budgeting and teaching entrepreneurial skills. However, she was never satisfied with working for local government because she felt that she had a deeper calling. Her deep desire to help people sent her to the University of Maryland, School of Law. While at the University of Maryland, she learned skills necessary to be an effective advocate.
Just as she did on the women’s basketball team at Bowie State, where she made CIAA history and was honored as the MVP of various tournaments, she always puts on a winner’s attitude for her clients. She is excited to use her skills that she learned while playing sports to be the MVP that resolves her client’s problems.
Beverly is a member of the Maryland State Bar Association (MSBA), American Bar Association (ABA), the National Bar Association, and the Fellowship of Christian Athletes (FCA) – Central Maryland. The Law Offices of Beverly Winstead, LLC, is affiliated with the accounting firm, Winstead Tax Group, LLC.
Attorney Beverly Winstead also serves as the Clinical Law Instructor for the Low Income Taxpayer Clinic at the University of Maryland, School of Law.
