In one of her first jobs, Beverly Winstead met a former head of the IRS Criminal Investigation division, who told her that more lawyers of color were needed to help taxpayers resolve their tax issues and that she should be one of them. That encouragement set her on the path to law school and to owning her own law firm, where she recently celebrated 10 years in business.
Winstead began her road to tax law in college, honing her teamwork skills on the basketball court and majoring in business administration. She found her tax classes in college fascinating and especially liked corporate tax, but initially decided to pursue a different course. Instead of heading straight to law school after graduation, she went to a tax accounting firm, where she met her first mentor in the legal field and developed an appreciation for tax work. Some of the clients she worked for there would later form the foundation of her legal practice.
As a student at the University of Maryland School of Law, Winstead developed a network of close friends and advisers who have remained important to her throughout her career and with whom she frequently collaborates. She is working on a project with one of her best friends from law school, Michelle Mendez of the Catholic Legal Immigration Network Inc., to create a webinar for taxpayers who would benefit from information about the Coronavirus Aid, Relief, and Economic Security (CARES) Act (P.L. 116-136) and economic impact payments in languages other than English.
Winstead also works with her former classmate Caitlin Ryland of Legal Aid of North Carolina on a project to help reclassify misclassified farmworkers so that they don’t run into tax problems. Working with law school friends is especially satisfying, she said.
Hanging Out a Shingle
One of the things Winstead likes best about being an entrepreneur is the constant new challenges, which started right from the beginning. Winstead’s venture into law firm ownership coincided with the market crash in 2008, and her first years in operation were marked by the ensuing recession. Looking back, she said it was a struggle to survive that early period because business was slower than she had expected, even though she already had a base of loyal tax return preparation clients. But her perseverance and the business development she did in those years paid off when even tougher times came.
Tragedy struck in 2011, when Winstead’s brother, grandmother, and two employees died. “That was the hardest period of my life,” she said. She considered closing her firm, but her support system of friends and family pulled her through. Although there was no time to do business development during that challenging period, Winstead learned that she had a strong personal network to lean on when she needed it. “In every tragedy you learn certain lessons, and 2011 prepared me for today,” she said. “It made me a much more compassionate and stronger advocate.” That difficult period also taught her the importance of having a support system of friends, family, and mentors, and she advises others to carefully cultivate their own.
Mentors have played a big role in Winstead’s professional success. “I’ve found that if you find the right people, they’re really in your corner and can advocate for you,” she said, adding that Caroline Ciraolo of Kostelanetz & Fink LLP, Tax Court Judge Tamara W. Ashford, Gerald W. Kelly of Kelly Dorsey PC, Arlene Blume, and Robb Longman all played an important role in advocating for her.
Having a group of knowledgeable and trusted fellow practitioners to provide guidance is especially important for new lawyers contemplating starting their own firm, because learning how to run a practice while learning the necessary law and procedure can be overwhelming, Winstead said. “Don’t think that you can do it alone,” she said. Her mentors have steered her into her current teaching role, as well as into new practice areas.
Winstead sees her nonjudgmental approach to clients who have run into tax problems as one of her strengths. “Clients choose me because I can relate to them,” she said, noting her own years of working to pay off student loans. She said helping noncompliant taxpayers and people who have run into financial challenges get back on track is intrinsically rewarding.
Winstead takes a holistic approach to expanding the services her firm offers. She continues to work with clients on a wide array of tax issues, including collection and assessment cases. She said one of her favorite areas is trust fund cases. But she is also expanding into estate planning and bankruptcy work, with an eventual goal of having a few more lawyers join her team. Winstead said she has found her mentors to be particularly helpful in getting that bankruptcy work up and running.
Social Media Star
Maintaining an active social media presence is the modern equivalent of a shingle on Main Street, and Winstead uses it to both promote her firm and help the community. Her weekly “Tax Talk Tuesday” posts on Facebook cover topics of importance to current and prospective clients and have resulted in invitations to other speaking opportunities.
Winstead began writing a regular newsletter earlier this year, and that effort quickly paid dividends as the coronavirus crisis hit because she had an established platform for disseminating information to her clients and broader group of friends, colleagues, and family about the resulting tax law changes and stimulus packages. “We’ve been able to be a resource for both our clients and our entire network,” she said, adding that “it’s time-consuming, but I’m so glad I did it.”
Teaching
For the past five years, Winstead has shared her expertise with students and clients as a professor with the University of Maryland School of Law’s low-income taxpayer clinic. As part of the clinic, she teaches a substantive class on tax issues, litigation, collections, and tax return examinations. One of her goals is for her students to see the interconnectedness of the tax code and taxpayers’ everyday lives. Winstead said the university’s clinic is special in that the professors and students do a lot of community outreach that both helps potential clients learn about the clinic and shows students the importance of their work there.
Winstead’s role at the law school also allows her to mentor students and help them discern the next steps in their careers. She’s had students who are thinking of starting their own firms as well as those who want to explore tax in a practice setting intern at her law firm. Despite the school and clinic closures, her current student intern has been able to help tax clinic clients file their tax returns and access their economic impact payments with support from her firm. Winstead said her interns get a firsthand look at the challenges and rewards of being an entrepreneur, which for the current intern means valuable experience in guiding clients through the crisis.
Scholarships for Students
Basketball is one of Winstead’s longtime passions, and she now pursues it by planning an annual fundraising game for the scholarship organization (Lewis “Eddie” Winstead Memorial Fund Inc.) she established with her family in memory of her brother, who was also an athlete. Winstead has played in the yearly game in the past. “It might be time for me to hang up my sneakers,” she joked, but she continues to enjoy combining her favorite sport with a good cause. The fund uses all the money it raises to provide scholarships to local high school students heading to college and planning a course of study in a STEM field. Every year on her brother’s birthday, February 19, the organization announces the new recipients. This year it awarded three scholarships.