Yladrea Drummond went from being “team no care about the law" to becoming a highly successful trial attorney and solo firm owner in Maryland and DC. She openly shares the grit required to get barred after a seven-year journey, how she transitioned her practice from family law to dominating criminal defense, and the non-negotiable value of complete autonomy that running her own firm provides. This conversation is a raw, honest look at the transition from legal disappointment to becoming a respected "big dog in court" who is truly building a legacy
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Yladrea Drummond's legal journey has been anything but linear, starting in a place far removed from the courtroom where she now thrives. Before establishing her highly-regarded solo law firm, the Drummond Law Group, she resided in Texas and spent her time in the fields of compliance and political work, actively not practicing law. The seismic shift in her life involved relocating her entire family, including her husband and two young boys, from Texas to Maryland in late 2020, right in the middle of the pandemic. This major move was the catalyst for getting her licenses and diving into the world of litigation, allowing her to ultimately practice in Maryland and D.C., in addition to maintaining her Texas bar status and federal bar admission.
“Being a first-gen college student, I just kind of figured it out," shares Yladrea Drummond on You Are A Lawyer.
The transition to the DMV area proved to be a rough and humbling one, especially as a mother who had to contend with the startlingly high cost of childcare, a factor she hadn't anticipated. Despite missing the South where she's from, Yladrea recognized the immense professional opportunities available in her new location, believing her move was perfectly timed to avoid political instability that could affect the South. Her firm has quickly escalated to the point where she has staff and has made a big name for herself, through consistent trial wins in tough counties, all while managing the demanding balance of a successful career and family life.
Yladrea's path to law school was not paved with a lifelong dream of becoming an attorney; in fact, she admits that she knew nothing about law school when she first applied. Her decision was less about a passionate career calling and more about the simple opportunity that was presented to her, causing her to jump in without a deep understanding of what the legal profession entailed. Once immersed in her studies, however, she began to find her footing, initially aspiring to practice family law after being heavily influenced and inspired by one of her professors.
“I never had this lifelong dream, but when I got there… I realized I really like this life now," reflects Yladrea Drummond on Episode 213 of You Are a Lawyer.
The real turning point for Yladrea was when she started viewing the practice of law, particularly litigation, as a "sport". This competitive frame of mind perfectly aligned with her personality, as she recognized that her deep-seated hatred of losing fueled her drive and competitive edge. This realization ultimately guided her career away from family law, a field she abandoned because of its inherent nature where "everybody loses," and towards the high-stakes courtroom battles that allow her to constantly fight for the win
For Yladrea, a law degree is the ultimate foundation for complete autonomy and the freedom to chart her own professional course, allowing her to control her schedule and her financial earning potential. While a law degree can lead to traditional roles, her experience shows that it is a powerful tool for entrepreneurship and building a solo firm that generates substantial income without the constant hustle for new clients. By becoming a panel attorney for the public defender's office, she uses her degree to secure a steady stream of serious cases, enabling her to focus on high-stakes courtroom work rather than business development.
“I'll never get tired of not answering to somebody else and always knowing that you're literally building your legacy," shared Yladrea Drummond on Episode 213 of You Are a Lawyer.
Beyond the firm's structure, a law degree equips you with the fundamental skills to navigate the profession, teaching you how to "figure stuff out" even when you feel unprepared. Her experience in her first job taught her how the degree can be leveraged to learn "the game" in court—how to finesse and connect with court staff—even if you're not fully trained in the law itself. A law degree also reveals who is "built for" the trial life and who is better suited for transactional work, emphasizing that the degree is a filter and a launchpad for diverse legal paths.
While Yladrea is a self-proclaimed "workhorse" focused on the rapid expansion and day-to-day operations of her successful trial firm, she also acknowledges the importance of creative outlets that serve as a side interest and a form of therapy. Her personal hustle is in the realm of writing, specifically fiction, which is a powerful creative counterbalance to the high-stress demands of her criminal defense practice.
“I love to write,” Yladrea Drummond shares in Episode 213 of You Are a Lawyer.
Although the fiction novel was ultimately shelved, Yladrea recognizes her love for writing remains strong. She notes that if she were to pursue a writing project now, after achieving success in her firm, she would aim to share her professional expertise in a non-traditional format.
Yladrea is licensed to practice in Maryland, DC, and Texas
This episode is produced by Skip The Boring Stuff, a podcast strategy company for business owners and creatives.
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