Why Winning Isn't Always Winning feat. Bill Reid

14 hours ago

4 min read

Bill Reid is a plaintiff's attorney, University of Texas law professor, and author of Fighting Bullies: The Case for a Career as a Plaintiff's Lawyer. In this episode, Bill shares how he discovered plaintiff-side litigation after years of exploring other legal roles, why law schools should expose students to more career options, and how prioritizing practical experience, mentorship, and meaningful work can shape a fulfilling legal career.

About This Episode

Background

Bill Reid grew up in New York and attended St. John's University School of Law before building a legal career that eventually brought him to Austin, Texas. His professional journey included a federal judicial clerkship, work at a regional law firm, and three years as a federal prosecutor. Although he gained valuable courtroom experience throughout those positions, he eventually realized that the outcomes he was achieving didn't always align with his personal values.

“I won twenty-four of twenty five trials," shares Bill Reid on You Are A Lawyer.

Despite his success as a federal prosecutor, Bill explains that securing convictions didn't necessarily leave him feeling fulfilled. He eventually transitioned into plaintiff-side commercial litigation, where he discovered greater satisfaction in choosing cases he believed were justified and helping clients obtain meaningful recoveries. Today, Bill focuses on complex financial litigation and teaches a course on the subject at the University of Texas School of Law. His experiences also inspired him to write Fighting Bullies, a book encouraging law students to consider plaintiff-side practice as a legitimate and rewarding career path.

Why Law School

Bill entered law school knowing he enjoyed debate and argument, but he hadn't given much thought to which side of a legal dispute he wanted to represent. He believes law schools often fail to explain the full range of career opportunities available to graduates, particularly the differences between plaintiff-side and defense-side practice. As a student at St. John's, he encountered a recruiting environment that largely emphasized traditional law firms and public interest opportunities.

“I knew that I liked debate and argument, and I didn't really give what side of the V I would be on much thought," explains Bill Reid on Episode 270 of You Are a Lawyer.

Bill argues that this limited exposure can lead students into careers they haven't fully evaluated. He believes legal education should do more to connect classroom knowledge with the realities of practicing law, including client relationships, litigation strategy, and the business of running a practice. That perspective influenced the course he developed at Texas Law, where he uses real cases from his career to help students understand how different legal concepts work together when solving actual client problems.

What Can You Do with a Law Degree

Bill believes plaintiff-side litigation deserves more attention as a career option for law students and young attorneys. While many students focus on Big Law or public interest work, he encourages them to consider representing individuals and businesses pursuing claims against parties that have allegedly caused them harm. His own practice focuses on complex financial disputes involving issues such as fraud, fiduciary duties, causation, and damages.

“I wrote a book about the third path that no one really talks about, which is the choice of becoming a plaintiff's lawyer, which I kind of had to figure out for myself," shares Bill Reid on Episode 270 of You Are a Lawyer.

For Bill, the appeal of plaintiff-side practice comes from combining challenging legal work with outcomes he finds personally meaningful. He enjoys solving complicated business disputes, but he also values the opportunity to select cases based on their merits and pursue recoveries for clients. He emphasizes that this approach isn't necessarily right for every attorney. Instead, he wants law students to understand the available options and think carefully about which type of work will sustain their interest throughout a long career.

Lawyer Side Hustles

In addition to practicing law, Bill teaches complex financial litigation at the University of Texas School of Law and mentors younger attorneys. His course takes a practical approach, using cases from his own career to show students how legal principles apply outside the classroom. He also invites defense attorneys, experts, and mediators to share their perspectives, helping students understand that opposing counsel can maintain professional relationships even while representing competing interests.

“I spent two years writing my book to fill that gap and reach a broader audience than my class,” Bill Reid expresses in Episode 270 of You Are a Lawyer.

Bill's desire to reach more students eventually led him to write Fighting Bullies: The Case for a Career as a Plaintiff's Lawyer. The book grew from a class discussion he called Advice I Wish Someone Gave Me, which focused on lessons he had learned through experience rather than formal legal education. Although Bill continues to enjoy practicing law, he finds mentoring particularly rewarding at this stage of his career. Through teaching, writing, and professional mentorship, he hopes to help younger lawyers make more informed career decisions and avoid spending years in positions that don't align with their goals.