Photo by David Cross

He is, to state the blazingly obvious, contrarian.

By nature. By temperament. By discipline.

He embraces the path not taken – a byway worth billions for his firm.

Bill Reid founded Reid Collins & Tsai 14 years ago. A unique private financial prosecution practice, it’s without question one of the great litigation boutiques in America, bringing novel lawsuits against institutional defendants for investors and trustees and winning billions for clients – with a healthy cut for the firm.

We’re sitting in the backyard of his new house in the hills outside Austin, where he’s throwing a ball to his dogs and I’m marveling at the family’s pet bunny rabbits. His son has tried to teach Reid the nuances of the language of teenage boys, circa 2023, on the drive home from school. His daughters are busying around the house with his wife, Misty, who’s packing up the whole crew to fly to the Caymans, where they have recently closed on a house. Reid has been handling litigation in the islands for nearly 23 years and is eager to open an office there.

Cayman litigation is one of those niches he’s mined brilliantly. Finding opportune jurisdictions and claims that other firms wouldn’t take or didn’t understand is one of his trademarks. Third-party claims arising from insolvency, accounting malpractice, and representation of offshore liquidators all grew from his work on the $325M InverWorld Ponzi scheme, which sent him to the Caymans early in his career. He continues to maintain a docket of Caribbean-related litigation and has also added a multi-billion-dollar practice pursuing foreign appraisal rights actions in Cayman and Bermuda, where his firm serves as a litigation manager and funder all in one.

Legal malpractice is also on his shortlist, a practice that flourished mostly because other law firms traditionally wouldn’t touch it. Although the size of such claims is often modest when compared with Reid’s financial cases, there’s no question they are showpieces for his trademark tenacity and bad-assery.

At 56, he’s achieved wealth, built a great law firm, and created a work-life balance that he revels in. His underdog ethos gives him the mien of someone a decade younger, as does his dedication to a paleo diet and a rigorous physical regimen involving regular workouts as well as hunting at his Texas ranch and Idaho elk lease. Big-game hunting is a particular thing – and not just the Am Law 100 firms of the world.

The past few years, he has added professor to his dossier, teaching a class he created called Complex Financial Litigation at the University of Texas Law School, and developing his thoughts about the legal profession – more specifically, how law schools funnel students to Big Law and how to be a happy lawyer.

Lawdragon: Were you born contrary?

Bill Reid: I guess so. I am often skeptical and a contrarian, but I’d like to think there is a bit more to the story. By nature, I am a creative thinker and see multiple sides to every situation. I surround myself with smart people so that I can group-think optimize every decision in business or law or life. I think that along the way, I have consistently been willing to reevaluate the course of my career while keeping satisfaction and enjoyment as my only true North Star. This approach has allowed me to be nimble in the practice of law.

LD: As a lawyer, there’s clearly some benefit to your approach. I’m thinking of early in your career, in 1992, while others were competing for East Coast clerkships, you headed to the border with 5th Circuit U.S. Judge Reynaldo G. Garza – himself a noted iconoclast.

BR: To be honest, Judge Garza was my first clerkship interview and I instantly bonded with him – so it was less strategic choice and more personal chemistry and luck. When he offered the job at the end of my weekend-long interview, I immediately accepted and never looked back.

I did, however, recognize that a NYC Big Law career was not for me. So, after my post-grad summer clerkship in Dallas, I chose to start my private practice at Hughes & Luce in Dallas, despite not knowing a single person in the State of Texas. When I felt that I needed more trial experience, I moved to Del Rio, Texas, to become an Assistant U.S. Attorney, even though I was a single 29-year-old with absolutely no contacts or friends there.

In short, in the early days when I saw the opportunity to pursue trial experience, I pursued it blindly regardless of the consequences to my personal life. After my three years as an AUSA, additional experience became less important, and I could truly focus on the enjoyment of law. After a decade at my former firm, I started my own firm in 2009. I simply wanted to have more fun, which was easier if I created the ideal practice for me – which is what I set out to do. Along the way, an incredible group of people have bought into our approach.

Each step I took, I was willing to bet on my own ability and I was willing to risk failure. Those are not common traits among many lawyers.

Over time I have become more convinced that my path is the right path for me and that the path so many other lawyers follow is not for me – and frankly it is likely not right for many of the people that choose it. And I’m talking about Big Law of course.

LD: Let’s talk a little about your own lessons along the Big Law path that led you to find a different route. First, what was your experience at St. John’s University School of Law. Did you feel funneled to Big Law then, as so many students are today? Did you already have a flickering that you might want to become a plaintiff lawyer?

Over time I have become more convinced that my path is the right path for me and that the path so many other lawyers follow is not for me – and frankly it is likely not right for many of the people that choose it. And I’m talking about Big Law of course.

BR: St. John’s was a great law school. It gave me a lot of knowledge and it had some truly great professors. I don’t think it overtly directed me to Big Law, although back then there was an institutional bias against plaintiffs’ law – and there still is. The problem is that the legal education system defaults to Big Law because students (and many lawyers) put starting salary as their North Star. Once you do that, you necessarily are led toward Big Law. So, it’s the quest to maximize starting salary that ultimately leads to careers that leave many lawyers feeling dissatisfied. Fortunately for me, I saw through the façade of the Rogers & Wells summer clerkship and realized that a full-time job at a NYC big law firm would be miserable, even though it would have paid a lot of money.

LD: You worked at Hughes & Luce in Dallas from 1993 to 1997 and then at Diamond McCarthy from 2000 to 2009. Do you consider those to be Big Law experiences? If you had a do over as a happy lawyer, would you still have spent time at Big Law?

BR: Hughes & Luce was a 175-lawyer full-service firm when I joined in 1993. The litigation department was about 40 people. So, I am not sure it was truly Big Law, but I take your point. It was a full-service firm, which in those days would have made it “big,” yes. Hughes & Luce gave me a chance to work on interesting cases and gave me experience on my feet in court and exposure to both sides of the V. I learned quickly that I preferred to be a plaintiff than a defendant. In the end, though, I had the itch to get more trial experience and become an AUSA because of the trials I witnessed at the district court in Brownsville during my clerkship with Judge Garza. Regardless of whether Hughes & Luce was Big Law, it gave me something few other big law firms actually provide – real responsibility and experience.

Diamond McCarthy was a litigation boutique of about 40 to 50 lawyers during the time I was there. It was formed by a bunch of former Hughes & Luce lawyers, and it was categorically not Big Law. There just came a time when I disagreed with the way the firm was managed and wanted to chart my own course with a focus on contingency-fee work.

LD: And, of course, your time as a prosecutor trying 25 cases in Del Rio was critical to your trial skills. Do you encourage your students to spend time as a prosecutor? Would you have been happy as a prosecutor for your entire career?

BR: I think young lawyers need to be aggressive about getting trial experience. For some, a short stint as a prosecutor could be very good experience – but beyond a few years it can quickly become a one-way street to a lifelong career in criminal work. And I would not recommend a lifelong career in criminal work to most people.

For me personally, my heart was not in prosecuting drug cases. I felt then and still believe today that our drug laws are extremely unfair because they do not penalize the greed factor fairly. In other words, white-collar crime is frequently committed by wealthy, educated people who take money that simply provides them with additional luxuries, whereas most drug crimes are committed by people who have very limited alternatives to make money. The white-collar kind of greed is far more nefarious in my view, yet the drug crimes normally lead to lengthier penalties.

The work I do today, prosecuting financial wrongdoing against bullies and Goliaths, is far more rewarding to me than prosecuting drug dealers. Often times, there is no other means by which to penalize financial wrongdoers if someone like me is not going after the institutional actors who perpetrate the types of wrongs my firm pursues. And, by the way, I could never have been happy within a bureaucracy long term. I pride myself on creating a firm that has virtually no bureaucracy.

But honestly, I lost my fear of being in the courtroom as an AUSA, but it was not until I met Dr. [Don] Nichols that I really began to learn the skills I needed to be a good trial lawyer. Judge Garza, a former plaintiffs’ trial lawyer, and Don Nichols were extremely important mentors to me. They both imparted their enormous wisdom to me, and I tried to absorb as much of it as I could. Bottom line, getting a great mentor is critical to career development.

LD: What caused Dr. Nichols to have such a big impact on your career? I think you’ve said you have never tried a case without him since you met.

BR: I have not had a jury trial in the 23 years since I left the government without Dr. Nichols at my side. He’s like my trial security blanket, and we are close friends on a personal level. Even though he is not a lawyer, he has a PhD in communications and has assisted lawyers in hundreds of trials in his career, which gives him a wealth of trial wisdom. Additionally, he has an uncanny ability to distill facts and produce themes. Thinking through what I call the multi-dimensional chessboard of complex litigation with him is very helpful to me as a trial lawyer. And quite frankly, the amount of wisdom that Dr. Nichols has bestowed upon me is too much to list in a sentence or two.

LD: What do you consider your greatest hits before Reid Collins?

What we have been able to achieve is due to a number of factors: a great business model, flawless execution, our willingness to take risk, and a really top-notch team.

BR: My first big case was InverWorld, where I singlehandedly pursued a complicated accounting malpractice case against Deloitte for about five years and ultimately settled for $25.8M. I had just left my job in Del Rio and taken a month-long cross-country trip on a motorcycle, and in my first week at Diamond McCarthy I began to work on InverWorld. I got on a plane to Cayman my first week on the job and have been going there ever since.

My first big civil contingency-fee case in which I got the client and led the show was the Grey Goose Vodka case, filed in Delaware Chancery Court in 2004. With Eric Madden and Lisa Tsai, I represented Grey Goose’s former in-house lawyer in his claim involving the $2.3B sale of Grey Goose Vodka to Bacardi, which settled.

And, although they were small, I did stumble into my first legal malpractice cases while at Diamond McCarthy. I realized instantly that there was a great opportunity in these claims because the firms that I viewed as my competition were largely unwilling to handle legal malpractice cases.

LD: You’ve also mentioned the $30M to $40M in settlements from law firms and accounting firms you wrested in the USA Capital case, alongside Madden and Tsai. Tell us more about that case, and how it led to you meeting Marc Dworsky, now one of your partners.

BR: USA Capital was a $1B Ponzi scheme involving a mortgage broker/servicer and some related funds. The crown jewel of the litigation assets held by the bankruptcy trustee was a legal malpractice case against the largest law firm in Las Vegas at the time. Marc, who was then with Munger Tolles, acted as lead defense counsel to the law firm. We had mutual respect for one another and, after we settled the case, we committed to working together. Frankly, I wanted to deselect Marc as an adversary. Today, we are partners and he is our resident naysayer. If we can overcome Marc’s doubts, we generally know we are on the right path. Meanwhile, the fact that our friendship grew out of an adversarial encounter shows that your opposing counsel does not need to be your mortal enemy.

LD: And then in 2009, you founded Reid Collins & Tsai. What was your vision then of the firm you wanted to create and what’s your assessment of it now, 14 years later?

BR: First of all, the “vision” I had in the beginning was no more ambitious than simply to be able to survive practicing law from Austin, Texas – where we launched the firm with literally no work. Our group had a pretty good run of about five years leading up to 2009, but we had no certainty where our clients would come from and we had no strategic clients coming with us, much less any guarantee that we could make it on our own.

As the firm began to gain traction as a national boutique around eight years ago, I began to realize that we were truly unique in a lot of ways, and that we were being recognized for it. From any vantage point, we have vastly exceeded any expectation that we could have imagined for ourselves. My assessment today is that what we have been able to achieve is due to a number of factors: a great business model, flawless execution, our willingness to take risk, and a really top-notch team.

LD: Of what cases are you most proud at Reid Collins?

BR: We had a massive $288M win for Highland Capital against Credit Suisse in the early days that put the firm on the map. Sadly, appeals have whittled the recovery to the bone, but the jury’s finding that Credit Suisse committed fraud still stands.

Our $300M direct-pay settlement for shareholders in the Renren derivative-securities litigation was also a big deal. It was a novel case that required the execution of an extremely difficult legal strategy that showed the strengths of our team.

The problem is that the legal education system defaults to Big Law because students (and many lawyers) put starting salary as their North Star.

The case that I am most proud of, however, was the acquittal that I got for Olga Hernandez in San Antonio federal court. Olga was a 66-year-old grandmother who was charged with bribery in connection with her position as a board member of the Bexar County School District (in San Antonio). My former office was prosecuting her, and it was my first (and only) criminal defense case in the 23 years since I left the government. My good friend and mentor, veteran San Antonio trial lawyer Alan Brown brought me in to first-chair the trial. It was truly an honor to represent such a courageous client and there is no close second to that case in my career. It was a pro bono win for a client who stood to lose everything, and the case changed her life.

LD: We have to talk about legal malpractice cases, of course. Back then, it was really frowned upon for one law firm to sue another. What was your first legal malpractice case and how did you weigh whether to go ahead and sue?

BR: InverWorld had a large legal-malpractice component to it, but I did not play a big role in it because I focused on the accounting claim. Shortly thereafter, however, I got a small bankruptcy case in which the trustee sued four law firms. The case presented a conflict paradigm that I have seen over and over: a dominant personality running an entity to the entity’s detriment but to his own personal benefit. For the lawyers in that case, and many others since, the inconvenient truth is that when the entity is the client, its interests must be prioritized over and above those of its majority shareholders and directors. When those interests diverge and the law firm follows the direction of the dominant personality, as so often happens, you have the classic conflict paradigm.

And yes, suing law firms was viewed negatively by many lawyers and judges when I began down this path. In fact, 20 years ago some clients would refuse to pursue their lawyers for wrongdoing out of some deranged sense of loyalty. I’m comfortable with it. I felt then and still feel today that a fiduciary is obligated to pursue a valid claim for legal malpractice. In other words, fiduciary duties override friendship or any sense of professional loyalty. I think that the prevailing view today among decision makers is much more favorable to suing law firms who have done wrong – although there are some people who still cling to the “old view” and look down their noses at us. To me, as a former accountant, I see no difference between suing accountants and suing lawyers. As it turns out, there is plenty of opportunity to do both.

LD: How many malpractice or other claims against law firms have you brought over the years?

BR: Frankly, I have lost count, but I have pursued at least 50 claims against law firms.

LD: What firms do you consider the greatest villains among law firms? Assuming you won’t name names, what are the traits of law firms that you most like to hunt? Do you have an observation, coming full circle, about the types of behavior that gets lawyers sued and the unhappiness that pervades Big Law?

BR: I enjoy holding institutions accountable for their wrongdoing, particularly where regulators or other law firms would not pursue them. I have a healthy dislike for the institution of Big Law, but there are many lawyers that work at Big Law firms whom I consider friends. As I mentioned, conflicts of interest are the number one reason that law firms get sued, although there are a number of cases where abuse of the hourly-billing model has been the primary cause of the litigation. And, you’re right. I won’t name names.

LD: What’s it all about for you?

BR: Justice, purpose, and a sense of accomplishment. If I don’t feel that my client deserves to win, I don’t take the case – that is not something every lawyer can say. By the way, I also love the strategy behind complex financial litigation, which I call the “three-dimensional chessboard.”

We teach legal ethics, but it’s rule based and rigid. Maybe we should teach the philosophy of law instead.

I get immense pleasure out of solving the riddle. I really enjoy being with my team and working through the legal and practical obstacles together. I love the camaraderie and the open and active exchange of ideas that lead to a successful outcome. I also love mentoring now almost as much as anything I do in my career, which led to my teaching.

LD: Through your firm and your teaching, you’ve become a bit of an evangelist for finding a way to enjoy practicing law. Part of your message is to create a conversation about what no one at law school or at on-campus interviews tells you about the real practice of law.

BR: I think law school suffers from too much theory and too little of what students really need to understand to find joy and satisfaction in the law. In part, I created my class to fill that gap. My class is a case study approach to law, which is rich in real world advice. Because I can only reach 20-30 students per year teaching, I am now writing a book entitled, “How to Love the Law” with the hope that I can reach a wider audience.

More to the point, no one in legal education sits students down and makes them think about what they want to do with their career, much less what will truly inspire them. A law degree is just a passport to travel: It’s the destination you want to get to that’s important. Guidance counselors are well intentioned, but few of them have actually practiced law, much less enjoyed it. There’s no one asking students basic questions like: Would you prefer to be a plaintiff lawyer or defense lawyer? No one describes the real-world differences between the two. And yet there’s a whole world of different types of plaintiff and defense lawyers, each of which might interest or repulse an individual student, depending on a whole range of factors. How can students know what they’d like to do if they do not know what choices they have and the implications to choosing one career path over another?

We teach legal ethics, but it’s rule based and rigid. Maybe we should teach the philosophy of law instead, and ask questions like, “You’re about to spend three years and lots of money on your legal education. Would you like to use all the knowledge you’ll acquire to assist bad actors to evade responsibility, or would you rather hold those people accountable?”

Take tobacco lawyers, opioid lawyers, and toxic tort lawyers. In general, they do amazing things in changing the behavior of really harmful companies and products, but if you go into that kind of work, you’re representing victims and family members of those who have suffered some injury or wrong. Is that something you’d be excited to do? It’s not for me. It's difficult and demanding emotionally, but I have great respect for those who take those types of cases on. Also, the complexity that I crave in financial litigation is generally absent in toxic tort cases. Bottom line, students and young lawyers need to think through what will motivate them and inspire them as they pursue their careers.

I think law school should force students to think through questions like these. They should explore the different avenues of law they could pursue so that they can make better choices about their career path – which almost certainly would lead fewer lawyers to fall back on the default route into Big Law. In order to effectively accomplish this, law schools would really need to bring in practicing lawyers on the front lines and ask them detailed questions about their practices.

When you do not go through that thought process, you become an accidental tourist in the law. You go to a big firm because you maximize your starting salary, and then you go in-house at a company because you worked for the company while at the big firm. All the paths you go down in your career are dictated by where you start.

LD: So how would you advise students to become happy lawyers?

Law school suffers from too much theory and too little of what students really need to understand to find joy and satisfaction in the law.

BR: To focus their North Star metric on something that will motivate them other than money. The money will come, so don’t worry about it. Stay focused on your North Star. For most happy lawyers, it comes down to finding a practice area or areas that they are passionate about. Once a lawyer finds their passion in the practice of law, they are truly on their way to becoming happy lawyers.

LD: What do you envision as the future of law practice?

BR: I think the future will be very different with the advent of AI/ChatGPT/quantum computing. I actually think there will be a premium on issue spotting and strategy and people skills. All of those are critical now – but they may be all that is left after AI/quantum computing get truly going. This will be the biggest change we will have seen in our careers. Once these new technologies pervade the practice of law, I think the hourly-based model will have to undergo substantial change, which will fundamentally challenge the foundations of Big Law. I also think that most litigation will be handled by smaller teams who will be much more efficient. Imagine a machine-learning tool that could produce a first draft response to a motion to dismiss or answer the question: what did the board know about the drilling project on X date? These are the sorts of tasks that currently require lots of hours. In the very near future, they will not take nearly as much time or as many people. For a thousand-lawyer, billable-hour firm, that prospect is pretty terrifying. For a boutique firm of 40 lawyers that operates on a success fee and thereby benefits from efficiency, it’s exhilarating.

LD: Reid Collins & Tsai is a pretty great test of your philosophy about law practice. How did you recruit such an amazing group of lawyers and support them in creating their own achievements?

BR: We are fortunate to have an amazing team. I think having Austin as the main office helps –we actually do very little local work there – but it is really about giving young trial lawyers what they really want, which is opportunity and responsibility, and then mentoring them along the way.

Like everything else, we do it our way. I created the kind of trial law firm that I wanted to work for, and I think that resonates with the right candidate. If we have a team go to trial, our young lawyers can count on the rule that everyone gets to take a witness at our trials: There are no bag carriers.

We spend a lot of time ensuring that the candidates we hire will fit our philosophy. In fact, cultural fit is my number one priority in making any hiring decision.

All lawyers who come to us as potential hires must do a mock oral argument. Think about that. How many law firms require their candidates to perform on their feet? And although it’s true that the mock oral argument is in part a rite of passage, it says a lot about who we are as a firm. I think our track record speaks for itself.

To be honest, our recruiting process is somewhat self-selecting. We try to paint as accurate a picture as we can of what we do so that we can both attract the right person and dissuade the wrong one.

LD: Every time we talk, I’m struck with the fact that you are a particularly happy lawyer who seems to be living his best life. And appreciating that fact. What did you do right?

I started my own firm in 2009. I simply wanted to have more fun, which was easier if I created the ideal practice for me – which is what I set out to do.

BR: Wow, that’s a big question. I am a big believer in carpe diem. I try to attack every problem with all of my energy and strength. And I’m guided by keeping justice, purpose, and fun as my North Stars. I think my life-work balance is really critical to my happiness, but true to my North Star – I am passionate about my cases because I found a niche practice area that I love – holding institutional bad actors accountable.

My belief in group problem-solving and teamwork has absolutely helped our success and the buy-in across the board. I was fortunate enough to have some amazing mentors along the way, particularly Judge Garza (a former plaintiff's lawyer), Don Nichols, and Alan Brown. I was also very focused on getting as much trial experience as I could get as soon as I could get it – hence moving to Del Rio in 1997 at the age of 29 – and it has served me well. I feel sorry for the next generation of lawyers because the opportunities for trial experience are dwindling (as is the jury trial itself).

LD: What are you working on now? What do you think 10 years from now looks like?

BR: Now is the typical bag of interesting insolvency-related litigations, a half dozen legal malpractice cases, a cool docket of litigation against AT&T and several other fiduciary-duty type cases in Delaware, a new case that looks like Renren II, my docket of foreign appraisal rights claims (now several billion dollars in dispute), my law-school class, and my book.

The future will be far less labor intensive due to AI and quantum computing. Fraud and greed will not go away. It will take on new forms and infect new technologies and industries – but it will keep us busy for sure. And as long as we remain atop the national contingency-fee boutique heap, we will get our share of opportunities.

LD: And can lawyers ever truly be happy?

BR: I think there are a lot of people who end up accidental tourists in the law and never find their true passion. That makes it very difficult to be happy. There are others who get sucked into Big Law, become disenchanted, and quit the profession altogether. Of course, there are many successful Big Law lawyers and I presume at least some are happy. But lawyers who prioritize what they are passionate about can find very rewarding careers in the law – and yes, happiness. The key is to really think through what they want to do and make deliberate choices, rather than just drifting with the current. You can tell from the working title of my upcoming book that it’s intended to encourage students and young lawyers to pursue happiness by doing just that. For now, I’m calling it: “How to Love the Law.”