Episode 24: Harmeet K. Dhillon

Law Firm
Written By Third Boxcar LLC

Founder, Dhillon Law Group and Center for American Liberty

 01:05:39

Watch Full Interview

 

Show Notes

 Harmeet Dhillon, the founder of Dhillon Law Group and the Center for American Liberty, is a nationally recognized lawyer, trusted boardroom advisor, and passionate advocate for individual, corporate and institutional clients across numerous industries and walks of life.  

Harmeet describes her family's journey to the United States, her time at UVA Law School, a stint at the Department of Justice, a federal appeals court clerkship, a decade of practice at prestigious international law firms, and how she came to found her own litigation boutique and then a nonprofit legal center.  She provides tips on navigating BigLaw and founding a law firm. This is a dynamic and independent-minded guest you do not want to miss.

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Harmeet K. Dhillon

Harmeet Dhillon is a nationally recognized lawyer, trusted boardroom advisor, and passionate advocate for individual, corporate and institutional clients across numerous industries and walks of life. Her focus is in commercial litigation, employment law, First Amendment rights, and election law matters.

From an early interest in constitutional litigation to a stint at the Department of Justice, federal appeals court clerkship, decade of practice at prestigious international law firms, and then founding her own law firm in 2006, Harmeet’s legal career has been marked by a passion for justice, a zeal for attacking legal challenges, and an intense sense of satisfaction in helping her clients realize creative and practical solutions to seemingly intractable problems.

Following a clerkship with the Hon. Paul V. Niemeyer of the United States Court of Appeals for the Fourth Circuit, Ms. Dhillon’s practice in New York, London, and the San Francisco Bay Area has focused on federal and state commercial litigation and arbitration, with a particular emphasis on unfair competition/trade secret misappropriation, intellectual property (including trademark litigation and internet torts), complex contractual disputes, and First Amendment litigation (including defamation, trade libel, right of publicity, and anti-SLAPP motions).

Harmeet’s broad experience also encompasses securities, entertainment, employment discrimination and civil rights matters. Ms. Dhillon has developed a niche practice in representing clients across California in election and campaign law matters, ranging from general compliance and ethics representation for partisan and non-partisan contenders to ballot description contests and intellectual property matters pertaining to campaign communications. She is regularly retained by candidates and campaigns for advice on complex legal issues.

 

Transcript

I'm so excited to have, as a guest of the show, Harmeet Dhillon, who has her law firm in San Francisco and throughout the country and has different lawyers in different locations. She also owns a nonprofit venture. Welcome, Harmeet. 

Thanks for having me. 

I would like to start with your origin story in the law. How did you decide to study the law and that you wanted to become a lawyer? 

It wasn't the normal path of a lot of my colleagues. Everybody in my family was either a doctor or a surgeon. I was born in India and my family came here when I was two years old. My dad settled in a rural town in North Carolina. I grew up in rural North Carolina and went to public schools there. I always thought that I would follow in the family's footsteps of going to medical school and being a surgeon like my dad and a doctor like my grandfathers.

My course of life changed when I went to Dartmouth College. I got involved with the conservative Dartmouth Review newspaper. There were my predecessors as editor included Laura Ingraham, Dinesh D'Souza some other prominent writers and journalists. In the course of that time in the 1980s, there was a lot of turmoil on college campuses, similar to what you see about free speech issues. 

Our newspaper was constantly in trouble with the administration for things we wrote and said. I became the editor-in-chief. My predecessor had been suspended from the college for something that an article we wrote, which was mainly about the content of a music class. American Civil Liberties Union was up in arms about our case. There were a lot of prominent liberal lawyers around the country who thought that Dartmouth had gone too far in suppressing our speech.

I was leading the paper when we sued Dartmouth College, as I was an undergrad. I was blown away by the fact that 19 and 20-year-olds could sue an Ivy League institution. We won the reinstatement of our colleagues and their suspensions were expunged. The federal court ordered them reinstated. That changed my course in life from Medicine, which everybody I knew was doing, to Law, which in my community in the Sikh, immigrants from India, law is not an honored profession. It's a third-rate profession. 

My family hadn't encouraged it or thought about it. I didn't know any lawyers other than the ones that I encountered in the lawsuit but I decided to go for it and I never looked back. I did work as a journalist for a year between college and law school. I had an early marriage and that was how I had to start my career in Washington but I did not enjoy Journalism so much as being an advocate full-time. That's what eventually called me into the University of Virginia Law School, where I had an excellent law education. 

That is something I have heard from a couple of the guests about a pivotal moment where they experienced the power of the law in some way. They became exposed to that and wanted to be part of that. They saw what could happen as a result of that. I would say Lynn Schafran, who is a Director at Legal Momentum, has spoken about that as well.

One of her professors was Justice Ginsburg and Chris Durham from the Utah Supreme Court talked about that, saying, “This is helpful in terms of making an impact on society.” To start as a client [as you did] and say, “I'd like to be a lawyer.” That's a very direct encounter with the law. I have a question about how you originally found your way to the Review at Dartmouth. Did you write something that brought them to your attention? How did that happen? 

I grew up in the Deep South and rural North Carolina. Everyone said, sir and ma'am. Everybody knew their hierarchy in the social culture. I never had, as an adult or even a teenager, lived in the Northeast. My family moved me into the dorms there at Dartmouth. I went into the all-girls dorm, the only one they had left at that time. 

Somebody let the door slam in my face because I had boxes in my arms. I thought that was very different and that would never happen in North Carolina, where I grew up. I wrote a letter to the editor of the local newspaper that had been left in the hallway in my dorm room. I said, “This was a very bad first experience for me.” I was sixteen years old when I went to college. I had skipped a year at my public boarding schools in North Carolina School of Science and Mathematics, which is where I graduated from. 

I was pretty young when I graduated, so I was all alone. I was not fresh off the boat, though, because I'd been in a boarding school for two years. I was somewhat independent. It happened to be the Dartmouth Review and not the main daily Dartmouth newspaper. As a funny aside, Jake Tapper was a cartoonist at the daily Dartmouth a year behind me and he had a couple of unflattering cartoons about me when we were in college together.

 

The best judges are those who have lived a life of practice. They are those who advocated for clients, took risks, and courageously made arguments in front of a court.

 

They invited me to join them as a writer. I settled in first and saw what was happening on the campus. During that first semester of college, we had a lot of controversy on campus about students occupying the dean's office, library and controversies included investment in South African stocks and portfolio of the endowment. As well as the liberation theology movement and the fight in Central America between the Sandinistas and the Contras, which is something that professors would talk about in classes that had nothing to do with that issue. 

That's what brought me back to accept that invitation at the Dartmouth Review to be part of something that I felt was consistent with my values and upbringing to talk about why I went to college and getting an education in the things that my parents were paying for, not going off on issues that I shared. I wasn't there for those issues. 

This is probably one of the most pivotal decisions in my life in a positive way. It was a small group of very dedicated people who were interested in learning. One of our mentors and patrons at the time was William F. Buckley Jr. because our paper was modeled on the National Review Magazine. I say from an intellectually curious perspective, many conversations with my colleagues about history, philosophy, literature. I got more of an education from the Dartmouth Review than I did in many ways from my classroom education. 

I remember those same issues when I was at Stanford the same time as you were in terms of the political questions along with Western Civ and things like that. 

We’re reading books about dead White males and what’s the design of some of our buildings is oppressive from a feminist perspective. I grew up in rural North Carolina and my dad is a country doctor. It was very foreign to me. 

You went to law school and worked as a journalist for a bit. Where did you first practice? Was it in a small firm, large firm or government? 

I wasn’t sure what I was going to do after I graduated from Dartmouth. I had a lot of friends. I was the President of the Federalist Society. I had a lot of mentors in the conservative law, DC establishment. Everybody had different opinions during law school. My first summer was for The Center for Individual Rights, which is a conservative nonprofit that challenged affirmative action policies in major universities that included some winning cases in the Supreme Court and other issues like that.

I tried that for one summer. I worked in the United States Department of Justice Civil rights, Civil Division, Bivins Section for a summer and I didn't think about what that was. If you're a government lawyer, it's the opposite of what I am. The government’s perspective was defending gross abuses of citizens' civil rights. That wasn't for me either. They did offer me a position in their Honors Program.

I was at a bit of a loss. One of my good friends from who I'd met through The Federalist Society and a noted writer, Ann Coulter, encouraged me to spend a summer in New York before my clerkship. I had been hired by Judge Niemeyer in the Fourth Circuit to clerk for a year after my law school. I went up to New York and enjoyed my summer being wined and dined by Shearman and Sterling. That's where I decided to start my career after my year of clerking in the Fourth Circuit in Baltimore. 

I wanted to talk about the clerkship as well because that’s something that lots of students either don't consider or understand the long-standing value of. How were the clerkships? What was involved in that? How has it resonated across your career? 

I had two weeks before law school when I started to leave an abusive marriage. I had one year of begetting, a tangle with the law. I was a little disoriented. I didn't know anything about study groups, law reviews and clerkships. I had no lawyers in my family. I only knew one lawyer, which was my dad's medical practice lawyer.

I had a friend, Laura Ingraham. She was a third-year. I was a first-year. I had met her through the Dartmouth Review. She sent me down and said, “You need to get onto law review, not one of those other law reviews. You need to get a clerkship and do well in your school.” She schooled me. I had no clue but I respected her. She was a great mentor to me. I did get and wrote onto law review. I did all of those things and focused but it was hard, as you can imagine, going through a divorce at the same time. That was very interesting, juggling my 1st year and 2nd year of law school. 

With the clerkship experience, I don't know what it's like now but there was a specific date back then and all the judges adhered to it. I applied to the judges. We were told that the first judge that gives you an offer, you have to accept that, which looking back, that's a little rigid but I was blessed to have interviewed with Judge Niemeyer. He was the first judge to give me an offer. 

One of my classmates, Scott Harris, who's the clerk of the United States Supreme Court, as a career job was also with Judge Niemeyer the same year I was. Our third clerk was from Yale Law School. Our judge was a conservative judge. He was pretty new to the Fourth Circuit at the time. He had been a district court judge briefly before being elevated to the court of appeals. He liked having conservative clerks. I was a conservative clerk, Scott was in the middle and the more liberal clerks. I was explaining to my parents that I had a job offer from a Manhattan law firm for the grand old salary of $75,000 at the time.

I also had this job offer from this judge who was going to pay me less than half of that. My parents were like, “This seems like a no-brainer. Why would you do that? Why would you need this clerkship thing?” I explained it to them and they understood. I said, “This is going to be something good for my whole career. I need to do this.” They supported it and I did it.

It's one of the best decisions of my career. I wouldn't have known about or thought about it if I hadn't had a mentor to tell me, “This is something you have to do.” Laura had clerked for a Second Circuit judge and Clarence Thomas as well. I was on law review about in good law school, everyone was competing for the same clerkships and all of that.

The clerkship itself was different than what I had expected in the sense that you look at what lawyers and judges do on television. Any federal appeals court clerkship is very cloistered. Baltimore was where my judge sat. It wasn't the main hub of the Fourth Circuit, which is Richmond. There was one other judge when I started and there was a third judge who joined us in the courthouse in Baltimore. At that time, I hadn't decided where I was going to practice law. I hadn't taken the bar before my clerkship. 

It was an interesting rigorous experience. My judge had been a partner at a Big Law firm. He was used to managing associates and that's how he treated us. He had been a judge briefly before elevation to the Fourth Circuit. He had a very specific way. He wanted things done. The court at that time in the Fourth Circuit had an oral argument for all of the cases. 

In the South, after each argument, they would come down and shake the hands of the lawyers who argued. It was a very courtly old-fashioned type of deal. At the beginning of my clerkship, the judges were meeting in an all-male club to eat their meals enrichment. We got a female judge who joined the gang and they had to change their ways. That was one of the things that we talked about quite a bit, how some of the traditions of the court were quite old-fashioned.

We heard some very interesting cases during the clerkship, The Virginia Military Institute and the Citadel cases. My judge's panel heard those cases and we helped write those opinions and draft the initial drafts of the opinions. It was a very interesting and highly recommended experience. First of all, I managed to talk them out of going to law school for all the reasons that you and I both know how tough it is to reach this age. I tell them, “If you're serious about doing litigation and you can afford it, I strongly recommend a trial court clerkship, appeals court clerkship or both.”

The district court and the appellate court are so helpful. When you turn in your homework, that's who you're turning it into. It’s seeing all of that and understanding what's important to the court, what's helpful to the court, how to persuade the court. Honestly, as a new associate, even what a summary judgment motion looks like, when you first come in your 1st or 2nd-year, somebody says, “Draft a summary judgment motion,” you're like, “What is that? I've never seen that beast before. What are all the things that go together?”

If I had to go back and do it again, I might have done it that way or have done both but probably similar to your law school, all the jocks in the Virginia Law Review wanted to be in the Supreme Court as clerks and practice appellate law. You have that direction and I didn't. For me, I wanted to go and get the trial experience. I never left it. I was asking my paralegal when is that Ninth Circuit argument.

I do argue quite a few appeals. The style of my small law firm is we typically argue the appeals of the cases that we handled through summary judgment or trial. A lot of civil rights cases, which is a lot of my practice, are done on stipulated facts. There isn't a trial here. Summary judgment is the way. We are the people who are closest to the facts and we tend to argue them as well.

I have an associate who came to me from a district court who's a star. He doesn't have to be trained on what's going to be persuasive to the court. What's the standard? Is that crazy argument going to fly? Technically, you can make that argument but it is what's the judge going to say. It’s that type of fact check. They have pre-season for that.

Looking back, I was trained how to think, analyze and do things like that in law school but I was trained to be a lawyer by my judges. 

My judge would test us. We would come in as a group and have some of these more controversial cases. He would leave a debate about them and I would think about things from a different perspective. To be frank, over the years, I've had a few opportunities to be appointed to the bench. It's certainly been something open to me.

The glamour of the interesting cases is side-by-side with a ton of cases that are very important to the litigants and not necessarily very interesting to anybody else. That's one of the things you also see up close and makes you think carefully if you know yourself, “Is that how I want to spend my day every day?”

In the Federalist society set and the set of the people who hung out within law school, it's very prestigious. “Is it me? Is that what I want to do?” That may be something that I do later on in my career but for the bulk of my career, I wanted to be an advocate and that's how my career has evolved, advocacy on issues that I care about or can care about on behalf of my client.

 

You don’t have to feel dreadful going to work. You do not have to fit yourself into a round hole if you are a square peg.

 

An important piece of wisdom is to know yourself. There is a lot of impetus to pursue the next prestigious thing. It’s important to have meaning in what you do for yourself. You have the greatest impact when you combine what you're good at, what you enjoy and then where you can have the biggest impact on humanity and the world. You've got to think about those things for yourself.

For me and in the old fashion of you, being a federal judge is a lifetime career commitment. I see some people getting appointed to the bench in both Republican and Democrat administrations who are ten years out of law school or less. I didn’t know a lot ten years out of law school, certainly not to be judging other people's cases. That’s a mistake. 

For me, the best judges are people who've lived a life of practice and have had to advocate for clients, not be, frankly, a law professor. That's also a type of judge you see out there but having to take those risks, stand up and fall on your face and make arguments in front of a court is important. The wisest judges are the ones who've practiced, gone through that and had that experience. The ones I generally more look forward to practicing as a lawyer are a judge with some real-life experience of going through what I had to go through, representing a client with some arguments that they want to make and I don't necessarily want to make them but I have ethical duties. 

Let's talk about from the clerkship to the large firm where I assume you did litigation. 

I did litigation throughout my whole career. 

Did you go straight from Shearman and Sterling to your firm? 

No. A lot of my career has been shaped by the realities of who I was married to at the time, to put it very frankly. I was married to two doctors, both of whom were doing a medical residency in my twenties. They had to do their residencies. I had to support at least one of them quite a bit and that dictated a lot of my career.

At one point, we moved to California, my second husband and I. That was dictated by marital opportunities. The marriage did not last but my love of California lasted. I stayed here and continued my career here in Big Law because there's that brass ring. “How are you going to support the family if you're the breadwinner of the family?” Those are the things that kept me in Big Law quite frankly but many years after, I wasn't enjoying it anymore.

One of the pieces of advice I give to young lawyers is I had a great mentor at the beginning of my career at Shearman and Sterling. He'd been a former federal prosecutor. In the old school, Big Law, they tried to pair you up with mentors who may have something in common with you. There were no female litigation partners that I recall at the time. There might've been one but they may not have a subspecialty. I had studied Ancient Greek and Latin as I did at Dartmouth and that was why they paired us together. He was a great mentor and taught me a lot.

I learned some of the disciplines of putting in the long hours in the document review and going to depositions. He took me along under his wings and I'm very grateful for that. At some point, you learn all you're going to learn in Big Law. There's an abusive and exploitative aspect to it in my experience. Things are different for younger lawyers but my experience in the ‘90s and early 2000s was one where I felt like I had learned what I needed to learn.

Through various circumstances, I went out on my own and started my practice. I never intended to be a solo practitioner because litigation is a team sport. It’s a little different than appellate law, where if you were going to practice in a smaller team, you always have to have paralegals, associates and all of that. It’s hard to have a standalone litigation boutique, quite frankly. 

My experience in Big Law had been quite negative, including instances of sexual harassment and otherwise, which made me say, “I did not want to live my whole career like that.” I took a year off in between leaving Big Law and starting my practice to think about, “Did I want to keep doing this because I love going to court advocating for people whose cases I cared about?” 

I'm using a random example, napalm manufacturers. Not so much being on the wrong side of age discrimination, sexual harassment or other cases where I felt like this was morally important because the position I'm standing up and taking a court is inconsistent with my values. I ended up starting my own thing, joining with other lawyers and eventually forming a partnership with another litigator. My litigation boutique has been in operation for several years of practicing law with my name on the door.

Congratulations. That's a huge accomplishment. It's hard for anyone to found a boutique firm that takes on significant cases and has such an impact as you do. Not many women found those.

When I went back to my tenth law school reunion, more than half the women had dropped out by practicing law together. By the 25th reunion, there were very few people doing litigation altogether. People had gone in-house, gone transactional or something. I don't think there were any other women with a law firm of more than ten employees in my class. I have over twenty employees at our law firm and it's been a very interesting experience. 

When I went to law school, I never set out to be an owner of a small boutique firm because the stereotypical success is being a partner at a Big Law firm, doing glamorous cases, a lot of expensive artwork on the wall, expensive real estate and trial teams of fifteen lawyers. Among the hardest things, when you have that background, Ivy League, Big Law, blue-chip law school and all of that clerkship, you name it all the credentials, to leave that and start something almost bohemian in comparison to that, that’s the loneliest moment.

People look at you at bar events like, “What happened to that person? What caused her to leave the shelter of all the credentialed comfort, the big guaranteed salary to go sue the government daily and to take on cases of civil rights? Where did that come from?” I feel very happy every day, getting up and going to work because I know I'm going to enjoy what I did that day. I'm going to make a difference, go home, sleep and not feel bad about what I did that day. I did not have that feeling in some of my jobs in law. 

It's good of you to say about that lonely, vulnerable moment and make a decision that maybe others couldn't see the value of. That's true in life generally but especially in law, where there are a lot of wickets that you go through and the prestige value is quite high, especially when you've managed to work hard enough to be at that level, there's an expectation of what comes next and a view of what is appropriate or where you should go next.

For all the reputation of lawyers being largely liberal, politically, they’re very conservative in terms of career choices. People feel pressured to go into 2 or 3 different kinds of things. What's beautiful about my law firm is it is handpicked people who also know themselves well enough that either early or later in their careers, they realize, “This is how I want to practice law.” It isn't, “I have to pay my bills.” You can pay your bills, doing what I do pretty well. I have to pay my bills, perform for other people and not look bad at my 5th, 10th and 15th law school reunion. 

That peer pressure keeps people in jobs that aren't a good fit for them in misery. We all both know about all the substance abuse, misery and heartache in people's lives as lawyers. A lot of it is because people have a mismatch between what they are good at, want to do every day and can do with their law degree, which is a lot of things that you can do. 

They feel like they have to do to make ends meet, fit in or keep up with the Joneses. You have to have something to say at the cocktail party at the bar reception like, “What are you going to say?” “I like to start my law firm.” People look at you with pity and horror, almost. My career has evolved in a way but they did look at me that way years ago. 

As part of doing this show, I wanted to talk to a range of people who have done several things, even outside the laws so that people can have a bigger perspective instead of a narrow view of where to go. There are a lot of doors along that hallway that you could open or that are open for you that you might consider. I have a similar feeling as you do that we're in the lodge to make some impact on society as well as for our clients. I've been able to carve a path in Big Law firms and big boutiques with a significant pro bono practice doing a lot of cases that I care about in that regard. 

There's a downside to doing that. You don't make as much money and all of that stuff in Big Law. To me, without those, that's where I feel like my skills and needs of the world fit. Honestly, how I discovered appellate practice was doing a pro bono piece in the US Supreme Court when I was in my twenties. Forever, I feel grateful to the pro bono work for exposing me to what it means to be an appellate lawyer, as opposed to what we saw as appellate clerks. 

I'm good at this. I'm not good at trial work because I don't like confrontational cross-examination and things like that. I feel bad for people, so that's not my pathway but what could my pathway be? Pro bono showed me what that pathway could be. I feel that part of continuing that service is important as well. There are a lot of different paths but being true to yourself and using your skills to the utmost is why you want to do it.

I started in law school doing a legal clinic for victims of domestic violence. I went through the 40 hours or training required under Virginia Law. I counseled women who had been in that situation and advocated for them. That was my first experience. After my clerkship, Shearman and Sterling did encourage people to do pro bono. 

The fine print is you got to do pro bono on top of your hours. I built over 3,000 hours a couple of years in a row at Shearman and Sterling. The pro bono part was important to me. It's funny when people go to law school, everyone starts out wanting to be an international human rights lawyer. That’s a thing when I was in law school. People realize international human rights law doesn't pay anything. You can't pay your loans on that and there's no Big Law job doing international human rights lawyer. 

I did a little bit of that on the side. My first trial was a pro bono case for a Kashmiri refugee from my home country of India. One of the partners on the board of the Lawyer’s Committee For Human Rights encouraged me to take that case and he would be on the case. I thought that meant he would be active on the case but he was not. He looked at my pleadings occasionally but sink or swim, the person's life or death, depending on whether I won that case.

 

A law career is not for you if you are only motivated by money. It is hard to make money this way compared to other ventures.

 

If he were going to be deported back to India as a dissident in Kashmir, he would have been disappeared like members of his family. I did win that case. Thankfully, the order on that case is hanging up in my office here. It’s in Big Law in the ‘90s. I'm not sure what it's like nowadays. I know I've had a lot of cases where I'm opposite some Big Law. The fine print is maybe you get to do it but it will affect your compensation potentially depending on the firm and how much they care about the issue. 

In some of my cases, wherever I've done quite a bit of pro-life litigation, there've been nonprofit and Big Law lawyers on the other side of that case as well. Certainly, there are some causes. I’ve done bail litigation on behalf of one side and there's been pro bono on the other side of that. I don't want to paint with too broad a brush. It depends on the law firm but it is a terrific experience. A lot of law firms still view it as an opportunity for lawyers to get some training without doing it on their paying client’s dime. That's not how I looked at it but over the years, it's allowed me to take an appellate prosecutorial case. 

I had an opportunity to represent the Queens DA's office in an appeal. I've represented prisoner’s rights cases on two occasions in the United States Court of Appeals on abuses of prisoners in our prison system and other cases that are important that I wouldn't have had a chance to do because nobody's going to pay me to do that. I strongly encourage that at my law firm as well. Anybody who wants to take a case does not have to fit with Harmeet Dhillon's ideology or what I care about. They have to be willing to put in the hours and we do quite a bit of that at our firm. 

I have the same view about facilitating pro bono work for folks who work with me. That's something they want to do and care about. They're going to get good experience doing it than they should. I make sure that I am very involved with it in terms of training them and being involved in the case. Whether you're paying or not, that's how I would treat it.

I don't think of it that way either you do that to get experienced but it turns out a great opportunity to get that kind of experience and even the various clinics. I've taught in Ninth Circuit clinics for many years at different law schools. If they had that when we were in law school, Harmeet, I would have been all over it.

I don't recall any student getting up and arguing an immigration case in the Fourth Circuit. I was in court arguing an important qualified immunity case a few years ago. The three cases before me were all clinics of local law schools arguing immigration appeals. It was made great and I wish I'd had that experience. It never occurred to me to stand up in court as a law student to do that and it wasn't a thing I had. At most, you could work on a piece of a death penalty appeal that a professor would argue in the Court of Appeals but not argue yourself.

The whole range of clinics that are out there, especially the appellate ones where I'm interested in the most. It’s to graduate law school and say, “What have I done? I argued a case in the Ninth Circuit.” Before you even pass the bar is amazing and something that I always tell people, “Help me, help you.” If you have the experience, that helps me tell a client, “No, Your case is not the trial balloon for this person.”

They have argued things and are making opportunities for themselves so that there are more opportunities in the future too. In clinics of all stripes, there are so many opportunities to do that. One of my friends runs an Innocence Project Clinic as well, so that's pretty amazing. They've gotten a lot of people out of prison who did not belong there. 

It can be controversial at some law firms. I've been at law firms where the amount of time some people spend on that work was inconsistent with what the firm expected of people. When you take on somebody's life and death, that's a huge responsibility. No matter how old you are as a lawyer, you're probably the only lawyer helping that person and their liberty depends on you. You are not only putting the effort in but also winning. It's a lot of pressure. 

I do a lot of immigration and asylum appeals through the Ninth Circuit and those are life or death for a lot of people.

I did a few over the years, people from Kashmir, Tibet, Eritrea, India and it's pretty heavy. 

It's challenging but when it all comes together, it's amazing to help someone in that way. What I enjoy about it too is when we're appointed for the appeal, there’s a fabulous, nonprofit lawyer who's doing the work in the immigration court or handling all the other levels. When they're at a super high level of operating and strategy, you can work together across all of those courts, which is often necessary to get a result for a client. You have to work in tandem and have the strategy across that. It's satisfying.

I don't think it's something that people think about happening at that level and in pro bono work but it can and when it does, it's gratifying. We're like, “Let's put our heads together and figure out what we're going to do across all of this.” Even if we can accomplish something directly in the appeal, we can leverage something in immigration court that can create a new opportunity for the client and that's super exciting too. Do you have any advice for people who are considering starting their firm and hard-won wisdom that you would share? 

It depends on what your practice is. For me, I could never practice law as a solo practitioner because you're never able to take time off. I feel that during COVID. We took on the burden of challenging, even though I have seventeen lawyers at my law firm. A lot of the government overreach during this time. I've never had a day off since COVID started. You have to plan. The thing to think about is not the romance of practicing law but what about the business side?

It's a good idea if you're going to go out on your own, have some savings and fall back upon. Even at my law firm, if you hire new people, there's a dip in profitability because the time between the time you start paying them a salary and the time the clients start paying the bills, if at all, even if they're bringing clients is a gap. You have to think about how this is going to work and when you sign a lease, they're going to look at your credit. You're going to have to guarantee a lot of these obligations yourself. You're the bank.

It's your business. You have to leave money in the bank so that bills can get paid. That's me several years into running a law firm. You're the bank, in a way. If you're not cut out for the headaches of running a business or meeting payroll, complying with all of the regulations in California is the worst. Also, complying with all the regulations of running a business in a state, complying with bar requirements and making sure all the lawyers who work for you completed their CLE. There's a sticky note on my desk, “I'm DEM.” The first third of the alphabet. We got to comply with our CLE requirements.

There are a lot of little things that people don't think about but you can work through a lot of those things. There are a lot of practice guides that did not exist when I was a young lawyer. Even when I started my practice years ago, there were no internet forums and software. You're on your own to figure it out.

The biggest piece of advice I would say to somebody starting their practice, hopefully, with somebody else, is who is that person? Picking the right partner, support staff or colleagues will make all the difference between misery and feeling like you're working for other people versus making it a joy and work for you. 

Let's say there've been some false steps in my career. I'm very happy with my five partners and all the people who work with me and for me but it wasn't easy. It was a lot of trial and error. In my family, my dad had a small medical practice and he was a solo practitioner. He started and had a few others with him.

I learned a few things from him but not much because he had a wife who ran the business for him and that was my mom. I don’t have a wife. I got Harmeet. Those are some of the challenges that people need to think through. It isn't for everybody. Some people need the security of showing up, doing their law work, getting a paycheck or getting a partner's profit. 

For me, the benefits of taking all the risks, headaches and occasional tears at night is I only work on cases that I want to work on at our firm or that my partners want to work on. That's it. I only deal with clients who we want to deal with. If you have a lot of money but you're a jerk to my staff, you're fired. That's the liberty that you do not have at a Big Law firm or in a big partnership. If your job is servicing the corporate department's clients, you can't fire them. Those are some of the limitations. If you want to hire the Dhillon Law Group, you hire us on our terms. These are our rates and terms. This is how you treat our staff and how you treat us. 

I love being able to set those boundaries for how I practice law and what I do. I turned down work every day of people who want to hire us but they want to hire us on their terms. They want to make a spectacle out of their situation and use a lawyer to do it. That's not us. We don't play that. These are some of the choices but the risk to me is worth the reward. It's not for most people.

Look around, how many women balance having a family, which most of us have some a family and running a law practice? Litigation is extremely stressful, even in the best of times. The stakes are high. You lose 50% of the time statistically. Even when you win, you have appealed and you'll end up spending time and money. If you're doing contingency work, you don't get paid for a long time, if at all and this is very stressful. 

Most people, particularly younger people, I hate to generalize but I'm finding that they are more focused for better or for worse on their life and lifestyle. The lifestyle of owning a small litigation practice is very difficult. I am blessed in having a supportive husband who's not a lawyer. He's retired. He makes it possible for me to do that. I don't think I can do it without the support at the home of somebody who is incredibly supportive of what I do, proud of what I do and make sure I take care of myself, which I often forget to do. 

With the business aspect, understanding that you also have a significant business hat, not just a business development hat is even vastly different from running a group or a section within a larger firm. It's entrepreneurial and we don't have that bug. They're not interested in that. They'd rather outsource that. It's hard to have your firm. 

There are cultural barriers as well that have plagued my career. In Indian Punjabi culture, women are independent and educated. However, talking, promoting and pushing yourself like, “I'm great. I can do XYZ,” is considered a very poor taste in my culture. Guys do it but for women to do it is like, “What's wrong with her?” 

I had to overcome that. I didn't have to overcome it in Big Law because people were feeding me work and I was doing it. I was working hard and thought, “I've worked hard. That's going to be what I need to succeed and get to the next level.” It wasn't. I did not know about some of the barriers for women. Perhaps, you did not experience them or you overcame them. I did not experience a lot of barriers to being a woman in Big Law firms, including harassment, stereotyping, judgment and favoritism.

I'm also an immigrant. I could not break through that old boy’s network in some places but these are some of the challenges that people don't tell you about but when you go your way, you can chart your path. If I had known that self-promotion was necessary to succeed in Big Law or life, I would have started doing that a lot earlier. I did not have to do that until I was out on my own and decided, “Yes, I want to do this law thing.”

 

The law is not about you. If you cannot see that you’re just a player in a bigger drama, it will be hard to succeed in this profession.

 

I had no clients, nothing. I had to start from scratch. Run the copier yourself and figure out how to format that pleading paper yourself with your first client. No paralegal to figure it out but that hustle is not something they teach you in law school. It doesn't even come naturally to any normal person, frankly, but it is necessary to be able to have your law firm where you write the rules.

There are certain types of practice like insurance, defense or others, where a couple of big relationships can be set. You do not need to hustle. You need to do a good job for your insurance company that's paying the bills. That's not the practice of litigation that I have. It's a constant hustle. Even not all of my partners are the same that way. Some of them are more comfortable being service partners and that's great because there is a lot of business but the point is, there are so many different personalities. 

People don't realize that at the end of the day if you go home, you can't wait to leave. You're dreading going to work on Monday. It doesn't have to be that way. There are so many options for lawyers be it government, nonprofit law, Big Law or small law. You do not have to fit yourself into that round hole if you're the square peg. 

Tell me also about your nonprofit that you also found. You're amazing. It's enough to have your firm and to have grown to where it is. Was it in those years too that you also founded a legal nonprofit? 

The story of my life is that ever since college, I've been interested in principles and vindicating those principles. The reality of running a business and the reality of trying to make a partner at Big Law is the more you think about stuff like that, they almost see it as some betrayal like, “Pfizer is our client. What about Pfizer?” 

I'm like, “What about human rights violations? Why go over there that doesn't pay?” Over the years since I started my law firm, I did it anyway because it's my salary and money. At the end of the day, if I want to spend 50% of it on stuff that makes me feel good, that's fine but when you start to have partners, people have to pay their bills and maybe they have different values than you, you have to respect that.

I started casting around for funding. I had a major civil rights case against the state of California. Kamala Harris was on the other side of that case, where I was representing a seek civil rights plaintiff, who was denied a job in the California prison system because of his turbine and beard. In four years of litigation, nobody paid my bills. At the end of the day, we did win an attorney's fees settlement from the state of California but that's four years in. By that time, most people have given up. If I wasn't a seek myself with a father and a brother who has a turban and a beard, I probably wouldn't have stuck in that case for years but I did. 

I realized fee-shifting is good and nice but you can't pay the bills with that. At the same time, I took on some very prominent cases and people approached me to say, “How can we support you in suing Google over discrimination and employment.” I'd say, “This is a case and a client. You can support them if you want.” “Donate it to a nonprofit.” I'm like, “I don't have a nonprofit.” I looked into it and I'm like, “It takes a year to get a nonprofit started.” I did that.

I started a nonprofit and hired somebody else. One of the other pieces of advice I would give to people is because you're a lawyer, it doesn't mean you can do everything. You need an ethics lawyer and tax lawyer. If you're doing a nonprofit, you need a nonprofit lawyer. If you have an appeal, you probably want to consult an appellate specialist. I hired a lawyer to do that for me. He started the nonprofit.

I picked a name out of Latin, which nobody could understand. I had a false start there but we have a name that people can understand. Our nonprofit filed seventeen cases against United States’ governors during the COVID pandemic. I've lost track but we won several of them in the United States Supreme Court. The 3 of them were granted vacate remanned 3 times in 2021 in the United States Supreme Court. We're the only nonprofit in the country that had three of those religion cases granted at the Supreme Court. 

That's a business too and it's a different business. It's a business that relies on generating funding from the public for what you do, which is a completely different model and has different ethical implications to the client plaintiff's situation. In that case, the client is generally not paying any of the bills and there are ethical considerations around that. To raise money for a nonprofit, you have to get the consent of the client because people are interested in our cases. 

You have to make sure the client is okay with publicity or not. Not every case that my nonprofit handles have publicity but you have to figure out how you're going to pay the bills for that. We have two attorneys on staff, not including me. I'm the CEO. The demand is huge for the work that we do, which is civil rights work from a neglected perspective. 

We have all kinds of cases and there'll be a case announced that I'm doing. It's exhilarating because it's a whole different law practice of ethically bringing attention to issues in public advocating for them. Almost all of what we do is what they call impact litigation. I learned a lot of my ropes of nonprofit law from being on the board of the American Civil Liberties Union right after 9/11. 

It’s a little different for somebody with my political perspective but I learned so much about the pieces that you put together to run a successful nonprofit. How do you select the cases? How do you get good judgment and input from a board of people who share your values and care about your goals? How do you raise money to fund that? How do you recruit new board members and do development work? How do you put all of those pieces together? It is a different business than my law firm business. Different people care about that in different skillsets and professionals who help us. I do wear those two hats and they're both satisfying to me in different ways. 

From what I'm hearing, the commonality between them is the meaning of the work in each of them and the drive to do that work. You want to do that work badly enough that all of these hurdles, challenges, running a business and nonprofit is something you may have seen but hadn't run before in which you have side-by-side. Most people would say that's their worst nightmare but there's a common drive to, “I'm going to learn what I need to learn to make this happen.”

There have been a lot of lawyers come through this law firm and even my nonprofit, not a lot but a few. The practice of law like this is not for most people. Sometimes I have to sit down with young lawyers and tell them, “You're a great person. You have a career ahead of you. It's not doing this.” That's harsh but it's true. There's this peer pressure around what you do. With the nonprofit, what's beautiful about it is that we're hard on ourselves as lawyers sometimes but the reality is if you're even a lawyer, you're good at it or you're smart, there are so many better ways you could be making money than being a lawyer. 

Why do people do it? Why do you and I do this? There's some psychic, emotional and intellectual satisfaction at making a difference and winning. You have to be that person. If you're motivated by money, law is not for you. It's hard to make money this way, compared to other ways. If you're not getting that psychic reward and what you do every day, why are you doing it? There are easier ways to make money. That's how I see it. Every day, I'm blessed. 

I have a nonprofit so I can think about stuff that doesn't pay but I'd like to do it. I know that other people care about it and I can find a way to spend half my day on that. There is also a bunch of stuff that people would like to pay me for and I have a lot of lawyers at the firm who would like to do that. Some of them do nonprofit work and some of them don't. We all treat each client the same way. There's an intake process, discipline and a cost-benefit analysis. 

Nonprofit is, “Can we help this person and a lot of other people with this example in our firm? Can we help this person do it competently and have them be happy about our work, regardless of the outcome at the end of the day?” In litigation, there's a loser in every trial, generally speaking, on settlement. That's always nice to get a settlement in a case. 

Sometimes you don't always know the same thing with the appeals. You can think of it might be going a certain way and may not end up that way.

Even from what you saw in oral argument, you get something completely different and you're like, “How did that happen? What did I do wrong?” It isn't about you. The other thing is you have to have a certain amount of self-awareness. Pick up yourself and keep going that if you have a fragile ego, this is also not for you. If you are unable to divorce yourself from your job and realize that your whole worth in life is not, did you win or lose that case? It isn't about you. You can do your best but you do not control the outcome. I have a religious background that teaches me that level of equanimity. If you don't have some grounding to know this isn't about you, you're a player in a bigger drama. It's going to be hard to succeed in this profession. 

That helps you with perspective because, given the amount of time and heart that you put into things, it can be difficult to go above that. Having a bigger picture of your role in the world, whether that's from faith or something else, is very helpful. It keeps you humble and focused on how you can contribute in a larger way, which you do in many ways. That's why I wanted you to talk about both the nonprofit and the law firm because those are two paths that people might consider.

A very few people would have them side-by-side or parallel. You're probably the only people I could talk to who could talk knowledgeably about both of those things. One of the good things about either practicing law or having legal training is that there are so many different things you can do with it and apply all of your unique skillsets, not to be too narrow-minded or about what it is you could be doing and be open to that changing over your career as it has for you. 

I'll give you one anecdote, which is when I was in the Federalist Society set. There was a certain couple of judges who you wanted to clerk for and everybody did want to clerk for those judges. If you didn't get a clerkship with one of those judges, you felt like a failure but where are those judges? Let's say a couple of them are not practicing as judges anymore. All of that competition for those particular brass rings doesn't matter. 

You have to think about that as well. When your whole world is, “What are the other people doing in my small section,” it's very narrow. I would have made some different choices if I had more perspective but I didn't have any lawyers in my family. I didn't know. Nobody told me, “This is what it's going to be like at Big Law. It's different than your personality.” If your personality isn't good for big organizations, which is not everybody's personality, I am not. I am a free spirit in a way and focused on what I think is right and wrong, which was a big clash throughout my career with some of my bosses. 

There's something to consider and think about too in that year between when you were trying to assess. “What is it I want to do? What's a good fit?” That's an important thing to have. 

I was a journalist for a year and during that time, I thought about it and I came back to it. That was one of the best decisions of my life and I'm so happy I did that. 

You need that stillness to be able to make that decision for you instead of for others or what others are saying.

 

When you only look at what other people are doing, you narrow down your growth opportunities.

 

Savings allowed me to do that because being conservative allowed me to. I make a lot of choices because I know that whether I pay my mortgage or not, I’m not going to depend on that particular decision. That's something that is a unique piece of advice to women. Being financially dependent either on a man or a particular job is very limiting as a woman. 

For me, that freedom has only come in my life with financial independence to be able to say no to cases or clients I don't want to do, opportunities or people I don't want to deal with. It’s all about financial independence. In my view of what do, I need to feel comfortable, have a retirement plan that's on track, spending and living beyond your means or the fanciest handbag does not contribute towards that end. That's my perspective on life.

Financial freedom comes from discipline. 

I couldn't have done what I did and walked away from what I found to be a very stifling practice of law for me without the savings to think about it, decide to start my own and live off of those savings for a bit. It worked out for me but even a part of my practice here is financial discipline. There's no debt in this law firm or paying people new star partner salaries out of debt. We do not do that. I've seen a lot of great firms go bankrupt here in San Francisco itself from financial overextension to keep up with the Joneses. 

That's a good admonition at the law firm level but the savings and financial discipline are important because that can be tough. That's not something that's generally referred to or emphasized but that's how you have options. To wrap up, I like to ask a few lightning-round questions. What talent would you most like to have that you don't? 

Better time management. 

What is the trait that you most deplore in yourself and what is the trait that you most deplore in others? 

In myself, I can be impatient and judgmental when people do not meet up to my standards in my mind. I wish I could be bigger. I am as slow but not as fast as I would like. A trait I would deplore in others is a lack of honesty either to themselves or certainly to me. Dishonesty is something I have a low tolerance for. 

Who are your favorite writers? 

I am very fond of reading and writing. Unfortunately, with a busy law practice, I don't get to do as much as I do but I have been on a long-running jog of detective noir murder mysteries. I've listened to Robert Galbraith, which is the nom de plume of the author of the Harry Potter books and there's Peter May, who's a British author. 

I also have listened to dozens of books during the pandemic in that genre. Cleave is another author. In school, I was a Classics major, so I did read all of the Ancient Greek and Latin Classics, many of them in the original language. I composed a tweet that was based on something from one of my favorite authors, T.S. Elliot. I didn't post it, though, because I knew it wasn't going to get the engagement that I had in my mind.

That's an interesting point because some of your favorite writers could be on Twitter. There are amazing things there, Twitter threads and things like that. It wouldn't be in a traditional book. It's true. Who is your hero in real life?

I have a few. I would say the freedom fighters of history are my heroes. When India was occupied by the British, it was some of the Sikh freedom fighters who made a big difference in forcing the British to leave India and stop the occupation. Those people are my heroes. They're not probably known to your audience but people who were willing to step up and give their lives for liberty are our revolutionary war heroes in our country. The presidents would be willing to take those routes as well for liberty. 

What in your view is a freedom fighter? Can you define that? 

That's somebody willing to take those risks and put their life on the line for what they believe. 

For what in your life do you feel most grateful? 

I'm grateful to be an American citizen because anywhere else in the world, we could not be having a conversation about two women at this place in their career doing what they want. That is not possible even in the country where I was born. With the so-called democracy of India, there are no opportunities like this for women. Frankly, nowhere else. I've lived in London for a year. I practiced law there at Freshfields for a year. This is the place where every day I get up and thank God that my parents brought me to this country where I'm living as an American citizen. 

I remember a few years ago having that feeling when the Ellis Island medal of Honors Reception is at Ellis Island at night. My grandparents came through Ellis Island. I'm glad that they made this decision to come here. I’m feeling proud of them, the country and the whole tapestry of people who've contributed to it. 

When you talk about taking the risk, leaving your homeland where you were a prominent person, had money, success, name or prestige and coming here starting from scratch with nothing like my parents did is a whole other level of courage. I'm not sure I had that courage but that courage to be a pioneer in a new place, start from zero, is very tough to do. 

I would hope that if we had to do that, we would but I'm glad that we haven't been tested to have to do that. I'm glad that my relatives did that much earlier but yes, it's a different level of grit. Given the choice of anyone in the world, who would you invite as a dinner guest? 

This goes to one of our prior questions here. Abraham Lincoln is somebody who I would love to sit down, talk to and understand where he got the moral and physical courage to stand up, do what he did for our country, what was right and on principle. He's somebody who's a hero to me. 

What is your motto if you have one? 

It’s a joking motto but it goes off of your last question. I like to say I'm a simple country lawyer from San Francisco. 

Everyone should be very scared when you say something like that because I remember having one of my fellow partners who’s like, “I'm a simple rancher. I owned a lot of farmland and represented a lot of agricultural interests.” I said, “That scares me. Whenever you say that, means we better watch out because there's a whole lot more going on under the surface than that.” 

That's a little joke in our family wherein somebody will say, “I'm a simple country lawyer. I don't know anything. I'm not a big appellate lawyer. I don't know how this is going to go. I do my job here.” 

I'm so glad that you joined us and had this wonderful, rich discussion of so many topics, what an eclectic mind you have. We're lucky to have you. I appreciate you being here and talking about your life. 

Thank you so much for having me. It's an honor. 

Thank you so much. 

Third Boxcar LLC
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