Chris Dralla Of TypeLaw: 5 Things I Wish Someone Told Me When I First Became An Attorney

An Interview with Eric L. Pines

I wish someone had told me to slow down. Oftentimes, when you’re starting something from scratch and you’re giving it your all, you just kind of focus on it and move on from thing to thing. You don’t take the time to appreciate the small wins. It’s really important to celebrate small successes and milestones and to develop things slowly, more than it is to focus only on a big win.

As a part of my series about “5 things I wish someone told me when I first became an attorney” I had the pleasure of interviewing Chris Dralla.

Growing up the son of an attorney and a material scientist in Silicon Valley, TypeLaw Co-founder & CEO Chris Dralla has spent his entire life at the intersection of technology and law. After becoming an attorney himself, Chris found himself increasingly frustrated by the monotony of building tables and painstakingly formatting briefs to meet local rules of court — and acutely aware that time spent on technical details could be better spent refining the substance of his argument.

Chris found ways to automate his brief formatting process, and in 2014, he partnered with a technologist and founded TypeLaw, to empower others in the legal community to improve their briefing formatting, at scale. In recognition of TypeLaw’s innovation and contribution to the legal community, Chris was named a 2023 Fastcase 50 honoree.

Thank you so much for joining us! Our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in law?

It was about 4 years into my legal career, in about 2014, I was working with the number of lawyers, filing a lot of motions in California state and federal court, and I was just realizing the complexity that each motion required, and how much time and detail I was putting into the formatting, rule compliance, citation checking, table of contents, table of authorities, cover pages…and all these things were not handled well in Word or whatever we had at the time.

So, I did the math and estimated that I was spending about 500 hours a year involved in formatting and I just didn’t like the idea that over the next 20, 30, 40 years of my life as a lawyer I was going to be doing this over and over and over again. So, I thought about how technology could solve the problem and help lawyers write better briefs by giving them more time to focus on their argument — and that’s how TypeLaw started to come into existence. I just felt the pain myself. I was a lawyer writing a lot of briefs and I was frustrated with the process of getting it done.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

One of the most interesting cases I had was actually representing my co-founder, Andrew Baker, in his immigration denial appeal using TypeLaw software. So in 2014, I’d partnered with Andrew, a technologist who had recently graduated with a computer science degree from USC, to help me build out what would become the TypeLaw product. The problem was, his Visa was expiring, so I represented him in filing the immigration visa on behalf of the company we had formed.

It was denied for the wrong reason, so we had an appeal and used the software we were writing at the time to write the immigration appeal to the United States Customs Immigration Services. It was very complex appeal, so it was the first use case or proof of concept that showed this thing is really going to work: it’s going to save lawyers time because it’s going to let them focus on the argument more, it’s going to do the formatting instantly, and it’s going to give me more time to edit, more room to write, and be my assistant for me.

It was a very interesting transition from being an attorney, to being a technologist, to being an entrepreneur that was happening in that moment of having this product come to realization through using it for ourselves to help us where we needed it.

What are some of the most interesting or exciting projects you are working on now?

We are working on a solution for summary judgment motions at the trial court level. It’s going to be able to organize evidence, fact timelines, and the important moving papers into a single process. It will probably save attorneys and their teams from about 40 hours of time-consuming, important, and labor-intensive work.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential can you share any stories?

On a personal level, the story I just shared about my co-founder’s visa situation was the first time I had first-chaired an appeal, and it was a really difficult, complex issue. It was a narrow statutory interpretation and some really technical lawyering, so I was very proud of being able to do that on my own, mastering that independently about four years out of law school.

At TypeLaw, we’ve had the great pleasure of serving both sides, plaintiffs and defendants, in criminal and civil cases, state and federal appeals, and trials across the board, so we see a wide gamut of interesting cases. Attorneys for Leslie Van Houten used our services, Kanye West, Ticketmaster, the Church of Scientology, some really obscure capital murder cases have come through the door…we’ve handled approximately 10,000 briefs in 10,000 cases at this point, so we’ve really seen all kinds of different interesting angles and cases.

Which people in history inspire you the most? Why?

I tend to gravitate towards inventive, entrepreneurial people, so somebody like Leonardo da Vinci or Galileo, scientists who were just observant, and ahead of their time, and created wonderful inventions for society. That inspiration extends all the way to today’s technologists and entrepreneurs who are passionate about working on a problem and solving a challenge that hasn’t been solved before.

I also really respect Mike Bloomberg. Full disclosure, Bloomberg invested in our business, but I’ve always admired the way he’s conducted himself on both the political and business stage, and it was wonderful to be able to do business with him though Bloomberg Beta 10 years ago when they seeded our business.

What advice would you give to a young person considering a career in law?

The practical advice is: know why you’re doing it. Are you trying to be a litigator or a corporate attorney? Do you have a sense of what you want to do and why you want to study the law?

It’s not as glamorous as it appears on television, but it probably is just as rewarding. You get to do a lot of challenging work with interesting fact situations and respected people, so it’s really satisfying. It is a lot of work and there’s a lot of paperwork, and there’s a lot of writing, reading, research, stress, and anxiety, but at the end of the day, it’s really rewarding.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

1. First would be to move to a mandatory electronic filing system throughout all courts. I don’t think there’s any need for lawyers to have to print and publish paper anymore. It could all be digitally sent, notarized, recorded, and held in public domains in ways that make access to justice more accessible, quicker, fairer, and ultimately cost less. So I’d like to see more electronic filing and management of cases, service filing…all that could really reduce the friction of the legal system.
2. I’d figure out a way to get more attorneys involved in mediation or arbitration, or some sort of low-level small claims dispute resolution services for common disputes that people have outside of the court system. People need lawyers. I think there needs to be more access to lawyers, but I think that system is so competitive and costly and complicated that it just prevents people that should be using it from being able to. So, I’d love it if there were easier ways for disputes between neighbors or friends, family to get resolved in fair and amicable settings that ultimately preserve relationships more than they fracture them.
3. Finally, I’d require every brief to hyperlink a citation to an authority or a piece of evidence in the record, because I really want to hold lawyers accountable for their writing and to make sure that only good, detailed work is presented to the courts. And a good way to ensure that only good work gets filed is to force lawyers to cite their cases and reference the record and evidence that’s at stake.
4. At TypeLaw, we’ve seen many briefs that don’t take advantage of citation hyperlinking, and those lawyers are losing an opportunity to talk to the judge and jury in a way that is more compelling. It forces better legal analysis, and I think that’s one way we can start forcing the issue today.

How have you used your success to bring goodness to the world?

I think like most technology companies in the Bay Area, we aim to provide a low-cost solution to clients and customers who can’t necessarily afford to pay full prices, so we do a lot of work with the appellate councils in California that represent indigent criminal defendants in their appellate work. We give them a reduced rate, as close to cost as we can, so they can have access to the service that most of our customers pay full-price for, to make sure that our technology is available to everyone at a level that they can afford to pay for it. So, we’re trying to help out where we can. We work with many lawyers who represent clients who cannot afford to pay high legal fees and we adjust our rates so they can gain access to current state-of-the-art technology like everyone else.

I know this is not an easy job. What drives you?

I am driven by solving new problems that make our customers happy. Each day there is a new issue to solve, and so each day there is a chance to improve. When our customers tell us how much they loved using TypeLaw or how much time it saves them, it is really rewarding.

What are your “5 things I wish someone told me when I first started” and why?

See my related “5 Things” video: https://youtu.be/OOjth6GVP0I

1. I wish someone had told me how long it would take to build something successful. We started TypeLaw 10 years ago and every year has been a grind. It took a couple of years to build something that someone used and paid for, a couple more to get a real customer base paying real dollars, and a few more to scale it to a national market…and it’s all taken longer than I’d expected. It’s not just about building a better mousetrap, and I wish someone had told me how long it would take.
2. Related to that, I wish someone had told me how isolating it is to either start a law firm or start a business. I’ve done both, and in both cases, you basically just walk off a plank into an unknown world and it’s scary. You don’t have anybody but yourself to rely on, and you don’t always have support and companionship and help where you need it.

So, the way to get around that is to form a small trusted group of people in similar situations that you can be honest and upfront with about the challenges of starting a business. At TypeLaw, our investor, Bloomberg Beta, brought us together with other founders where, once-a-month, we could candidly discuss how things were going at a fundamental level, in a non-competitive way. Having that small group of people in similar situations across different areas was very valuable for easing that feeling of isolation.

3. I wish someone had told me to slow down. Oftentimes, when you’re starting something from scratch and you’re giving it your all, you just kind of focus on it and move on from thing to thing. You don’t take the time to appreciate the small wins. It’s really important to celebrate small successes and milestones and to develop things slowly, more than it is to focus only on a big win.

4. Not every client or customer is a good client or customer. In the early days, we would basically take any customer who was willing to submit a brief and run it through the system so that we could have experience and train our AI models. Over time, we realized that the best customer is one that has the pain, is ready to buy, is searching for something to solve that pain, and is open to trying something new.

So, today, we focus our marketing efforts on customers that are not just likely to file a brief, but likely to be good repeat customers, because the experience will deliver real value for them, so we invest our resources in a more intelligent way. I wish someone had told me that not every dollar is important, especially early on. You’ve got to find the right dollar.

5. This is limited to the appellate or motion for summary judgment or other dispositive motion where a judge is reading it and you really need to convince them of your client’s position. It’s the most underrated part of a brief: the table of contents and table of authorities.

They’re the first thing that a judge or clerk will look at to summarize your argument to understand the finer points on a broader level, and they oftentimes will rip it out of the brief or use it as a guide as they’re reading. So, if you provide clear, straightforward sentences, in nested headings, in an organized way, you can basically convince a judge of your position in a table of contents — and TypeLaw’s automated brief formatting platform makes it easy to produce quickly.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)

Well, not to be too glib, but I’d say Donald Trump’s or Hunter Biden’s legal teams — because they are both involved in a lot of complex, active litigation, they could be great, high-profile customers. But more seriously, I’d say John Roberts, Chief Justice of the Supreme Court. I’d love to show him how artificial intelligence (AI) can supply a handful of paralegals with enough power to produce every table of contents and every table of authorities and cite check every case and citation in every brief throughout the United States, because technology can be that much of a lever.

This was very inspiring. Thank you so much for the time you spent on this. We wish you continued success and good health!

About the Interviewer: Eric L. Pines is a nationally recognized federal employment lawyer, mediator, and attorney business coach. He represents federal employees and acts as in-house counsel for over fifty thousand federal employees through his work as a federal employee labor union representative. A formal federal employee himself, Mr. Pines began his federal employment law career as in-house counsel for AFGE Local 1923 which is in Social Security Administration’s headquarters and is the largest federal union local in the world. He presently serves as AFGE 1923’s Chief Counsel as well as in-house counsel for all FEMA bargaining unit employees and numerous Department of Defense and Veteran Affairs unions.

While he and his firm specialize in representing federal employees from all federal agencies and in reference to virtually all federal employee matters, his firm has placed special attention on representing Veteran Affairs doctors and nurses hired under the authority of Title. He and his firm have a particular passion in representing disabled federal employees with their requests for medical and religious reasonable accommodations when those accommodations are warranted under the Rehabilitation Act of 1973 (ADA). He also represents them with their requests for Federal Employee Disability Retirement (OPM) when an accommodation would not be possible.

Mr. Pines has also served as a mediator for numerous federal agencies including serving a year as the Library of Congress’ in-house EEO Mediator. He has also served as an expert witness in federal court for federal employee matters. He has also worked as an EEO technical writer drafting hundreds of Final Agency Decisions for the federal sector.

Mr. Pines’ firm is headquartered in Houston, Texas and has offices in Baltimore, Maryland and Atlanta, Georgia. His first passion is his wife and five children. He plays classical and rock guitar and enjoys playing ice hockey, running, and biking. Please visit his websites at www.pinesfederal.com and www.toughinjurylawyers.com. He can also be reached at eric@pinesfederal.com.