An interview with three legal tech founders

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In this episode, M.C. Sungaila interviews an esteemed panel of female legal tech founders: Nicole Clark of Trellis Research, Inc., Dorna Moini of Documate, and Jacqueline Schafer of Clearbrief. They discuss their respective businesses and the pain points that pushed them to move from law into the legal tech space. This standout trio is working on ways to use emerging tech to accelerate court processes, and impact access to justice. Tune in for practical tips and insights from the ones paving the way in the tech industry, where female founders still face significant barriers.

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Relevant episode links:

Trellis Research, Clearbrief, Documate, Beautiful.ai, Clearbrief Blog, 2020-survey-results-female-founders-in-new-law-legal-tech/

About Dorna Moini:

Dorna Moini is the CEO and co-founder of Documate, a no-code platform for building document automation and client-facing legal products. Prior to starting Documate, Dorna was a litigator at Sidley Austin. There, in her pro bono practice, she worked with legal aid organizations to build a web application for domestic violence survivors to complete and file their paperwork, which led to the idea for Documate.  Dorna is on the LSC Emerging Leaders Council and a member of LAFLA's Advisory Board. She has been named an ABA Legal Rebel and a Fastcase 50 honoree. She also teaches the Legal Innovations Lab at USC Law School.

Nicole Clark

Nicole Clark is a business litigation and labor and employment attorney who has handled litigation in both state and federal courts. She’s worked at a variety of law firms ranging from mid-size litigation boutiques to large firms, and is licensed to practice law in three states. She has defended corporations and employers in complex class action and wage and hour disputes, as well as individual employment matters ranging from sexual harassment to wrongful termination. Additionally, Nicole is the CEO and co-founder of Trellis Research, a legal analytics platform that uses AI and machine learning to provide litigators with strategic legal intelligence and judicial analytics. Nicole has an intuitive understanding of technology and is deeply committed to helping lawyers leverage technology to gain a competitive advantage and achieve a more favorable outcome for their clients.

About Jacqueline Schafer:

Jacqueline Schafer is the founder and CEO of Clearbrief, the 2021 Legal Tech Startup of the Year. She won the 2021 WA State Bar Award for Legal Innovation for her work founding Clearbrief as well as her 2020 law review article, Harnessing AI for Struggling Families. Schafer began her career as a litigation associate at the New York law firm of Paul, Weiss, Rifkind, Wharton, & Garrison, and spent the majority of her career as an Assistant Attorney General in the Washington and Alaska Attorney General’s Offices, where she specialized in appellate practice and complex litigation. Before joining the startup world, Jacqueline also served as in-house counsel for the national nonprofit Casey Family Programs, where she negotiated agreements with state courts across the country and managed impact litigation. In addition to her pro bono appellate advocacy for several nonprofits in the Northwest, she serves as a founding board member of the Washington State CASA Association, a board member of the Seattle Repertory Jazz Orchestra, and an advisor to the startup X4Impact.

Welcome to the show where we chronicle the journeys of women to the bench, to the bar and beyond. We seek to inspire the next generation of women lawyers and law students to think and dream big and sometimes think outside the box in terms of where their careers can go. I'm very pleased to welcome three women founders of legal tech companies. First is Nicole Clark, who's the Cofounder of Trellis Research, Jacqueline Schafer, who is the Founder of Clearbrief and also Dorna Moini, who is the CEO and Founder of Documate. Welcome, ladies.

Thank you so much. It’s great to be here.

Thank you for having us.

Usually, I start out with some questions about what caused people to be interested in going to law school, but I think the more interesting question is what was the spark that caused each of you to see a need and decide to fill that need with a company and with technology in the law. I'm going to start with Nicole first because I think you're the longest-founded company here with Trellis.

I was a litigator for a number of years. I did a lot of employment, class action wage and hour work. I found myself in state trial court constantly. I honestly couldn't believe how difficult it was to access information on my judges, cases, or opposing counsel. One night, I was writing a massive MSJ and complaining to one of my colleagues that I didn't know anything about the judge. It was a complicated issue.

My colleague said he thought he had previously appeared before the same judge on a similar issue. We went back, checked the file, the document management system and there was a ruling in there that was by my judge on my issue and on my motion. For me, that was the light bulb moment of I simply couldn't believe that I didn't have that to start with in terms of my research like, “Why wasn't I able to research the practical insights and rulings of judges I was appearing before, instead of only doing research at Court of Appeals level when I'm appearing in the trial court?”

It took a while. I won that motion. I wrote it so much faster than I ever would've been able to and simply set out to say, “How is no one aggregated our state trial court system yet? Why is it fragmented across thousands of individual county courts? How do we go about having a single searchable interface to access trial court data?”

That’s because they are so discrete and in part of how the court systems are run that each PJ's in charge of their particular arena and they're all run a little bit differently. That's very different. Jackie, you have Clearbrief, which is a very helpful tool for particularly appellate lawyers, but that's your background as well. Maybe you can talk about Clearbrief and where that idea came from.

I'm the Founder and CEO of Clearbrief. I have been practicing as a litigator for about thirteen years. I started out in big law at Paul Weiss, but I spent most of my career in government as an assistant attorney general, where I was regularly briefing and arguing appeals before the state appellate courts. I started thinking about the idea for Clearbrief on a pro bono immigration case. I happened to be pregnant during this a-ha moment and so is my client. We walked into the courtroom for the final hearing, where she would be sent back to Honduras and her toddler would be sent back if we lost.

I consent that the judge was frustrated with her. I was able to point the judge to one piece of evidence that I discussed in my brief, which was a therapist's report. I saw the judge change his mind about my client right there, and ultimately, we won. It was that piece of evidence. I couldn't stop thinking that moment we’re seeing the evidence firsthand was much more powerful than hearing me talk about it. I'd had that experience so many times as an appellate lawyer where the bench is poised to play devil's advocate with your position no matter what it is. The thing that I always found the most persuasive was if I could point them to that spot in the case, point them to that piece of factual evidence that would change their minds.

That's where Clearbrief is doing something very different. It uses AI to help the writer select any text in Microsoft Word and then you upload the factual documents and the record in Clearbriefs. AI will suggest the most relevant pages from the discovery and the record that relate to your sentence. This is to inspire people to add more factual sites in their brief. We have a number of courts using it. It’s very cool to see their clerks using it and the judges to find factual support for their orders. It was very cool to talk to so many judges throughout the country and learn that they also put the factual sites in the order until the last minute when they removed them before publishing, but they are worried about the facts. That's the story of Clearbrief and it’s based on my years of practice.

The other part I love about Clearbrief is an easily generated table of authority that is the bane of everyone's existence. All this fabulous legal assistance and everything is so challenging. That's the most immediate payoff for those frustrated lawyers and legal assistants trying to generate tables, but the others are also quite helpful. There's an interesting aspect, which is your initial idea and sense of a need and then where that goes. There may be other needs and populations that haven't been interested in your initial idea, a use for it and the need to remain open to that.

You have your initial spark, but there are other things that your company can help others with. Courts have a need for this as well and an interest in it, which is a timing question because having a need for it and recognizing and wanting to invest in using it for the court is different. That's the question of timing too. Dorna, I wanted to ask you about Documate, which is a little bit different from the other two tech tools we've been talking about. It empowers lawyers themselves to create some custom tech for their firms. Maybe you can tell us about that and how you came up with that idea.

Similar to Nicole and Jackie, I came across this within my own practice. I was a litigator. I did mostly employment litigation and trade secret litigation. I was at Sidley Austin. I was also doing some work pro bono. The pro bono work that I did mostly was with domestic violence survivors. A lot of the areas in domestic violence can be complex legally and factually, but at the end of the day, what I was seeing in the pro bono work that I was doing was that it was very rules-based. It was a set of rules that I could almost build a technology tool for to solve, get me and get our clients at least 90% of the way there until I would need to come in and represent them at court, take them to the next phase or potentially do it through their appeal. 

At the time, I lived in San Francisco. Half the people I knew were engineers. I got together with one of the engineers on my team. I asked him if he wanted to help me build this tool. I said, “Do you want to help me build a TurboTax-like model, but for domestic violence and not for tax?” We built that tool. We launched it. We had a few different types of customers. Internally at our firm, we were using it. We had legal aid organizations using it and we had consumers using it. We started to get a little bit of press for this tool and we're thinking about how we can expand it into other areas.

What happened was we started getting all the inbound interest, not necessarily from consumers that needed domestic violence services, but rather from other lawyers who wanted to build similar tools in other areas of law and other jurisdictions. On the first day after, we got this one article that was published about our domestic violence tool. After that, we had someone in Arkansas who wanted to build eviction defense tools. Someone in Malaysia wanted to build child support tools. Someone in Canada wanted to build a Family Law platform.

There were all of these different areas that they wanted to build it. That led us to take a step back and realize that we had been trying to solve this gap between consumers and lawyers and deliver legal services through technology in a more efficient way. We could best solve the gap with our knowledge and expertise to enable those same lawyers to build tech tools because there was this gap between lawyers and technology. That's exactly what we are now. We no longer build a nice specific content area, but we're a no-code platform for any lawyer in any area and jurisdiction to be able to build full-fledged legal technology applications on the platform.

That provides access to customized legal tech tools to smaller firms and solo lawyers because some multinational law firms have their own arms for technology or their own separate incubator for innovation. There's a gap between that and a lot of other firms that could probably benefit from having some things that would streamline some of the work and also maybe save their clients some money in that way in terms of their number of hours working on the case. It also seems to solve that question of like, “Who's the customer and how can you accomplish that goal?” It’s because you're still ultimately working towards the goal you talked about in terms of access, but who is going to use the tools and use that for access is maybe different than what you first thought.

If we're really going to change the justice system and get everybody working more efficiently, we’ve got to get the courts to use it too. 

We're very much focused on those small and medium-sized firms. We're seeing that start to be adopted by even the larger firm because it does cut down on development time if you can start to build something on a no-code tool, have it launched and have the toolkit that you'd necessarily need to use if you were going to hire a developer.

That's the divide. You happen to be in an area where you're like, “I know lots of people who are engineers or developers, but most lawyers, we hang with those types.” Finding that connection with someone you trust would be maybe a little bit harder. Nicole had a question for you in terms of some of the things that we've talked about in terms of the market. What you originally thought was the market and originally the use, which is still the case, but now you've expanded to other states around the US, gathering the state information. In the period of growth, have you found that there are more uses that you didn't think of originally indifferent customers?

Most certainly. Particularly with a startup, part of what you're doing is testing, iterating, seeing what works and then doubling down in that area as much as possible. I started the company and very much thought we were going to be a direct sales enterprise to the marquee law firms only. If one person at the firm wanted to have access, the entire firm would have to. It’s B2B but enterprise sales. What I found was that the enterprise sales cycle was incredibly slow. For a young startup, it's a difficult road for a young startup because you have a limited amount of time to prove that what you're doing is valuable and that the market cares to keep moving forward.

You mentioned the SMB and focusing on it. It turns out that 75% of lawyers are at firms ten and under, which always surprises me. The SMB market is the larger market in law, but we all think of the large AM 100 firms as the market. What we've done is basically open up to allow bottoms-up individual sales into both SMBs and large law firms. Individuals can come and sign up on our website. These range from, “I am a solo,” all the way to, “I am a partner or chief knowledge officer at the large law firms.” The journey is a little bit different. The journey for a solo is they come on, they love it there, put their credit card down and looking up analytics on the judge that they are appearing before and they're using us as a brief bank, etc.

For the larger firms, what we see is an individual will come on and there'll be a champion. They'll spread it to other people at their firm. We watch when we see a certain number of folks from the same domain, then we say, “There might be something that's interesting here as an enterprise sale.” Other than that, we let it get into the hands of the people that it's going to make their life easier immediately and grow from there. We're seeing that even from outside of legal, there are a lot of use cases for state trial court data that you wouldn't necessarily think about that are data sets that have been locked up for a long time and fragmented, so it’s not usable. We see pull from insurance to real estate to financial services.

It's always interesting because I feel like I'm continuing to be educated by our market about the use cases of our data. I go in with my idea of, “I think this is going to be useful. You're going to want to look at the analytics on your judge and then you're going to want to look up opposing counsel.” They'll come to say, “I'm renting a place to a tenant. I want to look at landlord-tenant eviction records.” I'll be like, “That's an interesting use case.” You're always watching to see what your users think and then listen as much as possible to build for them.

That question of adoption, the legal profession is not known as being in the vanguard of adopting new things, but also it's the org chart of the law firms too who's making the decisions. The people who find it useful, which generally would be, let's say, associates who are doing the work directly are not the ones who are making the buying decision.

You have to work up from there. Individual sales make a lot more sense even though, on the outside, you would think, “This would be a tool that everybody should be able to access in the organization.” The connection between understanding the value and who's paying for that takes a while to filter up and for people to understand that. They need to have the internal use case from people who've used it already.

It's interesting because having come from the law, we know it, but we think about it from the business perspective with internalizing it. With the business hat on, you have to think about that in terms of how that happens. The data side is useful for so many. I think about it as having done a lot of work with RAND and other organizations that do research that has had access or trying to get even deeper access to federal court pieces or research. They're very excited because the state data has been locked up and they haven't been able to look at that or study things related to state courts from a pure geeky academic standpoint of think tanks. They are excited about that opportunity as well.

Reducing the administrative burden is how we should be thinking about emerging tech. 

That collection of data is of interest to a range of people beyond that. Jackie, I wouldn't have thought initially in terms of, “Let's ask the courts if they want to use this.” After you said that, it seems natural. It would be helpful to them. They're very busy and it can help them get accurate sights on everything that's in the record on a topic, but how did you morph into thinking about that as a potential partner?

We have a good problem, which is that pretty much anyone who does legal writing in the entire ecosystem could use Clearbrief to benefit their writing process or review opposing counsel's brief or review other legal documents. We had to make tough choices about, “Where should we put our focus?” As a very small team, we can't just serve everybody at once. Early on, we did exactly what Nicole was saying. We focused on the small firms where I am very proud to say that Jack Newton, the Founder of Clio, is one of my advisors and investors. I looked at Clio as a model of they've built this venture scale business by focusing on the small firms.

At the same time, it's also part of my mission because of my appellate background. I love working with courts. I understand government because that's where I came from and spent most of my career. I know that if we're going to change the justice system and get everybody working more efficiently, we got to get the courts to use it too. One of my advisors told me, who's a very big titan in the legal tech space, “I will buy you a car if you can get a single judge to ever try a startup product.” I sent out an email that was like, “Please send me the keys to a gently used Tesla.”

I'm so proud of our team. What is cool is that my friend and former colleague at the Alaska Attorney General's Office, Janell Hafner, joined our team. She was Alaska's solicitor general. She is an amazing writer and also deeply understands how courts and government agencies think. She's been leading the onboarding of court systems. We now have multiple courts and multiple attorney General's offices because they're the power users of the justice system because they're filing so many briefs. They're reviewing it.

If courts can review the underlying evidence while they're reading the party's briefs and writing their opinions, my vision is that we will have a more fair justice system. That's at the heart of our mission. I am focusing on profit for sure with the private sector, but it's about achieving that goal of reducing the dockets or having exploded because of COVID, the backlogs. We need to give court systems more tools that are modern to deal with it.

There are two things out of that. One is you're very comfortable talking to judges because that's what we do as appellate lawyers. You understand that dialogue.

It's my favorite thing.

You are talking to them about some other tool that could be helpful to them and you know it could be because you saw it as helpful in one case, but it's also pushing off of a trend that the courts many courts now have electronic filing and bookmarked PDFs. Many years ago was the beginning of when some of the courts started having hyperlinked briefs. You'd scan everything and hyperlink the record to the brief.

I literally have paralegals calling us and emailing us with these tearful stress messages because they're like, “I got an order from this judge and I have to create a PDF of the brief that links into every single document. How do we do it?” With Clearbrief, we're like, “There's a much easier way.”

In the beginning, I know there were paralegals or legal assistants who had to teach themselves how to do that kind of thing and create those briefs. There were companies that did the hyperlinking and prepared those briefs. More importantly, from that is the concept of the helpfulness of that is starting to be incorporated by the judges themselves into what they're asking the attorneys to do and if you have a tool to help them and the attorneys in that way. It does take time for lawyer adoption of new tools, but it's a concept that was moving through the system. This is a very user-friendly way to do that. There's something in the court's minds. I wouldn't be surprised that you're going to get potentially a new Tesla.

I do think that it's part of also my philosophy about how we should be using AI. Let's use AI for the low-hanging fruit of figuring out which things are citations, hyperlinking them for us and creating that. Let's not use AI to determine how long we should sentence. Let's be a lot more hesitant about that kind of use of AI. Reducing the administrative burden that we all face and that our teams face how we should be thinking about emerging tech.

There's always that nagging thing when you've read the record and you're like, “I can see the page in my mind's eye. I know exactly where it said that.” You're then like, “Where in this 10,000-page record was that?” Sometimes despite your notes, all of that stuff, you don't remember and then it's this long journey to find it, but now you could ask Clearbrief to help you find it.

I'm not replacing your analysis and that work you had to do to read the 10,000 pages initially to know what to argue.

There's a trend in the different generations of judges. The newer judges or even judges in our school era are more open to technology. They use it in their own practice of judging whether they're putting everything on iPads. I've seen it in action and I did a show with Judge Owens from The Ninth Circuit, who's one of the most tech-savvy people I know. As a result, it is a little bit scary to argue in front of him because he's so on top of things.

If anyone says anything and the advocate can’t find a particular piece of the record, he'll say, “Counsel, are you referring to this page of the excerpts?” You're like, “Yes, that's it.” You want to be 100% accurate when you say anything because he'll find that page. It shows how on top of it they are and that they're used to that being able to be responsive to that and find the piece of evidence, but they're thinking of it quickly as well. You want to be as on top of it as they're going to be. If some of the judges are going to have that technology, it would be nice to be on the same page with them.

What I see a lot is that even for judges who are like, “I'm not into tech, but this will help my clerks.” We've had to learn that. We should be focusing on the clerks because it's easy for the judge to come in and use Clearbrief after the fact when they've done all the prep work. They just look at the sites. It's thinking about the whole team of the court.

Clerks are grateful for that help. That's also good because there are a lot of cases to deal with. You want to keep them focused on the challenging part of the issues that require that kind of analysis and help get as much of that evidence in the document as possible. Dorna, I wanted to talk about your process. It’s a creative agency for law firms.

We don't do any of the work ourselves, but we are still a product. We call it more of a platform because, in the same way, that you could go on something like WordPress or Webflow and create a website, you can come onto Documate and create a legal application.

The skills you've gained as a lawyer translate to what you need to do within a tech company. 

I hope that it’s more user-friendly than WordPress.

I can't tell you the number of people because the nature of being a vertical tool that services lawyers specifically means that you have a very specific toolkit that you need to play with and there are designated things you want to do. Every lawyer wants to start with capturing information from the end-user, guiding them down different pathways, providing them either a decision or a document and then pushing that out into other systems and potentially taking payments, having further communications with that client. Each of those modules can be like a click of a button for the end-user and for the lawyer to be able to use.

Did you find some novel uses or other things that you hadn't thought about, like who your particular market was and then other people that might want to use it in a way you hadn't anticipated?

In our very early days, because we had launched that domestic violence platform, we started working with a lot of legal aid organizations. We still continue to love to work with legal aid organizations. We provide our software for free or at almost no cost to legal aid organizations, but they were very good initial users for us because they have a necessity. They have to use technology to serve the communities they need to serve because there will never be enough pro bono attorneys or legal aid attorneys to serve that population.

As a result, they also put up with a lot of our very early day bugs. They were good at being thankful and being like, “Here are all the ten things that you need to fix ASAP,” which was super helpful for us to grow the product. We need to generate profits and grow our team to be able to continue delivering features to our users.

Over time, we have shifted over to that small and mid-size firm market because we found that they also have the necessity for our tool. They are seeing a lot of cost pressures and demand from their clients to price in different ways, whether that be flat fees, subscription fees and there's an opportunity for them to build things on Documate and have everyone win. Consumers can access a more low-cost service, but still through an attorney. The attorneys can build technology that scales to deliver that same service to ten people instead of one in that same amount of time.

That's a good point about legal aid there. They're looking for tools to help funnel things through, from the self-help clinics to other things to have first contact and find out where to route someone to an attorney. It is so important. That's definitely an important need for them.

It's always interesting because there's a Legal Services Corporation conference every year whenever I go to. It's called the Innovations in Technology Conference. There are so many interesting novel tech-forward ideas that come out of this group of people because it's a bunch of legal aid organizations who are trying to figure out, “How can we move into technology and serve more people?” The rest of the legal field can be inspired a little bit by some of their work as well.

They're providing their experience in building those too. They’re like, “Here's what would be helpful.” How do you think your skills from practicing as a lawyer translated to what you're doing now or even starting the company? We think that as lawyers, we are business people and we are entrepreneurs to some degree, but we don't often think of ourselves that way. You three are clearly entrepreneurs. We definitely think of you that way at this point. How do you think that your particular skills as a lawyer translated?

Legal research is so critical no matter what you want to do.

Leaving the law to go start a tech company, you have so many new hats that you wear. When I was at a law firm, there were always new cases, new challenges and new case laws that came out. You don't know lots, but for the most part, your core skills, you know how to do at a certain stage of your career. It was very scary to dive into the entrepreneurial world, but at the same time, I did see that. In my company, I do almost everything other than engineering and some customer support, but marketing, sales, and product are all hats that I wear. I've seen so much how the skills that I've gained as a lawyer have been able to translate over to what I need to do within a tech company.

For example, legal research is so critical no matter what you want to do, like going in and researching what you can do with your product, talking to engineers, and knowing which issues to talk about. Witness interviews are similar to doing anything within products, talking to your users and determining how you need to map out that product. I was not an appellate lawyer. I was a trial lawyer, but planning out the sequence of putting witnesses in front of a jury, how they're going to take that in and make them feel is similar to how we put products in front of our users. We are trying to optimize for them, feeling a certain way and getting to a certain result.

There are elements of persuasion in business all around. Sales, partnerships, all kinds of things and funding, as we had talked about. Having good persuasive skills is helpful in that regard.

Sometimes when I talk to law school classes, I tell them, “With the skills that you're gaining in law school, you could do almost anything.”

That's the part of that that I hope by having our discussion will be eye-opening because what you said is true. Unless you're managing a practice group or managing a law firm, even if you're a partner, you know your clients, business and legal work well. You're hired to do that work very well. Outside of that, we're not maximizing some of the skills that we could be. It's also very challenging because being a lawyer is like an identity. Jennifer Friend, who was on the show previously, moved from being a big affirm partner to running a nonprofit that was not a legal organization.

She said that one of the hardest things was, “I'm a lawyer. I knew who I was like. That's my identity to many people. I know what to expect.” When you transfer skills to something else, you're no longer a lawyer per se. Even though you still are, but you're not practicing, that was a mental shift that she had to do. That's unique to our profession in terms of how we think of ourselves. Doctors are doctors. Lawyers are lawyers and that sphere. It would take a lot of courage to decide to step out of that. Also, probably a sense of contribution, inspiration or need. I think that what I am doing would be helpful to others and there's a real service to be done from what I want to do because you do have to push yourself off the cliff a little bit. We're here to manage risk and reduce it.

Honestly, a lot of venture capitalists push back on the idea of lawyers as certain owners. I've seen on Twitter someone says, “I would never invest in a startup led by a lawyer.” It's like this misperception that we're so risk-averse. We understand risk pretty well and we know how to handle it. I definitely have a little chip on my shoulder and maybe it's part of that competitive spirit we have as litigators where I'm like, “ Do you think I can't do this? I will do it.”

We're competitive, that's for sure. That's part of it. We are competitive and we have a level of excellence, both of those. I wanted to raise that because I'm going to encourage those who are reading who might have an inkling or might not even think about doing this that it's possible. We're not taught this in law school. We go through the career office and they say, “Government this way. Big law that way.” That's about it or maybe a clerkship. Those are kinds of avenues. They're willing to open people's minds to things that they can accomplish. To your point, Jackie, it still is things that people have perceptions about lawyers as well that you need to think about.

When you have the companies, “l have taken risks, I've gone out on edge,” and people are like, “You lawyers, I don't know about that.” In the legal tech space, in particular, there's a need almost for at least one of the founders to have legal experience in order to understand where the need is, how to position and how the whole legal system, law firms and all of that work. That's something that you add to the equation that would take others a lot of time to ramp up to. I want to ask Nicole about your tiptoeing and then going out with Trellis. What was going through your mind? What made you take that step? How is it different than you thought it would be?

Ask me any day of the weekend and it's going to be a different answer on that one. It's funny because it fits into what we're talking about, which is I, as a litigator, was very myopic in my view about what I thought my career could be. I thought if I wasn't happy at my firm, then my option was to change firms. That was the only way I saw a tunnel of what my career would be. It wasn't until I started to deep dive when I realized that there was this massive aspect of the law in the entire court system that nobody had structured and aggregated yet. It blew my mind that nobody had done it. Once I started to realize, I keep digging in, “Is someone working on this? What's going on?”

It almost became like a compulsion where once I saw it. It was so obvious to me that I knew someone was going to do this. Will this exist in five years? One hundred percent. Why not me? It's a cost-benefit analysis, a very lawyer thing to do, which was like, “I continue litigating. What does my career look like if I go to the highest rungs? What is the potential of this product that I envisioned to scale and build a meaningful business?” The opportunity just felt so much greater than I remained litigating. For me, in this weird way, it was the less risky choice and I felt compelled to suddenly do this thing.

I couldn't sleep. I’m always thinking about it. That was what got me in, but the truth is it took me a number of years to jump. I got the idea and I knew one developer. I basically had them start aggregating data. I used it in practice. I was terrified to jump from practice. Over that number of years, it became so obvious to me that the data was a competitive advantage. My motion practice became way more successful that it was obvious once I proved the value to myself and my own practice that it would be valuable to others. That's what it took for me to decide, “I'm ready.” Now we can jump in and let others use this product that I've been using for many years.

Sometimes once you've seen that opportunity, you can't unsee it. In that setting, when you're aggregating data, you're going to be the spot for that data. Somebody else aggregates first. First-mover advantages are paramount. I know I've had that kind of feeling about things too. I have an idea and I go, “Somebody else may be able to do that. Maybe I don't want to do that right now, ” but it's out in the ether and somebody is going to grab onto it. After a certain point, you're like, “Nobody else has done it. I might as well do that. I can see it.” I do think that's true about aspects of innovation. They're out there to be pulled from the ether to some degree and have to be clear enough and brave enough to grab it and be the one that does it.

That's also something that was a prime mover advantage. It's not something that the law rewards. It's more challenging. We believe in stare decisis. If you're going to exceed that, it's a worthwhile challenge. Many of us enjoy that. We are changing the law in that regard, but it's solid, tested and all of that stuff. We like to start there and then move beyond. It is that mindset to be open to a different approach.

When I talk with especially female founders, I see that there are more institutional barriers that are the bigger problem.

I was going to talk about that too because you are lawyer-founders. That's an unusual beast, but any kind of startup founder, particularly in the tech space, with three of you, it seems like, “There are lots of women, but it's all not true.” That's a different barrier. I want to explore with you guys a little bit why that is because it's an access question. It's access to capital and a lot of things to grow the company, but is there something else that I'm missing in terms of the barriers?

It was tough for female founders. I was the main income earner in our household. l had an agreement with my husband that my career was so important to me and he stayed home with the kids, but in order to go out there with Clearbrief, there was a period where I wasn't taking a salary before we were able to raise funding. That's a very big risk for a lot of people that they don't want to take it at a time in their lives when we need stability when we have kids, partners, parents depending on us and our steady income.

Tweet: It’s important to see more investors get into the earliest stages of funding women-led startups. 

It's important to see more investors get into the earliest stages of funding women-led startups because getting that first check in the door that can help you take in some salary, no matter how small, helps make the case to your family of like, “This is something that makes sense financially.” Childcare is a huge thing. Also, I'm seeing some startups who are raising funding and it has in their investor agreement that the lead investor will pay for them to have childcare. I'm like, “That is the future.”

I got to go back and build that in.

I did not have that as my agreement. My husband is our lead front-end developer. We're both all-in on the startup. We've had to handle the pandemic and not having childcare for certain stretches of time and still needing to put our full focus and work probably way more than we even would in big law or something in terms of hours to get the startup off the ground. Those are the kinds of barriers that prevent people. They might have good ideas. They'd be amazing leaders, but it's, “Who's going to manage the household?” It's something that we're all still doing.

There are various layers here, even in law firm life. You don't see a lot of female equity partners. If they do, their husbands are home or they don't have kids. One, it's hard to see the path that it can be done. If you don't see the path, you don't feel inspired to continue on because what are you moving towards? It's very similar in technology, except it’s the opposite for venture-funded startups, where investors pattern match how they decide to deploy capital. Their last five startups that became unicorns all dropped out of Stanford. They followed a very specific path and there weren't founders on them by and large.

It is important for us to continue to be successful to show both investors and female founders that this is a real Bible path if you put your heart into it. As for investors beyond pattern matching, why there's such a small percentage of capital that goes to women, there's a big picture there of a lot of things that go away. Some of which are women not asking, not having the ego to go out there and say, “These are completely unrealistic numbers.” Women are often going to go with what they think is more realistic. When you're not saying, “I'm going to build a $100 million company in my first six months.” The investors are used to hearing that and it takes time there.

I was listening to something about women following the job applications and whether they would submit their resumes for it. I thought this was fascinating. It was that if you list five requirements, guys will have two of those requirements and will apply and women won't apply unless she has all five. It's mindblowing for the standards that we hold ourselves to and our level of confidence before we'll go in and even apply, even throw our hat in the race for something. There are huge pieces all at play.

That's why I wanted to ask you because there are a lot of different moving parts to it and it all layers on. I wanted to say that you are very supportive and tangibly supportive of other women founders. It's very nice to see that. That's very good. One way to help with that is to pay it forward in terms of supporting other women in terms of access or advice, “I've been there to consider this.” Those are all ways we can all help each other and be open to doing that, whether we're law firm partners or founders. The other thing that shocked me and maybe Dorna, this is not going to shock you because you're in San Francisco.

I took a business class. It was the business of space law, but we're talking about the business of space, which is all the new space companies that are being watched. We're talking about venture capital-funded companies. We had some people come and do their pitches to us so we could see what that was like and 2 or 3 years down the line, what is their company doing based on the pitch? I saw exactly what you're talking about, Nicole, and they are way puffing about what would happen now. It turned out they made it happen. They said it, spoke it into existence, got the funding and then it happened. Based on the case I was being presented, I was like, “I am not sure that this is going to happen.”

The other thing that I noticed was that it's a very small world. Some of these founders were also partners in venture capital firms. They already have a pipeline to the money, know all the folks to ask and then they say, “You're an investor. You must know how to do this stuff.” It was self-perpetuating itself over this small-real group of people over time. That wasn't surprising in terms of how it all works there, but it surprised me when I saw it because it was showing up. Based on that experience, I was thinking access was the key. You need to have access to whoever the golden funders are or the people who have this kind of perception because perception is important in the beginning.”

We need to continue to be successful just to show both investors and female founders that this is a real viable path if you put your heart into it. 

What I've seen as the counterweight to that are women funding networks or women who fund women founders intentionally and they bet on the particular founder and what she can do, betting on that person in terms of their integrity and ideas, what they see in that person. It's a very personal kind of funding and for the future of another woman, her company and we hope to have many more founders as a result of that and allow well beyond the seed round of funding. I wanted to check with you on that in terms of what I saw in my little mini class about the very tight connection between a lot of these funders and founders.

I completely agree with you that the network aspect is so crucial. For all of us sitting on this show, we've all gone through this process of realizing that for hiring, raising venture capital and getting customers on board, all of those relate to the networks that we've had. When you're raising funding, there's this concept that you should never reach out to an investor cold. You should always get a warm intro because part of what the investor wants to know is that you can find the connections to get a warm connection to that person. That probably exacerbates the issue even more because, for us, we've worked in places where we've been able to create those connections and build those relationships.

For many people, there's no realm of possibility, no matter how smart they are. If they're ever going to make that leap into that traunch of folks who have those connections. For that reason, these groups that exist where women have gone out and have decided that they now want to pay it back to communities, whether that's women, diverse communities or people at specific schools. That's what's going to get us past that hump and be more inclusive more generally.

It's a relatively new phenomenon as far as I've seen, but it's an important one. It follows the value and the importance. The founders are essential to companies, especially at the seed round in the beginning. Having faith or expressing faith in that person and in what they can do also powers that person to accomplish even more than what they see in themselves and have the company move forward. There's something gratifying about doing that, about helping someone achieve the most that they can do to contribute to society. If that is by having a group that helps another founder in a seed round, it's very gratifying.

I’ll say some practical tips in case anyone's reading. I didn't get my first traction and supporters from existing networks. It was from LinkedIn and cold-messaging on LinkedIn. It took cold messaging, getting rejected a lot, and refining my story over time. This is where your legal writing can also come into play because you get better. I have had people say, “I never normally respond to LinkedIn messages, but something about your message got me to respond.” A number of men responded and gave me that help because, in some ways, it can be tough.

We put a lot of pressure on the women networks and they're already stretched to capacity. We're never going to get there if we're only relying on those women's funds. There is still a small piece of the VC pie. Don't underestimate the ability to send cold emails. They are telling your story and dealing with that rejection and not being ashamed of it. It's how everybody gets off the ground.

As a law firm partner, I feel the pain. You want to be proactive and reach out. Jackie and Dorna, I first encountered you through LinkedIn years ago. You're both very active and doing it very well. Especially during the pandemic, you're not going to be able to go to some cocktail party and chop someone up. You have to use the tools that are available to you. When you're building a company or business, we have to do that. We can't wait for whatever is going to happen with COVID. That's leveraging a network through technology, the network that's LinkedIn and being unafraid to do that.

This also comes back to the question of how does our law degree helps us within this realm? We do a lot of LinkedIn marketing as well. One of the things that have been most useful is knowing how to craft that initial message in a concise enough way to be able to immediately both demonstrate to the person what you're trying to provide them and capture their attention. I'm sure we all get so many of these spam messages on LinkedIn.

You click into the LinkedIn message and you have to scroll up for one hour to see what they're even talking about. Sometimes I wanted to respond to these people and say, “If you gave me a two-sentence description, your rates of responses would skyrocket.” That comes from having to have done that in front of courts where there are word count limits and you would love to say everything you want, but you want to make sure they're reading it.

Good writing is good writing and it can be used in a lot of different realms. Persuasive writing is persuasive writing. You can use those techniques too. Communicating is something that we do. It's good to be able to use that and analytical skills, critical thinking, and analytical approach to problems the company might encounter. It’s what I've noticed sitting on nonprofit boards and things like that we break down issues and work through them in an analytical way.

Many business people and other people without legal training don't look at problems the same way or break them down the same way. There are some problem-solving skills and issues spotting that are helpful on the business side as well. Jackie, do you have any particular tips based on your experience for those who might be interested in starting up a company? What are lessons learned or tips that might help some people get a leg up?

A very practical tip would be to get experienced with Beautiful.ai. You need some basic graphic design skills to get your pitch deck. VCs have many decks and they're snobby about it and they don't look beyond the surface. I'm embarrassed. For my first decks, I was doing them in PowerPoint. They were so bad and ugly. This is related to my previous tip about some startup founders in the community here in Seattle who were generous with their time. They looked at my deck and gave me feedback. It can be very tempting to be like, “They don't get it.” Listen to them because people who have been out there in the trenches raising money to understand what investors will ask you.

I had one amazing legal tech founder who introduced me to like a bunch of Angel investors. He was like, “Start pitching and doing it. You're going to get rejected by all of them. Maybe you won't, but you probably will, but that will give you the feedback you need to improve your deck.” Especially women founders, there are hundreds of pitches you have to go through usually before you get a yes. Know that and don't let your pride stand in the way of learning. That's going to be like our biggest lesson as lawyers where we're so used to being polished. Having all the answers, we have a persona of being very knowledgeable about everything.

That's not going to serve you when you're trying to just figure out, “How do I frame my idea in a way that makes sense to somebody who is not like me at all and doesn't understand legal?” When I was pitching Clearbrief, I had to explain citations. You can imagine the level of interest I got from VCs. You have to figure out a way, “How can I make this story compelling?” It's coming back to the storytelling ability that you get from your training. The other thing is my mental catchphrase like, “Get in where you fit in.” If someone is giving you good feedback and helping you focus on that person and that stream, instead of, there are going to be some people who are never going to want your idea or they're never going to believe in you. That's okay.

Focus on when you get the positive signal. Someone described it to me when you're trying to find product-market fit as tapping into veins of gold. You'll find something that works and you don't understand why it's working or why people are liking it. You need to keep following that. It's what you have to do the whole way. Don't take it to heart when people don't like you or your idea. You're not a fit for them and there are going to be people who will support you.

There's a certain level of intuitiveness to that. You hit something and go, “I don't know where it's going to go, but I'm going to follow it. I don't even know why, but I'm going to go that way and follow that road one step at a time.”

There's also sort of this intuitiveness that's bred in us from the legal profession to listen to the haters. It's fighting that and just thinking, “I'm not good enough.” I had people tell me early on who are not lawyers and not venture capital people, “We looked at legal. We didn't think there was anything there.” There's no venture scale. This was before all these legal tech companies, IPO and everything. You're going to have people who are going to say things to you that cut you to your core. Don't listen to them.

We don't understand why there'd be any technology in that particular area. That area gets funded a lot and that's all we want to see. It's like the flavor of the month, things like that. You got to have a strong core, a strong sense of yourself and the value that what you're doing provides and not be waylaid by that kind of attitude. Dorna, any tips?

Don’t let your pride stand in the way of learning. 

I would say, “Think big, start small and iterate rapidly because to get yourself off the ground, into a new field and in your team and everyone excited, you need to have a huge vision for what you think you're going to accomplish with what you're building. At the same time, when you start out, you need to take it in bite-size pieces because that will allow you to launch something, get it into the hands of your customers, and get some feedback. You need that negative feedback in order for you to move forward because there's no way that the first product you built is going to be perfect. If anything, often people say, “The first product that you build should be embarrassing because otherwise, you don't know that you haven't launched quickly enough.” I know that's true about us. That's maybe true about Nicole.

If it’s too perfect, you waited too long. Is that it?

Exactly. Starting small and getting that feedback will allow you to build that platform, tool, or company that you want to. The third step is iterating rapidly. Don't stop iterating. Every time you get a bit of feedback, take that internally and decide whether that's right for you and then apply it so that you can move quickly because startups are an area where you need to get out there and there could be potential competition-beating right behind you at any moment. The way that you're going to win is to be harder working and to move faster.

That's the most succinct bit of advice in each aspect. In terms of the feedback, sometimes people will say one thing and you have to dig under that a little bit to see what's going on. That's another layer to what you said. You might discard part of it because they don't know what they're talking about or legal doesn't work that way, but when maybe there's something under there that gives you an idea to iterate in a different way as well. Being open to that feedback is also open to iterating that feedback yourself in terms of, “How can I improve this or what are they getting at?” Maybe they're getting to something they didn't state away that was accurate or helpful, but they're definitely onto something that we could do.

That goes back again to our legal skills. What follow-up question do you ask to appropriately get out the information and tease it out of this person who maybe hasn't stated it in the right way but also gets you to understand why there's that objection and whether there is some level of validity to it?

You got to be curious. Nicole, what is your advice?

To double down on what we were saying, I entirely agree that you have to move fast and iterate. In terms of feedback and all of the noes, see if you can find one piece that could be interesting or that you at least want to explore with other people to see. A lot of it is noise. Cut out the noise and try and take one piece of it that could be something to work on and think about. In terms of super early, testing as much as you can to the extent that you can test and validate before you jump, do so.

Nicole, you tested it on yourself for a while.

Any way that you can build out tiny pieces of the vision that you have, try and test those are going to set you up for success when you're ready to build. The final piece, if you're out there early and you're thinking about fundraising and let's say your very first folks, initial Angels, remember that when you go in, you're not asking people for money. You're bringing them an opportunity. Shift the mindset a little bit there. There's definitely a lot to the way that you go in and your level of confidence. People can feel that. The more that you recognize that you're doing them a huge favor. You're potentially bringing them on something huge is in everyone's interest.

Tweet: Think big. Start small. Iterate rapidly. 

It’s how do you view it or what you're doing because it can be challenging to do that. Asking for money and the amount can be a little bit hard if you think about it that way, but if you flip it and think about it, “This is a good thing. This is a good opportunity, especially in the early part, that I'm inviting someone to be involved in. If I hadn't invited them, they wouldn't have that opportunity.” It shows your faith in where things are going as well that you think this is a positive thing that you should be involved in. It can be hard. In my experience, none of those were things that we learned in law school unless you have business or sales training. That's something you have to grow into and recognize for yourself and get comfortable with. You all have done that and grown. Nicole, I've seen over the longer haul of her company.

It’s an early conversation for us.

I know about those conversations. It's wonderful to see where you're at now, Nicole. The company, yes, but to also see you as a person and how you've grown and contributed to others. You are very generous with what you have learned and that is always very gratifying to see.

Thank you. I appreciate that.

I'm going to end with a short lightning round, which is usually we have a little lightning round of questions at the end of each. I'm going to start with Dorna. What talent would you most like to have that you don't have?

I wasn't sure if it was a magic power or it had to be a real thing, but to stop time, I'm going to go with the magic power.

Nicole, what about you?

Continuing to get better at delegating, letting go and accepting good rather than perfect. That is a work in progress and it’s important.

Perfectionism is ingrained in the lawyer. Jackie, what talent?

I would like the talent to teach my three-and-a-half-year-old to sleep through the night. That would provide the biggest benefits to my life.

What is the trait that you most deplore in yourself and what's the trait you most deplore in others? I'm going to start with Nicole.

It's funny because it's one of those things where probably the one you most deplore in others is the same one that you most deplore in yourself. I'm trying to think about it that way, but I would say regret generally. Spending any time looking back and wishing, “I made a different decision.” Also, too much time forward over-analyzing if something is worrying you, but spending more time in the present is important.

Dorna?

The one I was thinking goes along with that is letting go of things because things in the past you can't change and dwelling on them will keep you from moving forward. If it’s a concrete action I can take to change what happened in the past, then I should do it. If not, I need to move forward. Mine and the one that I deplore in others is not one that hopefully, personally, possessed, but it's twofold, non-responsiveness and lack of attention to detail because those are so critical to anyone that I enjoy working with so I look for those and others

Jackie?

What I struggle with a lot is caring a lot about what other people think and being on my phone too much is related because with how important social media is to a startup. It's something that I wish it didn't occupy so much of my brain space because there are so many other things that you might need attention too. In terms of a trait that I deplore in others, the biggest thing, especially as I've gotten older, is I love being around people who have self-awareness of their own behaviors, problematic behaviors and weaknesses, in general.

I deplore people who don't have any self-awareness and who haven't taken a moment to think about what they're putting out there impacting other people or what others might be going through. It becomes a very strategic muscle to develop if you're talking with a lot of customers or talking with investors. You want to always be thinking about having self-awareness and awareness of other people. If you don't have that, it's a problem.

That helps in your relations with others all around, if you have that. It takes some self-introspection to get to the point and to be aware of things. You got to grow internally first. Who is your hero in real life? I’m going to start with Dorna on this one.

I would say two. My mom is very inspirational to me and now I have an eight-month-old baby who has completely changed my perspective on life. For very different reasons, they are my inspirations.

Just remember that when you go in, you're not asking people for money. You're bringing them an opportunity and shifting their mindset. 

Nicole?

Mine is similar, which is I have an eight-year-old little girl. You get to watch them be present and filled with joy. It reminds you what's important, so it helps to ground you.

Jackie, your hero?

I have a number of heroes, my mentors in law, my previous coworkers and my bosses who have taught me so much about leadership and legal writing. I wrote my very first blog post. If you go to the Clearbrief Blog, I wrote about my biggest mentor, who inspired me. Any female founder who's out there, you all are my heroines.

You could choose anyone in the world. Who would you invite as your dinner guest?

I always am super fascinated by whatever is happening in the news and whatever defendant is standing trial for some kind of murder or crazy situation. I would pick three probably. I want to talk to Elizabeth Holmes. If Jeffrey Epstein were alive, I'd be very interested to get his thoughts and Robert Durst.

Do you listen to true crime podcasts and things like that, too, Dorna?

I don't. I wish I had time for that, but I follow all the headlines and would love to dive deeper with them in person.

Jackie?

I'm a musician and that's a big part of my life. I would go for Brandi Carlile. She lives here in Washington State. She's such an incredible singer-songwriter. Her songs are absolute works of art. I also love her voice, her performance and how she writes about her journey as a mother. She's incredible.

Do you sing? Is it in a singer-songwriter kind of genre as well or is there an instrument?

I am a singer-songwriter. I write original songs on my guitar and sing, but I also have a jazz band that I've been performing with my husband for a while. We did a little mini performance at a cidery. We brought the whole family and it’s super fun. I always try to keep music in my life, no matter how stressed I am.

If it's something you enjoy and gives meaning, you need to keep that in your life. We're holistic. There are many aspects to us and you don't want to give that part of you up. It's an important part of the expression as well.

It was hard during the pandemic because we weren't performing. There's been very little live music, but this particular venue was one of the first times that I performed in years because it's an outside venue. It was awesome to be there and connect with people. They don't care that I'm a startup founder, the law or anything. They love music.

You connect with people in a different way in a different part of your gifts and personality as well. That can be so hard to keep that going and it must have been gratifying after COVID to be able to be out there because it'd been such a long time. I enjoyed music as well. I like to sing. It's still on my list is to learn the drums. That's the instrument I would like to learn. One of my friends, for her birthday, lived in Austin. We all came in for a weekend to celebrate and we went to this girl’s rock school. 

Women wanted to do this so badly because we didn't get to do it when we were girls. They'd have these weekends. The women could go and do this. You got to try out three different instruments for over one hour each to see which one you liked. You got to try everything. You'd get broken up into bands and you would write the lyrics for your song and then you'd practice the song. We performed in an Austin club all in one day. It was a lot of fun and it's definitely something outside your comfort zone, but I was the drummer for the band.

It's not easy to pick up in a day. How did you do that?

I picked it up in the day. Understandably, we were a punk band because it only required three chords. I had the job. They're like, “Whatever you do, don't mess up because if the drummer messes up, everybody goes down.” I was like, “No pressure. It's all good.” It was a lot of fun and it was awesome. We were taught by other women artists in Austin, a real rock band of women who would teach us during the day. I distinctly recall that one of them was then on KCRW the next week with her new album.

I'm like, “These are real people. I liked their work.” They were so kind to say that we were doing a good job when clearly we were not at their level, but it was very encouraging of them. That idea of we're in a whole different zone. No one there would know anything about us and that’s fun to have a different role. Nicole?

I would want a rotating list. Probably some of your guests to be women that have made it to the judiciary, to the upper levels to the Supreme Court. It's fascinating that path there. I'd love to learn more about it. I need to listen in.

 We have a number of amazing people. I've learned so much from talking to them and their journeys. The last question for all of you is, what is your motto if you have one? I'm going to start with Dorna cause she's super succinct. I think she's going to have one.

I would say, just to always be stretching yourself. Part of the scary reason I left my law firm is that I felt like there was so much more to grow and learn. I'm always trying to encourage that within my team as well.

Nicole, are you ready for this one?

I'm ready for this one, maybe because it goes counter to what I was saying previously, which is you have to test everything. It's just as a part of it, which is, jump and the net will appear. At some point, you get to a place and if you don't jump, you can't allow the universe to provide the net to continue living forward.

Jackie?

Mine is talk to people because that was something that I got some good advice early on where like, “You can be so focused on building your product and you're waiting for the reactions.” You have to get out there, talk to people and hear their feedback. That's how you're going to get those golden nuggets that you need to improve the product. It doesn't matter who you hire. No one's going to hand that to you on a silver platter. You can only really get that from building relationships. Talking to people is how you're going to move your business forward.

For appellate lawyers, in particular, that's a real challenge outside the box, “Talk to people. Get out of the library and the research.” We are used to doing that. Thank you so much to all of you. I enjoyed it and hearing about your journeys and what it's like compared to practicing law to run companies. Nicole, Dorna and Jackie, thank you so very much for joining the show.

Thanks for having us.