Accessible Justice with Sonja Ebron of Courtroom5

Startup Savants Podcast header with hosts smiling in front of microphones.

Summary of Episode

#7: Sonja Ebron joins Annaka and Ethan to share her experience creating Courtroom5, a legal-tech platform designed to help those representing themselves navigate the legal system. Sonja shares her insights on using AI to solve problems, building customer trust, and leveraging your personal story to organically grow your venture.

About the Guest:

Sonja Ebron is the founder and CEO of Courtroom5, a SaaS startup that assists users trying to navigate the legal system. Having started two other companies prior to Courtroom5, Sonja is not new to the startup sphere. Sonja’s own personal experience in court propelled her to create a product that strives to increase access to justice. Although she is not a lawyer herself, Sonja has a PhD in electrical engineering and draws on her academic and engineering background to develop the tools needed to help others tackle the complexities of the legal system.

Podcast Episode Notes

Who is Sonja Ebron, and why did she start Courtroom5? [0:30]

The difficulty of navigating the legal system —  how Sonja’s personal experience dealing with the courts prompted her to create a legal-tech startup [2:30]

What does access to justice mean to Sonja Ebron? [5:30]

Sonja’s prediction for the future — if people cannot afford to pay for legal services, they will need resources to learn how to litigate for themselves and only pay the necessary legal fees [7:55]

One way to improve access to the legal system, enable people to pay for legal services à la carte. Both lawyers and everyday citizens could benefit from this business model [13:02]

Using AI and machine learning to improve processes and create solutions [15:30]

Robot lawyers? It’s going to take some time before we see any of these [19:21]

Creating a product designed for your users [20:36]

From a blog to a full-fledged product, the process of iterating and building various prototypes  [24:54]

Consider starting with a blog to generate buzz around your business and your niche [28:00]

Sharing your own experience and transparency are key to establishing trust with users [29:50]

Sonja’s advice: share your story. The best business ideas often come from personal experience [31:34]

SEO (search engine optimization) can be an effective tool for connecting you to your target market [32:28]

Tips for developing a pricing model [34:00]

Sonja’s experience with entrepreneurship accelerators and incubators [37:43]

How to manage freelancers and create a steady stream of content [41:41]

What’s it like running a business with your spouse? [49:54]

The difference between managing and leading a team [52:35]

Questions that are always lingering in a founder’s mind [55:20]

Check your ego and be sure to find other perspectives [58:26]

Sonja’s advice for entrepreneurs: don’t wait. Find a problem, and go get started! [1:01:50]

You will fail — learn how to get back up [1:03:05]

Ethan: Hey everyone, and welcome to Startup Savants, a podcast dedicated to helping aspiring entrepreneurs and startup enthusiasts by bringing you news, insights, and stories about the startups and founders that are out there every day, planning, plotting, and putting in the effort to one day take over the world. I’m your host, Ethan.

Annaka: And I’m your other host, Annaka.

Ethan: Our guest today is Sonja Ebron of Courtroom5. Sonja is a PhD electrical engineer and entrepreneur with a background in utilities and artificial intelligence. Her LinkedIn bio reads as follows, “pro se litigator, social entrepreneur, unconventional educator, energy and utilities expert.” It then goes on to say, “transforming the legal services industry, constant learning, thinking outside the box, asking why to singularity, and turning chaos into opportunity, making it all look easy.”

Now I’m sure we could do a whole podcast on just a few of those line items, but today we’re going to drill down on Courtroom5 and your story as a founder. So, for listeners who don’t know, can you start by telling us a story about Courtroom5 and its mission

Sonja Ebron: Ethan, hi. Annaka, great to be here today. Courtroom5 is designed to help average people navigate our very complex civil justice system. And so if you are familiar with Judge Judy or Judge Joe Brown or all of the court TV shows, don’t believe the hype. Real court is not like that. Oftentimes, people are handling somewhat complex issues, whether it’s a nasty divorce or a debt collection or foreclosure case, medical malpractice. We’ve seen, oh, several dozen types of claims that people bring to us.

But if you are handling one of those cases, chances are there’s a lawyer on the other side, very experienced in managing the court process and prepared to beat you up. Litigation is a battle, where one side wins and the other doesn’t generally. And so, our app, Courtroom5, is designed to help people level up, compete with those lawyers, and navigate the civil justice system, so they can get a fair hearing in court.

Annaka: I love the idea. And can you tell us a bit about the history behind Courtroom5, and how in the world did you come up with something like this?

Sonja Ebron: Yeah, as you mentioned, I’m a PhD electrical engineer. I’m not a lawyer. I don’t have any legal training at all, other than what I actually experienced in court. So I was a college professor, managing my life, got into some financial trouble, as many of us do. I ended up getting sued, and I had a really good income, as it turned out, but I could not afford a lawyer. Quickly realized that lawyers are, on average, about $300 an hour. And for any type of complex claim, your lawyer’s going to spend a couple hundred hours managing your case. And most of us don’t have $60,000 just laying around, particularly when you’re in financial trouble.

So I quickly realized I couldn’t afford a lawyer, but I felt like I had some good defenses to the claim, and I’m fairly smart, thought I could figure it out on my own. Well, I realized that it wasn’t true. It’s way too complex for the average person to deal with, or even someone with the educational advantages I had. I got my butt kicked really quickly.

And thinking back on it, lawyers go to graduate school to learn how to do this. It’s not a simple thing. We have courts that are designed by lawyers, for lawyers, and they look at people who don’t have legal training like, “What are you doing here? Go get a lawyer.” And unfortunately, as I mentioned, most of us are not able to do that.

At any rate, that happened to me a number of times. And each time, because I’m a learner, each time I picked up just enough to do better in the case and eventually started winning. And I realized during those experiences that there were a whole lot of people handling issues much more serious than I was handling, who just didn’t have a chance. They didn’t even understand what was happening to them. I saw people coming into court like it was a business meeting or something, like the judge is going to sit back and explain the law and ask you friendly questions and just sort it all out. That’s not the way it is.

It is an adversarial proceeding. You’re there against a very experienced litigator, oftentimes. And the judge is really a referee. They’ve got to be neutral. They can’t help you at all. And so, the average person just gets no fair chance to explain the facts, apply the law to their cases, none of that.

And so this happened also to my wife of 20 years, who is a PhD librarian. So we had separate tracks, and we realized at some point, we’ve got to do something about this. We’re both educators. We both learned to navigate the system ourselves. Let’s stop just going to court and watching these people get screwed and see if we can’t provide a solution that all of us can use. So that’s the origin of Courtroom5.

Annaka: Yeah. We were doing research, and I was like, “Man, I love this.” And in other interviews and in our research, we’d seen this term pop up, “access to justice.” It’s used a couple times. And what does that mean to you?

Sonja Ebron: Access to justice is really being able to use a branch of our government, is ultimately what it comes down to. So we’ve got a tripartite system in the US and many other countries. You’ve got your executive branch, you’ve got your legislative branch, and you’ve got your judicial branch. And it’s interesting because the executive and legislative branches, we collectively go on election day, and we pick our representatives. All well and good.

The judicial branch is different, though. It is designed for people to go one on one and use their government. You can actually, on a distinct, unique set of facts, go into court and petition the government through court to get a court order that speaks to your unique circumstances. And that’s unusual in the other… That just doesn’t happen in the other two branches. That judicial branch is the key to what makes our democracy work.

There’s majority rule in the executive and legislative branch. You can be a minority of any kind, an individual, and go into the judicial branch and get the government to work for you. Not for a collective, but for you. And without that, you just got majority rules. It doesn’t work.

And so access to justice, for me, means access to democracy, ultimately. We’ve got to enable the average person to be able to petition their government, the way they go and stand outside polling places on election day. We’ve got to be able to use the judicial branch in the same way.

Annaka: Yeah. It’s the interactive branch, if you will.

Sonja Ebron: Yeah.

Annaka: And everyone at some point is most likely going to be in there, whether as a juror or however.

Sonja Ebron: That’s right.

Annaka: And our legal system is often seen as behind the times in many senses. What do you see as the future of a more equitable US legal system?

Sonja Ebron: Yeah. That’s a great question. We’ve got something like, I think, 1.3 million lawyers in the country.

Annaka: Wow.

Sonja Ebron: Right. That’s a lot of lawyers, but it isn’t actually enough to handle all of the claims that hit our judicial system every day. That is, if everybody could afford a lawyer, not everybody would get a lawyer. We just don’t have enough of them.

And so what I think is happening is about half those lawyers are in small and solo firms. Often many of them are consumer facing lawyers. The other half work for corporations. They work for bigger law firms that serve big business, generally. But those small and solo law firms, believe it or not, can’t find enough work because the people they serve can’t afford to pay them. If you’re a corporate lawyer, if you work for a big law firm, you love your profession, you are doing great. But small and solo law firms are in a lot of pain.

Again, we’ve got the biggest market failure in the history of the United States, where all of these lawyers are prepared to sell their services, very valuable services. And you’ve got a huge demand, people who need them but can’t afford to pay them. And so they are going into court because these are serious claims. These aren’t things you can generally just ignore. Somebody’s trying to take your kids. Somebody’s trying to garnish your wages for years on end, those kinds of serious issues. Somebody’s trying to take your inheritance, whatever it is, you’ve got to go in and fight those claims. And so you’ve got millions of people in the United States every year, trying to navigate this very complex judicial system on their own. Meanwhile, there are lawyers patrolling the courthouse, trying to find clients who can pay them. It’s a disaster. It is a disaster.

And so what we’d like to see is a way to make better use of those lawyers. Lawyers go to school, and they learn a business model where somebody walks in the door, and they have a problem they explain to the lawyer. And the lawyer says, “Okay, I can take your case. No problem. I just need $5,000 to get started.”

Annaka: Yes.

Sonja Ebron: That’s a big stop sign for most people. Even those who do have the $5,000, write a check, sweating and wondering what’s going to happen next. That money’s gone in no time. And then the lawyer says, “Oh wow. The other side filed something I didn’t expect. It’s going to take another $15,000 or $20,000.”

At any rate, they drain your pocket books in very short order. As a matter of fact, at Courtroom5, we get refugees from that business model all day, every day. It’s really, really sad. People who were able to hire a lawyer to get started but quickly ran out of money to pay them in the middle of a case. They have no idea what’s been going on. And they’ve got to then step in and take it the rest of the way, if it’s possible.

So at any rate, what we’d like to see at the end of the day is people managing their own cases. If something has happened to you, no one’s going to understand that better than you, than the individual it’s happened to. So the client, it turns out, has the best grasp of the facts. If you can manage some basic stuff in litigation, as it turns out without a lawyer, you have to know what to do, you have to know what things mean, what’s relevant, what’s not relevant, what the procedures are.

In every litigation, there’s going to be a complaint or a petition that starts the case. There may be a trial at the end of it, whether using a judge or a jury, and possibly an appeal. But the flow of litigation is pretty much the same for any case you’re going to handle. And so, if you understand that and understand some of the rules, you can do the basic stuff yourself if you have the tools and some basic education.

That’s what we do at Courtroom5. What we want to do, though, is on those more difficult pieces, if you can’t figure out what evidence to collect, or if you are about to go to trial and you don’t know how to pick a jury, there are some difficult pieces in every case. We’d like you to be able to hire a lawyer piecemeal just for that specific task.

Annaka: That would be awesome. Yeah.

Sonja Ebron: Yeah. And then go back to handling your case when the lawyer’s done that job for you. And if the lawyer’s done a great job, the next time you get into trouble or need some really good advice legally, that lawyer will be available for you. Again, for a few hundred dollars is a shot rather than dumping $5,000 and your life savings, if you have any, on that lawyer.

And this is something that would work great for lawyers as well, who many of them can’t afford to maintain their practices because they have no money coming in the door. This will be a way for a lot of people to be able to pay them, to maintain their practices. And they would actually, as it turns out, be able to practice the stuff they went to law school for.

Like I said, there’s lots of stuff happening in litigation. There’s a whole bunch of paperwork that piles up really quickly on you when you’re managing a case. The vast majority of it doesn’t take a legal education to do. There are things like, for instance, if you want to schedule a hearing before a judge, you have to file a notice of hearing that lays out which judge, what courtroom, what time and date, basic stuff. My dog could do it. Anybody could fill that out. You don’t really want to waste a lawyer’s time doing something like that. But if you’ve retained a lawyer, that becomes part of their job, and they do it. And they’re going to charge you your $300 it took them to do it.

So we want to enable people to do that basic stuff and understand the wider context of their cases and use a lawyer on an a la carte basis.

Ethan: So that’s an excellent vision for a future of the legal system. To make that happen, is everything that we need within Courtroom5? Or do we need larger laws to change? Do we need societal change? Do we need a mindset switch? What is it that we need to do as a people to move towards that vision of the future?

Sonja Ebron: I think lawyers have seen this model as the solution. It’s not unique to me, certainly. They’ve actually lobbied their state bar associations and bars to enable them to serve clients in that way. And many of them purport to do that. Unfortunately, it doesn’t work very well. The reason for that is because your average person has no idea what to ask a lawyer to do. They don’t know how to task a lawyer because they don’t understand the civil justice system. They don’t understand the litigation process or anything about it. Most of us, when we think of a lawyer, and certainly wealthy people who can afford lawyers, you get into some legal trouble, what do you do? You call your lawyer.

Ethan: Right.

Sonja Ebron: You tell them what happened and they’re after the races. Exactly.

Ethan: Exactly.

Sonja Ebron: Right. You don’t have to know anything about litigation, and most of us don’t. This isn’t stuff that we learn in school. What Courtroom5 does is prepare people to task lawyers for those a la carte services by putting all of the tools necessary for them to represent themselves at their disposal.

Ethan: That’s a great answer. All right. I’m going to move a little bit into more specifics of how your product works, or at least one part of your product. But I’m going to ask the question a very vague way. And I think you’ll have a good answer. Can you tell us who Sylvia is?

Sonja Ebron: Sylvia is our intelligent chat bot. She’s a robot. She does lots of things. She handles some aspects of customer service, if they’re simple. But she also, for those people who are actively using Courtroom5, she tracks the progress of your case. She knows what’s happened in your case, and she can point you to the most relevant training for you, the things that we think is best for you to understand based on where you are in your case. That’s her main job is just to keep track of our users and make sure they’re getting the most relevant training necessary for them to make good decisions in their cases.

Ethan: That’s a great answer. So you’ve got a history in AI and machine learning. Do you think that any founder… Take Courtroom5 as it is now and put in a different founder with a different background than yourself. Do you think that they would’ve implemented an AI tool into the platform? Or do you think that some of the steam behind her creation was your background in AI and machine learning?

Sonja Ebron: Yeah. Good question. It’s really difficult in 2022 here to build an innovative technical solution, online web-based or mobile-based solution, without AI. And even if you do, it’s not going to be competitive because somebody’s going to come right behind you and build it with AI, which means their cost will be lower, and it may be a more powerful solution. So, if I knew nothing about AI or machine learning, I would absolutely adopt it in some form or fashion to deliver the services we do.

One of the benefits of having that background in AI is that I recognize some of the failure points, maybe better than other people do. And so I’ve seen… The landscape is really littered with AI failures, people trying to apply this very powerful technology to problems without an adequate understanding of what it can do and what it can’t. With machine learning in particular, and there are lots of different algorithms for it, some unsupervised, meaning you don’t have to tell the thing the right answers. They’ll figure it out on its own. But across the board, you have got to have data that maps to the problem. You have got to have data from actual users who are making some progress on that problem.

If you don’t have that data, you can fake it till you make it, maybe. But you have to be very careful about doing that because bad data leads to bad solutions, and you really waste a lot of time and energy if you do that. And time most importantly for entrepreneurs. Because again, we live in a competitive environment. So if you’re not fast, you’re not making good decisions. If you find yourself going down rabbit holes that are a waste of your time, then you are accelerating your competition, essentially.

So I say all that to say, we’ve been very deliberate and very careful about the way we collect and use data to be able to give Sylvia her power.

Ethan: That’s a fantastic answer. Sylvia sounds like a real nice lady.

Sonja Ebron: She’s wonderful.

Ethan: I would be glad to have her by my side if I get into some courtroom mess. So quick follow up question, how far are you from building a robo lawyer?

Sonja Ebron: Yeah, it’s going to take a while. It is going to take a while. And I say that because the problems that we are working on, again, we’ve got folks handling everything from contested bankruptcies and divorces to medical malpractice and civil rights claims. There are some peculiarities to all of those cases that Sylvia can handle only superficially. Until we get adequate data on all of those problems in all the jurisdictions, she can only operate at a certain level. And so we’ve got a lot of work to do. It’s probably going to take us a matter of years before she gets to the granularity we think we would expect of her.

Annaka: Yeah. And every state has different handling of different laws and doesn’t even have laws that exist elsewhere. And…

Sonja Ebron: Exactly, exactly.

Annaka: That’s going to be a mountain, but I’m really excited to see how y’all transform and keep growing with this.

Sonja Ebron: Absolutely.

Annaka: When you were building the tool out and in the planning stages, how did user experience play into that? And how did you take into account that most of your users have zero background in law? And how did you design to be sensitive to that?

Sonja Ebron: Yeah, it helps to have an academic background and to understand that people get to an aha moment in every class. No matter what you’re trying to teach, there’s a place where somebody goes, “Oh, now I know what she’s talking about. Boom, okay.” And we’ve all experienced that, hopefully multiple times. And so we’ve tried to embed that in our training, in particular. We used our own experience, and directed to your question, we developed very sophisticated customer discovery and customer feedback practices. So we know when people get to that aha moment. “Okay. I feel like I can handle this. I can do this.” Right> No matter what the topic is. And so, we developed… And I have to credit my co-founder here, Debra Sloane, my wife and PhD librarian. Let me just digress for just a second.

Annaka: Yeah.

Sonja Ebron: I grew up… many of us, we go to the library, public library. And I never really realized for most of that period, that there is oftentimes a person in the library who is responsible for answering any question you’ve got. It’s called a reference librarian. You can walk up to the reference desk, and you can ask, “How far away is Mars?”

Annaka: Oh my God.

Sonja Ebron: Right. Who designed our penny? Who decided it should be made of copper? You can ask a librarian anything. These are people with master’s degrees, and they learn where to go get that information. They don’t know it right off the top of their heads, but they know how to find it for you.

More importantly, once they’ve got that information, they are trained to make it accessible to a six-year-old. They can tell you any type of information in a way that’s appropriate to your understanding.

So Debra, our chief product officer, is in that role because she taught librarians how to do that. All right. She is really, really good at it. She spent 20 years in public libraries herself and got a doctorate and started teaching it. Just brilliant.

But when we’re looking at something as complex as litigation, it’s so important to be able to take these very, very difficult, technical, legal topics and make it accessible to regular people. And so, we’ve got a large suite of video-based lessons on everything you’d want to know about litigation. Where to sit in the courtroom when you go, depending on whether you’re the plaintiff or the defendant. How to address the judge, what to wear. How to write a motion, how to collect evidence, how to pick a jury, how to prepare for trial. All of that stuff is available in very short, accessible videos. Not a whole lot of legalese unless it’s explained to you.

But that is her work. That is what we’ve done. And in fact, that is the library that Sylvia picks from to point people to the right training at every step.

Annaka: Yeah. And I did sign up for an account and poked around, and I was like, I don’t really have a case to go with, but I filled in what I needed to fill in to look around. And I also have a background in education. And one of the biggest things that I learned was scaffolding. So you start at base, what is it the user absolutely needs to know from point zero. And then you can build on top of that. But if you jump into how to pick a jury, when we don’t even know where to sit in the courtroom, we’re missing those pieces. So I did pick up on that in the structure of your training and videos. And I was like, “Ah, going back to education school right here.”

Sonja Ebron: Scaffolding, you bet. Yep.

Annaka: Yeah. So what was the process like when you were actually developing this? Most are iterative, so I’m sure you … 

Sonja Ebron: Exactly. Yeah. That’s why I’m giggling, yeah. Many, many iterations. That’s right. That’s right. We started off with a blog, to be honest with you, just trying to share some of the things we had learned that were shocking to us. We would just write about and share in really layman’s terms, not a lot of legalese unless it’s explained. So that’s really where we started. And we found people willing to pay for that, just for that basic information. But they also gave us lots of feedback. Again, going to the feedback loop. Oh, well, I had this problem. How do I handle that? And so, we don’t give any legal advice, but we could tell them how we had addressed certain problems.

And we started hearing common stuff all the time and just decided to build tools for it. So folks were like, “I got this cardboard box at home and all this stuff, and I can’t keep anything organized.” And so we just built a filing system, essentially. And so that anytime you file something or get served, as it is, get delivered something that’s been filed for from the other side, you have an online place to store it and just keep track of it that way. And it became very valuable. Because I remember in some of my cases, I’d jump up at 3:00 AM in the morning, waking up from a nightmare. “Oh no, did I say that? Or did that person say that?” And then I’d be digging through my cardboard box, trying to find the specific filing.

Now you don’t have to do that. Store it online. You just go back, you can sort it any way you want, but it became very valuable just to have at the ready a history of your case, so that you could read through it and find any information, search for it if necessary, right there online. That was one of the first things we built. We’ve got much more complex tools than that, but we took feedback from all of our users and the problems that they were experiencing and just built tools for it. And so Courtroom5 just developed in that way.

Ethan: I really love that it started out as a blog. And I don’t know how long it was a blog before it started turning into tools, but I feel like that’s such an accessible entry point for so many entrepreneurs out there and so many people who don’t necessarily have either the funding or the experience, or really as many of the tools to go out and start a big business. They can start by starting a blog or starting a YouTube channel or anything like that. It’s really amazing to hear that something that started off, and I’m not going to say a blog is a small endeavor, because I’ve done a couple of them. It’s not. There’s a lot of work that goes into it, but it’s accessible. People can do it. And so, I’m just so glad to hear that something as awesome as Courtroom5 really blossomed out of something as “simple” as a blog. That’s awesome.

Sonja Ebron: Thank you. It’s great. It is actually… I’ll just follow up there. It is actually a great place to start because we still see a lot of folks finding us through the blog, free blog, free versions of the content that we produced. Folks are online, searching for any kind of solution to something that’s been filed or something they need to respond to. And Google has been very good to us. You won’t find this kind of content in many places.

Ethan: No, it’s very niche content. So building off of that, how do you decide… When you’re making new content, does everything new go into Courtroom5, or do you still make new things to go onto the free blog?

Sonja Ebron: Yeah. We still make new stuff to go onto the free blog. The way it developed is there’s a free version of the content, and then there’s one that is dedicated to our users, which is placed in an online community. We have a community where people can share their experiences and ask questions and that stuff of each other. Our staff doesn’t get involved because we don’t give legal advice, but we let people freely exchange any information they want. But we also, just as way of moderating those discussions, provide very in-depth guides on certain topics that folks are interested in. And so, that’s a paid version of the content, and then we’ll make a free version of it as well.

Ethan: That’s fantastic. So let’s go back to the user for a second. For any startup, building trust in a brand is an undertaking. It’s a big deal. And your company offers a product that’s a bit more intimate than most products out there. And this transaction is something that requires an extremely high level of trust right out of the box. How did you go about and how do you go about building a foundation of trust with your users?

Sonja Ebron: Yeah. Yeah. It’s by being transparent, being open. You’ve heard my story. Most folks wouldn’t want to tell you about their case and litigation. Most of us don’t want to talk about that stuff, but it is part of my experience. There’s no shame for me in it. It’s something that happens to millions of people. I know that. I know folks that need to hear from other people who’ve gone through that. And so, just one of the things that we did… It wasn’t to gain trust necessarily, but it was just to share because we saw so many people needing this information. You have to talk about your own experience, otherwise, where is it coming from? I don’t have legal training. I gained the knowledge that I have through actually experiencing it, having to learn it on my own.

So you got to tell that story. And people, we found, were just really… Gained some trust in us because of that. But also from their own experiences, they really needed to find other people who had gone through this experience. It’s a very isolating experience. We found folks who are in court, whose spouses don’t even know that they’re dealing with this issue. Parents don’t know. And so, we wanted to provide a place for people to be able to share their experiences in court when they couldn’t do it with their friends and family.

Ethan: So sharing the story, is that the advice that you would apply to other startups who are struggling with establishing 

Sonja Ebron: Absolutely. Absolutely. Absolutely. I’ve heard, and I agree with this, that the best business ideas come from your own experience. You want to solve a problem that you’ve directly experienced because you know it well. Particularly when you found a solution, even when you haven’t. You can be in search of one, that can be your entrepreneurial journey. But nonetheless, yeah, you absolutely want to find your tribe, and you do that by sharing your own story. You’ll find people who are happy that you did and want to join you on your journey.

Ethan: Let’s step to marketing for a minute. If I have ever heard of a product for a niche audience, this is it. You’re marketing to an extremely narrow band of people, and not only demographically, but also you need to catch them at the perfect spot in their timeline.

Sonja Ebron: Yeah.

Ethan: So how do you find these people and get your message in front of them without blowing your entire marketing budget out?

Sonja Ebron: Yeah. SEO. SEO again has been a great friend. And so just sharing our knowledge in the way we do, with the intimacy, in layman’s terms. We’re not a law firm trying to find clients, and so that sort of thing. And I think that’s been very attractive to people when they find us.

We’ve also invested here and there on Google ads, on Facebook ads. Those organizations have some algorithms that can find people who are looking for banana peels. It’s amazing. They can get as niche as you need to go. And so, we’ve developed some confidence in those areas as well.

Annaka: Yeah. We’re familiar with SEO over here, search engine optimization and keywords and all that fun stuff. So I’m glad that the algorithm is going in your favor.

A little bit off the beaten path here, but I was a little curious… Words, words… Because we were talking about you could spend $20,000 on getting a lawyer yourself, and one of your focuses was to make this accessible, and your pricing structure is very accessible. Can you talk a little bit about how you arrived, we don’t have to talk specific numbers, but how did you structure this based on who’s going to be using your tool?

Sonja Ebron: Yeah. It’s, again, iterative. Pricing is its own discipline in entrepreneurship. You have to figure out what your market will bear, essentially, and charge accordingly. For us, we also had an interest in making this as accessible as possible. And the beautiful thing about technology is it scales beautifully. You build a product, and millions of people can use it. So you don’t need to charge the highest prices, what the market will bear, in order to do this.

We’re also lucky that we don’t have any competition yet. It’s on the way. It’s on the way. We’ve scoped out a few organizations who’d like to do what we’re doing, and I welcome them. One company is a hobby. Two companies is an industry, so we are looking forward to having an industry here soon.

But to pricing, we want to make sure that folks have the ability to access it. This is a very much middle-class problem. We talked about niche marketing a moment ago. You’d be surprised how little of a niche this is. It turns out there are about 30 million people representing themselves in court every year.

Ethan: Oh my gosh.

Sonja Ebron: It’s insane. This is from the National Center for State Courts and some other organizations who’ve tracked it. I didn’t see 30 million people when I went to court, but I did see a lot. And so, it’s just a very broad based problem.

Now we have legal aid organizations, wonderful organizations who can provide a lawyer for people with very low income. As it turns out, they are only able to serve, on average, about half of the people who are qualified financially to get a free lawyer.

Ethan: Wow.

Sonja Ebron: But then anybody who is a dollar over the federal poverty line just is on their own. Has no… So this is very much a broad middle-class problem. Nonetheless, we’re in a stressed economy. We want to make sure that we can get this into people’s hands, and that they still have enough, if necessary, to hire lawyers on that a la carte basis.

So we give people a couple of options. They can pay by monthly subscription, and we generally recommend that if you think you’ve got a case that’s going to be resolved in a matter of months, then just pay monthly. And when you’re done, you’re done. But for others, and frankly, for most people handling this litigation, once they understand the process and are using our tools, it turns out their cases are going to last a lot longer than they may have thought. And so we want to give them a one time pricing. Just buy the thing, use it until your case is over. Some cases can last five, 10 years. Divorces never end right?

Annaka: Yeah, exactly.

Sonja Ebron: These sorts of things. But many other cases… You’d be surprised, the foreclosure, for instance, once the homeowner understands the process, these cases… And they’re able to fight back against their bank or mortgage servicer, these cases can last a long, long time. So we didn’t want people stuck on paying monthly, and so we give them the option. Start monthly if that’s comfortable for you. Once you feel like you’re going to be using this for a while, you’re free to switch over to a one time pricing. And you just own it, and they can stop paying us at that point.

Annaka: Yeah. It’s just a perfect opportunity to fill the gap. I was impressed. And going back to when you were really just getting off the ground, what made you decide to go through an incubator?

Sonja Ebron: I’ve been through a number of incubators, as it turns out. And so I’ll tell you, entrepreneurship is hard. It is really the most difficult work I’ve ever done — professionally, at least. And so, it’s something you can’t ever stop training.

I’m a natural learner. I learn something every day. I’m humble enough to just say, “I don’t know this, let me go learn it, see how I can apply it and make things better.” Accelerators package that for you, though. And their job is to change your trajectory. So you come in one way, and hopefully at the end of it, you’re at a higher trajectory and growing faster.

So I think probably the first experience we had was with, here in North Carolina, the NC IDEA Foundation gave us a grant. And along with that grant, just educated us on basic startup principles. That was very, very helpful. Even though… by the way, I should mention this is my third startup. I’d had two earlier energy-related ventures. There’s always more to know.

Annaka: Absolutely.

Sonja Ebron: In fact, yeah, I’ve learned so much more with Courtroom5 than I ever did, frankly, with those. Because I thought I knew it all right. But at any rate, NC IDEA provided the first incubator experience. We went from to the Duke Law Tech Lab has an incubator for access to justice-oriented ventures. And we certainly qualified there. So went through that wonderful experience. We also went through, LexisNexis has an incubator for legal tech companies so we also qualified there. Yeah. So wonderful experience there. In fact, they took us on a tour of Silicon Valley right here from North Carolina, really wonderful experience.

We went through Techstars a couple years ago. I think it was a couple years ago. Yep. Very powerful experience. I guardedly would call it hazing, if through a fraternity or sorority but really powerful, really wonderful experience to go through Techstars.

And so, I take those opportunities wherever we can. We’re working with one of our investors now in something we could characterize as an accelerator. They’re working, just rolled up their sleeves and are pairing us with all-star technical talent, marketing talent. And again, the goal is to change our trajectory. We’re doing something, as you all expect, very unique here. And this is a long game, a very lofty mission. Takes a lot of work, a lot of iterations. And so, accelerators are designed to just help you form the right experiments and to grow from them quicker than you would on your own. And so, really happy and grateful to have gone through all of those experiences.

Ethan: That’s absolutely amazing. I love the idea that you can jump into one of those and just get beat up for a couple months and then come out the other side, just so much better off. It’s really amazing.

Sonja Ebron: It’s awesome. It is. It is awesome. Absolutely. Techstars in particular is something I think most entrepreneurs should aspire to do. It’s a great experience. You really will come out of it… If you apply yourself, you get out what you put in for sure, but you can come out a whole different company, and many do.

Ethan: Fantastic. All right. I want to turn to something that is near and dear to my heart. And that is content creation. In some of your other things, you’ve mentioned that you outsource development, content creation, and some other aspects of your business. I’ve been in content creation for many years now, and dealing with contractors and freelancers and the… You’re always balancing the speed and moving things off of your table for quality. And not necessarily that they’re creating bad quality, but rather that you need to have an eye on quality control all the time, because you need to make sure that they’re communicating exactly what you would be communicating and that it’s just not flowing out of your fingertips, it’s flowing out of their fingertips. So, how do you manage that process and ensure that the quality and accuracy of the things that are coming from those freelancers is up to the standards that you yourself would produce?

Sonja Ebron: It’s great. You do a lot of work when you are dealing with freelancers. A lot more work, I think, than people expect, but certainly more than you would if you had employees. We have content development cycles. And so certain periods of the year, there’s a lot to do. Other periods of the year, there’s not so much. We ride and coast on what we’ve developed. And so for now, outsourcing has been the way to go.

What we do to make sure that it is quality, though, we start with the style guide. That is probably the most valuable piece. We’ve got to have a style guide that if you’re not following it, you don’t get paid. The job isn’t done. So you have to have a very solid definition of what done is. And be transparent about it in the hiring process. So if you are hiring somebody that’s not really feeling your style guide, they don’t get the job. It’s that simple.

So we start with a very, very detailed style guide, because all of our stuff has to be consistent, has to come from the same voice. And that’s what you embed in your style guide.

Secondly, when you’re dealing with freelancers, reputation matters a lot. And so folks have done some comparable work, we like to see it, we like to evaluate it, and we choose from folks who’ve done similar types of work.

And then, the third thing is you almost have to do half of the job yourself.

Ethan: Oh my gosh, yes.

Sonja Ebron: Yeah. And that’s fine. This is all about getting the right outcome here. So we’re happy to do that. And Debra is our expert on this in terms of content development. But what I’ve learned from her is that you create a template. For instance, we may need a course on doing legal research. Debra will write the syllabus, what material is going to be covered. Organize it, so this amount will be covered in one video, and that amount will be covered in another video. And you just work it down till you’ve done essentially half of it, of the work. But then you turn it over to your expert freelance contract developers, and they put some gloss and some polish on that thing that makes it all worth the effort. And most importantly, you can use a lot of those folks, and they are very prolific.

So you can develop a legal research course, but you can also simultaneously develop a process for picking a jury, for instance. And syllabus there, style guide, do half the work, and then you just turn it over and wait for something beautiful to come back.

So it does take a lot of work, probably more than if we were to hire folks outright and train them. At this point of our development, I think we’re probably getting a better outcome doing it this way than we could if we had to hire and train. You still have to supervise employees. So yeah, it’s worked out really well for us for now.

Ethan: All right. Can we roll it right back to that style guide? I don’t know if you saw Annaka and I were both just like, “Oh my gosh. Style guide, yes.” So, I’ve gone through a number of freelancers in my colorful past of having things written. And after about the first five, where I’m like, “Well, it just must not have been the right freelancer,” I decided it’s probably my fault.

And so I went into Reddit and went into a group of writers, and I said, “Hey, I’m not looking for any of you to come and jump onto my writing team right now. But I would really love to know, what is it that you need from me in order to create excellent content?” And they said essentially the same thing, it’s style guide. It’s that communication of really asking what it is that you want and getting that back.

So I started out to write a style guide. And I think I still have it, it’s 6,000 words of a style guide. And I’m asking these freelancers to write 1,200, 1,500, 2,500 word articles. So it’s almost three times, maybe four times the length of the thing that they are doing. And I’ve gotten some better results since then, but I still don’t… I don’t know. Maybe I’m just not telling them hard enough, “You better read that darn thing.” So it sounds like you’re getting better results than I was from your style guide. So more power to you, I really appreciate that.

Sonja Ebron: Well, it didn’t pop out all at once. Again, it’s an iterative process. You have some experience with freelancers, and you get what you get, and you change, you upgrade your style guide. Ours probably is upgraded three or four times a year. Yeah. So it’s constant. It’s a piece of content, like anything else. So you definitely want to take feedback from your experiences there.

But the other thing is in your hiring. Again, reputation matters. And the conversations you can have, that you should have with these contractors matters. But at the end of the day, again, if you haven’t followed the style guide, then you’re not done. You haven’t delivered what the job requires, and you don’t get paid. When people understand that going in, you get much better results.

Annaka: I got so excited. I live and die by a style guide. I’m a designer. It’s like, do go here, don’t go here. Say it like this, don’t use this word. It’s perfect.

Sonja Ebron: Exactly.

Annaka: We both got really excited.

Sonja Ebron: Content is one of those words, as well. So, it applies to the blog. It applies to some of our features. It applies to technical development just as well. So we have a separate style guide about what goes on in our app and how, and just how things work and so forth. So yeah, whenever you’re working with contractors, and we do that on the development side as well, you’ve got to provide the guidelines for them.

Annaka: Yeah. Yeah. So we’ve talked about Debra a couple times already, your wife of 20 years? Over 20 years?

Sonja Ebron: Over 20 years. I’m going to be in trouble because I don’t remember. Let’s see. Yeah. 2000. So almost 22 now. That’s right.

Annaka: Congratulations. That’s amazing. And she is an expert in qualitative data analysis. Don’t mind me, I might Google that real fast. But first off, what is it like working with your spouse?

Sonja Ebron: It’s really interesting. I’ll say it that way. Really tough, but you all may know the primary cause of startup failure is team dynamics, co-founder drama. We don’t… We have plenty of that, for sure, but we also, because of our relationship, have ways of dealing with it. So we have to silo a lot, constantly. I’m actually here in my home office, we often work at home. Not always, but often work at home. And so, we are constantly having to separate work from the rest of our relationship, just constantly. And it’s over the years gotten to be pretty natural. So, not a lot of struggle there, but there are times when, during work days, I’m the boss. I get to say what happens. I’m the decider. I can’t carry that into the other relationship. I’d get knocked down just brutally all the time whenever I forget. I’m not the boss. I’m not the boss of her in that way.

So yeah, just, it doesn’t happen often, but those are some of the dynamics we have to just traverse on the day to day. But it’s great. I wouldn’t have founded this company with anyone else. It’s just been fantastic. She brings just a huge amount. And I didn’t pick her as co-founder because she’s my wife. Picked her because she’s brilliant and she brought just the ability to curate very complex information. The main feature of what Courtroom5 does is to make the law accessible to people. I couldn’t have done this without her, for sure. So just really glad that this worked out.

Annaka: Yeah. Well, you both sound like incredibly smart cookies. Do you have any go-to strategies when you’re like, “All right, we’ve talked about work enough. We need to go back to our life as non bosses.” What’s your strategy for that?

Sonja Ebron: Yeah, so we have a 9:00 AM standup with the entire team, every weekday. And then we have a founders meeting once a week. Frankly, most times we miss it. So we might actually meet only a couple of times a month as co-founders. The rest of the time, I’ve got my stuff to do. She’s got her stuff to do. She’s got her own team. I’ve got folks that I lead. And so, we don’t really have a whole bunch of dynamics outside of 9:00 AM on the weekdays.

Ethan: All right. So this question might be… It’s definitely going to be interesting to you because this is your third startup. And of course, we heard just a little bit about your first two startups, that they were both in energy, but you’re now on number three. So you’ve got a little bit of experience going into this, but what was something that surprised you when you launched your own startup? Was there something that was 10 times harder than you thought it was going to be? And was there something that was 10 times easier than you thought it was going to be?

Sonja Ebron: Oh, we’ll be here all day. Yeah. I think probably the most interesting thing to me has been the difference between managing and leading, is the most fascinating thing for me. I am by no means an expert in it. I am very results-oriented. I like to get work done, just churning through and being very productive. I do that as an individual, I do that as a member of a team. But what I’ve learned and continue to learn is that I can manage… I’ve learned to manage a team. Leadership is a different animal. Leadership is almost like you pick a team, you task a team, you hold them accountable for sure. And then you let them do the work. You let them manage themselves. Leadership is about turning the folks you work with into their own leaders, their own leaders.

And that is a human development skill that I’m still learning to do. So, yeah, right now I lead by working hard and expecting everybody else to work hard, but that’s just the most superficial level of leadership there is. And so I’ve got a lot to learn. I’ve got some mentors that I’m working with, some fantastic leaders. I watch how they lead their organizations. It keeps me humble and understanding… I’ve got a lot to learn in that area, but it is one of the most fascinating things about entrepreneurship, and I’m really enjoying the lessons I’m getting there.

Ethan: All right. Now this next question, it’s going to take you to a deep, dark place. As a founder, what keeps you up at night?

Sonja Ebron: I sleep really well. I sleep really well, even though we’ve got just tremendous challenges. Anybody more intelligent would probably not sleep as well as I do, because we’ve got… There are lots of things that could keep me up, but I take a lot of solace in understanding that I do the best I can. I throw the best I’ve got at every problem this company has. And so, I sleep really well at night.

But we’ve got huge challenges. So we’ve talked about Sylvia, and we have a roadmap for her, for growing. It may be that the data that we are collecting and using for her is completely wrong. And I won’t find that out for years. I may not know that for years. That’s something that ought to keep me up every night, but it doesn’t because there’s nothing I can do. We’ve made really good decisions around that, I think. You do the best you can. So I don’t stay up worried about that.

Oftentimes it’s whether to take a check from an investor, to keep me up more often than it does. We’ve taken a number of checks, and we’ll be taking a good number more, but there is persuading an investor that you are investment worthy, worthy of their investment. There’s a separate conversation where this person’s going to be a part of your company’s family forever. You’re getting married, and you really… I think folks ought to perform due diligence on investors much more than we commonly do. So I do a certain level of it, but there’s always more to know. And so oftentimes I wonder, should I have taken that check or maybe not. Once I cash it, I don’t worry about it anymore. But those are things that ought to keep me awake more often.

The same with members of the team. Did I hire the right person? Am I rewarding them as well as I can? Am I leading them as well as I can or ought to? Am I being as transparent as I want to be? Lots of those questions. There are just a huge, huge number of questions. Are we building the right product for the market? Is this feature necessary or a waste of effort? Are we moderating our community properly? Am I having the right conversations with the regulators?

I could go on and on and on. There are lots and lots of company killing issues that, if you don’t really focus on them, you’ll be in trouble. But there are too many of them. I can’t focus on them all. I try to catch the things turning into fires and put them out. So yeah, we could be here all day on those issues, but long and short, I sleep really well. I don’t worry about too much.

Annaka: That’s so good to hear because I feel like… Yeah, all of that laundry list of stuff would make you insane. So hope you keep sleeping good.

When you initially filled out the questionnaire for us so we could learn more about you and your company, you said at one point, “Entrepreneurship forces personal development. I’ve had to get over my ego more times than I can count.” I’m going to applaud that. But this isn’t the first time we’ve heard something like this from entrepreneurs over the years. Can you tell me a little bit more about what that means?

Sonja Ebron: You have to have a huge ego to want to lead a startup. It’s necessary. You got to go into it like you are going to change the world, and only you can do it. it’s just a part of the mindset that you have to carry with you. At the same time, it really gets in the way. It can so easily turn into arrogance. I’m not the only one. The reality is I’m not the only one that can do this. If you’re not cautious, if you’re not checking yourself on that ego all the time, it will lead you astray. It absolutely will take you down the wrong path. And so, I try to… I practice humility and just actively check my ego and just question myself all the time. Not in a way that introduces doubt about what we’re doing but just get a different perspective. Just take another look at it from somebody else’s eyes. It has been so helpful for me.

Annaka: Yeah. And I love the awareness. It’s like, okay, all right, go sit in the corner, ego. We’re done with you for now. We’re going to listen to this person, or we’re going to take advice from somewhere else. So, I just really loved that quote, and I wanted to hear a little bit more. So, since you’ve been doing this for a while now do you have any customer success stories that stick out to you as favorites that you can share with us?

Sonja Ebron: One of the best things about this job is that we hear regularly from people who are handling some tough situations.

Annaka: Absolutely.

Sonja Ebron: Through the courts. And they tell us about… I hear, “You saved my kids,” that sort of thing, or…

Ethan: That’s amazing.

Sonja Ebron: Yeah. We get that all the time, and it keeps us working harder. Nothing in particular. We post some of the testimonials we get publicly on our website, so always happy to just refer to those and share those. But yeah, like I said, there are lots of ways to make money. Entrepreneurship is not always social entrepreneurship. And so, we are really happy that we’re able to do our work in a way that serves people and to be able to hear about how we’re serving people all the time. So I wouldn’t share anything in particular. There’s lots of great stories available, though.

Ethan: You’re such an inspiration. I just love this. They say to never meet your heroes, but you know what? In this case, I’m okay with it. So what is your spice… Wow. Wow. A spice.

Sonja Ebron: Cinnamon. Cinnamon.

Ethan: Yeah.

Sonja Ebron: Thanks.

Ethan: What is your advice for aspiring entrepreneurs?

Sonja Ebron: Aspiring entrepreneurs. Just to check that word. Every entrepreneur is aspiring. Every one of us. You’re never done. As long as you’re doing the work, you are always aspiring. And there are people on the fence. I talk to them all the time about, “oh, I’m waiting for the right idea, or I’m waiting for this, I’m waiting for that.”

Sonja Ebron: Don’t wait. Don’t wait. Go get started. Wherever you can start, that’s where you start. It’s going to evolve. So many people… I say this to my team all the time. We are pouring sand, not concrete. It’s going to wash away. What we’re building right now will look completely different in six months. And that’s true, no matter what you’re building. So don’t let the perfect be the enemy of the good. Just jump in and get started.

Find a problem that you want to solve for somebody, and then find the people who like your solution. That’s really all there is to it. Go for it. The solution is going to evolve. The people you’re serving are going to evolve. All of it is going to evolve, especially you. But you never start until you start. Just get started. Just do it.

Annaka: Just jump in.

Sonja Ebron: Just jump in.

Annaka: It’s another recurring thing we keep hearing. So you all are so consistent.

Sonja Ebron: It’s true.

Annaka: Yeah. I’m going to sit here and continue to be a designer because I am not on that level.

Ethan: We believe in you, Annaka.

Annaka: Do you have anything else you’d like to share with our listeners before we wrap things up?

Sonja Ebron: One other piece of advice is don’t be afraid of failure. You’re going to fail every day, guaranteed. No question about it. Get over it. The key to winning is to get up after you fall. That’s all there is to it. Just go for it.

Ethan: Can confirm.

Annaka: Yep. And then as far as getting in touch with you and/or Courtroom5, do you have social media handles or email or any way that users can reach out to you directly?

Sonja Ebron: Absolutely. Absolutely. So the best way to reach us is at It’s the number five, but if you spell it out, it’ll still come to us.

Ethan: Nice.

Sonja Ebron: No worries. Yeah. But we’re also on Twitter, Facebook, Instagram. The handle there is Courtroom5, that’s the number five, legal, L-E-G-A-L. Yeah. Just come and visit us.

Annaka: Sounds good. And for anyone listening, we will put all of those links in the show notes, but that’s a wrap for us today. We’ve reached the end of yet another episode of the Startup Savants podcast. We want to thank everyone for listening in today, and thank you so much to Sonja for joining us.

Listeners, do you have any thoughts for us? Good or bad, let us know in the comments. We love hearing from you, and we read every single one. Your input really helps us continue to be better. If you want to learn more about how to get your startup started with tools, guides, videos, and even more startup stories, head over to That’s, Bye, everyone.

Ethan: See you, everybody.

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