In the latest episode of “The Geek in Review,” Marlene Gebauer hosts a fascinating conversation with Sonja Ebron and Debra Slone, the dynamic couple behind Courtroom5, a pioneering startup in the Justice Tech space aimed at empowering pro se litigants. As part of the “Love & Legal Tech” series we discuss the personal and professional relationship that propels Courtroom5 forward, providing valuable insights into the intersection of love, partnership, and innovation in the legal tech industry.

Courtroom5 stands out in the Justice Tech sector by offering a unique platform designed to educate, encourage, and empower individuals representing themselves in court. Sonja, as CEO, orchestrates a broad range of responsibilities, from technical leadership to marketing efforts, while Debra, wielding her expertise as a PhD Librarian and CTO, focuses on managing the extensive content that forms the backbone of Courtroom5’s service. Their combined efforts have earned Courtroom5 recognition and awards, underscoring the impact of their work on providing accessible legal support to those without formal legal representation.

The story of how Sonja and Debra met over a game of spades in Durham, North Carolina, adds a personal touch to their professional narrative, highlighting the serendipitous beginnings of their relationship and eventual collaboration. This personal bond, fortified by shared experiences and a mutual understanding of being “screwed over in court,” has been instrumental in shaping the vision and mission of Courtroom5. Their complementary skills – Sonja’s technical acumen and Debra’s information management prowess – enable them to tackle the challenges of running a startup while fostering a shared passion for justice and empowerment.

Working together, however, is not without its challenges. Sonja and Debra candidly discuss the continuous effort required to balance their professional and personal lives, emphasizing the necessity of intentional scheduling and the discipline to separate business discussions from personal time. This ongoing negotiation between their roles as business partners and life partners is a testament to their commitment to both their relationship and their venture.

Their advice to other couples considering a similar path is poignant: prioritize the personal relationship, ensure a solid foundation before embarking on a business venture together, and select a partner who can significantly contribute to the business’s success. Sonja and Debra’s story is not just about love and legal tech; it’s a narrative of resilience, mutual respect, and the unyielding belief in their mission to democratize legal support. Their story is an inspiring reminder of the power of partnership in navigating the challenges and triumphs of entrepreneurship.

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Music: ⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠


Marlene Gebauer 0:05
Welcome to The Geek in Review. The podcast focused on innovative and creative ideas in the legal profession. I’m Marlene Gebauer, Greg is not going to be on today. So I’m just gonna get started, we have our second Love and Legal Tech feature. And today we have with us, Sonja Ebron, who is the CEO of Courtroom5, and Debra Slone, who’s the CTO of Courtroom5. So Sonja, and Debra, welcome to The Geek in Review.

Sonja Ebron 0:30
Great to be with you.

Debra Slone 0:32
It’s good to be here.

Marlene Gebauer 0:34
So, you know, just for clarification for the audience regarding this series of discussions, you know, we’re going to use the term Legal Tech as the standard phrase for the discussion. But we’re using a very broad definition I’ve mentioned to both of you to include innovative processes, like you know, practice strategies, process improvement, project management, and you know, all kinds of other innovations that may not fall into the pure technology definition. So, you know, we don’t want anybody calling us later and saying, that’s not really technology. Right. So. So, let’s, let’s get started, you know, what do you both do in legal tech space?

Sonja Ebron 1:16
I’ll start off, let me just say we’re, you know, I’m taking off your comment about legal tech, we’re not actually in legal Tech, we provide a legal technology or form of it for pro se litigants as opposed to law firms, which is what most legal tech does. And so we are firmly in the Justice Tech space as it’s known. Courtroom5. As you may know, Marlene is one of the founding members of the Justice Tech Association, along with several dozen other companies, serving consumers directly with technology solutions. And so it’s just really happy to be in that space. So what I do as CEO is, I’ve got my hands in some of everything I need the the technical team. I dabble in some of the marketing, do everything pretty much the Debra doesn’t do. She’s sort of a strong horse here.

Marlene Gebauer 2:10
Yeah, and I think I think since last night, we last spoke, so I knew like you guys have gotten some some awards and some quite a bit of recognition. If I were, if I remember correctly,

Sonja Ebron 2:18
It’s been a good, it’s been a good time. Absolutely. We’ve got a long way to go. Always, this is a tough nut to crack, we think in the industry, but are just really passionate and happy about the progress we’ve made.

Marlene Gebauer 2:30
So Debra, tell us about what you do.

Debra Slone 2:33
Yeah, Courtroom5 is a very content heavy company, we’re trying to educate as well as encouraged and instill some confidence and empowerment. And so my task, my job is to… I’m totally responsible for all the content on the site. So I’m, I’m to create it, I’m took a lead that, handed out, store it, preserve it, manage it, maintain it, all that stuff, all the knowledge base for Courtroom5,

Marlene Gebauer 3:06
and that must be quite a job, I would imagine it is a huge shock.

Sonja Ebron 3:12
A lot of people busy Debra, for those who don’t know, as a PhD librarian. And so that’s really a perfect role for her. You know, I just one of the things I tout to some of our investors and other folks who’d be able to got a PhD librarian, and how we think of the solution that we provide for consumers is really just in time delivery of the legal information they need. Right? So the tech really just distributes all the great work that Debra and her team do.

Marlene Gebauer 3:41
So tell us a little bit how the two of you met and I’ll I’ll let whoever wants to start start.

Debra Slone 3:50
We’ve met in Durham, North Carolina, over a spades game, which I won. It was it was a long game it was three hands spade three people and that’s how we met and after that we’ve you know, we’ve not we’ve seen each other every cent so

Speaker 1 4:10
Long a long time ago. barely remember that game because I rarely lose. I rarely lose a spades game and so I’m sure I’m blocked it from memory.

Marlene Gebauer 4:21
Had you met one another before? Or

Debra Slone 4:23
No. It was so the very first time

Marlene Gebauer 4:26
it was that third person was that the person who brought you together?

Sonja Ebron 4:30
No, actually it’s a long story but she was actually a girlfriend of mine and so.

Marlene Gebauer 4:39

Sonja Ebron 4:44
As we were, absolutely.

Marlene Gebauer 4:46
Well… sometimes those things happen and you know, it’s just seemed to work out for the best for everybody. So

Sonja Ebron 4:55
it’s been a lot. It’s been a couple decades and so it worked out very well.

Marlene Gebauer 4:59
Good. So what’s been the best thing about being in the same profession, and not even in the same profession, but I mean, the same company, for the two of you?

Debra Slone 5:14
For me, it’s been the ability to say something and have her understand it fully. You know, I couldn’t do that as a librarian, and she, and she did it. But as as, as two people working together, we have the same goals, we have the same out pretty much the same outlook, we know the same people, we can talk about things and we just know what’s going on, we just keep each other abreast of what’s going on. So I think that’s a wonderful thing, a wonderful part of our working together,

Sonja Ebron 5:51
I would just say, I do know, we’re both, we both got into this, because we’re, you know, found ourselves being screwed over in court. And to be able to, to see people succeeding with the solution we built for them. It’s just really satisfying. And it’s just incredible, to be able to share that with with Debra, you know, it’s been we’ve been working on this, it seems like since we were both in kindergarten, a good long time now, but just to, you know, just to see folks who really wouldn’t have an option to get any kind of justice in court without a lawyer, you know, have have a better day in court with our solution and share that with us. You know, it’s great for the entire team, but certainly, it’s something that is, you know, really makes our day when we get that kind of feedback.

Marlene Gebauer 6:40
So a shared passion, but I also imagine complementary skills. And that probably helps the two of you where, you know, one is strong, maybe the other is less than if the other strong, and vice versa. So do you find that happening?

Debra Slone 6:55

Sonja Ebron 6:56
I think so. Absolutely. I mean, I didn’t understand. And I know Debra, for a long time, you know, I knew she was a librarian. And I didn’t, but I didn’t really understand what librarians do until I was working with one and this way, right?

Marlene Gebauer 7:09
You’re not Alone.

Sonja Ebron 7:10
That’s right. I mean, it’s, it’s really, it’s really amazing the skills that librarians have, and the way that they can apply it, and we’re in the knowledge, you know, era, and to see these professionals, just curate information and and figure out what people need and deliver it to them is miraculous. And so it’s been very educational continues to be educational for me on a daily basis, I think, you know, we get to sort of approach the problems that we have as a business, from very different perspectives. I’m technical, I’m an engineer, you know, I don’t think like a librarian, Debra doesn’t think like an engineer. And so for us to just sort of sync up on the business problems that we have from those very different perspectives is just, it’s really joyful.

Marlene Gebauer 7:58
So I’ll flip it then. So what’s been the most challenging thing about being in the same profession in the same company?

Debra Slone 8:05
Being at work all the time.

Marlene Gebauer 8:08
Work, work leads, work leads over I guess, yes, yeah, it does.

Debra Slone 8:15
Yeah, so we have to spend a lot of time or at our scheduling, we have to schedule our personal life, and we have to schedule our work life and we have to schedule, you know, just just mundane things that people wouldn’t normally schedule. We have to do that. Because we just otherwise we just be in work mode all the time. So that’s, that’s the most challenging thing for me.

Sonja Ebron 8:39
And for me, as well, it’s like, we’re, we’re in a constant business meeting you like, the lights never go out at the business? Right? We’re just always working. And so we’ve had to develop some skill, around siloing different conversations. There are conversations you have with a business partner and their conversations that you have with life partner, and, you know, you’re not careful, they can lead into each other, and you’re just always doing both all the time. And so we’ve gotten really skilled, I think, at naturally understand, okay, am I talking to my business partner? Or am I talking to my wife? Right, you know, and just just keeping the lines clear there.

Marlene Gebauer 9:22
What are some? Oh, sorry, go ahead.

Debra Slone 9:24
Oh, I’m sorry, we just code switch sometimes, we just slip right into work business and vice versa, personal business.

Marlene Gebauer 9:33
So I was I was gonna say if you could share some sort of tips in terms of how to silo those things, because, I mean, even I think even couples that aren’t in the same professions, like you know, you start talking about work and then you can’t stop talking about work and like, how do you be like, alright, you know, time to stop that and move to personal things.

Sonja Ebron 9:54
You know, I would say you have to be very intentional about it. So Debra mentioned having to schedule you know, things and we literally put everything that happens for us personally and professionally on a calendar. Right. And so in that way that light switch off and on. But also, we’re both very strong willed people, very assertive people. And so, you know, Debra will say, at 3am, I don’t want to have a business meeting right now.

Marlene Gebauer 10:26
Why not?

Sonja Ebron 10:27
Right, that’s exactly what I’m saying.

Marlene Gebauer 10:31
Come on, I’m thinking about this.

Sonja Ebron 10:33
About it. Right. And so, you know, she, she does this more than I do. But just drawing lines, right. Okay, no, we’re having dinner, let’s have dinner. Okay, you know, let’s just enjoy, you know, ourselves, and we could talk about business at the, you know, tomorrow, or schedule it, it’s on the calendar, we’ll do it, then. You know, so you have to be very intentional and willful about it. Because it is difficult it is, it is a very challenging thing. And you get burnt out on certainly running a startup, right. And it’s really easy for that to bleed into the personal relationship. And so, you know, and you just, I mean, it gets messy, that you don’t draw those lines.

Debra Slone 11:12

Marlene Gebauer 11:13
So what kind of reaction do you get, like, when you tell others that you work and you work for the same company?

Sonja Ebron 11:22
Oh, I could never. I could never work with it. Right? I hear that a lot. But also, I hear people who, those who like their spouses, I guess I should say, we’re like, wow, that would be so cool to be able to spend the whole day, you know. Most days that that’s true. But you do have those tough days, too. So yeah, so I hear I hear a variety of responses personally.

Debra Slone 11:50
Yeah, most of what I hear, is it? Oh, that would be nice. You know, yeah, I don’t have to drive over a where they buy? Yeah. But, ya know, they’re, they’re thinking it’s all rosy.

Sonja Ebron 12:04
Yeah, there’s a lot of work. It’s an extra layer of work, in fact, and

Marlene Gebauer 12:09
That sort of leads into my next question, you know, how do you handle situations where, you know, you know, you don’t agree on on how to handle something, you know, that you’re, you know, both facing, you know, both personally and professionally?

Sonja Ebron 12:27
Yeah, we constantly business meeting, again, we, you know, we’re both pretty much equal owners of the business. And so, very rarely do I get to say, Well, I’m the CEO, I’m going to do it this wayl It doesn’t work that way, for a variety of reasons, including this is my life partner. I can’t do that. So often, you know, it’s difficult, we talk a lot, we reach consensus. And I think over the time of the business, we’ve come to understand that that consensus process, you know, it tends to, tends to help us reach better decisions. Over time, we think things through and we’re both over educated, both PhDs. And so we think about things 360 Anyway, for AI, again, adds an extra level of work to the consensus process, but we think things through and we do that in collaboration with each other, and we keep talking about it, unless there’s an emergency unless something has to be done today. Right? And that’s mostly on my you know, that’s mostly my call. But if it’s a big decision, sometimes really small wins, like what should the email campaign look like this week? But but you know, we talk it out, we talk it out. And so there’s a whole lot of words exchanged to get to some of these basic decisions.

Debra Slone 13:49
Yeah, we there was, there was one about two years ago, there was a on a change that we wanted to make. And Sonja really wanted to change. And I was like, Oh, hell no. And we talked, and we talked, and we talked for days, and we just talked about it. And we finally came to a consensus, but Oh, that was just it was we both had to make some compromises. We both had to give a little on our on each side. And, you know, it worked out. Okay. But that that was the longest time we’ve ever had a consensus session. I mean, it just went on for that. I think, like a week, week and a half or something.

Marlene Gebauer 14:30

Debra Slone 14:31
Just know, we talked about?

Speaker 1 14:33
Yeah, you do. I mean, we’ve gotten good over the over the years at planning our roadmap. And so we do that as owners and then once we come to some very high level decisions, you know, we engage the team and we get a, you know, a more granular level of what’s going to happen when, and so we rarely have these sorts of issues, you know, on a day to day basis, right, but then there are opportunities that come up, there’s a new challenges that come up, you know, that throw those plans out the window and we have to have to have these very long sometimes week long conversations about how to deal with them.

Debra Slone 15:10
It helps when the when the team can sound in on some pot on it, sometimes.

Marlene Gebauer 15:15
They can they can be the tiebreakers?

Sonja Ebron 15:17
Yeah, absolutely. And there are always things that we just haven’t thought about. Right. And so yeah, it’s good to good to engage as many people as we can.

Marlene Gebauer 15:29
Well, it seems like anything else, like communication is key, right?

Sonja Ebron 15:33
Yep. You got it.

Marlene Gebauer 15:35
Alright, so tell me some of the interesting things that you guys are working on now?

Sonja Ebron 15:40
Ah, everything is interesting. We’re still a startup. We’re tech startup, right? I think, for me, personally, we are continuing to build out our AI roadmap, which we have to do very carefully. We hear a lot about AI and legal tech these days, obviously. But, there’s AI, again, that’s built for law firms, right. And then there’s AI for legal consumers, which is a different level of effort, you have to build in guardrails for people who aren’t skilled in this area at all. They don’t know how to fact check, or, you know, gut check, or any of the stuff on the legal information and analysis that they’re doing. So, really excited about the progress of that we’ve released a couple features already, which are doing really well serving our customers really well. But we’ve got, you know, about two thirds of the process still to go. And just really excited about that. And I’m, you know, again, leading the technical team, but the bulk of it, as anybody any AI knows is that is the data, is the training. And that’s where Debra is having a really good time, and I’m having a good time watching her.

Marlene Gebauer 16:47
And Debra, is in charge of the data strategy, right?

Debra Slone 16:50
Yep. Sometimes it’s, you know, trying to get him to say what we want it to say is, is a challenge, but we manage on a daily basis.

Marlene Gebauer 17:03
I mean, or can you share any of some of the new tools that are there? Or is that still top secret?

Sonja Ebron 17:08
I think I’ll just share most of its top secret. So we can’t really talk about it until it’s released. But we have released a couple chatbots. One for members of the public folks just wandering through. And so we get to watch the bot just converse with them about their specific issues. As you might know, pro se litigants don’t really know what’s relevant to their issues, or how to even think about some of their issues. Sometimes they may not even know they have a legal issue. And so we saw the bot just sort of crystallizes, the brain dump, they do, right

Debra Slone 17:43
We’ll throw in everything.

Sonja Ebron 17:45
Exactly. Yes, it’s sort of an organized list of where you got to consider this. And, and I know about that, and now and so just watching the AI that we’ve built, speak to the public in that way. It’s been really exciting. You know, and we continue to train with that information to continue to train and correct where necessary, but that’s been fun. We have a similar bot, though, that talks to Courtroom5 customers. Courtroom5 members about their specific issues and can’t say a whole lot about it. But that’s a different level of excitement. And just to see the guidance, I’ll put it carefully that the bots provide to our customers to help them find the right tools and information on our platform has just been really exciting.

Marlene Gebauer 18:33
I imagine that’s gonna be helpful. I mean, just in both situations, because, you know, we kind of hear about prompting and how challenging prompting can be about like, I’m thinking about pro se litigants where it’s like, again, they don’t know how to have a problem. They don’t know, the terminology. And this, this has got to be an incredible help for them.

Sonja Ebron 18:50
We think so we’ve heard that from, from our customers, for sure. And so, you know, things are, you know, things are better. With AI. I’ve been excited for it I’ve been working at well, not directly, but I was involved with AI very early on. I’ve been looking at it for 30 years and watching it grow, and just really excited to see the successes that it can have on a very difficult problem like the one we’re solving. So just excited for the future of it.

Marlene Gebauer 19:21
Very good. So, Sonja, you know about our crystal ball question because you’ve been on before, but we’re sort of doing this a little bit differently. So instead of a crystal ball well, we basically are asking everybody, you know, what advice would you give another couple who are considering working in the same field or working together in the same business like you are?

Debra Slone 19:44
My first would be, just commit to staying together. Just commit to your personal relationship first.

Sonja Ebron 19:53
You’ve got to have a basis in that relationship that’s, you know, solid foundations. If you’re going to build a business relationship on top of it, because it is, you know, it’s difficult. We’ve talked about some of the challenges and trying to silo conversations and keep things in their own lane. It’s, you know, building a startup in particular, is a very difficult enterprise. And, you know, if you don’t have a solid personal foundation to build that on, you know, it’s going to be more difficult. Both of those are going to be more difficult, but the personal and professional. On the flip side, though, if you do have a solid relationship, personal relationship, when you’re thinking about it, at least in our case, starting a business with your partner. Now, don’t do it, because it’s your partner and you want to spend a lot more time. That’s not the reason to do it. Right. That’s a great benefit, for sure, great benefit, but it’s not the reason. You want to choose a business partner who can add something significant to the business, right. That I think is really the secret to our success. Here. You know, we got Courtroom5 wouldn’t exist without I think either of us. But certainly Debra’s skill set is critical to what we’ve been able to deliver. And so you know, I get to think about who if I didn’t have Debra, who would be the co founder, I can’t think of anybody, honestly better suited to, to build this for Courtroom5. So you’ve got to have you know, you’ve got to satisfy yourself that you’ve got the right co founder, not just the right partner, if you’re going to do this work.

Marlene Gebauer 21:29
Well, it sounds like you both do have the right partners both in life and in business. So Sonja Ebron and Debra Slone. Thank you both for coming to The Geek in Review and sharing your love and Legal and Tech story,

Sonja Ebron 21:42
It’s been a pleasure to be here. Thanks so much, Marlene,

Debra Slone 21:45
Thank you for inviting us.

Marlene Gebauer 21:47
And of course, thanks to all of you, our listeners for taking the time to listen to The Geek in Review podcast. If you enjoy the show, share it with a colleague. We’d love to hear from you. So reach out to us on social media. I can be found on LinkedIn. And Greg can also be found at on LinkedIn and threads at @glambertpod. And as always, the music you hear is from Jerry David DeCicca. Thank you both. And thanks everyone. Have a great day.