Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

I met Ben Chiriboga, who is the guest on today’s podcast, when he reached out to interview me for his podcast, which is called This Legal Life. He interviews lawyers who are now working in legal-adjacent jobs.

So we met and recorded for his podcast, and in the context of that conversation, he shared some of his story, and I knew that it would be a story that would be helpful for a lot of our listeners.

So today I am sharing my conversation with Ben about his experience going from lawyering to being an executive in legal tech. Legal tech is something that comes up a lot with many of my clients as a possible career path. So I think that, and many other things that Ben shares, will be very helpful and interesting to many of you who are listening.

So without further ado, let’s get to my conversation with Ben.

Hey, Ben. Welcome to The Former Lawyer Podcast.

Ben Chiriboga: Hey, how are you? I am so excited to be speaking with you again.

Sarah Cottrell: I am excited as well. So for the listeners, so they have context, I recently spoke with Ben for his podcast, which he can tell us more about as we’re having this conversation. At the end of that conversation, I was like, clearly we need to have a conversation on my podcast, because you and I have a lot of, I think, similar experiences and also just thoughts about the experience of being a lawyer. So before I go on and on, let’s just start with you introducing yourself to the listeners.

Ben Chiriboga: Okay, if you go on my LinkedIn, it basically says: left lawyering at 30, found my home in legal tech. Today I help grow Nexl and create content about how legal careers specifically are evolving.

I think that’s a pretty good summary of where I find myself today. I used to be a lawyer. I found what my career path is within the legal industry and building legal technology companies.

My passion project is really understanding what’s going on with careers in legal. "How are they evolving?" I think it’s just such a fascinating thing to look at. And that’s, I think, a lot of what you and I resonate with.

Of course, there’s that post-lawyer but still adjacent kind of thing. But yeah, that’s kind of me in a nutshell right now, at least.

Sarah Cottrell: Amazing. Okay, so, well, I do want to talk more about the specifics of what you’re doing. But as you know, on this podcast we tend to start in a similar place, because many people have similar stories.

That is, can you tell me a little bit about what made you decide to become a lawyer in the first place?

Ben Chiriboga: So I know, you and I, like you said, we have very similar journeys, and our journeys specifically are very, I think, archetypal for many people who go to law school.

When I graduated from undergrad here in the United States—this was the mid-2000s, so 2004, 2005—I didn’t have a strong sense about where I wanted to go. I had gotten a dual degree in biology and art history. That’s only because biology—I was very interested in things like genes and evolution. My parents are both STEM people, and I was really interested in that, but I was also very interested in culture at the same time, kind of the evolution of culture and how things are going.

But I didn’t want to be a research scientist in biology, and I didn’t want to go work in a museum. So, like many people, I found myself gravitating toward legal, not so much because I really knew what lawyers did.

I didn’t know lawyers in my personal life, but very anecdotally in terms of what they did. And I had really no sense about what they did on a day-to-day basis.

At this point, I was only 21. I was fairly young in terms of my life experience. What I had done at this point in time was mostly just excel in school, excel in sports, and try to follow this path. So I landed in law school with this idea that, “Well, it’s kind of the next thing. Lawyer seems to be a profession that…”—both my parents are professionals, so it was something to kind of land into.

That’s kind of how I went through law school. When I got out, I was kind of given the career advice, "You can either go work for the government, go work in-house at a company, or go work for a law firm."

I just so happened to pick the law firm route. That’s really the entire driving impetus—at least externally, that was the driving impetus—for why I went into becoming a lawyer, basically.

Sarah Cottrell: Yeah, it’s so funny. Well, I don’t know if it’s funny. It’s funny to me because so many people—even though often we have very different backgrounds—have a somewhat similar story about how we ended up in law school, which is kind of like, “I was good at school, and I graduated with some degrees that I wasn’t 100% sure what I wanted to do with. And law school kind of made sense as a next step.”

I think for a lot of us too, we have that experience of not really having a good sense of what it is to be a lawyer. I didn’t have any lawyers in my family. It wasn’t like I was going to law school with some super well-formed idea of what I was going to be doing.

I’m curious for you, you said you ended up at the law firm. A lot of people will say that they ended up at a law firm because they went into law school without a particular idea, and that’s just the “easiest” path that’s presented.

I’m wondering if that was the case for you, or if it was a little bit more like, “Oh no, I definitely want to go in this specific direction.”

Ben Chiriboga: No, it wasn’t. In my case specifically, I basically got myself into the law firm path because, after law school, I came back down to my hometown of Miami, Florida. I had a lot of people in my network back home. I was back home, it’s obviously a fairly big metropolitan city.

I happened to already know a lot of lawyers, specifically lawyers who had their own practice. So again, I followed the path of least resistance, let’s say.

So the first factor was a lack of a clear path, a lack of a sense about what should or should not be done for myself specifically in terms of my career path. I wasn’t really thinking in that sense about what was best suited for me or my personality.

This is a bigger motif in my life, which is kind of an awakening and a sense of starting to be much more reflective in my life. And this aligns a lot with my career journey.

But I’d say the last thing is that at that point in time—this is 2007, 2008—there was such little exposure for myself, even coming out of law school, to what was even tangentially possible with a legal degree.

On the one hand, I was so underexposed to what was tangentially possible, which in the end, I had no idea that there was an entire industry called technology that sold things to lawyers, or even legal innovation, which was just having its first kind of foray, which would have been such a better fit for me.

But I was so underexposed to that, and I was never steered to it. And also, I myself—as I was saying—was very reflexive in terms of what I was doing mostly.

I was looking for a path that I could perform at. And this was part of my overall inner journey. What I realized is that I was looking to continue a path that provided me the opportunity to perform.

As I’ve gotten older, I’ve come to understand that in the past, I’ve used performance as a way to feel safe, in a way. I’ve naturally gravitated throughout my life into arenas that were very high-performance because I’ve equated performance with the idea of giving myself safety, by effectively getting gold stars and all of this kind of thing. I can say a lot more on that.

But to answer your question very succinctly, it was more the path of least resistance and a real underexposure in terms of what else was possible at that point in time, with a kind of, let’s call it subconscious drive toward things where I felt like what came very natural to me was competitive, performance-type environments, effectively.

Sarah Cottrell: Yeah. It’s interesting. I want to amplify that point about performance. I think we talked about this a bit when I was recording for your podcast.

By far, one of the most common things that comes up for people who I work with when they’re starting the process of trying to figure out, “I don’t want to do this. What is it that I actually want to do?” Most people will have a realization—or have already had this realization—that a huge part of the decision-making process for them, in terms of going to law school and becoming a lawyer, is that approval through performance piece or approval through achievement.

I think the legal profession in particular, and I know I've talked about this on the podcast before, but the legal profession in particular is so prestige oriented that I think if you are someone who finds safety and security in performing, which lots of type-A/gold-star-getting/twice-exceptional/gifted kids/whatever do, the legal profession looks very safe.

I think the challenge becomes, once you’re making a series of choices based on how you will be perceived by others, it creates a trap where you then have to continually perform in order to feel like you are a valuable person. I wonder if that resonates with you.

Ben Chiriboga: Of course. That’s a completely accurate depiction of exactly my own journey, if I could put it in my own words, even though you did such a good job of summarizing it, at that point in time, my ego, let’s use psychological language, because it’s a good way to ground my ego, which in the first half of your life, from basically the time that you're, let’s say, six or seven years old until mostly your 20s, you develop an ego mostly for purposes of helping you exist in the world.

Now, depending on where you exist in the world and what you’re doing, that ego will also drive you to be part of a culture and fit in with a culture. Sometimes people stop there in terms of their development. Then sometimes people break through, where they start to have a realization.

In my case specifically, my ego had really driven me to understand a very simple algorithm, which is—because I grew up in high-performance environments previously, in terms of high school and friend groups and competitive sports and just a competitive environment all around me—I came to understand that good performance equals psychological safety and approval, effectively.

So that’s what I totally subconsciously chased toward. And now I see that’s what brought me into law firms, legal industry, all of this because it was a familiar territory.

Now, I love your extension, which is: fear-based motivation and external approval is basically the quickest way to burn out. That’s what we see a lot today in the industry, which is a lot of people kind of driving themselves through performance right off the cliff, effectively.

And in my case of myself, basically, by the time I hit 30, I was really struggling with this paradigm. It really wasn’t working for me. My ego was overdoing it and driving me into ditches.

Then, what typically happens is there’s a small voice inside of you that starts to whisper in your ear. It’s something else. There are lots of ways to describe this, but to use—to keep up with the psychological language—it’s something like your more true version of yourself. Or, let’s say, your soul, if you like this kind of mythological language.

I do, because on my podcast, I use the Hero’s Journey. So this mythological language resonates with that part of ourselves. But basically, it’s something like this. And many of us go through this but sometimes find ourselves trapped in one way or another.

So I’ll leave it at that. But it’s the ego overdriving that eventually puts you into this place. What served you earlier in your life ends up not serving you later in life, effectively.

Sarah Cottrell: Yeah. And I think it creates a lot of confusion for people. I mean, certainly speaking from my own experience, it created a lot of confusion for me because I had a similar trajectory to you.

I went from college to law school, got out, started practicing. Pretty quickly, I was like, "Eh, I don’t love how this feels." But I really had no context for something not feeling right, but being something that I was good at.

And that sense of, "Oh, well, if it doesn’t feel right, then maybe that means something else is better." But there was just no category for that in my brain.

That’s why I’m wondering for you what the experience was at the law firm in terms of how quickly you started to think, "I’m not sure that this is exactly right for me." What did that look like?

Ben Chiriboga: Yeah. In my sense, I think that on the outside I was performing well, all those things. Making high income for a person in their 20s and performing well. All of those check stars and those gold stars that you would pursue on a professional path.

What I quickly realized was that I was leaving a lot of myself along the road whenever it came to creativity. Whenever it came to a certain performativity in terms of the way that you had to look, act, sound, whenever it came to being a lawyer.

In my case specifically, I really wasn’t able to bury that much. And so, there started to be a really big dissonance in my life between what is the high-level performity that I’m doing—just in terms of even my own values, what I wanted to see in the world, etc.—versus my day-to-day within my career.

Now, I want to back up and say, this is something that lots of people in their 20s go through. I just think that in the context of something like the legal industry, these things become very attenuated very quickly.

And it just depends on how poorly—not poor—but how much there’s a, to use a fancy word, a dialectic between what you’re doing externally within the context of your job, versus what you more feel is a more unique version of yourself, which you start to understand a little bit more as you get into your 20s.

So these two things tend to start to run up against each other. Now, you’ll see that what I jumped to in my 30s is something that’s at least a little bit closer to what I think, at this point in time, is a closer version.

It’s technology. It’s about progress. It’s innovative. It’s transcendent. It’s reaching for the difference. It’s always trying to make change.

So this was what was being confined and needed an outlet. And that’s why it was rubbing up against me. It was really an identity thing, specifically around how much I had to package and pull away, vis-à-vis what I was coming online with and asking for an outlet, if that makes sense.

Sarah Cottrell: Yeah, I'm wondering. I tell people, among other things—and this is such a common story, I mean so, so, so many lawyers tell me something similar—but I literally would cry every day, either on the way to the office or I'd get an email that was a completely innocuous email. It wasn’t like someone was being how sometimes lawyers are. My window of tolerance was so small that pretty much anything could trigger it.

I fortunately had a husband who was like, “Hey, this isn’t normal, and also, this isn’t happening because you are a bad person.” Because, of course, a lot of lawyers have this sense of, “Well, if I can’t 'hack it' in some way,” whatever that is—I’m doing air quotes that the listeners can’t see—“then it’s a moral failing on my part.” I really had him as an external observer to say, “This is not good for you, and that’s okay.”

I'm wondering if you, in your time at the law firm, had similar things? And then, what ultimately got you moving in a new direction?

Ben Chiriboga: Yeah. In my case specifically, I think it was that I didn’t really have external validation. I only had my parents, who are professionals, and of course, as parents do, they want to keep you safe, effectively. That’s their core coding.

In my case specifically, I had a lot of friction against the idea of leaving and all of those kinds of things. I had come up in a culture around professionalism, both in terms of some of my friend groups and let's say the class and culture in which I had grown up.

Specifically, really the idea of sunken cost—the time and effort that I’d put in—and then even more deeply, psychologically, this idea of performance. That performance keeps you safe. You are worthy if you're validated based on the type of performance and the type of output you are able to do.

There are different types of outputs, and professionalism within a certain culture and a certain time is like the highest of value. So a lot of good, positive, extra recognition.

I had all of that that I was pushing up against. And yet, the reality was I was engaged in some pretty destructive behaviors myself in terms of trying to deal with this dissonance, when it came to alcohol, etc. Just ways to numb myself in this context that I eventually realized, "This is not sustainable from this perspective," and something had to change.

My 30th birthday, as you know, to be so cliché about it, I traveled. I go travel abroad. And of course, throughout the ages, traveling abroad and getting out of routines, I took two and a half weeks off after a very large case. It was kind of like a Julia Roberts Eat, Pray, Love moment, which travel tends to do. It gives you this ultimate window.

It was the combination of three things: one, a milestone; two, the ability to get a little perspective; and three, an understanding that I woke up and saw, “Wow, I’m doing some really destructive things to myself in order to cope.”

At that point, I wasn’t married, didn’t have family, and all of this, so I just took a risk and jumped into this new life. And that’s where I found myself, effectively.

Sarah Cottrell: How did you decide where you were going to jump next? Was it just anything-that’s-not-this that seemed like a decent option? Can you talk a little bit, of course, for the listeners, about what your process was, if any?

Ben Chiriboga: Sure. Let’s use mythological language, we have very old words like fate. We love the fate story, which is the strange thing that happens that puts you onto this path and some of our greatest, oldest stories of humanity are all based on twists of fate because it's basically deep and you could almost say that it's something that happens to all people.

The case that I was working on, maybe for a year or year and a half—this is 2015. While this whole dissonance of “what’s going on for myself” is happening, in 2015, this was the first wave of early artificial intelligence starting to creep into law firms.

Specifically, it was getting its use cases in things like e-discovery. As a litigator at that point in time—a senior associate litigator, basically steeped in discovery—I quickly ran into this idea that: one, discovery is just a broken process. Secondly, somehow, some way, we got into some e-discovery tools that applied early artificial intelligence.

Just to nerd out for a second, it was natural language processing, a subset of machine learning that basically you teach it to look for certain things. In this case, the e-discovery had been able to find semantics.

It was like a movie. I’d been working for months and months, and this computer came in and did in six hours what I hadn’t been able to do in six months.

So I saw this writing on the wall, while this psychological story was also playing out. These two twists of fate happened just so—and I say “twist of fate” because there would’ve been no reason for it to happen except for the fact that it was a large case with an inordinate amount of e-discovery.

Somehow, they made the decision to basically bring this date. This had never happened in my five and a half years prior—even though we had similar levels of discovery in all of that—so it was just a twist of fate, some random thing, some random time that they had gotten this sniff that like, "Oh, let's try this e-discovery thing," at this point in time and I saw it.

That laid the groundwork for where I felt I could be because I saw the application of what I had been doing and done in a completely new way through technology and I just put two and two together and that really allowed me this jump. So I left, I left Miami, I packed my bags, I moved up to New York and in New York right at this time is just this first wave of kind of what I call legal tech 2.0, which your listeners will remember as this is 2015, 2016, it's like the time of early applications of AI for reviewing contracts, it's like chatbots, it's like automation for workflows, it's CLMs like contract lifecycle management, it's like updated practice management systems like Clio are starting to gain.

So this whole thing is gaining momentum. It's happening a lot in New York specifically because of the confluence of money and venture money in New York, large law firms that are all based in New York, as well as technology kind of starting to poke out and get into these firms at this point in time, and venture type of companies, which are venture backed legal tech companies starting to poke their head above water, which really hadn't happened in the previous 10, 15 years before that.

Sarah Cottrell: Yeah, I'm wondering, you talked about having this realization of like, "Oh, I like go to performance because that's something that makes me feel like emotionally safe." I'm wondering like, where in this trajectory of moving over to a legal tech type job and all of the other things that were going on, did you start to have this realization? Was it like concurrent with the whole, I'm turning 30, I'm using alcohol in ways that I don't want to, which is very common for lawyers, like exceedingly, exceedingly common, or was it sometime later? Can you talk a little bit about the relationship between those two?

Ben Chiriboga: Sure, I think it was happening really, I map it like this. Like my 20s is basically where this kind of breakdown starts to happen in terms of, wow, what I'm doing on the outside doesn't really match what I'm feeling on my inside.

I make this break in terms of my 30s and in my 30s, I really pursue what I think of as a more unique version of myself working, working in legal technology. The what ends up happening—and this is, I mean, you remember maybe from your hero's journey—you know there's always a call to adventure at some point in time which really affords kind of like an off-ramp. If you happen to take it, it affords you this off-ramp into what you're being called.

Because The Hero's Adventure is just one big story about psychological transformation effectively. That's where you have this kind of like realization and you kind of have to like take the off-ramp to eventually get to a point in time where you build yourself up to what's a more unique version of yourself, let's kind of say. Did that answer your question or do you want me to go a bit deeper?

Sarah Cottrell: Yeah, I was going to just say, do you want to talk a little bit for the listeners about what you were doing in legal tech over that time and then maybe after that we can talk about the relationship to some of the things you were just mentioning?

Ben Chiriboga: Sure. Okay, so I jump into legal tech and I just want to set the record straight, I feel called to be, as at least from my perspective, as specific as I can to this. The transition from going from a maritime lawyer to working in legal technology and now eventually helping start a company and become an executive at a fast-growing company and all of that, that transition is not without its ups and downs.

To be very blunt about it, you’ll basically have to relearn most of your skills to be able to get into sort of, let's say, a position like that. Now, you have one thing, and I'm breaking the fourth wall and speaking to anybody who wants to get from a lawyer to tech and eventually a leadership position in a technology company—you really have the one thing.

Skills can be learned. You are smart people. You have something that many people within legal technology is incredibly important, which is this idea of, you have legal industry culture acumen, not legal acumen. You have legal culture acumen, which is much different, which is a lot of what you and I are just talking about. You understand the inherent structure, the power relationships, just the overall zeitgeist of what it is to be in legal, and that's very, very important for this.

So I'll go back to speaking more narratively. So I jump into legal tech, I come into New York and of course, the first thing that I try to do is I just try to be a lawyer for legal tech companies. And so that's my first foray. I have to pay my New York rent, all of this. I have a little bit of money saved up from my legal job, but that's effectively what I'm trying to do within the first year.

You know, I'm not really getting any place. One, because I'm a maritime litigator. What do I know about being an in-house tech lawyer? So there's not a lot of credibility. Let alone, I sort of—this is just me, you know, if you're on this path, let's say, let's use my Hero's Journey thing—if you're on this path, the first part of this path is you're always met with a lot of resistance because you have a lot of baggage from your previous life and a lot of impostor syndromes.

If you're following me, it's natural that you fall back on what you initially feel most comfortable with even if you're trying to do something new. You get a lot of resistance from this—because basically, and I know that this is in your story too a little bit, I remember a little bit—so basically, it's never going to work out. What your—let's use myth language again—what your soul wants you to do is cut ties and do the scary thing, which is walk into the dark, effectively.

So the lawyer-for-legal-tech thing didn’t really work out. So I had to effectively—I was basically running out of money. I was draining my savings down, just kind of living in New York trying to get into this thing, simultaneously trying to get like clients that kept me above water but not really like wanting to do that.

So I was kind of like putting up barriers for myself while also trying to teach myself all of these skills to see what was I going to do in tech.

Eventually, again, a twist of fate. This always happens in the second act of The Hero's Journey, which is right when the hero is almost about to fail, there's some very strange synchronicity that comes along and saves them. But it's only after they've kind of committed themselves to do it.

In my case, I was down to literally the last, like my last rent check of my whole savings. So I had spent all of the money that I had made. I was like 32 years old and I was down to basically my last rent check.

Now, that's okay. I wasn't married, didn't have family, da-da-da-da-da. So what's the worst that could happen? I go sleep on my friend's couch or something like that.

Yeah, but I was basically down to like my last rent check, effectively. And wouldn’t you know it, some random card, I had been passing out flyers a year and a half prior at New York Legal Week.

I passed out some flyers to some legal tech company which was talking about how to accelerate sales. I was just putting out offers about accelerating sales and revenue and things that legal tech companies care about.

Wouldn’t you know it that somebody kept—for a year and a half—one of those flyers that I handed out to some random legal tech company. They called me because they were looking for basically somebody similar with my profile to take up a sales job. Their first sales job that they needed to have a litigation kind of like background and a lawyer background, and that's the profile that they were looking at to fill this role. And they just had looked at me and they called me out of nowhere.

So I was dating my now wife, and I was down to kind of like our last rent check. And I get this call. And I end up getting this job that basically allows me to continue to pursue this, effectively.

Sarah Cottrell: You know, it's interesting because I think a lot of people would hear that story and be like, "Oh, well, that is not very encouraging because it was so random and it was such a one-off and et cetera, et cetera."

But one of the things that I have seen in the stories of people like over and over and over and over and also lots of the lawyers who I work with is that I think as lawyers we often think the way we get to the next thing is by pre-assembling some perfect attack operation, right?

Ben Chiriboga: Yes, exactly.

Sarah Cottrell: Ninety-eight percent of the time, the next right thing comes through some type of networking that you don't necessarily expect to result in a thing. That can be really difficult when you're still in the process and you don't have a lot of clarity about what you want to do because you can kind of feel like you're just waiting for something to happen and you don't know what that thing is.

But I think it also is really helpful for people who are thinking about, "Yeah, I do want to leave this eventually," that you don't have to do these extremely complex, convoluted things. You can literally just be making connections with people.

Ben Chiriboga: Yes.

Sarah Cottrell: That ultimately is in many, many, many cases what's going to result in the next right option for you in terms of a job.

Ben Chiriboga: Yes, totally. Let me put some more meat on that actually because it's so deep. I talk in terms of myth language and synchronizing and all that just because it's the most, I feel like the most encouraging storytelling way to say this and it gets to us at a deep level.

But I liked what you said on our podcast, which was we think that clarity drives action, but actually action tends to drive clarity. You said that and that's pointing at the exact same thing.

But let me even be more specific about this, which was, in my case, I basically tried this very strategic, kind of like, "Okay, so first I'm going to become a lawyer for legal tech, then I'm going to become their general counsel, then I'm going to go from general counsel to being the COO, and that's going to be the chart of all of this," and basically all of that failed.

All of that didn't work out. What did work out was just trying a lot of things, just actioning things. Eventually, yes, my whole thing is like, "My God, down to the last rent check, I could never, all of this." But that's just maybe my personal version of this. You've heard so many versions of this that basically it's this action affords clarity of next right step.

I think that when you're still committed to this very "clarity equals action," it's what needs to be unlearned effectively to get there. So again, in my case, it's like I had nothing to lose because I tried the very strategic, plotted-out thing that had worked previously and it didn't work, you know? So I had nothing else to lose except for try things, effectively.

Sarah Cottrell: Yeah, and I think a really important piece of this too goes back to what you were talking about in terms of having been conditioned to see performance and achieving as what creates safety for you.

It is very hard to take action without clarity, which is what you have to do in order to get clarity and move forward, if you also have a pathological fear of failing and therefore not getting approval and therefore not being emotionally safe. This is the case for so, so, so many lawyers.

This is why, in the process, in the Collab that people follow in the framework, one of the most difficult parts for people is when they actually have to start taking action. I don't say this to be like, "It's so ridiculous because it's so easy to take action." It is not.

There's a reason that I created this podcast and the framework and all of the things. It's that if you are not aware of the degree to which you rely upon performance and achieving in order to get approval and emotional safety, it will be very hard for you to take the action that you need to get the clarity that you want.

Ben Chiriboga: Yes, totally. You know, to use my language, I've gone deep in this now that I've had the space and kind of the maturity and quite frankly, the life story to map onto this.

Your ego is there. It's so strongly coded into you. We're basically born to develop an ego that effectively keeps us safe. Then we are encouraged by almost every single incentive around to stay within these bounds.

So there's nothing wrong with you if you feel resonance. In fact, it's completely normal to feel this because it's psychologically wired into you to form this kind of architecture.

Some of us, because of our own life story and our own life path, tend to overdrive this maybe a little bit and get a little too calcified and stuck in that, but it's completely natural. Everybody feels this tension to some degree or not.

I would just say that the legal industry tends to maybe attract a certain type of people, effectively, and then filter these people through so that only people who resonate with this kind of structure are the ones that end up being in there.

But yeah, this is just to say it's completely normal. There's nothing wrong with you. In fact, everything's kind of working right, except until it doesn't serve you anymore.

Sarah Cottrell: Yeah, the legal industry is full of people who have learned that performance and achievement is what keeps them emotionally and otherwise safe.

Ben Chiriboga: Yeah, and the validation that they get from it, which is a lot of the cultural bedrock on which the industry is built upon, works to revalidate that over and over and over again.

Sarah Cottrell: Yes, which, of course, it's one of the many reasons why I'm always talking in the podcast about how, "If you are not in therapy, please, please, please, please, please see a therapist. My personal preference is for a therapist that practices from an internal family systems perspective, and you can Google that if you want to." But yeah, this is why. Because it's just so huge.

Ben Chiriboga: Just really quick, my own therapy journey was incredibly important in helping me understand this, you know? It's like the coaching and the frameworks for basically making subject object, which you can then start to work with and grab a hold of and, quite frankly, stop allowing it to dramatize you into spirals is one of the greatest gifts you can give yourself, quite frankly.

Sarah Cottrell: It is, it really is. Ten out of ten, I approve this message. Okay, can you talk a little bit for the listeners, can you catch them up to where you are today and what you do today and all of those things?

Ben Chiriboga: Yes. Okay, so today, if we go out all the way to the beginning, today I'm an executive at a legal tech company called Nexl.

Now Nexl tries to solve one specific problem, and we try to do it in a way that is really simple. That is, we try to help lawyers understand their relationships with their clients on a deeper level.

Now we do that by creating a software called a CRM. A CRM is a customer or client relationship management software, and basically that's a really fancy way of saying this is the best address book and the deepest address book you will ever have.

The legal industry is basically an industry that is based on relationships. In a world where artificial intelligence and automation and competition and global competition effectively is going to make the work product, I think, of most law firms really come up to a parity, what we think is that at the end of the day, the quality of the relationship that you have with your clients and with your network specifically is going to be the differentiating factor.

Now, this is an old software that we are taking a new take on because we've built it in the modern era using modern technology, but that's basically the problem that we're trying to solve.

As an executive at this company, I'm really responsible for thinking about the future growth of the company. Now I can start to go into a lot business lingo but it's effectively like what type of next products and services are we going to deliver? What's the next market we're going to go after? What problems are we looking to solve that we're not solving today. So I start to put myself in—where to use the Wayne Gretzky American sort of thing—where the puck is going, and I try to skate to there and try to get us there.

So today Nexl is about 75 people. We have over 100 law firms that are using—10,000 lawyers use the system—and it's really with one single thing: to give you a better, deeper understanding about your relationships and the quality of your relationships with your clients and with your network.

Sarah Cottrell: Awesome. And how long have you been there? Can you talk a little bit about your roles that you've moved through as you've been in legal tech?

Ben Chiriboga: Of course. So I'm part of the founding team at Nexl. I've been there since the beginning and really, I mean, I've done everything there from, in the beginning, handing out flyers.

Sarah Cottrell: I was going to say especially when you're on the founding team, you're like, "I have done all of the things at the same time."

Ben Chiriboga: Yes, exactly. So it's been fantastic. I would recommend anybody who's really interested in moving into a technology role, if you're a lawyer, really just getting in on the ground floor.

Again, you'll have to confront some of your insecurities around not knowing things. That's basically the whole name of the game. But at the same time, you'll really get the chance to stretch yourself both intellectually and operationally by doing this, and you'll eventually garner all the skills that you'll need to push yourself very quickly into what you want to do next.

In the context of specific stuff that I've done, you know, it's everything across customer success and sales and marketing and growth and building teams, hiring, firing, building technology, product development, all the rest of it.

That's really what it takes to work at an early-stage company that's hoping to grow very quickly. So it's truly such a generalist role that affords you a lot of stretch opportunity.

Sarah Cottrell: Okay, Ben, as we're getting to the end of our conversation, is there anything that you would like to share with the listeners that we haven't talked about yet?

Ben Chiriboga: You know, as I look back—I'm now 40 years old—Sarah and I share a very, not the exact same birthday, but very close birthday, right, almost birthday twins.

So for all my Gemini people—no, I'm just kidding. Outside of Gemini, we love all signs here. This is like a, of course, Gemini personality.

But, you know, I would say that as I look back now at 40—to put a very fine point on it—in my 20s, I started to feel kind of like an emotional dissonance between what I was doing versus what I felt was a more unique version of myself.

This was totally fair and something pretty realistic for most people as they go through their 20s. In my 30s, I made this jump and I went into technology, and I really tried to grab the more aspirational versions, more creative versions of myself, and that's been fantastic as well.

As I enter into my 40s, I'm really starting now to think a little bit more about things like meaning and what draws the most meaning for me, especially as it relates to other people, and really try to get to know myself a little bit even deeper from parts of me that I've been ashamed of or that I just haven't integrated into myself.

This is all basically to say that, as I've thought about all of this, I came into my professional world thinking that my value was in my output and in my performance as it related to things, and I thought that that's all that mattered.

And now, as an executive at a successful tech company, having done all of this and made all of these transitions, I really have come to see that truthfully, I think what we all truthfully give one another and into our professions is just our unique story and our unique life. That's what we really put in.

So that's a long way of basically saying that your story, your life experience, is ultimately what is most valuable. And that's through the ups and downs and everything in between. That's really what you donate into the world—I think the professional but also the personal world—at the end of the day.

Sarah Cottrell: I love that. Ben, if people would like to connect with you, where can they find you on the internet?

Ben Chiriboga: On the internet, well, the easiest place would probably be LinkedIn, where I'm the only person—except for my cousin—who has my name. So Ben Chiriboga, you can get it in the show notes and stuff.

So hit me up on LinkedIn. I would love to be connected to you. I would love to hear your story at some point in time. So if you're out there and what we've spoken about—Sarah and I—has resonated with you, and you have something to share, and you would like to share your story, like I just said, I would love to feature you on the podcast. So please reach out to me.

Otherwise, you can email me: [email protected]. Those are probably the two best places.

Take a listen to the podcast where we really try to go into the story. So if you are a lawyer or somebody in a similar career—obviously, you're listening to this podcast for one reason—if you want to hear what other people are doing in their lives, in their legal lives that are legal-adjacent, check out the podcast.

That's why I do it. I do it to a younger version of myself that hadn't been exposed to this. My hope is that if people hear this, they can get on this path and get themselves to where they feel like they need to be.

Sarah Cottrell: That is amazing. Well, as you know, I am a big fan of story. For the listeners, can you share the name of the podcast one more time so that they know what to look for in their podcast app?

Ben Chiriboga: It's This Legal Life. So you can just look This Legal Life. Probably just search my name actually, and you can probably find that as well, but This Legal Life, yeah.

Sarah Cottrell: Amazing. We'll link that in the show notes, et cetera.

Ben Chiriboga: Awesome.

Sarah Cottrell: Okay, well, Ben, I really appreciate you coming on the podcast and sharing your story. I think that there are so many things that you shared from your experience that I know so, so many people who are listening will relate to. So thank you.

Ben Chiriboga: Thank you. You are a wonderful host. It's so good to sit down with you, my Gemini twin. It's awesome. We got to do it again soon.

Sarah Cottrell: Yes, for sure. All right. Thanks.

Ben Chiriboga: Thank you.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.