Kevin speaks with Andrew Arruda, Founder and CEO of ROSS Intelligence. Together they discuss the difficulties facing startups, the growth of ROSS Intelligence, and the company’s latest Clio integration, at the seventh-annual #ClioCloud9 conference in San Diego.


Kevin O’Keefe: So who am I talking with? 

Andrew Arruda: Talking to Andrew Arruda. 

Kevin: And what do you do Andrew? Pretend like I don’t know.

Andrew: Well for folks who are tuning in who might not know, uh, I am the co-founder of a company called Ross intelligence and we operate within the legal research space. Our big thing was bringing in a kind of the latest and greatest in artificial intelligence into our industry. Um, that happened around four and a half, five years ago. Folks thought I was crazy. I think people think I’m still crazy.

Kevin: Maybe in and amongst lawyers you do.

Andrew: Uh, but, uh, today we announced the big Cleo integration and we continue to do some amazing things in the team is, we’re just honored to have been growing the way we have been.

Kevin: What were you doing before you founded the company?

Andrew: So I was a, a lawyer. I was an attorney. But the way that I like to say it is I’m a first generation immigrant and growing up my parents told me I could be anything I wanted in the world. So long it was a doctor, lawyer, engineer.

Kevin: That’s about right. My dad was an engineer. My mom was saying, you know, you can grow up to be a doctor or a lawyer or president of the United States.

Andrew: (0:59) Yes. Yeah. That, that could have been another option. And so I feel like, um, that was ever since I was a kid, I wanted to be an entrepreneur and I feel like, I do think you can learn aspects of entrepreneurship, but I do think a lot of it just comes innately from within you. And right when I was a kid I was, you know, setting up, um, a stand selling soda outside of, you know, the baseball park near my, in, in the local park. Uh, I had a lemonade stand, I was doing yard sales. I was always kind of doing something 

Kevin: So when you say “first generation immigrant” from where?

Andrew: So actually, yeah. So from Portugal, but the islands of Portugal. So there are these tiny archipelago in the middle of the Atlantic ocean. Two hours plane to Europe. Yes. So, yeah um, kind of in the middle of nowhere in many ways. And I think actually that has helped me in my entrepreneurship. 

Kevin: So has your family moved here. Your folks?

Andrew: Yeah, my folks, yes. So my, both my parents were born there, moved to Canada, um, met each other in Canada actually, which is funny cause they were both actually from the Island but uh, grew up in little Portugal. So I think that ingenuity and some of that, um, grit came as well. But I would say ever since I was a kid, I wanted to be an entrepreneur. I became a lawyer. And then once I started seeing, um, what was happening in law, I figured I could build a company in this space.

Kevin: (2:08) When, I mean at first off, Portugal is, Portugal and Greece are the two finest countries in Europe. Last year in the UK, we got on a plane and said “we’re going down to Portugal”. Yeah. For a week. Great great country. 

Andrew: It’s Beautiful. Yeah. 

Kevin: Um, so from the entrepreneurial standpoint, what did your folks do? I mean you saw the entrepreneurial thing and what, where did you see it?

Andrew: Yeah, I think, uh, my, my dad is in aluminum and my mom was a banker, so not necessarily entrepreneurial that way, but I think I got from them the entrepreneurship just being, uh, immigrants and from my grandparents who kind of brought everyone over in my community that I was living in. It was all about kind of thinking of ways to kind of start with nothing and kind of build up, you know, how are you going to buy a house if you like, just moved somewhere. How are you going to learn a new language? So there was a lot of that mentality kind of you’ll figure it out and hard work and um, being trustworthy and being someone that people, you know, respectable and all those types of characteristics that I think I got from them.

Kevin: Yeah, it is. When you talk to people, you talk to families that come to the States, we take for granted everything.

Andrew: Yeah. Yeah. 

Kevin: Some come that have professional degrees and come to the United States and they have nothing because they don’t have that professional degree anymore. They’ve got to find a way to support their family and like you said, “how am I going to own a house?” 

Andrew: Yes. 

Kevin: “How am I gonna allow my kids to go to college?”. Obviously, they all know it’s going to happen, but they aren’t certain how. 

Andrew: And I think actually that actually segues perfectly into kind of entrepreneurship because you are certain, you might find a problem, you don’t, you know what you’re hoping to do but you don’t know how. And so I think I’ve always kind of directly thought of that as my training, with this kind of burning desire ever since I was a kid. Um, coupled with, I think there was this moment where I, I actually remember the moment when I first started using the internet. I would sign up at a local library near me and I would, the first time I was searching before Google came out, I was on like Alta Vista. I was on like this and that. And then I, a librarian came up to me and said, “Hey”, cause they knew me cause I was always like trying to sign in for the internet. They’re like, “have you heard about Google?”. And I remember I typed in my first search and it changed my life because I was like, “wow, there is technology that is linking us all together and this is going to be fundamentally change. This will fundamentally change what it means to be human”. And so I think once I graduated law school, um, I was a lawyer so my parents were happy. Um, and also I think it provided me with a really good kind of, 

Kevin: (4:37) Where did you go to law school?

Andrew: I went to law school up in Canada up at University of Saskatchewan, which was amazing and I’m proud to be working with them still. Um, but yeah, so I finished there. I was at a law firm, actually. I was working at a small law firm, um, from the first year of undergrad. And actually I would take night courses at university and I worked there during the day in an administrative capacity, um, kind of filing things, uh, making coffee, anything they needed me. And I actually worked there for my first year of undergrad all the way until I finished law school. So by the time I graduated law school, I had been intimately aware of some of the challenges that lawyers face, particularly solo small law firms, um, in what they face. And so that’s kind of what was the impetus behind me collaborating with my cofounder Jimoh in starting Ross. 

Kevin: How’d you find your co-founder? How did you find each other?

Andrew: So that actually is kind of a fun story too. So, I was at an event in Toronto and a friend of mine, I was talking about how my original idea was by being at my law firm for, at that point six -seven years, as I was graduating law school, I said, “look, I want to build a small law firm that is connected potentially with other solos and small law firms so we could swap precedent documents, we could collaborate and we could start referring to each other. I just thought that technology could help facilitate that”. And so I was talking to a friend of mine who was in banking and he said, “Hey, you know what, if you’re passionate about technology, you should meet Jimoh. Jimoh is an AI researcher. And he’s really passionate about technology”. And so I went to an event, I met Jimoh and I started telling him about how I thought law should change. He was really passionate about changing law based off of some, some of the things that, uh, from his childhood. And he said, we went back and forth and then I started explaining to them how we did research. And I remember he was like, “wait a minute. So this takes all these hours from…?”. I’m like, “yep”. And he’s like, “you know how like, why don’t you do it this way or why don’t you do it that way?”. And I was like, “well, I mean that should happen”. And then he looked at me and was like, “why don’t we do this?”. And I remember there was this concept between he and I that we said, “someone will do this and kind of rethink the way you do research using AI”. And we just said to each other, “why it could be us?”. Because at that point, and I think that was that belief and whatever and just kind of, I think it was naive. We just didn’t know as big of a challenge ahead of us was. Kind of foolish. 

Kevin: (6:56) Whereas years ago when my best friend back in Wisconsin about, and we talked about getting things done and he goes, “you know, it gets harder the older you get cause you see the brick walls and you see the hurdles that you got to click”. Yeah, you’re younger, you have no idea how the pain points are going, what they’re going to be and how hard they are going to be. A clear, Oh you can see it. There’s the Valley on the other side of the mountain. It’s as clear as it can be like, “Oh of course we can do it. Why not? Somebody has got to do it. So we’ll just do it”. And then you have all these challenges. How did you, how were you able to fund that additional thing to say, “okay so we can live without, without food, without rent, we don’t have any money”?

Andrew: So at first we had moved into a basement and a lived off of, we had zero savings. So what we did was just started opening up different credit cards.

Kevin: Yeah. I did that three times. My first company, I took a $200,000 twice. Yeah. LexBlog went to about 50 or 75 a couple of times. 

Andrew: So you know what it means. 

Kevin: And back then we used to get 0% interest too.

Andrew: (7:57) Well ours was not zero percent. Like we were very happy when we first got our first investment to then pay off all that debt. But uh, that’s what we did. We kind of, we sat around it. I think it’s funny that you say that. We genuinely, I remember was sitting there and I’m sure if we had taped ourselves, people might’ve thought we were kind of crazy or delusional cause we were sitting there and we would say, “okay then when we do this, um, in a year or two this will happen and this will happen. And of course it’ll work out like that”. And I almost kind of like it. I’m glad that me and myself wasn’t there because I would’ve said, “Hey, that’s not how any of this is going to work out”. But it was, I mean, it’s been an extremely, uh, rewarding time, but it’s been so difficult in entrepreneurship. I think sometimes folks sometimes see the funding announcements or they see integration announcements or they see all these different partnerships and, and testimonials from our users. I’m so glad that we’ve been releasing more and more of this, but they don’t see like all those nights of sleepless nights and hard work, which makes it worth it. But as you know yourself.

Kevin: (8:50) Right? I mean, hell, I remember one time, we were probably a year and a half or two years in and we’re walking up the street stopping at a park bench and crying because I wasn’t sure I can make payroll and like three more payrolls. Yeah, pretty rough. 

Andrew: No one talks about that when you’re coming and going through their life.

Kevin: You figure it out somehow because you know you’re going to make it, you figured out a way. The next morning you wake up, next morning woke up and I go, “wow”. Rather than nuisance my clients by having them pay once a month, I can have them pay once a year. Yeah. So we’ll just email them and tell them as a courtesy to them. They can have 10% off if they want to pay by the year. Sure. We got a whole bunch of money within like two weeks and I go, “that problem is long sung”. 

Andrew: I love that story because it reminds me like sometimes when Jimoh and I are going back and forth on something that a problem we’re trying to, sorry. He’ll look at me sometimes and I’m usually kind of the, I’m the worrier. I’m like, “Oh, Jimoh”. He looks at me. He goes, “Andrew, you do realize that like two years ago we didn’t have this, we didn’t have this, we didn’t have this and we still weren’t as worried as you are right now”. 

Kevin: Yeah, that’s right. You just somehow you wade your way through it. And if you guys end up having a family, it’s a great role model for the family to watch. Their parents deal with this, this crazy fiasco of entrepreneur, entrepreneurship. You got married, how long ago? 

Andrew: (10:19) A few months ago. So earlier this year. 

Kevin: Oh, I was going to say like a year ago. But I’ve been able to see you do a little bit more to try to enjoy your life.

Andrew: That’s right. 

Kevin: You know, I was able to follow it on Facebook. See you guys take some trips. You know, when you get a chance to be happy. 

Andrew: Yes. Well I think that’s the most important thing. And I think if there’s anything for the folks who are listening in now or even gonna return and view this afterwards, I think one of the lessons I learned the most was how um, part of the amazing thing about being motivated by an idea you love is, is some of the danger as well. Because I could work for 24 hours straight on Ross and then I have forgotten about myself, my friends, my family, et cetera. And I think over the last, even before I got married, I think it was one of those things where I start to say to myself, how can I be more thoughtful in my life? Prioritizing myself? And I think part of that, and I was joking with you before we started the interview, that part of it has also come via our success. Once we’ve become as successful as we are, especially over the last year or two years, we’ve been able to hire such amazing people that have taken that burden. But that being said, it also is a decision as an entrepreneur that you have to make and how much of this are you going to be plugged in and taking those thoughtful breaks. And I’ve been really lucky to have an awesome life partner and we go out and we hike and she isn’t in legal. Um, and uh, but very good to bounce ideas off. 

Kevin: She’s a doctor, right? 

Andrew: (11:35) Yes, she’s a doctor. 

Kevin: I mean to just to get a whole different take on life. What do you think of coming to Clio?

Andrew: I’ve been coming for many, many years and I did the morning run this morning and I think it’s a fun story to kind of show. 

Kevin: I saw you guys. I was coming back and I saw these people, 20 or 30 people. I’m out running, uh, coming back and I said 20 or 30 people. I, this must be the Clio group or something.

Andrew: Yeah. But what was funny as early when those early morning runs would happen at some of the Clios in the past there’d be, you know, three or four of us, Jack included. Like it was more like, “Hey”, it was more like a conversation. “Do you want to go for a jog tomorrow morning?”, “Yeah, sure”. Whereas this one, there was coaches, there was sign up, there was so many people and why I think that really speaks to how much Clio has grown. And I think Jack’s opening keynote did a really great job in talking about how I think Clio has been one of the kind of indicators that you can easily check to see the health of the legal technology community at large. Like them getting this funding and what’s happening I think shows that our industry is maturing and I think this environment.

Kevin: (12:40) It is, but they’re a unique bird. Jack is a unique person. I remember meeting him before Clio launched. Um, there are a lot of things and we’re just sitting there talking in a Starbucks and he’s talking about, we’re talking about running watches. He’s like, “I really like this Garmin watch. I got”. He goes, “you know, I’ve, I’ve been running every day for X amount of years” and I’m going, “Really?”. I looked at Jack and I’m thinking “your a big guy, tall, big” and he has, he’s one of the people that inspired me to start running everyday three and a half years ago. But he’s a unique person. 

Andrew: He is.

Kevin: He, he sees things that other people do not. He’s really smart, very much a people person. People are just attracted to just hanging out with him. Like developing that mission that all of us have. But can you recruit a strong way as they do it to get people to leave better places to say, “I got to go to Clio because of the mesh that I don’t know anything about space”? I don’t even know anything about this space. I don’t know about this technology. It’s a very unique thing. I don’t know that it always happens. 

Andrew: (13:42) I agree. 

Kevin: Especially in legal tech. I mean, I think my gut tells me that you have that, that 250 million, that’s like a magnet. You’re going to have the people in the financial circles that can pick up distressed assets and legal tech and try to get Clio to buy them. 

Andrew: Oh yeah maybe. I mean, I think, well first of all, I couldn’t agree more about Jack as a leader. And as a matter of fact, a few months ago, we announced that Jack joined our team as on our board. 

Kevin: I saw that. That’s great.

Andrew: So why are we ducked out? 

Kevin: I was jealous. I said, actually, “why didn’t I do that a long time ago?”

Andrew: Well, well thank you. Yeah. So of course, part of that was because we hope to grow, in a similar way as Clio. And I feel like we’ve been making strides towards that, but I also wanted to ensure that we brought in someone that’s thoughtful, um, and as, um, just unique and just as special as Jack, uh, to help us guide because, uh, that’s come with, uh, as Jim and I have continued along with rosters where we’ve realized is there’s a lot of things that we do great. Um, but there’s a lot of shortcomings that we have as leaders and how can we bring the right people around that? And so, I couldn’t agree more about Jack, but I also think, um, what, what this has indicated to me is that, um, financially, uh, for folks to make that bet on legal, I think that’s huge. And I also think just once that announcement went up, uh, my inbox was absolutely inundated with almost any investor that has ever talked to me ever wanting to throw some additional money, which is actually, I mean, if you don’t do the right job with that, I think that’s a problem. Um, but I think, uh, that has certainly been something awesome because it allows us to kind of continue to expand and it shows that there are huge successes in our industry and in a very relatively short amount of time. I think we, if feels long with Clio, but things take it’s time. And it’s very fast. 

Kevin: (15:26) You just have 2000 people here.

Andrew: It’s amazing. 

Kevin: And that’s fast. Guess you could ask 10 years or 200? Could there be 5 or $7,000? It’s more like 5 or 7,000 more people here within another two or three years. 

Andrew: Yeah, I think so. 

Kevin: And then you take a look at, um, maybe even some of that stuff coming together as far as the inefficiencies and improvements in delivering legal services. Yeah, once that tilts, the model goes away, the model based on hours. Having a team of people that are billing $400 an hour so that you can make two and a half million dollars. You’d have a model based on inefficiency. Once that tips, using technology like yours, using technology like Clio, I probably could open up, I may be too shortsighted. Maybe I became more cynical than I thought it was going to happen. I number of years ago, lookin. 

Andrew: I mean we all wish it happens quicker, but I think like for example, the other day I realized that this like a, like the iPhone recently celebrated just over 10 years itself.

Kevin: It’s funny, right.

Andrew: Right. So I mean that’s something that if you think about on a subway or public transportation platform and someone had a smart phone now, everyone, we all just staring at our smart phones. But if you thought about five years ago, eight years ago, no one had one. And then the empires that were built on that, um, like Uber and this and Twitter, all this stuff. So I just feel like things happen faster than we think, but when you’re in the eye of the storm, especially cause we’ve been coming to Clio and we’re in the industry sometimes we obviously want it to go faster. 

Kevin: Thank you very much. It was great. 

Andrew: Absolutely.