At ILTACON 2018 in DC,  Anand Upadhye, VP of Business Development for Casetext, shared the perspective, not of a founder, but of a lawyer quitting a good job at a good law firm to jump on a legal tech startup rocketship.

Kevin O’Keefe: Who am I talking with?

Anand Upadhye: You’re talking to Anand Upadhye, VP of Business at Casetext.

Kevin O’Keefe: Okay, so you answered that question. I have a question for you. What causes someone to leave a job as a lawyer and go work for, at that time, a startup company, which you did in the case of Casetext. What causes that to happen?

Anand Upadhye:  What causes that to happen is realizing something is gravely broken in the way that business currently operates and for me as a litigator at a large firm that was legal research. What I was finding in my thousands of hours of legal research over my six years as a litigator was it was incredibly inefficient. It was prone to being inaccurate and attorneys were prone to missing cases. It appeared to me to be a space that could be really, really changed and changed fast.

Kevin O’Keefe: Why you? What made you click to do it. I mean you got all these legal tech companies that are sitting back out here. Different startup legal tech companies, and you have thousands and thousands of lawyers with real jobs that they went to law school to get.

Anand Upadhye:  Sure, real jobs. I had one.

Kevin O’Keefe: So you had one and you’re saying, “okay, I think I’m gonna leave this and go work for this company.” What was it beyond just what you saw that made you do that?

Anand Upadhye:  So being in Silicon Valley, it’s very much a culture of, if not me, then who? And so, as someone who had a lot of the experience, someone who felt the pain – another trope in silicon valley is no one can solve for pain better than the person who’s felt the pain – and boy had I felt that legal research pain. This was 2015, and the legal tech ecosystem was not nearly as developed as it is now. So, you know, uh, uh, the legal tech ecosystem was not nearly as developed as it is now. It was certainly hardly in its nascent stages, but you know, Casetext was brand new. It was a seed funded company, and there wasn’t a lot of buzz about that. So for me it was new, it was novel, and it was time for me to step up and try to fix it.

Kevin O’Keefe: How’d you find Jake, Pablo, the other people that founded the company. Did you find them or did they find you?

Anand Upadhye:  Yes. So I certainly found them and I found them because I was really looking for solutions providers in that precise area. As a litigator, I wanted to solve problems that attached specifically to litigators, and Casetext was doing a lot of very exciting things at that time and so I found them like a lot of other people in Silicon Valley on Angel List, which is a site where you could find startups. They had some very early press. They were in this incubator called Y Combinator in Silicon Valley. A lot of early signs of momentum. And when I met with Jake and I met with Laura in our office, I was sold. I mean, this was a team I wanted to be a part of.

Kevin O’Keefe: So you told them, “hey, I want to come work for you?”

Anand Upadhye: That’s right.

Kevin O’Keefe: Now will Jake say it was that way?

New Speaker: I hope so, I hope so. It was a point when Casetext was so early that they were getting a reasonable number of applications, but nowhere near the number of job applications as we get now when we post anything and a third Silicon Valley trope that I’m going to include in this three minutes is when you see a rocket ship, just get on, don’t worry about where you’re sitting. And that’s what I took to heart. So I applied for whatever nontechnical position I could get, and I got it. And since then I’ve kind of moved on to new roles with progressive responsibilities.

Kevin O’Keefe: What did peers back at the law firm say? Your parents, whatever. Did they say, are you sure about this? You went to law school?

Anand Upadhye:  Absolutely. In fact, one of the partners that I used to work for, great guy, told me, “hey, when this doesn’t work out, just come on back. Just please come on back.” And you know, it’s been almost four years.

Kevin O’Keefe: What do you tell somebody that’s in a law firm today? They’ve done okay in the law firm, they’ve been practicing for a few years, and they think there’s something greater out there.

Anand Upadhye:  The reading online about legal tech companies, there’s more on legal tech companies than there ever has been before.

Kevin O’Keefe: And a lot of that’s thanks to you Kevin.

Anand Upadhye:  Now, I don’t know about that. These peoples’ ideas is what it’s part of. What do you tell them? As far as starting to look around and start talking. Where do you tell them to go?

Kevin O’Keefe: I would really restrict it again based on the pain that you feel as an associate. And there’s so many different verticals or categories where associates are experiencing pain, and that’s why there’s this big boom in legal technology, whether it’s billing, analytics, document review, e-discovery. I found my little niche and that was legal research, but so many people out there are constantly trying to find out their niche.

Anand Upadhye:  I’d really focus on what, as a law firm associate, makes the practice of law troubling, or boring, or inefficient, or inaccurate for you.

Kevin O’Keefe: Today you could go around and find those companies that are starting to work on that stuff. You might find that somebody has just started. There’s people wandering the hallways here who aren’t exhibiting, are just here to take it in.

Anand Upadhye:  Absolutely, and there’s a lot of resources for this and we were just talking to Bob Ambrogi about this. LawSites has an excellent, excellent repository of legal technology, startups, and companies doing great work. Angel List still, and you can sort by legal technology. Find companies that are doing great things and if you are really experiencing pain, and you think you could create something that no one else has, think of a think of being a founder.

Kevin O’Keefe: Think of Michael Sanders, and Docket Alarm alarm, right? And we talked to another person here today from Singapore, with PING, who just couldn’t believe how silly it was, the inefficiency going into certain document preparation. All of a sudden you realize I’m going to start this.

Anand Upadhye:  So frequently. I think when people ask the question, “why has no one done this before,” there’s no good answer, and that that’s really a door opening for you to go start it.

Kevin O’Keefe: Thank you, sir.

Anand Upadhye:  Kevin, I appreciate it. Thank you.