Speaking with James Pittman, co-founder of Docketwise, fast, intelligent and intuitive immigration software for preparing your immigration forms, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

James Pittman: I’m James Pittman co-founder at Docketwise

Kevin O’Keefe: And what is Docketwise?

James Pittman: Docketwise is a web-based platform for preparing immigration cases. So an attorney creates an account on Docketwise, and then we have a system of online questionnaires for collecting biographical data from the lawyer’s clients, and then seamlessly populating that into government immigration forms, creating tremendous efficiency for an immigration lawyer.

Kevin O’Keefe: So as opposed to a lawyer coming in and getting a legal pad and jotting down all types of stuff, or going on word documents, or filling in blanks form after form. You’re asking the types of questions that will be needed to complete a whole series of documents that could all ultimately decide the track of what forms should even be needed.

James Pittman: Well, we have our bundled questionnaires which have some decision-making features within that, and we had those for family immigration and for US citizenship cases which we call naturalization. And the idea is to dispense with a paper questionnaire. Right. And the idea is to dispense with a paper questionnaire. So you know, the attorney staff can either be entering the information into the database or you could send the client a link, and they can enter it remotely on their side. Data goes into the account, it’s recognized by the account, and then when you create a form that asks for those bits of data, it’s populated into the form.

Kevin O’Keefe: When did this start up?

James Pittman: We’ve been around for about four years.

Kevin O’Keefe: What were you doing before?

James Pittman: I was an immigration lawyer, practicing immigration lawyer, at my own firm. I did that for about 15 years. And with various types of cases I had a lot of family immigration, removal defense, humanitarian cases, business immigration.

Kevin O’Keefe: Did you ever see yourself, when you started being an immigration lawyer, that you’d be starting a legal tech company at some point?

James Pittman: What I was interested in was going to the next level, after helping hundreds of individuals with their own cases, I was looking to take it to the next level, and whether that was going to be in the policy realm, I wasn’t sure. What had happened was a former client of mine came to me after his case was completed and said, “you know, I’m a tech entrepreneur, I have an idea for a company, a new startup around immigration. Do you want to be part of it?” And I thought this is an amazing opportunity. Here it is, this is the answer, right? So now I have a chance to have an impact on the field as a whole, which is just amazing

Kevin O’Keefe: So when you started this thing, how’d you guys get it off the ground? You have a former client come to you, you look at this and go, well, it’s really cool.

James Pittman: There was about a year of solid backroom planning of the logic and doing the development of the aesthetics of the site, the basic coding involved, before it actually went live. And then ultimately it went live, and first it was reaching out to lawyers that I knew, to sort of get them on board, to have them try it out. And we beta tested it with some immigration lawyers that I knew, and then after that the next step was to just start selling and go around to conferences, lawyer conferences, and other events. And then, you know, marketing.

Kevin O’Keefe: Who did that, who went out to the conferences and did the selling?

James Pittman: I did. Sometimes my partner, Jeremy Peskin, who’s our CEO, would come to the conferences as well, but mostly it was me.

Kevin O’Keefe: Was Jeremy the coder side, or the tech side?

James Pittman: He is, yes. He is the head of the development team and, coordinates all of our software developers. We’ve got people in a couple different parts of the world working on it. And he keeps that altogether and plans their priorities.

Kevin O’Keefe: So you’re out there and just said, “okay, now I’ve got to go out to conferences.” How did you take to that?

James Pittman: I liked it. I mean, I like interacting with colleagues, especially immigration law colleagues. I really do. And I used to go to a lot of conferences back when I was practicing, so they were events that I was already familiar with, so I was in a position to really know how to capitalize on that, so I quite liked it.

Kevin O’Keefe: When was the point during this process where you said, “I think we’re going to pull this off, this is really going to work. This could be a business.” Or maybe you knew it from day one?

James Pittman: I kind of had the feeling we were on the right track right from the beginning. And that’s because I knew the technology that was out there for immigration law – most of it had not been updated for quite a long time and some of it was pretty old fashioned, let’s put it that way. The field itself is due for an upgrade. Making the aesthetics more modern, making things more intuitive, easier to use. So I knew there was space for us and then, when my colleagues were interested in trying it out, when we were in Beta, we just had a very easy time acquiring users. So I thought well, we are actually filling a need here. So from the beginning I was optimistic.

Kevin O’Keefe: That’s cool. Was there ever a time when you thought maybe we won’t be able to overcome this hurdle? Or you got thrown a curve ball, and you didn’t expect it?

James Pittman: One of the things that happened was that the government occasionally updates it’s form versions and when they do that then sometimes we have to update our questionnaires. And if it’s minor changes, that’s not a big deal. If it’s major revamping of the information that they’re asking for, then that’s a lot of work for our team. So some of the forms had not been updated for years and then there was a slew, there was this period where they were just issuing new versions every couple of weeks and our entire timetable had to be readjusted to take care of this huge project now that they created for us. So that was one point where I thought, wow, this is really creating. And then, you know, there were, I would say, occasionally you find that you think a feature is going to be really well-received and then people start raising additional concerns, or want additional things included within it, where we have to take it back to the drawing board and then relaunch it. There were one or two instances like that.

Kevin O’Keefe: There’s a lot of lawyers here, that are probably a little bit different than your average practicing lawyer and that tend to be more innovative and looking at new stuff. Some of them are probably with here with ideas of “I’d like to be one of those guys like you, or somebody else.” What do you tell those lawyers about if you got this idea? Should you do something, not do something if they were asking you?

James Pittman: Well, I think first of all, it’s going to be more work than you think. I mean, you might expect it to be a lot, it’s going to be even more. There are going to be complications that you can’t foresee. I mean don’t just to put all your eggs in one basket. I mean, plan carefully and do some market testing, stick around in Beta for a while, do a feature light version in Beta, see how that’s received, and also adequate capitalization is needed.

Kevin O’Keefe: So the market testing can be as simple as you’ve got that Beta and going and showing it to people, right?

James Pittman: I mean, you want to have proof of concept, right? So yes, you want to have a feature light Beta and you want to at least have several dozen users using it regularly and telling you, yes, this is helping, this is fulfilling the need.

Kevin O’Keefe: What do you think about a lawyer keeping their job, and going whole boat into this?

James Pittman: I mean, if you can afford to take that kind of a risk. Certainly the more time that you can devote to it, the faster it’s going to get launched, but that’s just an individual consideration. Certainly have a few months’ rent saved up if you’re going to do that.