Attorney Gabe Levine of Matchstick Legal has found an interesting niche: Helping creative people run their businesses. Being surrounded by creativity—and the content creatives produce—inspires Gabe daily.
We tend to think of attorneys as experts who comb through case law or draft reams of documentation. But could artificial intelligence absorb this time-consuming work? Gabe isn’t ready to predict that.
According to Gabe, no machine can take into account the thousands of real-time variables that inform legal decisions and negotiations. For now, anyway.
Gabe Levine is an attorney and Principal at Matchstick Legal.
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Note: This transcript may contain some minor wording and formatting errors. Apologies in advance!
[Voiceover] Welcome to The Future of Content, a podcast exploring how we create, manage and distribute content. Brought to you by Four Kitchens: We make BIG websites.
[Todd] Welcome to The Future of Content. I’m your host, Todd Nienkerk. Every episode, we invite a guest to explore an aspect of content and to make predictions about the future of that content. If you create, manage or publish content, welcome! This podcast is for you. Today we’re talking about the law. Our guest is Gabe Lavine, attorney and principal at Matchstick Legal, a firm that specializes in working with creative businesses. Welcome to The Future of Content, Gabe.
[Gabe] Hey, thanks, Todd. Glad to be here.
[Todd] So, first things first. How did you get involved in law?
[Gabe] Oh, I didn’t have any better ideas [laughter]. When I graduated college with a so-so GPA, I started driving a cab, and I was like, “How am I going to make some money?” So, I took the LSAT. Did pretty well, applied to some law schools. And both my father and stepfather were attorneys or are attorneys. So, by default, I guess.
[Todd] So, what does a typical day look like for you as an attorney?
[Gabe] A lot of emails, phone calls, and contract drafting and revising because I am primarily a transactional attorney as opposed to a litigator at this point.
[Todd] I see. The litigator is somebody who shows up in court and defends and— See, I don’t quite know the words. Does stuff in court as opposed to working with negotiations and documents and things like that.
[Gabe] Yes. Accurate? Yeah.
[Todd] Got it. Okay. Now, your firm, Matchstick Legal, has a specialty. And that specialty is working with creative people, creative businesses. What does that mean?
[Gabe] I mean, primarily, it’s people creating content for the web and applications, but we have a handful of traditional graphic designers, people who write, people who design physical products in the world, from chairs to televisions. And then an outlier set of clients that do things totally unrelated to that but might fall under the creative umbrella. So, think designers, developers, writers, things like that.
[Todd] So, these are people who are producing, largely, like creative or technically creative work for other clients?
[Gabe] Right. Yes.
[Todd] And how is working with a creative agency, for example, different from working with other types of businesses like manufacturing or architecture, doctor’s office or whatever?
[Gabe] It’s a lot better.
[Todd] How so?
[Gabe] Well, the clientele, the owners and operators if you will of these types of businesses, at least in my experience and in my partner’s and our third attorney’s, are just better people to work with. I haven’t thought too deeply about why, but I think it’s the types of people that are attracted to doing that type of creative and technical services work. In terms of the actual counseling, there are unique issues because the ephemeral nature of this sort of intellectual property that’s being created. But by and large, it’s not that different in a sort of day-to-day and counseling-type perspective from the work you might do with other types of services business.
[Todd] And so when you say that it’s better, and I know you haven’t given a lot of thought to this, but it’s such an interesting comment. Is it that they are more approachable? Easier to work with? Or is it that the work that they’re doing just appeals to you more?
[Gabe] Better people. I’d say the level of appreciation and trust for the work that we do as attorneys is much higher and the level of engagement and desire to sort of learn and participate in the process is much better than what I’ve experienced in other industries in general.
[Todd] That’s interesting. Would it then be safe to say that in other industries they either think like, “Oh. Just send it to the attorneys. Don’t bother me with it. Just make it happen,”? And you’re just kind of at their beck and call?
[Gabe] Yeah. I mean, I’m overgeneralizing, right? And this is my personal experience, but yes. I mean, that’s more of the sort of you’re a box to be checked.
[Todd] Is there a difference—since you work with both creative companies and technical agencies—is there a difference even between those two that you’ve run into?
[Gabe] In terms of, like, how good is the client? Not really. No. I mean, no. There isn’t.
[Todd] Interesting. So, people who make things perhaps just have an appreciation for the law and all of the output of law as a thing that is made. That has creativity in it. That has a process to it.
[Gabe] Yeah, maybe. And I mean, our client base is younger and tends to have not spent a lot of years in professional schooling, and I don’t know what else it is that goes into it, but it’s really very good. And in any service-based business, your job is as good as those people you work with and for, right? That you have to spend— So it really makes the job a lot better.
[Todd] So, I’m curious because the legal profession strikes me, as a layperson, as one of those industries/professions that involves a lot of content. Doctors kind of strike me as similar in that there is a lot of having to keep up with, in your case, case law and trends and decisions and analysis and all of that. What kind of content is most important to you, as an attorney?
[Gabe] We all work on developing our own form agreements from a transactional lawyer perspective. And litigators do, too. It’s just different types of forms of pleadings and things like that that they’re going to get filed in court. So, our most important content is that work product that we create and rely on and improve and extract from over time. But we also rely quite heavily on what you might sort of think of as like cookbooks, reference materials, and form databases, which have improved dramatically over the last decade or so.
[Todd] Break that down for me so I understand exactly what you’re dealing with when you say a “form database.” What does that look like to somebody?
[Gabe] Okay. Yep. So, how do I explain this? The one that most lawyers use these days is called Practical Law, which is owned by Westlaw, Thompson West, where it’s just that massive conglomerate. And so if you go into Practical Law you will see a menu of—assuming you subscribed—the price for all the different type areas of law. You’ll see a menu that has, like, intellectual property and technology, labor and employment, corporate securities mergers, and acquisitions. There’s different ways to search it, but that tends to be a very efficient way so you would click the box that says intellectual property and technology, and then you can drill down on that by type of resource or by state, and, ultimately, you can enter natural language and bullion search terms either generally or within that subset that you’re searching. For example, intellectual property and technology might be the area of law. You might select California, and you might enter a natural language search for “employment agreement,” and it might pull up a dozen resources including a couple different standard forms of employment agreements for California employees in working with the development of IP.
[Todd] So, this a tool that you, as an attorney, use to find some of the forms that you use as a basis for what you do or snippets of language or both.
[Gabe] Yes. Absolutely.
[Todd] Got it.
[Gabe] And it also contains guidance and reference materials. Like, if you wanted to figure out— You needed to look at three or four states because your client has employees in three or four states and you want to try to help them develop a paid time off plan and you need to check the box on all the various states, there might be a table showing what the paid leave laws are of those various states and that sort of thing. Or an article about how it’s changing.
[Todd] One of the things that strikes me about a public perception of law is every TV show, every movie, every commercial that I’ve seen where there’s something about a law firm or a lawyer, they’re in a wood-lined room full of books. How real is that?
[Gabe] Surprisingly real. Although, I mean, in our Portland office, there are plenty of books. My partner, Josh, likes his books. And in every larger and mid-sized firm that I’ve worked for, we’ve had lots of books. And what those are, are those practice guides, those cookbooks in print form. But they’re both, for someone like me— I’m 42. I kind of grew up with the advent of the internet if you will, it is a lot more efficient and, frankly, less expensive to do it online now at this point.
[Todd] Right. So, there’s a tremendous amount of digital content and digital work that happens in law right now. Do you feel that the legal industry was ahead or behind the curve when it came to digitizing content?
[Gabe] I’m going to say ahead. I mean, if only because I went to law school in 2002–2003, and even back then, learning had to navigate LexisNexis and Westlaw as search engines to find the content you needed to conduct case law research or to find these types of forms that I’m talking about, was a huge part of practice. Looking up cases trying to find that needle in the haystack case that would help your argument required some pretty sophisticated searching of sort of those natural language and boolean terms within those— [crosstalk].
[Todd] What’s an example of that? Some of these more sophisticated searches? What are the things you can do in these tools?
[Gabe] Yeah. So, turning again to sort of labor and employment. So, again, you select California case law and you want to find out— You talk about laws about non-competition. And so you’re like, “Yeah. I know that I want ‘employee’ in the same paragraph or same sentence as ‘compete’ or ‘competitive.’” Some variation on that word. So, you could type “employee” and then “w-s” would be within sentence, or “w-p” would be within paragraph, and then put “compete” or just stop at the “t,” and then put an explanation point at the end of it, which would then give you every variation of that word “competing,” “competitive”— That sort of thing. And you would return a search for the cases that showed up with “employee” in the same sentence or paragraph as the word “competitive.” Or you could drill it in any variation of “compete.” Or you could also drill it down to within two, within three, within four words. That sort of thing.
[Todd] And so this is how attorneys are able to structure an argument for their case or their client using what might be otherwise extremely obscured decisions and arguments and cases, right?
[Gabe] Yeah. Hundreds of thousands. Especially a place like California where there’s so much, which makes it both good and bad. Or Texas has a lot of case law, too. It’s just a big state with lots of litigation, so, yeah. For well over two decades, or maybe two, three decades, it’s been done like this online and before that, to a certain extent, that same sort of search just minus the technology is done in books.
[Todd] And so there must’ve been, before you could do digital searches of all of this case law and everything, there must’ve been hours upon hours or people and just huge amounts of time and effort went into reading and actual physical case law, right?
[Gabe] Yes. Westlaw and LexisNexis developed systems to sort of provide case notes so you could, for example, look at a statute and know that you’re thinking about that non-competition provision in California’s law of business and profession code 16-600 and look at the case citations and then break it down like this— It breaks it down in sort of a menu of types of decisions. So, I want to look at something that has to deal with mergers and acquisitions or something that has to deal with, again, sort of employment and then break it down further within that space in books and tables. And there was still a lot of that, too, early in my career and when I was in law school.
[Todd] There must be something happening then on the more— As these competing services are trying to win more subscribers, right? LexisNexis versus Westlaw and the rest to predict what attorneys are looking for, right? To try to not just rely on complex searches of this word plus that word within the same sentence or any variation of this word plus that. There must be some degree of what, in the web industry, we might call things like “suggested content” or “predictive content.” Things like that. Are you seeing that already in these tools where once you start to look for things it’s suggesting stuff to you automatically based on some kind of algorithm?
[Gabe] At least not within practical law. I mean, it’s the same sort of functionality it was 20 years ago. It’s sort of like “here’s your recent searches.” But, no. That’s interesting. It is not.
[Todd] Well, somebody should take note.
[Gabe] Yeah, good call. Good call. I mean, there is maybe something out there, but certainly not in practical law, which is what— I would guess a percentage, but the percentage would be very high of lawyers and firms that use that tool.
[Todd] Well, let’s take a short break and when we return, let’s pick up this topic of what’s essentially artificial intelligence and machine learning in law.
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[Todd] Welcome back to The Future of Content. Our guest today is Gabe Lavine from Matchstick Legal, a firm that specializes in working with creative businesses. So, I’m curious to hear about how technology has impacted law. I want to get to artificial intelligence in a moment. But something that’s been on my mind, because here we are, we’re in a podcast and lots of podcasts are sponsored. This one is. But one of the common podcast sponsors I’ve heard from is LegalZoom and services like that. So, there are these online services for people to get some of these forms made for them relatively cheaply, like LegalZoom, Rocket Lawyer, and all the rest. How are those services changing the legal industry and the role of an attorney?
[Gabe] Not insignificantly. I think a lot of those types of forms are becoming standardized.
[Todd] And when you use the word “forms,” you’re talking about, like, contracts and things like that. That’s a general word for your industry for those kinds of things?
[Gabe] Yeah. Contracts and incorporation-type documents such as bylaws or LLC operating agreements. Those things like LegalZoom and even Clerky is used for startups a lot. Y Combinator uses Clerky as far as I know. So, you see the same forms over and over again. I work with a lot of executives and professionals, individual executives and professionals that work in Silicon Valley as well, being where I am in the Bay Area. So, I am frequently negotiating compensation packages and also working with professionals in sort of the creative field that try to make sure that they can continue to own the IP that they’ve developed or that they’re working on to develop. And so I am looking at these forms that are varied. So, there’s that, right? You see these same forms over and over and over again. And then I think probably it’s reduced that type of work, that type of form work. I’ve never done a ton of it in corporations and LLC organizations, that sort of thing. And we still do a lot of it regularly. Not a major part of the practice but that’s probably reduced that work for us and made people more able to do it on their own, which to a certain extent is a good thing. I think those services are very useful. If you have a good tax advisor, those services are very useful for individual business formations. You’re an individual, you want to form an LLC, fine. Where they fall down significantly, I think, is when there’s more than one person and they’re not— They can’t coach you on the prenup. The operating agreement, the partnership agreement, that sort of thing.
[Todd] So, it’s good when there’s one person and it’s relatively simple. But when you’re dealing with multiple parties, then these things kind of fall apart.
[Todd] Got it. It’s so interesting how in the legal industry there’s LegalZoom and Rocket Lawyer and Clerky and all the rest. And then in the web design industry, we’re receiving a lot of, I wouldn’t say pressure, but change as a result of services like Wix and Weebly and Squarespace and all the rest. Yeah. So, as these things become more standardized and automated, it’s kind of picking off the low-hanging fruit, right? And then you have to continually elevate your own offering, your own service to keep up with that. Interesting. So, on the topic of technology and law, how are you seeing artificial intelligence impact the legal industry?
[Gabe] Not a lot yet. There’s one company that I’m aware of because I was an early advisor called LegalSifter. And not a legal advisor but sort of a product development advisor. And LegalSifter, it’s an interesting company and product that helps identify issues— I mean, it does more than this, but its principle thing is identifying issues with contracts. So, you feed a contract into it and sift it. And the machine tells you what the issues are in the contract dealing with this is something that you ought to be aware of here in this contract and here’s some commentary from one of our attorney advisors about what this means. And even maybe sort of what might be “market,” i.e., what’s sort of normal for this type of agreement. And LegalSifter is being used, as far as I know, by law firms and I think some in-house corporate law departments to sift documents and provide a set of eyes, if you will, on those contracts. From an ethical standpoint, it’s not enough. The lawyer has to put eyes on it, too. But there’s certainly nothing wrong with doing both.
[Todd] So this service, it takes a contract that I wrote for you. You’re hiring me to do something, here’s my contract. You can take this contract, run it through this system, and it’s going to tell you, “Oh. This stuff seems pretty normal. This clause is unusual.” And it’s flagged it as unusual because it’s not— The limitation of liability is too low or it just, for whatever reason, it doesn’t seem to match what is typically seen in this context. And then it just throws a flag to allow the attorney to say, “Oh, you should probably pay special attention to that.” Does it then go on to say, “This is what’s typical”? Or does it just flag it as atypical?
[Gabe] I haven’t used it or worked with it in a long time but I believe it does. And I believe it has suggestions.
[Todd] And so it’s doing this based on, I imagine, some pretty serious machine learning in the background having sorted and reviewed thousands or hundreds of thousands or maybe millions of contracts that are out in the wild.
[Gabe] I think so. The guys have started this company, if I’m recalling correctly, are Carnegie Mellon engineer or scientist-type guys with AI degrees and backgrounds that program this stuff. Or I suspect. But early on I was working with them to, I like to say, “pair program” it. But feed in that sort of legal information. But they’ve worked with lots of well-known attorneys in the field of contract drafting preparation and things like that.
[Todd] Do you feel that there are areas of the law in which AI is or will be more effective than a human lawyer?
[Gabe] I can certainly imagine some day that being the case. I mean, an AI, as far as I know, doesn’t get tired or emotional or invested. And so it can certainly— [crosstalk]
[Todd] Unless you want it to be.
[Gabe] Right. I suppose. With enough information and development, I can’t see why it couldn’t get better at the coolly analytical part of it.
[Todd] Do you foresee a time when an AI can become a paralegal or a lawyer? To be licensed as one?
[Gabe] No. You don’t have to be licensed as a paralegal. But, no. I mean, I’m a sci-fi geek—we may have talked about that at some point—so, I can sort of play with, in my mind, a future where there are robot attorneys that are licensed. But realistically, I don’t know if my vision is far enough out perhaps, but I kind of can’t see that because, in my mind still at least, there are some things that it can’t do as well as a human. And reading sort of emotion is maybe one of those things, which is a lot of the job when it comes to negotiation, for example. Bluffing, taking into account hundreds of thousands if not millions of real-time variables that are coming in your head and making those decisions as you do it. But it wouldn’t shock me if there was some way to preserve my conscious for a thousand years.
[Todd] Since we’re just spit-balling sci-fi ideas. What do you think will come first, an AI attorney or an AI judge?
[Gabe] Oh. I mean, the notion of an AI judge scares the shit out of me. Sorry to— But you know, right? Then again, there’s a lot of judges on the bench these days that scare the shit out of me. Man, I would bet a judge, I guess, before a lawyer.
[Todd] I’m just curious. Why is that?
[Gabe] Well, looking at the sort of— The judge’s job is to be coolly analytical, right? It’s just look at the facts, the law, and spit out a decision. Lawyers are advocates. We’re supposed to be “zealous advocates”—that’s part of our job for our clients. Judges aren’t supposed to be zealous advocates. They’re supposed to be neutral and interpretive and logical.
[Todd] That’s fascinating. One last topic. Earlier we were talking about how all this content shows up in things like Westlaw and LexisNexis. These forms and bits of language that you can use. Is there any kind of movement to “open source” legal content so that that kind of stuff is more freely available to people?
[Gabe] Yeah, certainly. I mean, a lot of the large firms have those forms that I was talking about that you see over and over again. They’re out there and they’re open-sourced. Y Combinator put out all the— Why am I forgetting it? Oh, SAFE. Simple Agreement For Equity. To kind of try to do away with all the back-and-forth of convertible notes in early-round investment. Remove the debt feature and just kind of make it easy for people to take investment early. And there are some other open-source forms from the— I think it’s NVCA, if I’m getting it right. National Venture Capital Association or something. For later round investments like series A and that sort of stuff. So, yes. There certainly is.
[Todd] Interesting. Well, thank you so much, Gabe for your time. This has been fascinating. This is a world I know so little about and as a result, mystifies and terrifies me. And the amount of content that you have to manage and sift through and look up is just overwhelming and it’ll be interesting to see how artificial intelligence and predictive searches and things like that might alter that experience down the road.
[Gabe] Yeah. Well, it’s my pleasure. Thanks for having me, Todd.
[Todd] Cool. Well, until next time, everybody. Enjoy your content.
[Voiceover] You’ve been listening to The Future of Content. A podcast from the Web Chefs and Four Kitchens. Hosted by Todd Nienkerk. Produced by PJ Hagerty. Theme song is PAFRATY by DJ Listo. Find us on Twitter at focpodcast and get in touch by email email@example.com.