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Dennis Garcia

Dennis Garcia is an Assistant General Counsel for Microsoft Corporation based in Chicago. He provides a wide range of...

Conor Malloy

Conor Malloy is a partner/founder of Chi City Legal, a law firm dedicated to Chicago-area landlords. He’s a graduate...

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Jonathan Amarilio

Jon Amarilio is a partner at Taft Stettinius & Hollister in Chicago. He represents individuals, small businesses, state and...

Catherine Sanders Reach

Catherine Sanders Reach is Director for the Center for Practice Management at the North Carolina Bar Association. Formerly she...

Episode Notes

In this edition, our hosts Jon Amarilio and Catherine Sanders Reach talk with Dennis Garcia, Assistant General Counsel for Microsoft Corporation and Conor Malloy the Founding Partner of Chi City Legal about the ever-evolving, hot-button topic of artificial intelligence and how its impacting the practice of law. Should lawyers be fearful that AI is coming for their jobs? Should we resist AI in the office? Can AI be embraced by lawyers to make their practice easier and more productive?



The AI Edition: Resistance is Futile



Jon Amarilio: Hello everyone and welcome to CBA’s @theBar, a podcast where young and youngish lawyers discuss legal news, events, topics, stories, and well, whatever else strikes our fancy, really.

I am your host Jon Amarilio of Taft Stettinius & Hollister, and co-hosting the pod with me today is Catherine Sanders Reach of The Chicago Bar Association. Say hello Catherine.

Catherine Sanders Reach: Hello. Catherine.

Jon Amarilio: Perfect. This is the AI Edition: Resistance is Futile. The question we will be answering today, exactly when will the Skynet, Matrix, the Borg Collective, whatever we call it destroy and enslave us all? Just kidding, I think we know that Donald Trump and Kim Jong-un will do that long before AI.

Well, anyway Catherine, this subject, AI, it’s been in the news a lot lately with the latest dustup between billionaire business icon and obvious Johnny Depp fan Elon Musk and billionaire Internet icon and probable future cult leader Mark Zuckerberg. Musk, along with a number of other kind of smart people like Stephen Hawking, have been warning us that AI presents an existential threat to humanity, while Zuckerberg and the more hopeful set tell us that’s all nonsense and we should just hit the like button on this phenomenon.

Catherine, we are lawyers, we judge people, we judge things for a living, do you think we can resolve this debate today?

Catherine Sanders Reach: I wish we could resolve this debate today, but it is fascinating to continue to read what’s going on in the news. This is evolving constantly. It seems like it’s a threat, it seems like it’s a promise, and that’s what we are going to explore with our guests today, why is this such a hot topic? What are the practical uses? What’s in development? How is it changing the practice of law? And then, well, is it going to enhance law or are you guys going to be Silicon Valley’s next victim?

Jon Amarilio: That’s cheerful.

Catherine Sanders Reach: So these are the questions we are going to get to and to help us answer those questions we have several guests with us today.

Jon Amarilio: Who is our first guest?

Catherine Sanders Reach: Our first guest is Dennis Garcia and Dennis is an Assistant General Counsel at Microsoft. And before that, he was with Accenture and IBM. Since he has worked with several tech giants and he is a great guest to have addressing this topic, he has been talking and writing a lot about the subject lately.

Jon Amarilio: Excellent. Dennis, thanks for joining us today.

Dennis Garcia: Thank you very much for having me today, really appreciate it.

Jon Amarilio: So you have been with Microsoft, IBM, Accenture, few scrappy young startups before.

Dennis Garcia: Yes.

Jon Amarilio: Tell me something, is AI coming for my job?

Dennis Garcia: My view is I think we should view AI as being a friend of ours, not a foe. I think AI may result in some legal jobs going away, but I think there is always room for great lawyers and we don’t need fewer great lawyers, we need more great lawyers.

So I look at AI as really a tool for us to practice law, at sort of a higher level, if you will, to achieve more to get more done.

Jon Amarilio: So you said some of the jobs will go away, one of the parallels or the analogies I often hear used with reference to AI is that it’s the next Industrial Revolution, which when I hear that I think okay, that means long-term benefits, like you were just talking about, but probably a good amount of short and maybe even medium term displacement and pain.

Can you speak to that a little bit? What are we looking at?

Dennis Garcia: Sure. Well, I think and there is a terrific book out there by Klaus Schwab, who is the Founder of the World Economic Forum, he is the Chairman of the World Economic Forum, it talks about the ‘Fourth Industrial Revolution’, about how our society has entered into a whole new era, where we are going to see technology advance at a rapid pace.

And we have seen three previous Industrial Revolutions; I think AI is an important component of a new fourth Industrial Revolution. And as we have seen in the past with other Industrial Revolutions, jobs may go away, but there may be opportunities for other jobs and roles and responsibilities in our society. And I think from a legal perspective where AI may displace jobs or roles are for those tasks which are routine, maybe mundane, and which could be sort of mechanical, if you will.

Jon Amarilio: So give us an example of that, what do you think, are you talking about discovery?

Dennis Garcia: I am thinking about perhaps document review. Perhaps, let’s say, if you are going to be merging with another company, you need to do an extensive review of documents, perhaps that’s done by younger associates in the past, perhaps that can be performed by an AI system.

Jon Amarilio: So that due diligence kind of work.

Dennis Garcia: Due diligence work, maybe basic contract review. So, much of what I do and my team does, we are constantly reviewing contracts from our customers, comparing contracts, looking at fallback positions, and I think there is a role for AI to play in that gap analysis, in that review, and to do that review very quickly and then provide that information to lawyers so that they can then negotiate contracts with customers and partners and what I view is practicing law at a higher level..


Also for maybe routine contracts, non-disclosure agreements as an example, perhaps there is an opportunity for AI systems to help business clients put those non-disclosure agreements in place and to plug and play certain key contractual terms.

So I think for what I look at as being, I don’t want to say necessarily the lower level work, but some of the more routine repetitive work which lawyers or paralegals, maybe younger lawyers have done in their careers, I think there is an opportunity for AI to do that work at a faster level, maybe more efficient and maybe a higher quality, depending upon the task.

Jon Amarilio: That can be kind of dangerous though, right? I have been reading in the news lately, Wells Fargo is in hot water again, because they mistakenly released, I think it was something like 50,000 customer records to the opposing side in a lawsuit, that included Social Security Numbers, bank account numbers and that was all done as part of a doc production run by AI.

So is that just a failure of the technology or failure of supervision, what do you think that bodes?

Dennis Garcia: In that particular example, I am not quite sure. Maybe it was all the above, who knows. But I do think AI, at least in the legal industry is still very much in its infancy. I think AI in general is still in its infancy. I don’t think we are going to see the impact, the significant impact of AI on the legal profession until maybe three, four, five, maybe even 10 years down the road. And I think with all technology, it takes time to get better and it will improve over a period of time.

So I do think we have to give it some time, but I think if you are thinking about test driving AI solutions, you definitely want to stay close to it. You want to monitor it and you want to oversee it.

Jon Amarilio: Okay.

Catherine Sanders Reach: I feel like there is still going to be a role obviously for lawyers to feed the intelligence and the facts and the data and the information and make sure the connections are made in the artificial intelligence bots for a while.

And the other thing I read the other day that while artificial intelligence may come to power, emotional intelligence is going to be where lawyers’ skill sets can really come into play.

Jon Amarilio: Because lawyers are so great at emotional intelligence.

Catherine Sanders Reach: Well, it’s something that you want to start working on now. That can be a learned behavior, it’s not something that — I mean some people are good at it, but it can be a learned behavior and so that’s an opportunity to get better.

Dennis Garcia: I think that’s a great point Catherine. And I think AI won’t replace lawyers’ empathy, their judgment, their creativity, their bedside manner with clients, if you will, building relationships with clients, those won’t go away, and I think what it means is that all lawyers, as we move into this new world, with the fourth Industrial Revolution, artificial intelligence, we need to embrace what we speak a lot at Microsoft of embracing the growth mindset and learning new skills every single day.

And I think for the younger lawyers, I think it’s also an opportunity for law schools to provide maybe better training for younger lawyers as they get out in the marketplace and they are going to maybe in some respects be competing with some of these AI tools, and how do they differentiate themselves and provide higher impact services to their clients.

Jon Amarilio: You are not actually suggesting that law schools teach law students how to practice law, are you, because that would be pretty revolutionary?

Dennis Garcia: Perhaps. I am a little bit removed from law school now, about 25 years or so ago, I don’t remember too much from law school. But I do think there is a real opportunity for especially, let’s face it, I mean these students are paying a lot of money for tuition, maybe jobs could be tough to get sometimes nowadays, and I think — I do think law schools owe it to law students and have a responsibility to provide better skills for a 21st Century lawyer.

Jon Amarilio: Let me push back, play devil’s advocate a little bit. Catherine, you said — you led in with the EQ thing and Dennis, you picked up on that and said there is always going to be a role for lawyers to understand their clients and be empathetic in their needs. But Catherine, yesterday when we were preparing for this pod, you sent to me something called an article about a Woebot. So was it Woebot?

Catherine Sanders Reach: It’s W-O-E-Bot.

Jon Amarilio: And its function was to essentially be a cyber therapist?

Catherine Sanders Reach: Yes, it is a Facebook messenger bot.

Jon Amarilio: I mean that just sounds so annoying and ridiculous, but if AI advances to the point where we see it in sci-fi films, will there be a need for lawyers to provide that kind of counseling and support?

Dennis Garcia: I still believe that’s the case. I mean it’s hard to predict what the future is going to be all about. So we are thinking 10, 15, 20 years from now, it’s going to be hard to anticipate those needs, but I am still of the mindset that there will always be a room for great lawyers and lawyers are so important to the fabric of our society and moving forward.


We saw the role that lawyers, great lawyers have played in the immigration ban several months ago with the Trump Administration move forward on and of great lawyers at O’Hare Airport helping immigrants and their families get into this country safely.

So I think there is going to be still a role for great lawyers in our society, but again, I think all lawyers are going to have to grow and provide a differentiated type of counseling to their clients, and it may not just be legal things, maybe it’s business counseling as well.

So I think it comes down to all professionals differentiating themselves, growing, figuring out how they build their brand basically and constantly learning new things and providing higher impact to their business clients.

Jon Amarilio: Let’s run with that for a second, because one of the things I have seen articles talking about the use of AI in the law and one of the things they mention is predicting litigation outcomes. And I know a lot of PE firms, private equity firms who are doing that kind of investment. They are also investing in technology that they think will help them predict litigation outcomes.

Is that going to push the law into like some kind of algorithmic exercise? You should or you shouldn’t sue? You should bring this claim or you shouldn’t bring that claim, this kind of claim is only successful in front of this judge, this often? It makes me wonder how the law can advance if we are reducing it to numbers like that.

Dennis Garcia: I think it’s an interesting question, a great question. We talk a lot at Microsoft in the legal department about the importance of helping our clients engage in smart risk taking, maybe even smarter risk taking. I think having those tools available to lawyers can help the business clients engage in that smarter risk taking and to try to quantify, and not with absolute certainty, but maybe with a high degree of confidence, the likelihood of prevailing in a legal action or not.

I think the key thing though with litigation, as we all know, it’s always a wild card. You never know what’s going to happen when you are in litigation, depending upon the judge, the venue, the lawyers, lots of variables involved, but I think to the extent that you have more tools, especially more algorithms and more data to help lawyers, help business clients engage in smarter risk taking and practical advice basically, I think that’s a good thing. I think it only helps providing higher client service to your business clients.

Catherine Sanders Reach: And I think you are still going to have disputes, and I already know several people who do mediation arbitration, who are getting more and more and more business. So maybe that’s the skill set you should build and not necessarily preparing to go to court, figure out how to do fee disputes, to do other disputes that come up that a bot probably can’t handle, because again, it’s got the emotional aspect to it.

Dennis Garcia: Right, that makes sense. It’s hard to imagine an AI doing mediation or an arbitration, yeah.

Jon Amarilio: All right, I think that’s probably a good place to break. Stick around everybody. We are going to be right back with our next guest. You won’t want to miss him.


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Jon Amarilio: And we are back. Catherine, who is our next guest?

Catherine Sanders Reach: Our next guest is Conor Malloy, who is a Partner at Chi City Legal. Conor is a graduate of the inaugural class of the Justice Entrepreneurs Project, which is a legal incubator that focuses on helping new lawyers learn to leverage technology and back office productivity, to offer predictably, and this my term, predictably priced legal services to modest means income clients.

And the reason I call it predictably priced is because I don’t like to say alternative fees or flat fees, because there is all sorts of fee agreements, fee arrangements that you can do, but what I think a consumer is looking for is something predictable; how long is this going to take, how much is it going to cost or some ballpark thereof, and not necessarily that it’s a flat fee, because that doesn’t work for everybody in every case, but that’s Conor, working with the modest means income clients.

Jon Amarilio: Yeah, I have tried those flat fees before, I always lose money on them, it’s tough.

Conor, welcome.

Conor Malloy: Thank you. And I lose money on them too sometimes.

Jon Amarilio: So before we get into the AI thing, tell us about the JEP really quickly, because Catherine mentioned it.


Conor Malloy: Sure, sure. So the JEP, it’s a class of usually new lawyers jumping into the game and learning the tools in order to practice. You were talking about before where law schools aren’t necessarily the best venue to learn how to practice law, so the JEP gives you some of the tools, practice management tools, connections, even touring the court and learning how to file and stuff like that and then there is some CLE built into it. But it’s a good place to start, and it allows some pro bono too, so you can get some substantive work as well.

Jon Amarilio: That’s great. And if people want to learn about that, where can they find out about it?

Conor Malloy:, they are doing some information sessions at the end of this month as well.

Jon Amarilio: That’s great. So let’s get back to AI. Conor, I logged on to your firm’s webpage yesterday and a chatbot popped out at me. I noticed there was the chatbot and also like a topic selection device essentially for why I was going to your website, what I wanted to talk about, what I was curious about, sort of a choose-your-own-adventure approach to finding a lawyer. Is that AI?

Conor Malloy: So when I think about AI, and we were talking before about the Goliaths out there that can throw tons of money at being able to create certain systems that you would think of as AI, like a Skynet type of thing, very high-level. We look at it as more of, if that’s the Goliath; we are more of the David.

When I think of AI, it’s really employing technology just to be able to handle some sort of a task, if you take it in a very broad term. So what you are looking at is basic AI, 1s and 0s, choose-your-own-adventure.

Jon Amarilio: So, on the back end, what does that look like? How does that help you in your practice? When someone logs on to your website and they say, I am looking for a lawyer to help me with this kind of business dispute, does it like direct that person to the lawyer in your firm who handles those kinds of disputes? What’s going on behind the scenes?

Conor Malloy: Sure. Not that I receive any sort of compensation from them, but the chatbot that we use is from a company called; they are out of Naperville, it’s just a new startup. And you don’t need to code. It’s just a WYSIWYG, what you see is what you get, dropping little segments along the way in order to create a chatbot, so that is pretty easy to put together.

But a lot of the tech that’s working in the background, so when somebody interacts with it and clicks on something or enters data, that’s getting fed back through sort of an infrastructure that I created, so I can get pertinent pieces of information, because in the area that we practice in, it’s very segmented.

Jon Amarilio: How is that?

Conor Malloy: Well, you were saying before that talking about distilling the law into the pieces parts. When it comes to landlord-tenant litigation, there is only so much wiggle room that you can really explore. So that’s what’s going on in the chatbot it’s, is it this or is it that, and it guides you along the way. So once I get basic information, I know exactly where they are, I know exactly where they are going to be going and how much it’s going to cost to get there.

Jon Amarilio: So it’s essentially an intake interview process.

Conor Malloy: Yeah.

Jon Amarilio: Do you use AI in any other aspects of your practice?

Conor Malloy: So there are certain things that I am working on right now in order to create a chatbots, essentially just for clients, to be able to check the status of their case, where they can say hey, what’s going on or what happened in court, and being able to take that natural language, throw it through our back end system, retrieve the data that we have from our public facing nodes and the like and being able to deliver it to the client.

Because that’s one of the things, especially for my practice, a lot of people in the landlord-tenant arena, the ratio of attorneys to matters might be very lopsided. So you might have one client who has 100 evictions, will have one client with one eviction, so we have many, many clients at any given time, and so we need to be able to leverage that ratio and increasing the communication is one way of doing it.

Catherine Sanders Reach: So instead of replacing you, your AI is helping you, and it’s almost acting — and we have seen this with Amy, and I can’t remember the male counterpart, you can sign up for a service for a bot that basically schedules appointments for you. So if you don’t have an assistant, or Cortana or Siri or all of these other kind of things that take data from one place and give it to you in another place because you asked for it and that sounds like kind of what you are going to be leveraging.


And that might be client facing, that might be just internal, but I think there are some interesting uses that aren’t scary, that aren’t taking over lawyers’ jobs, but actually help you do your job, which gets us to the modest means income client thing, because there’s been full service representation and then a whole lot of people who feel like they can’t afford legal services, don’t even know they have a legal problem, and I am seeing a lot of different technologies out there trying to solve for those issues, whether that’s — there is — the ABA put out a project for veterans so they can go through a kind of a chatbot and figure out, well, this is the problem that I am having and this is how I can start getting help with that problem and it’s leading it to information.

Jon Amarilio: One of the problems that we have seen a lot in the legal community lately, as you know is, there is a glut of lawyers and also a undersupply of lawyers who can do the kind of work of the JEP and serve the underserved. So you are saying this kind of tech could actually help bridge that gap?

Catherine Sanders Reach: I think so, because the other thing is, we have a very empowered consumer at this point. I can go online and do practically anything. In fact, right before I came down I went to the car dealership service website to book my own appointment. Back in the day you would call somebody, deal for someone else, you would sit on hold. You can do everything in the middle of the night online now.

So when you have got someone who, like for instance, I was a condo board president, when did I have time to work on the condo?

Jon Amarilio: Why would you do that?

Catherine Sanders Reach: Yeah. I actually had lawyers say don’t let friends be on the condo board. No one was my friend evidently. But it was one of those things where the time that I had to deal with that was not during my workday; that was at night, and my lawyer worked during the day, Monday through Friday 9-5.

Now, he was very good at responding to emails and things like that, but if I had been able to kind of self-help, put the dispute up, because we were constantly having little minor disputes between people and needed to have like — I used them as my King Solomon all the time, so anything that that could be automated, he would still my lawyer.

Jon Amarilio: Right. But I am kind of hearing two things. In the last segment Dennis told us that a lot of tech can do some of maybe basic legal work, like drafting contracts and that sort of thing. And in this segment what I am hearing a little bit is maybe it could actually help small lawyers and solo lawyers and small firms.

I am just — I think peoples’ hesitation is that we don’t know whether it’s going to wash out and it doesn’t seem like we have a good idea of where that’s going to wash out.

Conor, I mean obviously you are using some of it in your practice. How do you find it?

Conor Malloy: Find the AI that’s out there?

Jon Amarilio: Yeah.

Conor Malloy: I started searching for just chatbots and maybe I know a little bit more than the average bear when I was going out there and looking for solutions, but a lot of this stuff, Lawyerist is always exploring different things that are popping up, but the caught me off guard, because it was something that needed no programming, because once upon a time I programmed, I knew VB.NET, made stuff in Visual Studio and all that jazz, but I have to make money now. I can’t tool around with code all day long. So that was the perfect solution for me.

It’s really about thinking what ends you want to meet. So for example, to keep our costs low, we can’t really have any sort of front desk. So there is no paralegal, there is no secretary doing anything. We have a remote receptionist, a virtual receptionist and they pass data right through our system, but beyond that it’s just two lawyers knocking out the work.

Jon Amarilio: Who brings you like coffee in the morning when you are hungover?

Conor Malloy: The coffee in the morning?

Jon Amarilio: Yeah.

Conor Malloy: I want to get one of those cool 80s robots eventually.

Jon Amarilio: That would work, like with the mousetrap kind of thing maybe.

Conor Malloy: That would be a throwback.

Jon Amarilio: Okay.

Conor Malloy: Yeah. But we are not there. I haven’t made the big bucks yet.

Jon Amarilio: Well, Dennis is at Microsoft, maybe when he is back in the next segment we could ask him if he is working on that.

Conor Malloy: Is he working on a closet somewhere?

Jon Amarilio: Yeah.

Conor Malloy: But yeah, that’s how we run. You have to run a lean ship and I think you are going to see it happen with the larger firms too, that a lot of this stuff, it’s not proprietary anymore. I guess once upon a time if you had tons of money to hire a consultant and bring in programmers to develop a proprietary system, the day was yours, but now you can get all this stuff as Software-as-a-Service, and one of the big things that we use is Zapier to connect all this stuff together. It couldn’t get any easier.


Jon Amarilio: Right. You mentioned large firms. It seems to me in the go-go 90s the big firms were making just mountains of cash on doc review and things like that as a major revenue source; now, that’s pretty much dried up. How do you see large firms using AI to actually increase profits rather than just replacing their junior associates?

Conor Malloy: Now, I never worked in a large firm setting. I went straight into a solo practice, but it’s exactly what we were talking about before, to be able to knock out this really no-brainer work.

So, for somebody to mine some sort of a data source where you’re breaking down case law into its pieces parts and looking at probability, it doesn’t seem like it’s rocket science to me, especially if you have something parsing that language. I’m sure you could get judges with colorful language in certain opinions.

Jon Amarilio: Don’t think of any who used that.

Catherine Sanders Reach: I would never wish verdict searching on anybody.

Jon Amarilio: Can’t say I’ve done it but I trust you.

Conor Malloy: But it seems like that’s a great thing for a large firm to knock out and then you’re going to wonder honest-to-goodness what partners are doing at that point.

Jon Amarilio: Yeah, I’m a partner and I honest-to-goodness wonder what I do every day, so I think that’s probably right.

I think that’s probably a good place to take a break. We’ll be right back, stay tuned and we’re going to have both our guests back for a roundtable.


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Jon Amarilio: And we are back with Dennis and Conor. Guys, welcome back.

Dennis Garcia: Thank you.

Conor Malloy: Thank you.

Jon Amarilio: So, one of the things I want to do with this segment is just talk about what big issues do you guys see on the legal horizon with AI in the practice of law?

Dennis Garcia: Well, from my perspective one of the fundamental elements of AI is this whole notion of getting access to massive, massive amounts of data, and we’re living in a data first world in many respects and almost every organization is a data company.

So, I think there are some interesting questions or issues involving the protection and security of that data and large amounts of data. What laws apply as an example? In our country, unfortunately, some of the data privacy laws are a little bit dated, no pun intended, other places in the world, in the European Union we’re seeing a newer law come into effect called the General Data Protection Regulation come in May of 2018.

So, at times it’s unclear as to what laws apply where you have data scattered throughout the world in a mobile-first, cloud-first environment. So, I think data protection, data security, I think as a corollary point another issue is cybersecurity for all this data out there. How are you going to protect that data, and you are in a way, I think increasing the surface area of potential cyber attacks and cyber issues.

Jon Amarilio: So, that’s one of the things I’m really curious about actually because it seems to me at least from my layman’s knowledge of AI, that it works better-and-better the more inputs it has, the more it learns. Well, the more information you feed it to help people, the more information you’re giving it about people and the more you’re centralizing that information.

So, a really good hacker could hack into, I’m not saying this would happen, but Microsoft’s AI and gather probably just tons of information about people, what kind of security measures can be put in place other than trying to, well, I don’t even know.

Dennis Garcia: Well, I think what it means is a really good practice point is if you’re a lawyer or a businessperson thinking about moving to an AI solution, make sure that you are appropriately vetting your technology provider, understand what sort of leading best-in-class security practices or protocols are they employing to safeguard your data? What sort of compliance standards are they adhering to? Making sure you’re doing that extensive due diligence, if you will, and make sure that you’re only going to be working with a provider that you can truly trust nowadays.

But, I think and one great skill many lawyers have is this notion of doing thoughtful due diligence and that sort of investigation and evaluation.

Jon Amarilio: Not about our own lives.

Dennis Garcia: Not about our own lives, but —

Jon Amarilio: Yeah, just some are paid for.

Dennis Garcia: But for technology providers it’s an absolute imperative that you really do that that thoughtful due diligence. I am little bias working on Microsoft. We have what we think is an incredible trusted cloud narrative, more-and-more companies are moving to the cloud and protecting their data, but again, make sure that you’re doing that proper evaluation of any technology provider which can have access to, not just your data, but your client’s important data as well.


Jon Amarilio: So, how do you do that though? It’s, from what you described at the top of this segment, it sounds like it’s essentially the Wild Wild West out there? From a regulatory standpoint, how does a lawyer find out? How does a lawyer do that kind of diligence, I suppose, I’m asking?

Dennis Garcia: Well, what I think is making sure that you get the right people in the right place at the right time, and the lawyers need to play an important role in that. I think your risk management and compliance professionals have to be actively engaged. Your privacy leaders, privacy law is evolving and changing as we speak. Make sure you get people who understand that changing landscape, your security folks. You need to get a virtual team. I think of those four stakeholders involved early and often in doing that analysis. But that said, it’s still a little bit of a wild card, because there really are no AI-focused laws or standards out there.

But I think the key point is really scaling up in the area of privacy and data security, and I think that’s the area you should focus on first and then hopefully you can make a thoughtful smart risk-taking decision as to which technology provider you choose.

Jon Amarilio: And that seems to be like the area of the law right now that just has unlimited growth potential.

Dennis Garcia: And I think that’s a great point too because I think a lot of lawyers are worried about AI and how it may impact their future employment and jobs, but I think AI provides an incredible opportunity for lawyers to really get in on the ground floor of this growing area and to show their expertise or to have an AI-focused practice group and to really help shape the law, if you will.

Catherine Sanders Reach: I think kind of tangential is this concept of the Internet of Things, which I think AI is intersecting with so that you have the Terminator — there’s actually a Kickstarter out there for a kind of Echo-like device, but it’s the Terminator’s head so you can talk to Amazon, but when Amazon is talking with the Internet, getting data for you and then telling your refrigerator what to do, that all, and this stuff is happening so fast that that’s what kind of freaks me out.

There was already a case where somebody bought an intelligent garage door-opener and closer so they can do it from their phone. They gave a bad yelp review about the company and the company locked them out of their garage.

Jon Amarilio: Oh man. That’s fantastic.

Connor Malloy: Oh my gosh.

Catherine Sanders Reach: So, even at a very like low level, just like that kind of thing, how do you go about dealing with the legal ramifications of that?

Jon Amarilio: Right, and then on the other end it’s not quite a legal problem but I saw that article about Facebook, how they developed an AI system that started talking to itself in its own language, and they had to shut it down because that is Skynet scary, but even just the little mundane stuff like getting locked out of your garage by a begrudged company, that’s wow.

Catherine Sanders Reach: Yes.

Jon Amarilio: Wow.

Dennis Garcia: I think another issue; a corollary point to data protection is with all this increase of massive amounts of data when should government have access to that data, right? That’s a very — sometimes a little bit of a tricky subject and one hand government needs to protect us in the interest of national security to protect us, but also we have these timeless values in our country about protecting the privacy interest of individuals and we need to balance that appropriately.

Catherine Sanders Reach: So, looking at some other things on the horizon in terms of AI we were thinking about if AI starts practicing laws that UPL and how do you even go about dealing with that? So, there’s this little AI bot called DoNotPay that a non-lawyer and the UK came up with. It’s now been enhanced with thousands of different kinds of matters that can take on in the UK and across the US, and you go to the website and you type-in a couple of words, any words. It just says, “What’s your problem?” And then it starts asking you more questions until it gives you a rudimentary kind of response, and sometimes it doesn’t do so well at all; but, as this thing gets smarter that does seem like a threat. Is this a threat, Conor?

Connor Malloy: So – well, on the flip side too is my chatbot or at least some of the ideas that I have for mine if I’ve been accused of giving my chatbot unauthorized practice of law, their abilities; even though if a lawyer programs one to be able to diagnose something, in the same way I would interpret your facts and apply the law to it is that legal advice. It’s the same thing I give you, but I’ve looked at DoNotPay. I looked at it long time ago too when it was just handling stuff for the Brits and dealing with their parking issues. I think like millions of dollars maybe, it’s excused.


Then I started looking at it once they unveiled the new one maybe about a month or so ago, especially because representing landlords, I noticed that it’s very consumer-friendly. So, it’s looking at tenants and fixing issues inside of units. So it’s not necessarily doing any legal documents. It’s doing things that are of legal significance for now, but it makes my landlords that are nervous because they are renting the unit upstairs or things like that where they don’t have compliance.

So, if you get hit with something and you don’t know how to respond to it. Well, now that’s going to have some pretty serious legal ramifications. And so my thought is, to introduce a bot, to have the bad old bots, and essentially you just say, okay, well what happened? Well, I got a letter from my tenant. All right, here’s a letter to send back to him. I’m working on it.

So, that’s something that I’m trying to do to be able to combat it, but being able to draft legal forms, I don’t even know when that becomes unauthorized practice.

Jon Amarilio: It’s very interesting issue. As AI advances I think we’re going to need to look to the American Bar Association State –

Connor Malloy: If they are still around.

Jon Amarilio: — if they are still around, and State Bar Associations to maybe render Ethics Opinions as to what’s the rules of the road here, and what’s the authorized practice of law and what’s unauthorized practice, and I think we’re going to need some guidance from them.

As we know though that sometimes those entities move a little slowly, but I think we’re going to need some thought leadership from them.

Catherine Sanders Reach: Well, and I have also been reading a lot lately about kind of the protection of the guild. There’s a certain group of people who think that the Bar Associations and Ethics Opinions are all about kind of protecting the profession and not protecting in their interests in the face of emerging technology. And so, I think what needs to be the focus is protecting the consumer, not the protection of the profession, but protecting the end user of legal services so that there is not harm done on unintended consequences, and I think if that is the focus of these investigations then the UPL and the Ethics Opinions and all that, I think that — and that is made purposeful and distinctly clear from their investigations and not just knee-jerk suing because you’ve got something that competes with lawyers I think people will see that.

Jon Amarilio: I’m really wondering, just listening to this conversation, if this isn’t going to make pro se litigants even a bigger pain in the ass to deal with because they know just enough to be dangerous, and this is only going to make that phenomenon worse.

Catherine Sanders Reach: I got to tell you, having looked at all this e-filing that’s coming out in Illinois and thinking about a per se patron, even being able to put the filing together, the actual processing of the document, all the bookmarks and hyperlinks and things that are required. That’s going to take advanced training in word processing. So, I’m going to be interested to see how all of that really plays out.

Dennis Garcia: The other I think interesting legal issue is the intellectual property ramifications of AI and what’s patentable or not, and I could see a number of companies trying to file patents in the AI space and it’ll be interesting to see over a longer period of time or we’re going to see some of these smartphone patent wars we saw a few years ago in the AI space as becomes a more mature technology, but I think that’s also a sort of an interesting legal area, which is going to grow further.

Jon Amarilio: You have some insider trading knowledge on Microsoft for us, Dennis?

Dennis Garcia: I cannot share anything.

Jon Amarilio: All right, we will talk afterwards. So, before we wrap up today we’re going to play a game we like to call Stranger Than Legal Fiction. Each of us has done a bit of poking around the Interwebs and found some of the strangest laws on the books in this oh so fair country of ours. Catherine and I are going to summarize one of those real laws and another law we completely made up, and then we’re going to ask everybody, including ourselves, if we can distinguish which is the strange legal fact and which is fiction? Everybody got it?

Conor Malloy: Is this worth a CLE?

Jon Amarilio: Absolutely not, but you’re welcome to try to apply for it.

Conor Malloy: I will give it a shot, thank you.

Jon Amarilio: Okay, let’s get started. Catherine, you’re up.

Catherine Sanders Reach: Okay, so I’m doing The Chicago Edition of the Stranger With Legal Fiction.

Jon Amarilio: Appropriate.

Catherine Sanders Reach: So, in Chicago those who are under 21 can drink and serve alcohol legally but they must be enrolled in a culinary program to do so.

Jon Amarilio: All right, what’s the other one?

Catherine Sanders Reach: The other one is, you may be arrested for vagrancy if you do not have at least one dollar bill on your person.

Jon Amarilio: Dennis, what do you think?

Dennis Garcia: I think the second one is real.

Catherine Sanders Reach: Okay.


Jon Amarilio: All right, writing that one down. Conor?

Conor Malloy: As a solo practitioner, trying to make it week to week, I’m nervous about the second one, but I think it might be the first one; yeah.

Jon Amarilio: Conor, I think I’m with you, especially in this cashless society that we are in right now. I’m going to say one. What is it, Catherine?

Catherine Sanders Reach: Interestingly enough, both were laws.

Conor Malloy: That’s not the game.

Catherine Sanders Reach: But the second was repealed. And if you go and look at all the fake laws or the strange law websites this one about the dollar bill and vagrancy comes up over-and-over, but it is actually not on the books anymore; and in fact, no one can find it. I found where it might have been taken out.

Jon Amarilio: Yeah, vagrancy laws of running one or two constitutional problems over the years.

Catherine Sanders Reach: Bingo.

Jon Amarilio: Yeah, all right, next one. In Skamania County, Washington State, I hope I’m pronouncing that right. my apologies to everyone in Washington if I didn’t. It’s not only illegal to kill Bigfoot but anyone who ignores that law is guilty of homicide provided the coroner of Skamania County can prove that the creature is actually a humanoid.

That’s option number one. Can’t kill Bigfoot if you do, it’s homicide, but only if the coroner can prove Bigfoot is a person.

Option two, in South Carolina, it’s illegal to label for sale a sauce as South Carolina Barbecue Sauce or South Carolina Mustard Sauce, unless 51% of the ingredients are sourced from within the State.

Conor, what do you think?

Conor Malloy: I am guessing the people of South Cackalacky are very protective over their barbecue sauce. So, that’s got to be the real one on the books.

Jon Amarilio: That State is definitely known for that. Dennis, what do you think?

Dennis Garcia: Well, first off, I just want to thank you. I’m a Microsoft lawyer and Microsoft is incorporated in Washington State, so thank you for at least recognizing my Washington State in one of the laws; but, I’m with Conor. I would go for number two, I think number two is the real law.

Jon Amarilio: Catherine?

Catherine Sanders Reach: Gosh, of course, I think it’s number two, is the real law; but because I have to cut or break the tie here, I’ll have to go with one even if I’m losing.

Jon Amarilio: Catherine is the winner, believe it or not. I found this one on the website, did not believe it, went to the county’s website, looked up the ordinance, it’s there. You could be in real trouble if you shoot anything that you think looks like Bigfoot. So, for hunters in Washington, for all your Microsoft colleagues, Dennis, you should probably forward this pod to them and let them know.

Dennis Garcia: I will let them be aware of this interesting law.

Jon Amarilio: Yeah. And that’s going to be our episode for today everybody. I want to thank our guests, Dennis Garcia and Conor Malloy, for joining us today and putting our minds somewhat at ease about how we’ll be treated by our future AI Robot Overlords.

It was a lot of fun, guys, and I hope you’ll consider coming back to the pod again sometime soon.

I also want to thank everyone who makes this machine run, including my co-host today, Catherine Sanders Reach, as well as Jen Byrne, our exec, and our sound crew, Ricardo Islas and Steve Weirich.

Remember, you can follow us or send us comments, questions, episode ideas or just troll us on Facebook, Instagram and Twitter @CBAatthebar. Please also rate us and leave us your feedback on iTunes, or wherever you download your podcast, it helps us get the word out.

Until next time, for Catherine Sanders Reach and all of us here at the CBA, this is Jon Amarilio and we will see you @theBar.


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Episode Details
Published: July 2, 2018
Podcast: @theBar
Category: Legal Technology

Young and young-ish lawyers have interesting and unscripted conversations with their guests about legal news, events, topics, stories and whatever else strikes our fancy.

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