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I kind of turned the oh no, we're going to get replaced mindset on its head and say, replace me. How can I be replaced?
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Welcome back to CZ and Friends where we talk with legal leaders, technologists and operators shaping how modern companies work. I'm your host, Cecilia Zanitti. Today's guest is Jimmy Toy, chief legal officer at Articore Group. Articore owns Redbubble and TeePublic, two of the biggest online marketplaces for independent artists in the world. 70 million plus user generated images on those platforms. Jimmy is the lawyer. Jimmy and his team are the lawyers responsible for all of it. Jimmy's been using AI and ML in his legal work for over 10 years before Modern LLMs, which is a small group, self included. Jimmy has some takes on where legal is going, where legal is getting AI wrong, where legal is getting AI right. And it's going to be a potentially uncomfortable conversation for some of you depending on where you sit on the copyright spectrum. But, but it'll be good uncomfortable. So let's get into it. Jimmy, welcome to the show.
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Hi teacher. Thanks for having me. Thrilled to join. Talk about my experiences.
B
Awesome. Let's start with something you wrote to us before this episode that has really caught my fancy. So you said the best lawyers five years from now aren't going to be using AI to work faster. Instead they're going to not be using, they're going to be using AI to not do legal work at all. Lawyers and the teams that they lead will shift from authoring individual outputs to just reviewing them and being architects. That's consistent with what I see. It's what we see on the software engineering side. My co founder recently said, hey, I don't write code anymore, I just oversee it. Is that where legal is going and unpack that for us?
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Yeah, yeah, I definitely think so. Because I think software engineering has really led this sort of a transformation within their industry. And lawyers in the legal industry, I think we need to head there too. But I think we have a very unique resistance to that sort of a transformation because we are just because of the way we're trained and the way that we think. But yes, I think we'll either have to change or we'll get be left behind. I think being replaced is the fear of everyone. But I think we need to embrace that and figure out how we can get replaced in the right way.
B
You mentioned a unique fear that lawyers have and I want, I want to push on that. I'm not sure it's unique, but what do you think makes your lawyers uniquely averse to AI if they are.
A
I can speak for myself. I think in a lot of ways I represent a typical lawyer because I want to have flawless judgment and I want to work hard and show that I'm spending a lot of time working on this output. I mean, maybe not if you're at a firm, maybe not too much, not too little, just the right amount. And then you really become risk averse. And you know, you have this, this notion that exercising your independent judgment is, is key and that judgment needs to be flawless and you need to put in the time and effort of backing it up. But with, with these new tools that we have, it's, you know, it's really changing that because it's not. I think you still need to exercise your independent judgment and you still need to be right most of the time. But things are moving so fast and you can rely on AI, I think, to, to fill in some of those repetitive parts of what we do, like information gathering. Just, you can rely on it for that and then focus on maybe the higher level judgment. But I think it's hard to let go because as a lawyer you feel like you're responsible for everything, every output, every, every response. I think it does make it harder to embrace a new tool that is new and risky and uncertain, but has such potential, I think, to transform the way we do our work.
B
You said part of that aversion of that feeling of responsibility is trained how. Like is it just literally going to law school? Is it. We've been burned too many times. Like I, I want to get into like the psychology a little bit caus. I think it's a powerful concept. If you want to move past it is like, okay, I understand why it's the case.
A
Yeah. Well, I think a great example is the billable hour. I think I'm speaking not only to in house lawyers, which I have been for most of my legal career, but also those at firms. Because when you look at the billable hour, take this as an example. What if you spent a thousand hours doing something and you had this really great work product and the thousand hours you spent on it, it was, it was like a big deal. It was great. It was the right amount of time. You didn't spend too much time, too little time. So let's just compress that and say, what if you could, what if you, instead of spending that thousand hours re achieving that same output, you could have spent five hours or even zero hours. It's, you know, you, I think in the end you aren't measured by, you know, the amount of hours that you spent on it. You're measured by the output and how correct it was and how timely it was and the way you communicated it. But it, it's hard to separate that from the billable hour because how do you do you just give a client a bill that is 90% less hours than you normally would have spent on that task.
B
And so you, you made the transition in house, you said relatively early in your career. What is different about that instead of in house, if at all? Because I mean, I think for me, like, I agree with you that there's this like work ethic kind of pride of authorship of like, you know, we've been through law school, you know, if you clerked like what, whatever it is that you did, you build a ton of hours at the firm. It's like this like kind of dossier that you have where you're like, you know, yes, I've, I've done all those things and most people haven't and we're this rarefied breed, but in house, I feel like I shed that, that like just the pure hours based pride. Did you?
A
Yeah, for sure. Valued more on the timeliness of my advice and the work product documents I produce. Much more so than, yeah, the amount of time I spent on it. I think there is one aspect of this that I, that applies to in house probably more so than firms. So I think if you're a lawyer at a firm, you got this billable hours thing and how do you fit AI tools into that? But if you're in house, you know, you also, you want to build the trust with your, with, with your fellow executives and, and cross functionally across teams. You want to show that you're the person that they can come to that has the answers. You know, how do you, how do you deal with AI in the middle of that? Do you, do you tell them I, I used AI for this? Are you proud of that? Or do you, do you not make it very prominent in the response that you're giving to them? So I think that there is a little bit of a conflict there because when I'm answering a question, I want to feel like this is my judgment, you can only come to me. But actually they could have gone to the LLM and asked and probably gotten 80% of the answer that I gave them.
B
So what lives in that 20%? Any good stories? You've been using AI for a long time. Different platforms and what are the things, what does legal look like going forward?
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So I think that LLMs will have the most powerful transformative effect on the legal profession if we try to not just do things faster, but try to do things totally differently. And I think the differently, that's pretty generic, broad thing to say. But I think one way lawyers can really look at it and apply this new awesome tool in a way that is going to have a real positive effect on like their business that they're advising and the outcomes that they drive is just thinking about what you don't have to do. I kind of had this, I kind of turned the oh no, we're going to get replaced mindset on its head and say, replace me, how can I be replaced? And what are things I don't like to do, things that the LLM could do or something that we can use the AI tool to empower someone else to do. That could be somebody on your own legal team, it could be a paralegal, it could be a more junior lawyer. It could also just be somebody on the people and culture team, just like interacting with say a legal chatbot or something. And I think the way you get there is by identifying what you do repeatedly, what you don't want to do, what somebody else or some tool can do, and then kind of separating those things out and then trying to build a system around it. You know, the, you know, the system can be something that's, you know, involves a lot of the different tools and communications tools and LLM tools that you have at your disposal, say as an in house lawyer and then, and then building workflows, building policies and escalation. How are things escalated? Measuring the effectiveness of it and then capturing all of that and then iterating and continuously improving that system.
B
So let's bring it to your company. Redbubble and Teepublic are marketplaces. Artists upload designs, customers buy them on products. 70 million images, that's bigger than almost any marketplace. And so you create this platform for creative work and basically your legal exposure ends up being relatively high. Right. So obviously you have dmca, but you're printing T shirts, you're printing all kinds of things where if your users upload things that are have IP issues, you've got to not only police it, but you've got to have the consequences around that. So curious. Like on copyright, so are you a copyright maximalist? And how does that view or how does the company's view on copyright show up for your team? And then we'll talk about AI within that. But first let's start there.
A
Yeah, so Little background on Articore Group is that so we, we own three digital platforms. Two of them are marketplaces. One's a creator storefront called Dashery that we newly launched. We also announced recently that we are acquiring an Indian print on demand marketplace for the Indian market. And so that'll make four digital platforms that we have. All of them are user generated content catered to creators of graphic content that are trying to sell products like T shirts and stickers and merch with their, with their brand or their, or their art on it. And then because I'm a lawyer, I have to clarify one thing. We actually don't print anything. Chachilia.
B
When you talk about ip, it's like so I used to work on Amazon Alexa and this is public, but the name for the Echo device was changed from Dash to Echo so late they had already printed the boxes and so literally tossed the boxes, shipped Echo in a just like literally cardboard box. And it was brilliant because the users were like, wow, this is so stealth. You know, this is incredible, like secretive invite only thing. But it turned out it was just that it was too late to print the boxes. So it's true that IP is harder when you're dealing with physical goods. So do you use like a third party printer or how do you go from being a marketplace to.
A
So the, the. We had different participants in the marketplace. We have the creators who are selling the products and uploading the content and creating their art, their customers who purchase from them and then third party fulfillers. They're usually mom and pop printers who are located close to markets all around the country, around the globe. Because all of our marketplaces are global and so they're huge community of fulfillers that participate on our marketplace and they're the ones that do the printing. They aren't our employees, we don't have any equipment. They're just participants, fellow users.
B
Interesting. Okay. Yeah, so I like to, I dabble in photography. My mom has done a Shutterfly calendar for every year for however long. And you know, I did notice recently I went to go print something at Walgreens and it did have a copyright, an explicit opt in copyright said I own these images, et cetera. So is that the legal framework you're using? And I'm a former IP lawyer, so relatively deep on this, have pretty big views on OpenAI and copyright, which we'll talk about. But how do you all do it?
A
Yeah, and so that's a very standard way to kind of build compliance with the law. You know, when you're on A user generated. When you run a user generated content platform. So we have tens of thousands of uploads a day to our platforms. You can't possibly monitor it all. So yeah, you have to rely on people that are uploading that and selling their products to attest that they, to represent that they own the IP and that they aren't infringing anyone's rights, they're complying with the user agreement. But yeah, it's a, it's a huge area of risk for any platform whether you're, you're social media or you're more like graphic art platform hosting that sort of thing or you know, all the way to being like an E commerce marketplace that has its own special specific risks. And, and I never, I never did litigation when I was at a firm. I joined redbubble to become a, just become just a generalist and do corporate law. We'd never, redbubble had never been sued at that time. And then, and it was called redbubble before Article. So when we started acquiring companies we changed our name to Articore Group, became a group of companies. Now that I've within, within six months or so of joining the. We were sued and then we now Fast forward almost 12 years that I've been here. I think we've had maybe 40 or 50 IP cases around the world.
B
Wow.
A
Yeah. And I've been the one leading the
B
management what it sounds like I did.
A
Yeah. Although I don't know anything about filing or formatting court documents, that's all totally foreign to me. But yeah, the strategic side of it, the reviewing briefs and doing a lot of ediscovery, all of that I had to learn.
B
Does any one case stand out that you're most proud of?
A
You know, I like to say we win most of them, but we don't win them all. And I think that's actually very important observation for risk management. I think if we won all of them hand down, knocked it out of the ballpark, we might be managing risk with too heavy a hand. But I think the ones I'm most proud of, so I think one in Australia I'm very proud of. Hell's Angels sued us for trademark infringements. I like to say I testified against the Hell's Angels in federal court, but it was a trademark suit. Like somebody had uploaded their logos and rightfully so. They're very protective of who can wear a jacket or a vest or T shirt with their logo on it. We try our best to, to really keep that stuff from coming on the site and Very little of it did. But you know, there would be a couple of things that would get through our screens. And Australia didn't have a law, a safe harbor law to protect platforms around for uploading of trademark content. So they had one for copyright similar to the DMCA in the United States. But there really wasn't any settled law around what to do if somebody uploads a trademark that infringes someone's rights and there's nothing to protect the platform. So we actually lost our, our first round and then, but you know, this case went on 10 years and then we just in the last couple of years won on appeal and I'm very proud of it because it actually created law in Australia. Yeah. Similar to what the United States has where if we modeled around just notice and take down and you know, how sort of responsibility does a platform have for this user generated content? So now it very much mirrors what a lot of other countries around the world, you know, whether you're talking about eu, India, United States and so. But yeah, it was our, our cases that helped to bring that about, which helped all platforms operating in Australia.
B
Wow. So put us in the room, let's say seven years in or whatever you're. When you're deciding whether to appeal, what are you presenting to the team to make that decision?
A
A lot of balancing. So of course you weight the costs, likelihood of winning, disruption to the business. As the lawyer of managing these cases, you want to appeal and you want to win if you don't think it's the right outcome. But you have to take the greater business into consideration. In the case of this one, it was really. There wasn't much of a. I think this is true of a lot of appeals. If you lose, there's really not much downside to appealing and you can, Yeah, I think maybe you could use it as leverage to force a settlement or. I think there's a lot of different ways to look at it and usually on balance it's for an important case, it usually makes sense to appeal. So it's kind of our default.
B
Yeah. So back to the kind of AI theme you know, is it I have this. Well, I would say that being a litigator at a law firm, which I was more so firster and then as you know, in house lawyer and then now as a CEO, it does change my tolerance for it. So I gotta say seven years in to a 10 year litigation, I'm not sure how receptive I would be. But I guess in that, in that framework, like back to our Question about AI. Could AI have queued it up as you did? So you kind of said, okay, here's the balancing, here's the whatever. And you're saying, okay, replace it. Like is that the kind of decision? Like that most crucial decision. We had a, a litigator on the show a bit ago, Michael Jacobs, who was the former chair of Worst Enforcer and he said deciding to bring a litigation is like deciding to open up a business unit. Was how much he thought that that was a decision because it really was. It has to be managed, it has to be staffed, it has to be paid for and it has to be have the strategic decisions that you described. You know, but you're a defendant. Right. So a little bit different, but curious if you would agree with him. That really is fundamentally business judgment. And even if it is how that interacts with AI that you described of making yourself obsolete.
A
First of all, we just have an amazing in house team, all of us. I would say that we became a crack litigation in house team over the last 10 years across so many jurisdictions, so many countries, Europe, Asia, United States, Australia, and then in the external council that we use have been excellent as well across all our cases and jurisdictions. And then I think that it's so time consuming, especially the E discovery part. We've done class actions. When things get into class action area, it can become very, very time consuming, disruptive for the business. It can be very broad discovery. You have to bring in. If you don't have a system in place like an ediscovery system and you haven't been through it before, you just need to reach out to the CTO to ask them, is this how this part of the platform works? And they have to think about it. It takes time out of their day. They might need to get deposed. And then, you know, how do you deal with that? You know, they've never done that before. Yeah. Across all the teams, starting with legal and then extending out, if you're an Internet company, especially sending out to like the product and engineering teams, marketing, even finance. Yeah. It becomes an all encompassing thing that every buddy is working on together. It is like the launch of a, of a. Yeah. New business line or something.
B
How have you, you said your beer team became a crack team of litigators. You're encouraging AI, you're telling people to embrace the new. How do you do it and how do you find and hire people that are willing to make change and to be open to new things, challenge the status quo? Because I think if lawyers are kind of afraid of AI, the meta point would be more. Or a meta point that I might see there is that it's more just like they've had this great career, they're making good money, there's kind of not a reason to do things in a different way. And so how do you suss that out? The kind of psychology of it and how do you encourage and grow it in your team?
A
I think it's a push. Even if you're not a lawyer, but you work in the legal profession, I think those same sorts of ideas in training, you get exposed to it too. And that shapes the way you act and the way you think. As one example, we have on my team, we have an AI champion. She's our legal ops manager. So I. One of the things I told her, which kind of got her out of her comfort zone, was every week I want you to walk me through a tool that you created, like an AI tool. And I don't just mean a prompt that, you know, just, that's nice. It generates a good output. Like I'm, I'm talking about something that people can use to self help or you can use the self help that's built on our knowledge base. Say going back to the litigation example, one thing that was very time consuming and very, very hard to do was like bringing a new. So. So let's say you get sued in a new jurisdiction. Well, you want to maintain consistency with the arguments that you've made, you know, the way you describe your business. And so, you know, we would have to go back through just hundreds of litigation documents that we filed to try to find that one little passage where we may have described something or made an argument in a certain way that we thought was really good. And we want to like pass that on to this new council, get them up to speed, spending as little money as possible. Doing that before AI, you had to.
B
It's a needle on a haystack for sure. Yeah. And I even think, I think back to pre AI, the thing that's jumping out at me was meta about maybe five or ten years ago, posted a job role in legal and they called it. This title was crazy. You can look, we can look it up in the show notes or something. But they called it the VP of existing obligations.
A
I was like, that sounds about right. Yeah.
B
Like going through and looking. Of course, you know, META had the FTC consent decree. I'm sure they had a lot of state AGs that they were dealing with hundreds of things globally. So you can literally imagine like what have we promised to what regulator? And this person was a vp, they hired somebody and they failed within six months. Which is like, you know, kind of sad, but, you know, predictable. But you can imagine like, okay, at Amazon, there was another case where Amazon was arguing for purposes of going after an employee for their trade secret, that the handbook was not a contract. And then in a case literally like three months later argued that the handbook was a contract for purposes of the person violating it. So very clear conflict to your point. So have you solved that problem? Does AI solve this problem?
A
Yeah, one of the things that we've been doing is building a knowledge base around like all of our court filings that we've done. So they can be like affidavits, declarations, even deposition transcripts. That's the greatest thing about this. Like, you would never look at a deposition transcript for something or look for, you know, you may just focus on your briefs, like the big briefs that you file, but here you can really put it all in and create this excellent knowledge base that's comprehensive. And then you can just interact with it like it's a, you know, like a person. And so like we have built, put all of these court filings in and into these, just like into a Google Drive folder, really. And then you can also, of course, like some AI tools will have a, like a projects folder. You can also put them in there. There's a lot of different ways to do it, but you can totally leverage this extensive, decades long, multi decades long knowledge base and get the answers that you want and that you need without having somebody go and search through all of that stuff.
B
So it sounds like it, like, when that tool works well, what you're getting is a better result. Right? Because presumably in my example, Amazon is not, you know, saying one thing in one court, another thing in another. And then of course, what are the litigants in both cases gonna do? Take the other. How does that improve your outcomes? Like, do you, do you have any specific examples? Or like, is this work that previously your team would have just said, you know, don't mess around, don't, don't look for this because it's going to take forever. But I remember in that one case, blah, blah, blah, you know, like, is it additive? Like, what I'm getting at is like, I think what you said is like, it's not just saving time in this case, it's better outcome. Have you seen that specifically yet?
A
Yeah, yeah. So a lot of what you're just describing would fall onto me because, you know, I am the only one that really had the knowledge of what we said in a certain case in France and how that might apply to an argument that we're making in India. And the. I think it goes back to that idea of not of trying to figure out what do I not need to be doing anymore and trying to build a system around that. So it would fall on me to try to make sure everything was consistent. And then I might spend three hours trying to figure that out and maybe not come to an actual answer on it. But now I can just not even do that. And I think it's important it needs to be done because you don't want to get in a situation where you're contradicting yourself. But I don't have to do it anymore because I can just farm it out to the AI tool. And then of course, you go back and check, you know, you make sure that's actually what it's saying is true in the actual documents. But you never would have been able to locate those and find the exact passages without that sort of help.
B
So it's funny you say that because I think one of the original vision for GCAI was actually that the GC in this case, you, in Amazon's case, David Zapolsky, you know, in the various jobs I've had, David Zapolsky's been at Amazon for 25 years, seen the company through, you know, antitrust, labor and employment issues, expansion companies, you know, market cap to almost a trillion dollars, like all these things, and is one of the top 10 highest paid execs in the building, added tremendous value. And you think part of it is that institutional understanding of what is Amazon's risk approach. And so I'm like, if AI can do that, then it's like an aigc. Now, obviously you still need, you still need him, but that's kind of where I think this is going. Do you see the same.
A
Yeah. I envision a legal function maybe as short as five years in the future where, say, where you were the only one that could do something. You were the only one that had the answers and you were the gc, being able to decentralize that to people in your team. And I think we always have this sort of, you know, this idea of delegation and self help. I don't think those are new things, but the being we have this tool now that we can use that's very, very beneficial to our profession, legal, and to actually bring that about, to really delegate things that only you could do, delegate that to other people on your team and then. And Then create these self help tools for people on other teams to, you know, to just kind of replace you as the person they had to ask before and wait because you're a bottleneck and you're expensive. You know, it gives them an alternative. It's a lot cheaper for the company and a lot faster.
B
What is something that surprised you about this job or your tenure at redbubble?
A
I think how important relationships are. I think I'm, I'm very lucky because I like getting to know people and building relationships. I, I get a warm feeling when I, when I feel like I can trust somebody and they trust me and so I really thrive on that. And I don't think I really realized how much I enjoyed that and the importance I placed on it until I had the job that I have now. And I look back on the relationships that I've built over the years. All the people that have come and gone and come and gone again, like CEOs and CFOs. I've been here a long time and seen many of them come and go. But building that relationship and trust with each of them and, and then seeing how that translates into a really great legal product for the company, that's probably been the most surprising for me and things I've enjoyed the most.
B
Has your CEO or board or shareholders noticed that legal is a product and a good one?
A
I think so, yeah.
B
Any good stories there?
A
Yeah, I mean we like, you know, the litigation, I think people, the board has been pretty happy with the way that we've managed that risk and managed all that litigation. You know, like reorganizing from like restructuring our company from what started out as redbubble, this one marketplace into a parent company that owns a group of companies that, that I think was required some special skills. And yeah, I think people have been pretty happy with the way that all that has progressed. And you know, now we're in a, in an M and A phase, I think in turnaround too. We want to try to get our stock price up and grow and yeah, that's our next, that's our current challenge that we're trying to overcome and I think we're on track to do that.
B
In your time at redbubble, you had kind of an up and a down and it sounds like you're in a turnaround now. What's different about being a turnar, do you see?
A
I think you need to be very cost conscious in a way that you don't need to be. When your company is growing 30% year over year, doubling Every year, you know, in a hot area where there's a bunch of money being, being flowing in. Yeah, being a cost center, you know, you're not, you're not generating revenue, you're not helping to, to create profit directly. So cost becomes a real pressure. So you want to have the mindset. So on our team, we have three values that all of us try to live by. And it's light touch, no surprises, and make every dollar count. We actually had that before we were in a turnaround situation, but really we keep trying to add things to that list of three, but we keep going back to. Actually, that list of three is pretty much everything. Everything kind of goes back to it. And so we've really stuck with that over the years. And in a, in a turnaround, I think what is so important is the, is the make every dollar account for the, for the legal function, because you can't have, you can have a direct impact on OpEx, which does impact profits. It's hard to make your business grow just from the legal function. Of course, that's impossible. Can't do that. You can make it not grow, which would be bad, but you do have a direct impact on OPEX and spend.
B
So light touch. Make every dollar count. And what was the third one?
A
Sorry, no surprises.
B
No surprises. I love that. Okay, so literally, like, print this on a. Put it on a. Post it and learn it. So no surprises. That's a good one. Ever been burned on that one or where did it come from?
A
Yeah, yeah. It's like what you don't want as a boy is a, as a member of the board of directors, to be surprised by something. You want to make sure that, especially in the risk management area, that I'm not responsible for all the risks. I can't control all of them. But what I can do is make sure that because we're responsible for the risk management function, that the board is informed and they can ask the questions that they need to ask. So that really gets to the no surprises thing. I don't think we've been burned on anything there. These values have really always been a part of our DNA. I think it's more of just a fear of it happening. Yeah.
B
So it's, it's good. I mean, it, it definitely is. Like, you know, it, it, it's. I think for me, we've had as, as GCAI has grown. You know, I had a, a bad day. It happens, but I had a bad day last quarter, where for about, let's say, half the day, I thought we didn't have insurance. Like, I thought something had not been submitted. It was like one of these just like, oh, God. And we, you know, we ended up calling, you know, the broker, and it turned out it was something with. Ironically, their online portal wasn't showing the coverage, even though we had it.
A
Yeah.
B
But something similar happened, not on insurance, more recently. And my. My faith, I was like, you know what? I'm sure it's fine. I'm sure we actually have whatever it is. And it turned out that we did. And so it was one of these, like, you know, it was very, like a Zen moment for me. But the difference between those two times was actually that the first time we didn't have a gc, and now we do. And so actually, that was a nice. That was a nice, nice realization given what we do here at gcai. All right, that was fun. So let's do the lightning round. So anything that you would tell your early career self about, about succeeding as a GC or just about life?
A
I think. Don't be afraid of imperfection. Don't be afraid of making mistakes, especially me as a. As a junior lawyer. Emphasize the output more than the amount of time you're spending on it. And. And then the third thing I think is maybe a little more abstract but very relevant to what we're talking about here is, is always try to rely on a system and build a system and continuously improve your system. It makes decision making so much easier and consistent. You know, it makes you less likely to leave things out. I think it really does. And it makes it so much less stressful because you're not. You don't feel like you're starting from scratch every time. You're kind of reverting back to this framework that has worked before, that you're just executing.
B
I love it. What's a book concept or podcast that has shaped how you think?
A
I. I'm big into sci fi. I really like that. But I will choose a non sci fi book. What's really shaped me as a lawyer and an executive and manager and leader is this book by Peter Drucker. I think everyone's heard of the Effective Executive. It's just one of the classics of management, has so many insights. It's the Effective Executive in Action. It's a workbook that accompanies that book, and Peter Drucker wrote it also. But it's like a kid's workbook that you would, like, fill out in kindergarten, but you're an executive actually writing out, fill in the blanks. And doing exercises from it, and it's just forces you to apply these things to your actual life and career. And so that's had a huge impact on me. I still actually do exercises from it to this day. It's been years.
B
Love that. Favorite thing about being a lawyer, I think the relationships.
A
I wish I could say I would always know the answers to things and like, off the top of my head and be able to, like, help friends out with advice or when the CEO asked me or the chair of the board asked me or cmo, whoever, you have the answers and I'm right. I never really achieved that. And I think it's impossible. Yeah, just being relied on and trusted and being able to help them and help the company, that's. Yeah, that's the greatest thing.
B
Anything else that you want our listeners to know about you or parting advice?
A
No, just let's embrace this new technology and make our lives easier and let's make our. Make our companies perform better. And I think we can do that by just kind of reexamining the way that we do our work and how we think about it and where we place our value.
B
I love it. Awesome. Jimmy. This is a great. This is fun to catch up. I'm so glad you came on.
A
Thanks for having me. I really enjoyed it.
B
That was Jimmy, chief legal officer at Articor Group, the company behind Redbubble and Teepublic. If you want to see how legal teams are using AI to do better work and move to the future Jimmy describes, head over to GC AI, Follow Susie and friends wherever you get your podcasts. Thanks and we'll see you next time.
Podcast: CZ & Friends
Host: Cecilia Ziniti
Guest: Jimmy Toy, Chief Legal Officer at Articore Group (Redbubble, TeePublic)
Date: April 22, 2026
In this episode, Cecilia Ziniti sits down with Jimmy Toy, Chief Legal Officer at Articore Group, which oversees leading platforms for user-generated art (Redbubble, TeePublic). The conversation dives deep into how AI and machine learning are transforming legal work, copyright management in creator marketplaces, and the cultural psychology of lawyers facing an era of rapid automation. Jimmy candidly discusses his philosophy ("replace me"), his company’s real-world IP challenges, and frameworks for risk, culture, team-building, and turning the perceived threat of AI into a lever for growth and creativity in legal.
Mindshift in Legal: Jimmy urges the legal profession to embrace being “replaced” – not in a dystopian way, but by seeking out what AI and tech can do, freeing human lawyers to serve as architects of systems, not manual performers of labor.
“I kind of turned the oh no, we’re going to get replaced mindset on its head and say, replace me. How can I be replaced?” (00:00, Jimmy)
Parallel to Software Engineering: Like software engineers who now often oversee rather than write every line of code, the legal function is moving to an oversight and systems-design role. (01:09-01:48)
Lawyer Psychology & Resistance:
"As a lawyer you feel like you’re responsible for everything, every output, every response. I think it does make it harder to embrace a new tool that is new and risky and uncertain, but has such potential…to transform the way we do our work.” (03:25, Jimmy)
“I kind of turned the oh no, we’re going to get replaced mindset on its head and say, replace me, how can I be replaced?...and then trying to build a system around it.” (07:38, Jimmy)
Articore's Structure & Model: Jimmy details the company’s platform model (Redbubble, TeePublic, Dashery, global expansion). Articore doesn’t own the fulfillment equipment; utilizes mom-and-pop printers worldwide (11:38).
Massive IP/Vetting Challenge:
“I testified against the Hell’s Angels in federal court, but it was a trademark suit…We just in the last couple of years won on appeal and I’m very proud of it because it actually created law in Australia.” (14:40, Jimmy)
Building a Legal Knowledge Base with AI:
“That’s the greatest thing about this. Like, you would never look at a deposition transcript for something or look for…you may just focus on your briefs…the big briefs…but here you can really put it all in and create this excellent knowledge base that's comprehensive. And then you can just interact with it like it’s a…person.” (23:46, Jimmy)
Practical Impact:
AI as Institutional Memory:
Hiring for Change-Readiness:
Team Values in a Turnaround:
“Light touch, no surprises, and make every dollar count…Actually that list of three is pretty much everything. Everything kind of goes back to it.” (31:40, Jimmy)
| Timestamp | Quote | Speaker | |---|---|---| | 00:00 | “I kind of turned the oh no, we're going to get replaced mindset on its head and say, replace me. How can I be replaced?” | Jimmy | | 01:09 | “The best lawyers five years from now aren't going to be using AI to work faster. Instead they're...using AI to not do legal work at all.” | Cecilia | | 03:25 | “As a lawyer you feel like you’re responsible for everything, every output, every response…it makes it harder to embrace a new tool that is new and risky and uncertain...” | Jimmy | | 07:38 | “...try to not just do things faster, but try to do things totally differently...what you don't have to do...separating those things out and building a system around it.” | Jimmy | | 14:40 | “I testified against the Hell’s Angels in federal court...we just in the last couple of years won on appeal and I'm very proud of it because it actually created law in Australia.” | Jimmy | | 23:46 | “That's the greatest thing about this...you can put [all legal documents] in and create this excellent knowledge base...and then you can just interact with it like it's a...person.” | Jimmy | | 31:40 | “Light touch, no surprises, and make every dollar count…Actually that list of three is pretty much everything.” | Jimmy | | 34:27 | “Don't be afraid of imperfection. Don't be afraid of making mistakes...emphasize the output more than the amount of time you're spending on it...always try to rely on a system and build a system and continuously improve your system.” | Jimmy |
The future of legal, as articulated by Jimmy Toy, is defined less by individual heroics and more by systemization, openness to automation, and a willingness for lawyers to architect new workflows where their specialized judgment can shine—while AI takes on the repetitive, the redundant, and even elements of institutional memory. To thrive, legal leaders should “invite replacement” not as obsolescence, but as strategy.