Why Section 230 Won’t Shield Roblox: The Legal Strategy Behind the Predator Platform Lawsuits

Matt Dolman: Welcome to another episode of the David and Goliath podcast. Here with my partner in crime, Stan Gipe. Stan, how’s it going today, brother? 

Stan Gipe: Pretty good. We got ourselves a good guest today. 

Matt Dolman: Yeah, I was going to say, we’re pretty lucky today that we’ve got Joe Masterman with us. Matt, you can probably do a better introduction than I can, but I’ll just sum it up by saying I run into a lot of people in the legal circle. There’s very few of them that impress me quite as much as Joe does when it comes to his acumen, his ability to break down situations and really analyze legal topics. So that’ll be my short introduction. I’ll let you go a little deeper with it, Matt. 

Matt Dolman: Joe is far and away the brightest friend I’ve ever had. I think Joe looks at us as charity, like these two morons he’s got to hang out with. But Joe, I’ll give you a little history. Joe clerked for Justice Alito, and before that clerked on the Sixth Circuit Court of Appeals. Prior to that, he graduated from Yale Law School, and just before that, as an undergrad, he was editor of the Harvard Lampoon, which is a pretty damn good resume. I don’t have anything like that on my resume. So kudos to you, Joe. There’s a whole bunch of topics to discuss with you, and I’d only have so much time today, but I want to jump in. You started with the Harvard Lampoon. What was that like? There are so many famous alums who served on the Harvard Lampoon. It’s such an amazing publication. 

Joe Masterman: Well, thank you, Matt. It was amazing to be on, but guys, you can’t just invite me on here and embarrass me with a hagiography of my own resume. First, as a young lawyer, you have to Google statutes sometimes, Google legal questions. From 2017 until now, every time I would Google something, on the side would be Matt Dolman’s face, because you were just all over. I’d be sitting in my little office in DC representing some state government doing some sort of constitutional defense of its laws, and I would just see this guy, Matt Dolman. I knew that there are other types of lawyers out there, but the only other type of lawyer I knew was this guy, Matt Dolman. You were just everywhere. You’re a legend to me before I even met you. Then I meet you, and it turns out you’re also an athletic star at the University of Miami. I grew up in Miami wearing a Santana Moss jersey until the number six fell off the jersey. Little did I know you ran track with all those guys. 

Matt Dolman: Who ran after Moss? Who was the number six after Moss? 

Joe Masterman: Antrel Rolle, the great DB. 

Matt Dolman: Yes. 

Joe Masterman: So, you have also been in these circles, and Stan’s okay too, and impresses me as well. But no, the Lampoon was a really unique experience. I don’t know if you’ve ever Googled it, but it’s this sort of triangular castle in the middle of a street in Cambridge, and it’s sort of the most elitist Harvard thing you can imagine. It’s associated with Harvard College. When you get on, you get hazed like you would at any other secret society at Harvard, but all the other secret societies are not affiliated with Harvard technically. So when they’re doing their month of effectively fraternity rush, they would do stuff like make their initiates party all night and then tell them at 7 a.m. the next morning, “Hey guys, we signed you all up for the SAT and you have to go get a certain score or else you’re going to get cut.” But the Lampoon, because it was associated with Harvard and subject to all the Massachusetts hazing laws, actually couldn’t make the initiates drink. So they would do things like make us memorize a bunch of poems and stay up all night and just recite them endlessly. Then we did that, we got on, and yeah, you’re just writing jokes in this magazine that all of the most famous comedians ever have gone through, and it’s really humbling to do. Honestly, an incredible thing to be a part of, and it was certainly the hardest, silliest, and hardest thing I’ve ever worked at, until clerking. I know this has nothing to do with the law or what we’re going to talk about, but it was a fun part of life, and honestly was kind of good training for learning how to put things succinctly and communicate to audiences you never know how they’re going to react to what you say on the page. So it was actually good discipline for what I ended up doing. 

Matt Dolman: Understood. You think you learned any skills from that that served you now? 

Joe Masterman: Well, like I said, being concise with the writing. Humor is a good way of communicating. You guys are trial lawyers, right? An easy way to get into someone’s good graces, and to actually get them to listen to you and want to respond to what you say, is to try to disarm them by being kind of funny. So honing that, not saying I am, it’s always dangerous to say I’m a funny person because then people are going to say, “All right, tell me a joke, funny guy.” But it’s a useful tactic to communicate to people. It’s a package for getting whatever information you want to get to someone in a way that they’ll receive it. 

Matt Dolman: What’s the selection process like with the Harvard Lampoon? Is it, I imagine, just everybody who wants to work there can’t. Is it, do you submit written stuff? Is it a personal interview? Is it a good old boy network? How’s it work? 

Joe Masterman: It’s purely blind and meritocratic. There’s no social competition process. They last the semester, and you can try every semester until your senior year. For that semester, they open up the castle twice a week, and you walk in, and the only room you’re allowed in, if you’re not a member, is this big wood-paneled circular library. All of the current members of the staff are sitting in these raised, inset window seats in the library. All of the people who are trying to get on, there’s usually like 50 people who last the semester, or who keep going back. You spend whatever time you’re not doing homework trying to write comedy pieces, usually page-long comedy narratives or dialogues or something like that. You take your stuff in, you show it to the current staff members, who are all sitting there looking very intimidating and very mean, and they never laugh, and they’re all smoking. A lot of them actually don’t smoke, so they will actually exhale these big white clouds rather than the thinner blue clouds if they were actually inhaling. That’s a little too in the weeds, but they’re all doing this to look scary. You show them your stuff, and they’ll read it, and if they think a piece has promise, they’ll say, “This joke works, here’s how I’d restructure this.” If it doesn’t work, they’ll just say, “Thank you very much, come back next time.” You do that for a semester, and they weed out people over time, and as they’re weeding people out, it gets progressively crazier. One time you go, it’ll just all be dark and candlelit, and everyone will just be sitting there, not speaking, and you drop your stuff off and leave, and then they come back and tell you, “You can come back again.” Then, at the very end, they’ll come back and tell you if you made it or not. If you don’t make it, they’ll give you back your packet with these really nice, encouraging things, and say, “Please try again next time.” If you do make it, they’ll give you back your packet, they’ll tell you, you didn’t make it, you’ll open your packet and see that they’ve spit on it and crushed a bunch of bugs on it and said, “This is the worst ever.” Then they’ll come back ten minutes later and pound on your door, and then they don’t let you sleep for a week, and you have to memorize all these poems. You get put through the ringer. It’s a real cloak and dagger thing, but I was really appreciative that it was never about, because you end up with all these people who chose to work really hard to be there, and they have this incredible opportunity to inhabit this interesting space for as long as they’re there. All these famous people come back because they want to be there, because there’s all this history. To make an incredibly strange connection to our job, it’s sort of like a steering committee for an MDL. It’s people who have chosen to come together for this purpose and to work on this thing, which is the magazine, and you never expected to work with these people before. You don’t have pre-existing relationships with them, but you all just kind of get along because there you are. 

Matt Dolman: Pretty cool. Did you make some lifelong friends from that? 

Joe Masterman: Oh, yeah, for sure. A lot of people at my wedding party, you know. Me and Conan text all the time. 

Matt Dolman: I can’t tell if you’re being served. 

Joe Masterman: No, I’m not. Like I said, you sort of keep this ingrained deadpan sarcasm that you can never really get rid of. My own wife never knows if I’m being serious or not. 

Matt Dolman: No, I always try to be very witty. Did you ever think about writing comedy afterwards, or is that something that still interests you? 

Joe Masterman: It still interests me a little bit. Actually, as an early lawyer, when I was working at Cooper and Kirk with Chuck Cooper, he was invited to present an argument at the Harman Shakespeare Theatre in DC. The Shakespeare Theatre does this really cool thing where they’ll take a Shakespeare play and turn it into a mock trial. I think they still do this every year. Ours was based on Richard III. Chuck argued against another real appellate lawyer. It’s supposed to be funny, this mock comedy trial based on the play. We were representing the crown, and one of the other characters in the play was suing the crown about something that had happened in the play. You write a whole brief, and you’re supposed to make the brief funny, and then Chuck is supposed to get up there and give the argument. The argument happened in front of Justice Alito and Justice Breyer and these other judges, and it was great. I actually got to write a fully comedic brief, and it was a lot, that was probably the most fun I’ve had as a lawyer so far. Unfortunately, I couldn’t bill for that time. So I still try to keep that a little bit. It’s hard, we get busy, and you can only use comedy so much, but once I’ve had bench trials or stuff like that, when I’m interviewing a witness on direct or cross, I’ll look for little opportunities. I’ve been told by my senior lawyers over time that maybe I pushed the envelope a little too much sometimes with trying to get a witty repartee with an antagonistic witness. But you do what you can. I’ve never been censured. 

Matt Dolman: Excellent. It’s a high standard. 

Joe Masterman: Yeah. 

Matt Dolman: So then you went to law school, that’s boring, you’re obviously brilliant, and then you clerked for the Sixth Circuit, which is pretty exciting, and then Justice Alito. Take us through that. I’ve never clerked for a federal judge. What is that like? I understand the importance of it, I understand why it’s considered so revered in the profession. What is it like? What do you do? 

Stan Gipe: I want to ask something too on this, because when I was in law school, there was never a thought in my mind that there was a path from Stetson to clerking for a Supreme Court justice. When we were talking about what your plans were after school, no one was saying, “If you decide to go clerk for a Supreme Court justice, here’s what you need to do.” When is it, how do you end up realizing you’ve got that kind of potential, or that kind of analytical prowess, that you might belong in that circle? 

Joe Masterman: I never expected to, until I got the call. Honestly, Stan, what is it like to be smart? Tell us what that’s like. You guys know other smart people, don’t put me on the spot. It’s something that, look, being at Harvard, going to Yale, I was incredibly fortunate in those experiences, and I was incredibly fortunate to be around all the other 200 students at Yale Law School who were smarter than I was, and to be against those peers every day. You’re not against them, but you’re always working and doing your best, and there are limited spots for those kinds of things. So I knew it was an option that people were pursuing, and I just tried to do the best I could in law school, and if it so happened that it was going to work out for me, then great. The way it happened, I actually started out clerking on the Eastern District of Kentucky, for Judge Thapar, and I spent a year there at the district court, on the federal district court, and that was incredibly informative. You’re dealing with motions every day, you really have to get educated about how litigation really works very quickly, and you’re working really hand in glove with the judge. My last day of my district court clerkship was actually the day Judge Thapar got elevated to the Sixth Circuit, the day he got his commission to become an appeals judge. Appeals judges actually get one more clerk spot than district judges in the federal court system, so Judge Thapar had an extra spot left over. I stayed for the summer as his fourth, extra clerk. He let me work part-time while I was studying for the bar, which meant I worked from nine to six, and then studied for the bar after that. Then I went to go clerk for Judge Kethledge, also on the Sixth Circuit, which I was already planning on doing. I went to clerk for Judge Kethledge on the Sixth Circuit in Michigan. He is the most rigorous writer I have ever worked for. It was sort of like the Lampoon experience, honestly, only on steroids. He has this process where you bring your draft opinions to him. For people in the audience who don’t know, clerks will basically do whatever a judge needs them to do, and the most important thing they do is write first drafts of opinions. The judges obviously read all the briefs the parties submit and everything too, and the judges have final sign-off and the final pen on all the opinions they issue, but the clerks will also digest all of the briefs, they’ll give the judges memos about how they think the cases should come out. The judges will then hear, if there’s a hearing at the district court level, the judge will have a summary judgment motion, a motion to dismiss hearing, whatever. We also handle criminal matters, so there might be hearings on that. At the appeals level, a lot of cases reach argument before three judges of the court of appeals, and then when an opinion is assigned to that judge, that judge then has to write the opinion that will be the decision of the court. The clerk who is assigned to that case will write a first draft of that opinion and bring it to, every chamber works a little differently, but generally the clerk will write a first draft, bring it to the judge, and together with the judge will work on it, and at some point the opinion will go, the judge will turn it into their opinion, and it’ll be released. Every judge is different, and Judge Kethledge is truly a generous mentor, but his writing process, he himself calls it a sandblasting process, because you will get your opinion back from him, and he must have gone through like two pens worth of red ink, and he expects you to have Strunk and White memorized, because a lot of his annotations are just, “S dot W, seventeen,” you know, Strunk and White, rule seventeen. So that was really a grueling boot camp for learning how to write like a lawyer. In those two clerkships, Judge Thapar and Judge Kethledge, they’re younger judges, in their forties and fifties, so they’re super active, they’re really on the forefront of a lot of legal areas, their opinions are cited as really important in a lot of different legal areas, and I just got along with them really well. They’ve served as mentors for me the rest of my career, I still keep in touch with them, and they continue to do truly thought-leading work from the bench. They encouraged me to apply for the Supreme Court. When you apply to the Supreme Court, you actually apply to all nine justices, and whichever justices find your application interesting will invite you for an interview. Each interview process is different, each one of the justices is a constitutionally appointed officer, so they can do kind of whatever they want in how they run their hiring process. I was fortunate enough to get called for an interview with the justice. You go to the Supreme Court, they sit you down. 

Stan Gipe: No one calls Stan for these opportunities. We want to know what’s going on, I’m fascinated. 

Matt Dolman: You can edit. Please edit out whatever’s boring. 

Joe Masterman: They call you to the Supreme Court to do your interview, and they sit you down in the marshal’s office. The marshal is the court security officer, and they must do this on purpose, I’ve never had this confirmed, but there’s one little bench in the waiting area of the marshal’s office, and you sit down, and there are portraits of all nine justices staring right back at you, and you’re just sitting there thinking, “All right, okay, I get it, I’m in the presence here.” You walk through the halls, and the halls have the official portrait of every single justice, I think by the time I was clerking there had been about 108 justices, and you walk past all of them who have ever served on the Supreme Court. I got there and I thought, whatever happens, I’m going to tell my kid about this experience, and that was honestly very gratifying, or very alleviating, because it’s stressful, right? I knew I was getting the interview about a month before it happened. I read the Constitution every day before the interview, it’s only nineteen pages, so it wasn’t that hard. I was naturally a little stressed about what was going to happen, because it’s a kind of life-changing opportunity, but I got there and thought, you know what, my life has changed no matter what. I got to come to this building, I got to sit here, I’m going to get to talk to Justice Alito. In these interview processes, the justices usually ask, “Do you have a question for me at the end of the interview process?” I just asked, look, in each of these, my tactic was always to say, “I’m a young lawyer, I don’t know what’s going to happen, what advice do you have for a young lawyer?” I wanted to learn from these people. I enjoy learning from people like this every time I get to be around them, and that continues to be the case. You go to dinners with other lawyers and stuff. And now I’m a plaintiff’s lawyer, and I’m probably, you could count on one finger how many Alito clerks do what I do. So I get to run into a lot of different lawyers that other people from my background don’t get to run into, you guys and everyone else we work with. I get to ask them about their experiences, which are different from mine, but we’ve all ended up in the same place, and they’ve all created a bunch of incredible lawyers that we all work with. My background is incredibly blessed, incredibly fortunate, incredibly good legal training, and I look forward to telling my kids about it and having them live in awe of their father, but also I’m here with all these people who have also worked really hard in different ways. Stan, to go from wherever you were to come to be in my presence must have taken an incredible amount of work. It’s really amazing. But you guys are trial lawyers, you guys know trial, you know how to work with these clients, and you know stuff that I don’t know, because they don’t teach you that at Yale. So there’s a lot of stuff that I learned in a very specific way, and did well in a very specific way, that got me to the specific brass rings that I was able to grasp, and that I was fortunate to reach. But it’s also given, how humbling the experience is every step of the way, it also, if you allow yourself to be humbled by that experience, it also enables you to keep learning from everyone you’re fortunate enough to run into. 

Stan Gipe: It’s a great story. Have you ever driven a fast car before? Have you ever test-driven a fast car? 

Joe Masterman: Why do I talk fast? 

Stan Gipe: You’ll get to my point, but have you ever driven a fast car? 

Joe Masterman: My stepdad for a while had a Corvette that he let me drive one time. I didn’t crash it or anything, he just didn’t like how I revved the engine too hard. So, yes, obviously slow cars too. 

Stan Gipe: When you’re around Stan, do you feel like you’re in a slow car? Does it seem different when you deal with mere mortals like Stan? That’s where I’m trying to land the plane here. I always wonder, I get self-conscious when I’m around Joe. Does Joe just think, “God, this guy’s not very, he’s kind of dimwitted, what’s going on with this man?” 

Joe Masterman: Look, I’m sitting here in Williamsburg, Brooklyn, looking out at the street. There are some incredible Mercedes with these graphite wraps and incredible rims, and then there are some trucks that are bringing the bread to the bakery. It takes all kinds. 

Matt Dolman: So then after clerking for Alito, that’s when you started at Cooper and Kirk, right? 

Joe Masterman: So, basically, yeah, I actually worked for a year at Cooper and Kirk after clerking for Judge Kethledge, and then I clerked for Justice Alito, and then I went back to Cooper and Kirk. Cooper and Kirk, as you know, is a small Washington boutique litigation firm, small just in the number of lawyers, focused on the sort of Washington-y stuff, constitutional and administrative law. They have about twenty lawyers, a lot of them have clerked for the Supreme Court. It was not unusual to leave for a year and go back. Chuck Cooper, who’s the head of the firm, referred to it as my sabbatical. 

Matt Dolman: Chuck’s a Washington luminary for those who don’t know him, and I previously had Davis Cooper on this podcast, Joe’s less intelligent partner, and I say that lightly because Joe is brilliant himself, but his father’s Chuck Cooper, who I guess is one of the kingmakers in the Republican Party for years. His law clerks were Senator Tom Cotton and Ted Cruz. That’s an incredible place, incredible law firm, incredible establishment to start working for. 

Joe Masterman: Yeah, Chuck’s a legend, and is still doing it. The most amazing thing about Chuck, he’s an acute intellect, as you know, you’ve gotten the chance to work with him as well, but the amazing thing is that firm doesn’t shy away from taking on potential political third rails. They are right of center, they do a lot of stuff in Washington, and if you’re right of center in Washington, that’s going to lead you into some fraught political battles. But every single person Chuck has ever litigated against, as far as I’m aware, loves Chuck. He’s just such an honorable person and really embodies the idea in American law that everyone deserves a lawyer. Reasonable minds can disagree, but these causes need to be hashed out, and they need to be hashed out at the highest levels, and when you’re hashing them out at the highest levels, you need the best lawyers to do it, so that these questions can be definitively decided in the best ways they can be. 

Matt Dolman: Yeah. And again, I don’t judge based on politics, I fall on both sides of the aisle, pretty much a moderate, a little bit of conservative leanings I guess on some issues, but I get it. You guys represented DeSantis against Disney. What was that like? That’s such a newsworthy story, and such a polarizing story. What’s it like to be on such a polarizing issue, beyond that side of the issue? 

Joe Masterman: Well, when I was clerking at the Supreme Court too, a lot of what we did was in the news, and that was really the first experience I had. We had some big cases at the district court and appellate court levels, but nothing where it would be front page of the Wall Street Journal, like it was at the Supreme Court. The first time that I was involved in one of those cases, whether clerking or in the Disney case, for example, it is a little surreal to see what you’re working on reported on. Every time that you really know an issue, and you read a report about it, you’re like, well, they got that little detail wrong, or whatever. You’re invested in the details, but you kind of just have to shut it out, treat it as noise, because people are going to have whatever opinions they’re going to have, and that’s fine, people are obviously entitled to their views, and not everyone has to have the same views. That’s why we have an adversarial legal system, to work all this out. But working for state governments, we represent Florida at my new firm now too, working for state governments is really a special opportunity, because every one of our clients is important obviously, but when you’re working for the state, their client is their entire state and their entire population, and they need to do the best job they can, and they are really entrusted with making whatever policy decisions they have a mandate to make on behalf of their electorate. It’s really not my job to adjudicate what the people in Florida, or whatever other state we represented, are supposed to think about something, we got hired to represent the office. I think most people of common sense understand that you just have to represent your client. But as we sit here now, you’re on a couple of really cutting-edge projects. You’re on the steering committee in heavy metals in baby food, where the allegation is that there are such high levels of lead and arsenic in specific brands of baby food that led to neurodevelopmental disorders. I know you were leading some of the law and briefing there, and for those who don’t understand, that’s the subcommittee of the smartest people on the steering committee, and they put together the pleadings and forward-facing documents that go to the court. 

Matt Dolman: You’re doing that right now in Roblox. Roblox is really, I hate to use the word sexy project, because we’re talking about pedophilia and pedophiles and the predation of children, so I guess I’d call it just incredibly newsworthy. There’s two cutting issues in this case, but namely the biggest issue, besides Roblox shamelessly trying to force minor sexual abuse survivors into arbitration, is Section 230, the Communications Decency Act. My understanding of 230, you can correct me, is it serves as kind of a sword and shield for internet platforms, they’re not responsible for content posted by a third party. How does Roblox not fall under 230? What’s the argument here? I know we can’t get too granular, because we’re not trying to give away the secret sauce of what we’re going to argue in this case, and you’re at the center of that, but for those people out there who think this case is going to be blocked by 230, what is the avenue? How does that work? 

Joe Masterman: Yeah, sure. You’re right that we’re actively litigating it, so I’m not going to get too specific about litigation strategy or anything like that. But it’s interesting that you correctly identified the name of the statute that Section 230 falls under, which is the Communications Decency Act, and actually the operative language of Section 230 that really is supposed to, or has been held to, protect platforms is actually called protection for “Good Samaritan blocking of content.” Why does that matter? That matters because our argument is not that Section 230 doesn’t apply to Roblox at all. Of course Section 230 protects Roblox from some types of lawsuits. The whole point of Section 230, which was passed back in 1997, was to say these platforms, that even back then were having a lot of traffic, can’t moderate or police everything that happens on those platforms. If I were to post on any of these platforms, there’s this case that was the sort of first that Section 230 was a reaction to, it was called Stratton Oakmont, which was, ironically, the Jordan Belfort platform from The Wolf of Wall Street. The concern there was, okay, you have these big messaging platforms, what if I were to defame Stan on this platform, should Stan be able to sue not only me but also whatever platform I were to post that message on? That comes down to a distinction between a publisher and a distributor. What Section 230 basically does is say these platforms that can’t possibly police everything that happens on them are more like distributors, they’re more like the newsstand, right, they’re not like the newspaper, which chooses what goes into the newspaper, and the newspaper is the publisher. Historically, under the law, the publisher could actually be liable if I were to defame Stan in the newspaper, because the newspaper presumably saw what I wrote, said yes, this should go in our op-ed page or whatever, and chose to publish it. So they can be equally liable for what I said as if they said it. What Section 230 does is say, okay, say my defamation of Stan happened over Facebook, what Section 230 says is Facebook is not like the New York Times when I defamed Stan over Facebook, Facebook is more like the newsstand that just happened to distribute that, that is assumed not to actually know or choose what goes in the newspapers it sells, it’s just the distributor, it’s just the seller. The reason for that protection actually goes back to why it’s called protection for Good Samaritan blocking, is that what they were concerned about back in the day was that Congress actually wanted these platforms to be free to act a little bit more like publishers, and to say, actually, if we know that Joe is about to defame Stan over our platform, we’re going to stop Joe from doing that, or if Joe does defame Stan over our platform, we’re going to take that message down, but that doesn’t mean the platform is assuming liability for all the other defamatory stuff that might happen just because they caught the one bad message that I happened to send over the platform. So Section 230 serves an important purpose and definitely applies to certain types of things that you may try to sue Roblox over, but that’s just not our suit. Our suit is about the fact that Roblox, as we allege, designed its platform in a way that, Roblox doesn’t have to read anything that happens on its platform, we’re not saying Roblox is liable because someone sent some bad message over the platform, we’re saying that before any of that happened, Roblox chose to design its gaming platform in a way that makes it completely seamless for sex predators to find children, and that happens. I know you’ve talked about Roblox on prior podcasts, but just as a reminder, Roblox is this platform where you can go on and play games, and a lot of the branding of the platform, what separates it, is that you go on, and the users actually create the games that other users play. The problem is that Roblox has historically not done anything to verify who’s coming onto its platform. I could be a thirteen-year-old girl and pretend to be an adult, I could be an adult, I could even be a registered sex offender, and pretend to be a thirteen-year-old girl. It’s as if, in a real-world playground, we somehow had this magic technology that enabled sex predators to transform their bodies to look like thirteen-year-olds, and to interact with other thirteen-year-olds at the swing set and say, “Hey, you want to come be my girlfriend and come back to my house?” That is what is happening, because you interact as these digital avatars over Roblox, and we are just saying that’s a design defect, because that is below the bare minimum safety standards that have existed on the internet for twenty years. Even putting that aside, Roblox can’t advertise itself as the digital playground if it knows this is happening, and it definitely knows this is happening. It doesn’t even, again, Roblox can know this is happening without even reading what’s happening on its own platform. There have been multiple police investigations about this, there have been multiple huge reports about this, pointing out Roblox’s pedophilia problem for years. Even putting all those claims aside, given that Roblox knows about this from all these other sources, they at least have to warn people. At the end of the day, Roblox could choose to say, “Yeah, we like being a pedophile hellscape,” they can make that choice if they want to do that for their business, they just got to tell parents that’s what they are, they can’t keep not warning parents about the dangers to the kids who go on to Roblox. None of that should sound like anything I just said about what Section 230 does. Section 230 serves an important, narrow purpose that has nothing to do with design defect, has nothing to do with failure to warn, has nothing to do with negligent misrepresentations. Under the law, you have to look at what you’re actually claiming, you have to look at what duty you’re trying to impose on the platform based on your claim, and you have to look at what the platform has to do in order to fulfill the duty you’re trying to impose on it. In none of our claims does Roblox actually have to police the content, like it would be if our claim was, “You have to stop Joe from defaming Stan.” 

Matt Dolman: That was a great explanation, and yes, we’ve covered it with other people, no one did it as well. You go, Stan. Sorry. 

Stan Gipe: I’ve got a question, it has nothing to do with where we’re at, but kind of getting back to your clerking days. When you clerk for someone like Justice Alito, let’s take it back, you could knock me out, give me truth serum, extract every bit of information I have in my head, and the Dow Jones isn’t moving. When you’re working on an opinion for a judge like that, you’ve got information that truly the whole nation is interested in, you know these opinions before they’re put out, and you’re in the process of drafting them. What kind of training do they do, like, “Watch out for this, people are going to try to exploit you,” like, do they tell you stay out of bars, stay away from strip clubs, how do they train you to help avoid accidentally letting massive information slip? Do strippers often try to extract information from Supreme Court clerks? 

Matt Dolman: I guess that’s the question on that slippery slope, Stan, that would lead to, would they be smart enough to actually contemplate asking Joe what he learned when he had closed-door sessions with other clerks about cutting-edge issues going on in the United States? 

Joe Masterman: Well, look, there’s only so many things that motivate people to lie. Money, women, drugs. 

Stan Gipe: At least give credit, you’d figure it’d be a higher-end escort, not like a stripper at the local strip club in the middle of the afternoon, who put down the McDonald’s bag to get on the stage and ask Joe what it’s like. 

Matt Dolman: Who was it that talked about investors? It’s the three L’s, ladies, liquor, and leverage, right? It’s one of those three that takes down every great man. 

Joe Masterman: Well, fortunately, having spent a year at the Supreme Court, I watched the most amazing appellate advocates, so like them, I’m only going to answer the parts of this compound question that I want to answer, not including certain parts. They strike the fear of God in you about that. You may recall there was a rather famous leak of an opinion a couple years ago, which happened after I clerked, so I’m sure it’s even different now. It’s even to the point where the instructions you’re given are, if you have a roommate, you cannot tell your roommate which cases you’re working on, because even that amount of information could be used to glean some amount of information. If someone knows Joe is the clerk assigned to this case, they kind of know what Joe thinks, so they know what he’s going to recommend to the justice, so they can sort of glean from that some parcel of information about what might happen from the case. So you can’t say anything. It’s like being in the CIA. I can tell people I’m clerking for the Supreme Court, obviously, but beyond that, you really can’t say anything. Prior clerks can tell you what happened during their terms, because you kind of need that institutional information to do your job, but once you’re out of it, the people clerking then can’t even tell former clerks at the same justice’s chambers what’s happening at the court. 

Stan Gipe: Are you allowed to bring materials home? Do you have to worry about that kind of security when you’re working on an opinion? 

Joe Masterman: Yeah, the security is insane. I had never had to use one of those random number generator keys before, but you have to plug that in, you have to put in the number, in order to use the laptop at home, you’ve got to plug that key in, you’ve got to put the random number generator thing that pops up, within five seconds or else the number changes. There are all these locks and keys you have to go through just to access your own laptop for that reason. 

Matt Dolman: Wow. 

Joe Masterman: Yeah, no one ever cared about anything that Stan and I knew. 

Matt Dolman: This is really cool. 

Stan Gipe: To me, I feel like that would be almost a burden, like, “Hey, I let something slip here when I’m talking to Matt or my wife or something.” It’s not like that, I would almost feel like an overwhelming burden you’re carrying all the time, like you’ve got to be constantly careful you don’t share too much about anything when you’re hanging out with your buddy at a bar. Just, loose lips sink ships, but especially more so in that situation. I think it’d be hard. 

Joe Masterman: Yeah, even right now, there’s still someone right behind my laptop screen pointing a gun at my head, just to make sure I don’t say anything too much, a few years later. 

Matt Dolman: Any other brain busters, Stan? What else you got? 

Stan Gipe: No, that was the stuff that really plugs my mind. A little bit of a question, like, in the clerking job, when you’re clerking for a judge, do you almost have to train yourself to adopt his form of legal analysis, or his legal voice, and does that take some time to learn? 

Joe Masterman: Yeah, you are there to serve as kind of that judge’s agent, and in order to do the best job you can for them, you do have to think, “Here’s how I know they like to approach these types of cases.” Before beginning any of the three clerkships, I went through and read all of that judge’s published opinions, as far back as I could, just to kind of get into the mode and the style of that judge’s reasoning. It’s never going to be perfect, and honestly the times I feel like I did the most disservice to myself, and wasted the judge’s time, or the boss’s time, was when I actually tried to go too far and be like, “Oh, this is like a real gotcha or zinger that this judge might like,” and that kind of stuff, you’ve got to leave it to the experts. You’ve got to get in there, you’ve got to do your best job to process the information, give them what they need to help them do their job. But part of that is, you’ll do that better if you can do it sort of in the mode you think they’ll want to decide whatever type of case it is, and you learn that over time, you’re working really closely with them for a whole year, so you get better and better at it. 

Stan Gipe: Let me ask you, have you ever had to sit down, let’s say you’re in a judge’s chambers, and he thinks completely differently about an issue than you, and he thinks it goes exactly the opposite of the way your intuition says it should. Have you had to sit down and draft an opinion like that, and if so, is it hard to sit there and draft the side of the argument you don’t believe? 

Joe Masterman: I don’t know if it’s hard, because that certainly happened, but in my experience it has happened in cases where it’s a close call, and where I came out and said, “I just think it goes this way,” and a refrain in judges’ chambers is they’ll say, “Okay, see how it writes.” You’ll take a position, you’ll write the opinion to see how it goes, and then once you actually have it written out, these people are really smart, you’ll give them your work product, and you’ll try to hide the flaws in your argument, and they’ll look at one clause in the paragraph and say, “This is wrong,” and they’ll point at the thing that really unravels the whole thing, because they’re incredibly logical and incredibly smart. So it is hard, but it’s only hard because the cases are hard, I would say. I did have one experience where the judge didn’t think the case was hard, and it wasn’t a controversial case or anything like that, it wasn’t a Supreme Court case, but I thought it came out one way, I brought the draft, and the judge, once we had to talk about it, his first response was, “All right, well, Joe, I have one question, what planet are we on?” I was like, “Well, I guess I thought it was the one where this case comes out this way, but apparently not,” and I had to go back and redo it. But even there, these are the reason cases get to the appeal, and they become cases that you actually end up spending time on, is because there’s possibilities for going one direction or the other, and the reason these people are judges is because they’re good at making that call. 

Matt Dolman: What percentage of cases are taken up by the Supreme Court? Less than one percent, right? 

Joe Masterman: Yeah. The Supreme Court’s appellate jurisdiction is discretionary, so they get to choose most of the cases they hear. There’s a small category of cases that fall under their original jurisdiction, so for example, if two states are suing each other over land or water use rights or something like that, they actually have to hear that case. But for the most part, they hear like seventy to ninety cases a year, and those are all cases they choose to hear, because they’re the cases they think need to be decided for the good of the rest of the country. 

Matt Dolman: Because of an obvious constitutional issue, or a split between circuit courts, lower appellate courts, right? They don’t just take a case to take a case? 

Joe Masterman: No. These are very complex cases that get to this. 

Matt Dolman: My point is these are the most complex of complex cases. 

Joe Masterman: Yeah, they say the Supreme Court doesn’t really do error correction, as they say, it has to be an issue that other courts are divided about, and we need a single answer on, or it’s a question that, maybe the courts aren’t divided on it, but it’s a big constitutional issue, or maybe the government has done something really important and the court needs to decide whether the government can keep doing it. 

Matt Dolman: You are an interesting person. We’ve gone longer with you than any of our other guests, which isn’t saying much, we’ve had a low threshold so far. Although we had Christy Fed and Alex Walsh on, but we did have your partner on, so we didn’t have a high threshold for him. He didn’t mention Yum Yum Sauce or his restaurant, which by the way, I went to, so for those who don’t know Davis Cooper, Davis Cooper owns a fast food hibachi restaurant, where is that, that was like ten minutes from where I was staying in Reston, Virginia, what was that called, Asheville, okay, it was fantastic by the way, that was really, really good food, but Davis brings it up in every conversation. 

Joe Masterman: He’s not even here, and I’m talking about Yum Yum, I can’t believe this. 

Matt Dolman: Yeah, that’s why I brought it up. Is there any parting words, or any passion projects you’re working on right now besides Roblox and heavy metals in baby food? 

Joe Masterman: Our firm, I know you talked to Davis already, so I’m sure your listeners are all well familiar and have flocked to our website, but we’re still pretty young, we’re a couple years into this, we’re kind of unique in that we’re still pretty lean and mean, and at least I am trying to bring something to this space that I saw a need for, which is, I hope I have some amount of legal ability and learning from all these experiences I’ve just talked about, and obviously we’re trying to do a good job for our clients, but we’re also trying to help the plaintiffs’ bar. I think there’s a lot of legal service we can provide to other law firms, because as you guys know, it’s not just going to trial and having a cool cross-examination, there’s a lot of stuff that happens before you get to trial, there’s a lot of stuff that happens after you get to trial, and a lot of that stuff is very boring and involves sitting at a computer doing stuff with Word documents, and I can sometimes do a nice thing with a Word document, and I hope we can continue to do that for whoever is trying to win summary judgment, has a verdict to protect, stuff like that. We’re trying to bring that kind of quality, and obviously other people are doing that too, Keller’s got a great firm, Gupta Wessler has a great firm, Lieff has a great appellate team, but we’re trying to come in and be an additional resource, because kind of like I said about Chuck Cooper, he’s an incredible lawyer, and people love him because he really advocates for his clients, and presents the best possible side of an issue that you possibly can, and I came to the plaintiffs’ bar as sort of an unusual member of the plaintiffs’ bar, to try to provide the best possible arguments for the cases we’re involved in, because we’re going up against some of the most incredible lawyers on the other side, and they’re doing a great job too, and they’re giving the judges the best presentations of the issues that they possibly can for their clients, as they should. But we also need to give those judges the best presentations of the issues that we can, at the motion to dismiss stage, at the discovery phase, at summary judgment, at judgments notwithstanding the verdict, on appeal, maybe at the Supreme Court, we need to make sure that, with issues like Section 230, we’re going to run into all these complicated issues as business evolves and runs into more and more new and complex legal questions. We’re just here, I know this is getting a little salesy, but we’re here to try to help where we can, with those hard questions that are going to face our practice for the foreseeable future. 

Matt Dolman: You’re very humble. The word on the street from some of the top trial lawyers out there, you know who these people are, is that they think you guys are the best brief writers in the whole country. These are some of the best lawyers in the country saying this, so there’s a reason why you keep appearing on steering committee after steering committee. Kudos to your success, you guys are going places. I’ve got nothing left, I could keep Joe on for another hour, you want to wrap it up? 

Matt Dolman: Do you have a Conan story, or do you feel comfortable? I’ve got a wrap at five o’clock though. 

Joe Masterman: I don’t really have, I’ve only ever run into him at some stuff, he’s too famous for me now. 

Matt Dolman: Is he a cool guy or not really? 

Joe Masterman: Yeah, yeah, he’s a cool dude. 

Matt Dolman: All right, Stan, you want to wrap it up? 

Stan Gipe: All right, well, this has been another great edition of the David and Goliath podcast. We’ve had an extra entertaining guest today with Joe Masterman. As an attorney speaking to him, I find him to be just fascinating, and I think everyone else out there does too. Super lucky, thanks Joe for coming on, taking the time to speak to us and entertain our somewhat lowbrow questions, but I really appreciate you taking the time. 

Matt Dolman: I want to keep Joe in a cage and just study him, I find him so fascinating. Most of my friends have nothing interesting to say, they’re just my friends. All right, stop, I know, being honest. All right, I always love talking to you guys. 

Joe Masterman: I’ve learned a lot from you guys, I really appreciate the chance to work together, and I look forward to keeping it up. 

Matt Dolman: He’s learned that there’s a low barrier of entry into the plaintiffs’ bar, and there’s dopes like Matt and Stan making money, so he might as well go do this himself. All right, wrap it up. I appreciate you coming on today, Joe. And as always, Stan, it’s a pleasure doing this with you. Have a great day, and God bless. Thanks, guys.