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Legaltech Week

23 Sep 2026 · 59m · 24 chapters

Episode artwork

09/18/2026: OpenAI Launches Legal-Specific Model, AI Regulation in the news, and more

In short

Legal Tech Week episode focused on OpenAI’s “Astra for Law” launch (legal-specific GPT-6 configured for legal research/writing), AI regulation chatter, Microsoft Copilot adoption, and Clio’s push into the judiciary; includes a legal-hallucination story tied to Lane Kiffin/LSU using ChatGPT for legal strategy.

Guests (backgrounds)

  • Bob Ambrogi (host; Law Sites, Law Next).
  • Caroline Hill (editor, Legal IT Insider, UK; global coverage).
  • Nikki Black (Principal Legal Insights Strategist at 8am; writes for Above the Law, ABA Journal, Daily Record).
  • Victor Lee (assistant managing editor, ABA Journal; business of law/tech).
  • Rhys (editor-in-chief, Legal Tech News; mentions MCP/OpenAI connection).
  • Joe Patrice (Above the Law).

Key claims

  • Astra for Law moves OpenAI from “engine behind tools” to direct legal offering via chatGPT Enterprise + legal search index + plugins; targets AM Law 200 with “trusted access” and emphasizes governance/“zero data retention” (with fine print).
  • ILTA survey: most-used AI platform is Microsoft Copilot (76%); cost drives bundled adoption.
  • Clio hiring (Jim McCormick, Pablo/Bridget mentioned) signals judiciary-focused growth; courts are underfunded and need AI for judges/clerks and pro se litigants.
  • Regulation calls may be partly competitive moat-building.

Notable examples

  • Thomson Reuters plugin and Free Law Project collaboration for research.
  • Oz Ben Amram (Pillsbury chief AI officer) quoted on research+analysis “under one hood.”
  • Lane Kiffin/LSU nearly making a major legal mistake after relying on ChatGPT screenshots.

Written by AI. May contain mistakes.

Chapters

0:45

Panelist Introductions

The panelists introduce themselves and share their backgrounds.

“And that has been particularly the case this week with some of the stories we're going to talk about with involving San Francisco, where I don't think I've stopped working before about 1030pm.”
3:08

OpenAI Astra for Law Launch

Discussion on OpenAI's launch of Astra for Law and its implications.

“which has been configured for legal work.”
5:56

Industry Reactions and Competitors

Panelists discuss the reactions from the legal tech community and competitors.

“It's also interesting, too, because OpenAI has shares in Harvey.”
7:40

Legal Research Capabilities of Astra

Exploring Astra's legal research features and partnerships.

“So it seems like they have completely entered the industry in a way more direct way.”
10:35

Future of Legal Tech and Access to Justice

Panelists debate the future of legal tech and the importance of access to justice.

14:00

OpenAI's Legal Model and Access to Justice

Discusses OpenAI's focus on large law firms and their new API features.

“But the the the Astro for Law, the sort of enterprise API that they're talking about, they're really focusing on large law firms.”
17:00

Industry Trends and AI Integration in Law

Explores the integration of AI into legal practices and the industry's response.

“And it's interesting how everyone was like, okay, the only company I know for sure that doesn't do these types of plugins is Laxess.”
19:45

Challenges of AI Adoption in Legal Firms

Addresses the stress law firms face with multiple AI tools and the pursuit of consolidation.

“We now have trillion-dollar companies in the industry, and it's completely changed the game.”
22:25

Microsoft's Influence and Copilot Adoption

Analyzes Microsoft's Co-Pilot as the leading AI tool and its implications.

“The fact that when they asked everybody, what AI platform are you using?”
25:05

Perceptions of Copilot and Market Alternatives

Examines opinions on Copilot, cost issues, and market alternatives for legal tools.

“effort is sometimes, but hopefully it improves.”
Show all 24 chapters
28:00

OpenAI's Revenue Strategies

Discussing OpenAI's financial strategies and the legal industry's potential.

“a lot of money to Microsoft as opposed to going and purchasing another product.”
29:10

The Confusion of Copilot Products

Exploring the various Copilot products and their branding confusion.

“Again, I say they should name it Noonan after Amelia Earhart's co-pilot who did not succeed.”
30:40

Challenges of AI in Search Engines

Critiquing the performance of AI in search engines, especially Google.

“Like, it destroyed Google search, and it slows it down, and the answers are all wrong.”
32:00

The Impact of AI on Legal Tech

Examining how AI is reshaping the legal tech industry and challenges faced.

“I will say I find perplexity computer to be the most amazing thing I work with as a general day-to-day matter.”
33:50

Clio's Strategic Moves into the Judiciary

Analyzing Clio's recent hires and their focus on judicial technology.

“And people just don't know, like, how to respond at all to, like, what's going on.”
36:00

Funding and Future of Judiciary Tech

Discussing the funding challenges for judicial systems and potential growth.

“I don't remember how much money that was worth, like 300 million plus or something.”
42:00

Discussing AI and Court Funding

Explore the challenges of AI integration in the judiciary and court funding disparities.

“and best practices on AI I don't know how widespread that is and I don't know if there will be enough funding here in the States.”
43:35

Insights from Ed Walters and Tech Development

A deeper look at AI developments in legal tech and insights from industry experts.

“I was just reading that thinking, okay, yeah, maybe we should listen to Ed.”
45:38

AI's Impact on the Legal Industry

Discuss the implications of AI technologies on legal practices and challenges faced.

“And just from 2022 when the AAA really did a focus on AI tools, Like, they had a ton of tools that they came out with in a short period of time.”
47:12

Regulating AI: A Necessity or a Shield?

Debate the need for AI regulation and the motivations behind industry calls for it.

“Because, you know, in the comments, some folks were pointing out, like, are we going to talk about the way in which this week everybody in the on social media started going like we need to start regulating AI?”
49:54

The Intersection of AI and Sports Law

Analyzing the legal implications of sports law cases involving AI, using Lane Kiffin as a case study.

“It can't book a flight reliably, but it's going to murder us all.”
52:52

Generational Views on AI and Legal Work

Understanding Gen Z's skepticism towards AI and its implications for future legal practitioners.

“Well, and another really interesting issue that I think is discussed too much when it comes to the demand for these products is Gen Z hates it.”
56:01

Legal Tech Meets Sports Talk

Exploration of the intersection between college sports regulations and legal tech.

“Still raising billions of dollars through a public offer?”
57:38

Upcoming Events and Future Shows

Discussion on upcoming events, including the Kaleidoscope conference and future show plans.

“And we'll be doing some, not exactly a full version of our panel there, but we will be doing Vicki, Joe, Steve, and myself, right?”
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Transcript

Automatic transcript. May contain errors.

0:04Welcome everyone to another edition of Legal Tech Week. This is the show where we talk about the top stories of the week in legal tech and innovation. And we are here every Friday afternoon at three o 'clock and hope you'll stay with us if you're if you're a newbie and come back next week. My name is Bob Ambrogi. I have a blog called Law Sites and a podcast called Law Next. and a lot of interesting stuff to talk about today. So I'm looking forward to getting to it. So let's introduce our panelists, starting with Caroline Hill. Welcome. Hey, hey, everyone. Thanks. Nice to be here. Yeah, I'm Caroline Hill.

0:44I'm the editor of Legal IT Insider based in the UK, but we write about stories globally. And that has been particularly the case this week with some of the stories we're going to talk about with involving San Francisco, where I don't think I've stopped working before about 1030pm. Anyway, nice to be here. All right. And Nikki Black. My name is Nikki Black. I'm the Principal Legal Insights Strategist at 8am, the team behind LawPayMyCase, CasePure, and Docket Wise. And I write legal tech columns for Above the Law, ABA Journal, and The Daily Record. And if you have any doubt that Nikki is magical, every time she speaks, chimes start going in the background.

1:30I thought about that. We have a rubber band for like when it's really windy to close it so that they won't go off. But it broke during a storm recently and I couldn't find another rubber band big enough. So there's just going to be chimes going on because it's a little windier. So sorry about that. Okay. Very nice. Victor. I'm glad those are chimes and it wasn't just my ears ringing. You never know these days. My name is Victor Lee. I am assistant managing editor for the ABA Journal, covering business of law and technology. And yeah, glad to be here. All right, Victor. And next up, Rhys. Thank you.

2:11The chimes are actually awesome. I'm Rhys. I'm the editor-in-chief of Legal Tech News. and I too have a MCP connection through Cloud and OpenAI. So it's not just tech companies doing that. All right. And last but not least, Joe Patrice. Joe Patrice from Above the Law. Why, did something happen with Astra today? I don't know. Like my press releases haven't mentioned anything. I think my entire inbox is the word Astra today. Well, if you don't know what Joe is talking about, if you've been in a cave for the last 24 hours or something, probably, I think without doubt, the biggest news of the week in the legal tech world was the introduction by OpenAI or the rollout by OpenAI of its Astra for Law, which is a version of its latest model, GPT-6 Astra.

3:16which has been configured for legal work. It includes a legal search index that can do legal research, and it's been configured with custom instructions for knowing how to do legal writing and legal analysis. And there was also a rollout of a bunch of plugins from legal tech vendors, which is part of the reason our inboxes are all getting flooded today, I think, because weirdly, although we had a media briefing earlier this week, some of us were on it, not all of us were on the media briefing, but they only mentioned a couple of the companies that were providing plugins, and even when they put out their announcement, they didn't list them, and then no sooner did, for me, I'm sure others too, no sooner did my blog post go up, then I started getting all the emails from PR people at companies saying, you know, we got a moonshot GPT plugin too.

4:18Anyway, if this all sounds familiar, it all sounds a little bit like what Claude did not all that long ago when it rolled out Claude for legal. And I think it was interesting that during the media briefing, Jason Bomeg, who's the former, the founder of Ironclad, is now leading this effort at OpenAI, that he kind of bristled when somebody kind of suggested this was OpenAI getting into legal and he kind of made a point of saying, you know, we're not just getting into legal, we've been in legal from the start and this is just a different manifestation of it, which is probably fair. I mean, OpenAI was behind co-council and behind Arby originally and, as a matter of fact, invested in both of those and gave them early access to their products.

5:03So it's not at all inappropriate to say that they've been in this kind of since the beginning but but they've always been in it in more of a kind of supporting role you might say and here they're kind of taking more of a lead role so uh what do people think of us what's what do you what do you all make of it strange like they have been uh the engine behind you know like quite a few tools. And the release this week essentially means people can do stuff directly on chat APT Enterprise. So it is kind of like them directly offering something to the legal industry as opposed to just kind of like powering the tools behind the scenes.

6:01It's also interesting, too, because OpenAI has shares in Harvey. They have been a funder of Harvey. And it was interesting how in the press release they sent over, they were like, oh, this new configured large language model can be helpful to like Harvey and Cora too. And so like all these other, you know, startups as well, it's, you know, it's weird to see them like have a stake in Harvey and at the same time like have something out there that kind of could compete in like Harvey too and it, you know, like probably comes around the same time as Harvey announcing it, like, fine-tuned a Chinese open-source model to be like a legal specific model.

7:14It's strange. It's exactly the same approach that OpenAI has taken, too. So I'm not sure if they're doing the same things, if they're even talking to each other. What I do know is that we all were expecting OpenAI to enter the industry to have a direct offering to the industry. they hired I believe the former I can't remember his Rolex was like a really higher up at the CLM company like Ironclad Jason Bumick, he was the founder former CEO of Ironclad they hired him in the spring to like be the, I suppose, of their legal business. So it seems like they have completely entered the industry in a way more direct way.

8:28As quad and anthropic, I mean, Gemini and perplexity have as well, too. yeah yeah i was in the brief sorry i was in the briefing with bob as well and it was it was interesting um i mean i think reese you're bang on like this is not unexpected and to take jason's point they have been involved in eagle but i feel like this is a big bang you know this was make no mistake you know everyone's seen this on linkedin someone was just suggesting a drinking game for every time someone says the word astra because which i'm definitely in for by the way but um And so I think it's exciting. I think people, I spoke to somebody who is one of the community partners.

9:15There's so many pieces to this to unpick, I think. So one is this like co-opetition that you were just talking about. So they are competing in a meaningful way with a lot of the people that they're partnering with. I think that we've seen a lot of that. They're creating, they're going to want to be the infrastructure. What really fascinated me, and I would love to hear anybody else's take, was about legal research. We've probably got people from that field, I haven't actually looked who's on, but, you know, so they've said that they're providing more legal research capability within the platform.

9:50They're working with the Free Law Project, but they also said that that will complement the people's prevailing legal research tools, and Thompson Reuters, for one is one of the partner plugins they they made a point in the press release of saying you know that co-council um and other tools or high queue they referred to specifically provided the the sort of the that deep data um and that they would be relied on but sort of almost conceding that people would want to use open ai as the the interface um and the the sheer number of partners albeit was kind of strange that not all of them were mentioned and then we had the whole run of everybody going I'm on it I'm on it you know but so the the sheer scale of this at launch is very impressive I saw um you know um really creating that in sort of amazing infrastructure the community partners I spoke to Oz Ben Amram who one of the community community partners is Skills Law and I spoke to Oz who I quoted um on the night like on Wednesday night was it last night we did it last night um and he said oz benamram who many of you know he's now chief ai officer at pillsbury i spoke to him when he was on his way they did um they did an in-person launch with jason um uh so everyone was there and oz said it's a really important development um i also got commentary from sullivan and cromwell from john saver um who said um it's really he said it's very exciting in the legal research space they're seeing some sort of real he said um no model before has brought together legal research and uh ai analysis um and it's really exciting to have that all under one hood so there's lots and lots to unpick and not very long space of time not much space of time so far so i think i've got to do more I'm picking I don't know what anybody else thinks about any any any of it yeah well I mean I think I think it was um I mean obviously it was I mean it's not it was it was expected that they were going to come out with that and I think it's I think it's a great it was it was a great idea it was it was a good move for them because I mean I think was it you know um Nikki's study that she cited um with um well you know with 8am I mean it like Chachi but he already has a pretty pretty built-in advantage with as far as like people asking legal questions and whatnot they they tend to go to chat jbt first so this is sort of a logical extension of that um you know they already have that market but i was also i was kind of curious just what was brought up just now with like the idea of like convenience and having one thing that that um you can do everything on i mean and i think i think maybe maybe your article bob that talked about when google came out with uh the gemini for legal or whatever it was called gemini for i don't know um whatever gemini for lawyers um um just like their well the fact that like people use google for so much so much like it's already sort of like their go-to default for a lot of things that would give them an advantage over other potentially give them an advantage over other other over other um vendors because people are just used to that um that you know just going to google for for things and whatnot so you know it'll be just to kind of see to kind of see like yeah like as far as the convenience factor goes like who's going to win out um you know whether whether the whether whether google's um ubiquity gives them the advantage or whether the chat's you know brand recognition or the fact that people tend to default to it whether that'll give them um an advantage but yeah it's it is odd seeing like now whenever whenever we get one of these press releases it's always it's like and we partner with this with this with uh you know these people can plug in these people can you know integrate it in this partnership yeah like it's just weird seeing all this cooperation It was like, man, what happened to all the cutthroat competition?

13:38What's going on? You guys are all getting along too well. And they're coordinating us all in advance of the announcements. It is a really interesting thing. One thing I think worth noting is that there's kind of different parts of this in terms of what they've announced. And I don't know if they've done the best job, or maybe the reporters haven't done the best job of sort of parsing it all out. But the the the Astro for Law, the sort of enterprise API that they're talking about, they're really focusing on large law firms. And I specifically asked that during the briefing and Jason said, yeah, we're targeting the AMLA 200 with this.

14:18And at some point I asked him about access to justice and whether they're going to do anything to try and make this available to nonprofits or others. And he said, well, you know, that's he's very passionate about that. And OpenAI is very passionate about that. But that's for another day. That's not this announcement. And they rolled out this new, what do they even call it? Their trusted access program, which apparently am law 200 firms have to somehow apply to or be part of in order to get access to this, this API. and it was kind of an interesting point in the press briefing because they kept talking about the fact that one of the features of this is zero data retention, and they're talking about security and governance.

15:05And Stephanie Wilkins is not here today, but Stephanie asked, well, does zero data retention mean zero data retention? And they were like, well, it's like a 30 page agreement and you got to read it and there's like fine print. and it was kind of funny the way they did not directly quite answer that question when she put it to the... It was a very loyally answer wasn't it? It was like wow I think everybody's going to be round about happy with it it's very difficult to answer because it's 30 pages long and but you know we've worked very hard at it it's not you know it's obviously complex but yeah it was a very roundabout round the houses answer that one he was very impressed with your A to J sorry he was very you know I thought Bob you asked Bob asked about access to justice and you made that comparison with Claude and you know making to trying to do some good and he he seemed very touched by that didn't he Jason you know he said that this is something that's a big...

16:08I'm British and sometimes cynical about these things. Well, actually, we're all probably really cynical. I don't know why I said I'm British. But, you know, I think he seems... I think they really are trying. But with this release, it's not got an A to J angle. Not immediately, anyway. Yeah. So two, like, victors, you know, playing too. It's strange that, like, you know, like everybody is playing along.

16:37They kind of have to. If OpenAI does anything, it's the AI engine that's powering all their tools, as is Anthropic 2 and probably as is MNI as well. They really don't have a choice. And I'm pretty sure a ton of the companies that are partnering are also scared shitless too. these you know like huge AI providers are really hoping to become like the app store for Eagle Tech and we've seen the app store before with Raymond Court I believe the difference here is that you know you have like some of the largest trillion plus dollar companies in the tech sphere who have entered the industry and are like, everybody plug into us.

17:41And it's interesting how everyone was like, okay, the only company I know for sure that doesn't do these types of plugins is Laxess. And I asked them too and like they were like it's you know like it you know like um we have a very different strategy and people can come to like our tool um and they have like really good reasons why um it's just interesting like to see the industry after spending so much time trying to create like the end-to-end like one platform for the entire industry has to become like a, like, you know, plugin to a tool that OpenAI and Cloud had, like, you know, I have. And it's an open question, too, if, like, everybody can just play a log and if there's space for everybody.

18:49I do know from the conversations I have with firms, they are stressed out with the sheer number of tools that they have to go through and review

19:07and they're trying to decrease their surface and their tech stack. It seems like the entire industry sees that trend and they're trying to become like the one agentic or like you know like one like you know like comprehensive tool um and these giant um ai companies like seem to have the the cash and the scope and the you know the and what to kind of do all of that um and we always talk about like harvey and

19:43and how they have just ridiculous sums of cash in the industry. We now have trillion-dollar companies in the industry, and it's completely changed the game. I don't enjoy to predict stuff, but I strongly believe I think it's the start of a broader shift and potentially a broader consolidation too. Yeah. Julie, welcome. Put some cash on Kelsey and see if that pans out. I think we're going to talk about ILTA's survey, I think, maybe. And obviously Microsoft. First of all, let me just say welcome to Julie. Oh, yeah. Sorry. Hello. Hi. I'm right on time. Continue. Canadian, you know. Oh, yeah, yeah.

20:42Canadian journalist. Hey, when you become our 51st state, we're not going to tolerate this anymore. But for now, they're going to join the EU. Yeah, we're joining the EU. So we're good. Oh, that's right. I'm going to move to Spain. That's what I'm going to do. You can all do that. Anyway, sorry. Don't forget Microsoft, right? We're going to talk about Microsoft in the Ilticon survey, Microsoft Copilot at the top. We've, you know, I feel like we, I do not want to be the person to say nothing has changed because everything's changing. And but, you know, we have seen big tech sort of come into the sector.

21:22The one thing I would say about that is that Microsoft, I don't mind saying it publicly, has been extremely flaky. You know, like legal hasn't been a very big vertical or not enough of a vertical. Microsoft previously with SharePoint dipped in and dipped out. Firms thought that Microsoft, you know, was going to be the be all and end all platform. They invested a lot of money in legal. Then they kind of went off and didn't invest, you know. So I think that's obviously we've seen those kind of things happen before. I feel like before we I think it's exciting to see big tech coming to the sector personally.

21:55And I think something that we've been everybody's been thinking will happen. But, you know, what's going to be important is that consistency. I think that things have changed lots of things have changed you know for reasons we haven't got time to go into but but I think we've seen big tech before you know and yeah it'll be interesting to see what trajectory this this goes on. Yeah you talk about the ILTA legal tech survey that came out this week when it I thought it was interesting I think is what you're talking about The fact that when they asked everybody, what AI platform are you using? It wasn't Harvey.

22:34It wasn't Co-Counsel. It wasn't Legora for the most part. I mean, the greatest percentage of them are all using Microsoft Co-Pilot, Microsoft 365 Co-Pilot, which was by a wide margin. It was like 76 percent said Co-Pilot. The next one was like 44 percent or something after that. That was really interesting. It was also really interesting to try and sort out in the survey which copilot they were even talking about because they alluded to different versions of copilot in the survey. None of the names they used for copilot in the survey, several of them didn't actually line up with the names Microsoft uses for its own copilot products.

23:19It was kind of confusing on that point, but that just sums it all up for Microsoft. We're all confused about Copilot. It's super interesting. I'm totally curious on who actually is going to Copilot on their own and who goes to Copilot because their company basically says we only have Copilot. you know and apologies to anybody from like we're off on the call but you know I don't feel that it's the strongest an AI tool and I feel like everybody just says copilot because it comes with the office suite too and it's kind of like included in the package and like firms don't want to pay for some other tools.

24:11So like it's, you know, it's there because of like Microsoft's deep like foothold. You know, if we had a survey that actually asked people like, you know, what tool would you prefer to have like access to all the time, you know, like as opposed to the tool that your company tells you, you're only able to access because of a cost issue. And the cost issues were pretty high in the survey too. I mean, like, you know, people were for the first time, like, you know, saying that cost was like a huge challenge with these tools. And if cost is a huge challenge, then, you know, you're gonna go to the shiny-eyed tool that's basically bundled in.

24:59You know, it's strange, like, I really do like to enjoy Copilot. It's just, it drives me crazy effort is sometimes, but hopefully it improves. Yeah, and it was interesting though, and then kind of to the point we were just talking about with OpenAI, the other thing the survey said is that after Copilot, if I, let's see, was it, do I have this right? I think the next most used AI platform was Claude. It wasn't even one of the legal specific ones, although Harvey was right there in the same ballpark, but I mean, And I think that goes to, again, part of the reason why OpenAI is doing what it's doing.

25:42And I thought it was very interesting in the OpenAI announcement in our briefing. They spent a lot of time talking about their forward deployed engineers and what they are doing. to, you know, these are like, you know, their own tech people who go work in law firms and help law firms customize and adapt their product to their own particular purposes. And they spend a lot of time talking about that. And that seems to be a big, a big emphasis of their push into legal is that they want to be sending, they want their people in your law firm helping you use their product. I think there's still such a nervousness around privacy governance.

26:21and that's where Copilot has one of the edges I think and um as well as the fact that you know I it's interesting because I I actually love Copilot I know it's probably maybe an unpopular view but and then I've seen some quite cool work being done like Clifford Chance working with Epic um and helping people to surface their knowledge using Copilot um because obviously it's got amazing search natural language search search function functionality it's it's cool it's you don't have to worry about some of the issues that we're going to have to worry about in terms of where that data's being shared or stored i i feel like it's um you know there's a lot of reasons why i'm not surprised why i found where the adoption is higher than than some others personally i i just um and i'm sorry if this point has already been raised but just going back to the point of cost in Microsoft.

27:19We know how expensive Microsoft is, and we know how every law firm has it. And it just makes me think of the analogy as a millennial talking to you on a Mac who has no Microsoft products on my computer. Word perfect. Oh, yeah, we got to talk about that later. But, you know, like how there was a shift for this whole discussion of using Google products or using Apple products in a professional setting. And I just wonder, like it doesn't, I'm not surprised that Copilot is number one. I also do not like Copilot, but I get why people use it. It's the lowest barrier and your firm is already paying a lot of money to Microsoft as opposed to going and purchasing another product.

28:08At the same time, as somebody put in the chat, OpenAI needs to start making money. And the legal industry is a very easy way to go and take a chunk of cash for people who still are not sure what their strategy should be. I'm also curious if the question was, if you had unlimited resources, what would you choose? Because I've written about this before, about things like building private LLMs and building your own systems. systems um and i forgot to add this article to the list but i'll try and find it but there's a really good article here in the in canada of a firm that's doing this um and so i i think i take this survey with a with a little bit grain of salt because because copilot was always going to be number one and also this idea of like which copilot um how many products have the word copilot in it can anyone on this panel actually list all the different products with copilot because like to me it's just i just think of it as microsoft and then i can talk about gemini and open ai and everything but like copilot seems to be like branded on lots of things and i'm not really sure what the differentiator all the time and there's co there's paid copilot there's free copilot there's copilot for enterprise there's regular copilot it's it's it's just ridiculously confusing.

29:33Again, I say they should name it Noonan after Amelia Earhart's co-pilot who did not succeed. Clippy, I don't understand why they didn't. We've been talking about this in the chat over here for people who are listening to this who weren't in the chat. I don't know why they didn't stick with Clippy. I mean, Clippy was made fun of at the time but was, you know, adorable. And they should have brought Clippy back and been like, Clippy was ahead of his time. Now we got Clippy. Yeah, right? Like now we have a Clippy that works. That should have been their thing. I mean, look, Microsoft's always going to be ahead because, and this is a fight I've been having in a non-legal tech, in my role teaching education.

30:17There's a lot of people who are like, well, we got to get AI out of here, whatever. I was like, you can't. Some of these AI tools are now getting so baked into the products that you can't avoid using them. Of course, Copilot gets used. It's baked into the word processor, and so you can't, like, avoid it. And the same thing's true of how Gemini is running Google search these days. Like, it is doing terrible jobs of it, but you can't avoid it. Oh, it's awful. Like, it destroyed Google search, and it slows it down, and the answers are all wrong. And I'm like, I was— Almost always wrong. A teenager in Google search was stronger than it is today, and it's nuts.

30:58Yes, but I will point out, with Search, we know that Google shot itself twice in both feet before they ever put Gemini in AI. Search is a whole other thing. Again, this is why I'm saying, as I get why law firms will be like, I'm just going to use Copilot. Gemini sucks. We used to be a pro. What about Copilot, though? I mean, that's always been Microsoft's model, though, right? Like, they've never been about quality. They've always been about ubiquity. They've always been about, you know, commonality. Like the fact that like they're the easiest ones to use because I mean, I mean, that was that's the problem with Internet Explorer for a while.

31:32That was the only one you could use for the longest time. And and antitrust violations. Yeah, no. And yeah, I will say this was mentioned in the comments. I will say to anybody who was in this meeting with me, some of you might have been none of the panelists, somebody in the meeting in the chat might have been. I don't know. But I had a meeting in which I told the story. here's how we used to be a proper society but now i did a search the other day where i couldn't find i kept asking something i knew the answer to and google kept giving me the wrong answer and i went to bing and it gave me the right answer immediately we are so broken as a society that bing works like that we should not be here bing has always worked i will always be a bing supporter bing has always worked bing has always worked canada's running bing word perfect and everything that probably still blackberries good canadian company yeah all right i mean google is so broken i just when i really want to find an answer to something now i use perplexity i just find it it gets me the answer to something and it tends to get it right and it gives me the sources and I don't have to bullshit through all sorts of ads and other crap.

32:45I will say I find perplexity computer to be the most amazing thing I work with as a general day-to-day matter. I don't use it all the time, but whenever I do, I'm like, God, that does work better. Yeah, yeah.

33:01It's interesting how NAI has completely transformed the tech industry because like search is completely like, you know, turned around on its head. It's probably going to do the exact same thing to the Eagle tech industry. It is a young industry and we have had people at the top for quite some time. And, you know, it's basically anybody's game. And like, if you go to these industry conferences too, Like, people are scared. Like, the vendors don't take anything for granted. And there's always, like, a, like, weird desperation in the air, too. It's, like, almost anyone's game. And people just don't know, like, how to respond at all to, like, what's going on.

34:01And that's, like, true probably across the entire tech industry. Like, you know, like once huge companies like Google, who owned a search to the point where we would just say Google it, we still do. You know, it's just it's insane how quickly like they've been like upended. Yeah. I know we have a bunch of stories, other stories to talk about. I did want to I don't think we did we ever talk about the whole Clio getting into the judiciary thing? because I thought the fact that they hired Jim McCormick this week after just hiring Pablo or Orlando is like the major personnel coups of the year in the legal tech world.

34:44I mean, these are two powerhouse people each in their own right, neither of whom needed the work either, I don't think, who are teaming up to lead this whole push into the judiciary. very I mean it's it's sort of fascinating that that Clio is even trying to do this like apart from the hires that they even want to make this a focus of theirs because that's kind of way off track from from you know building tech for usually is not the same as building tech for law firms and. So I don't know. I think it's going to be really interesting. as evidenced by the fact that we have a mention in the chat that some judges are still using word perfect uh so yeah so building tech for judges is a very different game uh yeah no like it it does seem like cleo is putting together uh and they're like assembling the avengers over there although it's canada so i guess it's alpha flight but they're putting together uh anybody anybody get the uh no i'm just waiting yeah yeah all right good good good well look i i i loved a good alpha flight in the 80s uh yeah so it's um yeah but no they're going out and using the massive amount of money that they're sitting on uh to uh to gen to get some talent right like both Pablo and Bridget like Pablo and Bridget I'm just kind of like yeah kind of an impressive uh it's impressive because it not only adds talent but they're also big enough hitters that you kind of are like it generates like for us like as press it generates headlines like we want to write about that story like it is itself a PR move to hire these people on top of the fact that you're getting a value add in talent like it makes sense yeah it makes sense to me this this approach because I know people probably aren't aware that Thomson Reuters has a multi-million dollar contract with Ontario government to modernize their court system.

36:54I don't remember how much money that was worth, like 300 million plus or something. I just put in the chat the article I meant to add to the group this week, which is that the Ontario courts were hacked. And the hack is probably due to this upgrade that they're doing right now through tr so i i kind of get why um i really get why cleo would would start the judiciary to and by the way this hack affected 12 states 12 u.s states as well so they know that there's actually money to be had here with these modernization projects because if you're going to talk about ai i know the article is funny but you gotta talk if you're gonna talk about ai you have to modernize the legal system so do you know anyone else like i didn't write this cynical i'd say i'm more cynical on the panel than i am sometimes i just wrote a very plain piece but part of me wondered you meant you mentioned the big research providers like they've always been trying to you know they they want to work with the judiciary everyone's given lexus everyone's given thompson reuters and we know the reason why is because if the judges are using lexus and thompson reuters then the people will have then the people coming before the courts will have to use lexers and thompson reuters this is like the oldest thing in the book and sorry to anyone listening from cleo but like and actually there's nothing wrong with doing that right perfectly legitimate but i did wonder whether it's like hey we're going to build separate judiciary tech or what the kind of strategy is here like whether there's a kind of like i don't i don't really i don't really have a full sense of what this looks like or how clever it is or not clever i thought it was super interesting because I do think that there is significant demand.

38:39I mean, there aren't, the judiciary doesn't run around and constantly do PR about their, you know, IT needs and it's all these like isolated, you know, meaning like it's this county, it's that county, they all have their own IT systems and that's, you know, the state oversees it, but, you know, it's all these little bubbles of IT and they aren't really well funded. The courts are overrun with, you know, they have so much demand and they don't have enough staff to deal with it. And then with all the pro se filings now, especially in federal courts, but you know there's even more for them to be dealing with.

39:14And when I read this, what I immediately thought of was about a year and a half ago I was at a local bar event and one of the judges I know told me, you know, he's a little bit older than me, he's a Supreme Court Justice, which in New York is a trial level, told me that you know his they were already using ai and his um in his um why am i what is the word what do you what is the word like in his um chambers chambers why am i having this i'm not very i think it's really chimes but he's loving the timing nicky i'm sorry you know in his chambers and that they were really finding it to be incredibly valuable to help them move things along and that they were able to draft things with it.

40:04And so I think that they may be serving sort of a, and I'll use an AI word, quiet need. You know, AI loves the word quietly and quiet. But I think that it was a really interesting move. And I'll be really interested to see, as you alluded to, Caroline, what it looks like in practice. And actually, I should add, you know, from a, they've now got a lot of money and they're always looking for growth opportunities, you know, and this is, you know, an untapped, it makes perfect sense from a lot of senses, from the need and from the fact that, you know, they're looking for different, I don't know if you can call the judiciary market, but you know what I mean, like in terms of, they're looking for growth and this is an obvious avenue.

40:45And I'm afraid they can have it. Their motto is to transform the legal experience for all and I think they're going to do it just by hiring everybody. So there's no one to be a judge. Quick question, though. I'm all for Clio helping to create tech for judges. And it's totally something we need in our court systems, too. How strong of a growth opportunity is this at least in the States where our court systems are so ridiculously underfunded? and you know like the education on even how to use the tools is still not at the place it needs to be I mean every time I go to a conference and hear judges talk they always like you know discuss the need for education and there has like been some efforts the JAIC it's like a judges group to like help them share education and best practices on AI I don't know how widespread that is and I don't know if there will be enough funding here in the States.

42:17I mean, it could be very different in Canada in the UK. You probably have tons of cash to give to your courts because you're not spending it on testosterone for the army or God knows what we're spending it on. The miles from the Kennedy senator, apparently. Why didn't we think of that? All judges should be required to take testosterone. That makes perfect sense. I did talk to Bridget. I interviewed Bridget for my podcast, which will be up Monday, I think, and she talks a little bit more about kind of some of the specific tech they might be trying to build. But it is very much focused. I mean, her thinking right now is very much focused kind of on actual the work of judges and to some extent the clerk.

43:07But it's not they're not necessarily looking to like build systems like what Tyler technology they're not looking to build docketing and filing systems that sort of thing but somehow use the work of judges and they are also you know very much focused on the fact that 75 % of litigants in state courts are not represented by lawyers and if you're going to try and tackle the problems of the courts you have to try and tackle that issue in some way so that's definitely going to be part of what they're well look we have Ed Walters here in the audience of connection probably tell us a lot more about this.

43:36I was just reading that thinking, okay, yeah, maybe we should listen to Ed. Yeah. Well, and, and, and courts provide a long tail, uh, revenue stream too. Like it is difficult to get in, but once you are in, you're kind of in forever. So, uh, they, it is a nice business to get in. Yeah. Yeah. Plus, I mean, like, like, yeah, I mean, if they can figure out a way to like do this and price it right, then they'll have a, they'll have a basic, almost, almost a monopoly. I mean, like, I don't, I don't, I mean, I don't know if anybody else is really tackling this problem. And, but, but for the Judge McCormick thing, I thought it was interesting because it's kind of like when, what are they called?

44:13The ADR when, what was that? ADR, AEI arbitrate. Yeah. Because when they hired her, they made a big deal. Because when they hired her, they made a big deal out of it. Like, and that was a big, that was a big get for them. And so, you know, yeah, I wonder, I wonder what, you know, what, you know, what was sort of the impetus for, maybe, maybe, I didn't get a chance to interview with her. I wonder what was the impetus for her to do this. But maybe, maybe it was the fact that, yeah, what was pointed out, what Ed pointed out, that, yeah, this is going to be a problem for the judiciary and maybe she wanted to get ahead of it.

44:49I mean, he's always thinking ahead. But yeah, but yeah, like Joe was saying, if they can figure it out and price it correctly and whatnot, then pfft. I did ask her to build it in the AI judge. Again, And word perfect is still being used. Her answer was ask Pablo. So yeah, go ahead. Yeah, I know. Yeah. He and Pablo have like created some of the coolest tools I've seen. So like I'm super excited to see what they're going to do. And it's also like really cool to see like Pablo like creating stuff again. because he was really awesome at Case X. They really changed the space and the time too. So it's going to be interesting to see how far they all go.

45:42And just from 2022 when the AAA really did a focus on AI tools, Like, they had a ton of tools that they came out with in a short period of time. And the ADR space, like, quickly changed to, oh, it's like, you know, probably two of the strongest, like, hires, I would assume. It's high stakes, too. I mean, like, we're all going to pay close attention, too, because, like, there's high expectations. it's going to be cool because we're going to be are people here going to be at ClioCon? I'm going to send somebody in from my team yeah so it'd be so cool to be able to go and have more content I'm sure this will feature quite highly I'm sending my team yeah like I have a team I'm sorry we're just jealous that's all I can't be jealous all right we have to get to the oh go ahead i'm sorry finish oh no no no i was just repeating so it'd be great we'll no doubt have lots of conversations about this and be able to explain more unless ed just wants to spend on we had a couple of other stories i did joe had had the sort of the bonkers ai story of the week uh i thought uh legal ai story anyway legal hallucination story or whatever so i thought we ought to at least talk about that yeah uh and it's useful Because, you know, in the comments, some folks were pointing out, like, are we going to talk about the way in which this week everybody in the on social media started going like we need to start regulating AI?

47:23It's the most dangerous thing in the universe. And I was like, all right. So my story does touch on that. My story, I honestly think this is my magnum opus as a legal tech person, because as I put it to a private chat that like a chat I'm in with, like, some other journalist folks like Ellie and all. I'm like, this is this is a story in which I talk about A.I., Lane Kiffin, Dario, the Protect Sports Act, Ted Cruz, conference realignment and open weight language models. I go into all sorts of little weird rabbit holes here. But the impetus for it is Lane Kippen. And for those who aren't sports fans, LSU nearly got kicked out of the SEC a couple weeks ago.

48:06And they were, you know, because they decided they were going to sign a bunch of NFL players to their college team. And they thought they could get away with this. Not the Security and Exchange Commission. Not the Security and Exchange Commission. No, no. This one has power. Anyway, so they attempted to do this. The SEC said you can't do that. There was a lawsuit. It was seen by a Louisiana state judge who has LSU season tickets who thought it was all fine. Then there was a federal case that did not. Anyway, so Louisiana talked a big game about this. And then once they finally got to real court, they started to fold like Superman on laundry day, as they put it.

48:49But the issue of this insane legal theory that came out yesterday in an ESPN deep dive is that Lane Kiffin, the head football coach, seemed to have been actually running the legal strategy. Not a great look. Running the legal strategy, and he was running it by asking ChatGPT whether or not he was right. And his lawyer friend kept telling him this isn't right. And he kept sending his lawyer friend screenshots of ChatGPT going, sure it is. So this nearly was a billion dollar mistake for this university. And it's now quasi resolved. So I start writing about that. And then I kind of go off on a different tangent, which is this week we had with Dario from Anthropic kind of writing this paper.

49:41But, you know, Sam Altman agrees with him and then Elon does. All of them are asking for we need regulation. You know, we need we need to slow this down. It's an existential threat. Like literally, AI is going to murder us all. It can't book a flight reliably, but it's going to murder us all. And they're talking about this. Well, and we need to slow down. And we also have to be worried about China because we're in a race toward what? Nobody knows. Anyway, they need regulation, and their pitch to this is what major revenue-producing industry ever asks to be regulated itself? I mean, that proves that you should trust us.

50:19Well, one, no, don't trust them. And two, industries ask to be regulated all the time, and it's because, well, one, this industry doesn't actually make any goddamn money. But if they did, the reason they're asking for it is because they want regulation for two purposes. to shield themselves from liability for things and to throw up entry barriers to competitors. They want regulation that will say, AI is so dangerous, but don't worry. Open AI, Anthropic, Gemini, and maybe Grok are fine. Just don't use anybody else. That's what they want. And that is what they're going after. And I say this accelerationist nonsense that blew up this week.

51:03And I say this coming off of this Lane Kiffin story, which got me realizing that this is the exact same thing that's currently going on in college sports, where college sports is pushing for a new regulation over everything so that they can stop paying the players. Because now that the SEC and the Big Ten are on top, they're like, well, we need something to stop all of this craziness that we ourselves caused. And so now they want that. And it's the same damn thing. It is exactly what LSU is privy to as part of the SEC. It's what they were fighting the SEC over in this Lane Kiffin case. And it's what the AI industry, Frontier Lab industry is doing now.

51:43They are trying to use the government to build the moat that they can't build themselves, which is partially because nobody actually wants to pay for any of this stuff, because people think normal people outside of this conversation, where we're all like tech savvy and see enterprise value to it, personal people are like Lane Kiffin. They like to ask their legal problems for answers to their legal problems and they don't want to pay for it. They will ask the free version for answers. And if you put even the minimal price tag on it, they won't buy it, which is what we know from the data. And that is where the problem is for these companies who have thrown, burned piles of cash chasing this stuff, built physical infrastructure to get bigger and bigger and bigger.

52:31And they are starting to see their lunch get eaten by models mostly, but not exclusively out of China going, what if we just make you run Excel a little bit faster? And it's like, great, I will do that for cheaper. And that is how somehow I covered all of these topics in one article. Well, and another really interesting issue that I think is discussed too much when it comes to the demand for these products is Gen Z hates it. Like my kids and their friends, and when I went and spoke to my law school a couple weeks ago and was on a panel, it was during orientation, my alma mater, I'm not in law school now, but it was during orientation.

53:16And so we spoke to the entire orientation class and they had their arms crossed when we were talking about AI at one point I said and by the way you know um how many of you are you know kind of reluctant to even use AI and like more than two-thirds of the room raise their hand like they hate it they think it's taking their jobs they think it's taking their future they don't trust it my daughter's offended that it's you know stealing work from artists and you know it's it's kind of ridiculous but that's a huge subsection of um tech savvy young people that aren't using it so I think there's so many problems I think that's this sort of um undiscussed or not as often discussed challenge that they face.

53:55But I thought all the things you raised were super interesting, Joe. And sort of that overlap was also really interesting. And of course, funny because everything you write is. Oh, thanks. Yeah, no, like, look, my new mission in life, my life, my crowning achievement will be, I'm going to be watching game day tomorrow. There is a law school at Ole Miss. If anybody has a sign making fun of this Lane Kiffin chat GPT thing, I am going to consider myself vindicated. I am really looking forward to scanning the game day crowd tomorrow. For those who don't watch football, you don't necessarily understand this.

54:34Point is, it's a big deal. Signs are a big deal. No, I love this article. It brings together my two favorite topics, sports and technology. This really is your magnum opus. No, but I really is. And I don't think people understand how huge the LSU story is. That is a huge story right now. And the fact that a head coach who is making millions of dollars, by the way, has a lot of power within LSU is using chat GPT for legal advice when there's a whole LSU legal team right there is the funniest. Like, there's a good Netflix, like movie out of this, you guys. But I want to go back to what Nikki said.

55:15I was talking to a pre law student a few days ago, who's doing her undergrad in criminology. She said she doesn't even want to be a lawyer anymore, because she doesn't want to practice law on zoom. And I'm like, we've, yeah, this is I have, she's not the first person to say this to me. I think the tipping point came with the data centers and the environmental. We forget how much Gen Z is like, we are destroying the planet and you want to destroy it faster with data centers. Like there are people, there are municipalities banning data centers and this is a huge movement right now. And so AI companies are reading the room.

55:55What about the IPOs? I haven't heard a lot about those IPOs lately. Are we still doing that? Still raising billions of dollars through a public offer? No, we're not. Because we need regulation to do what? And then, like you said, the perfect marriage with the SEC and the NIL and how that has evolved, like, it really is actually, it's funny how college football is actually, I'm losing the words here, but it's like the Trojan horse for legal tech. Like, they've got to learn from what's going on with SEC. Too bad it was in the U.S.A. Too bad it was in the U.S.A. I mean, he did work there. Yeah, that's right.

56:42Well, no, but here's the thing, right? Like, it's an incredibly smart thing to think of, okay, well, how do I get around the NCAA rules? I'll bring in professionals because I can pay them now and it's not banned anymore. So that's an incredibly smart thing to do. Like, I'm not excusing it. I'm not, you know, whatever. But it's a smart thing to do. and then it's just like but then i'm i'm not gonna i'm not gonna consult my lawyers and i'm gonna i'm gonna uh consult chat gbt not a smart thing to do but he probably he probably i mean lynn kiffin i mean i don't i don't i mean wasn't he the one who got into the dispute without davis i think like uh when he was in uh uh over like over like his contract whatever so he might not have the most respect for lawyers you know he might he probably had some bad experiences with them so um i've always said this show is like sports talk for legal tech but now it's like legal tech talk for sports talk for legal tech yeah all right unfortunately our sports talk for legal tech has to wrap up i know we got a couple of stories victor nikki sorry i didn't get to your stories but uh uh they're evergreen enough we could talk to them i can talk next week although i don't know if we're going to do a show next week because i'm going to be flying home from kaleidoscope i think i may be home by then i don't know go figure that out some of us will be at kaleidoscope next week the 8 a.m conference in beautiful downtown Las Vegas, which is one of the most favorite cities in the world.

58:09But that'll be fun. And we'll be doing some, not exactly a full version of our panel there, but we will be doing Vicki, Joe, Steve, and myself, right? Is that it? We'll be doing a panel there where we do what we do. Are we posting that? Are we going to post that panel? I don't know. Anyway, whatever. Yeah, maybe that's the next week. Yeah, my attempt to record the last one we did wasn't all that great. It worked. It was fine, I guess, but I don't know if anybody watched that recording from Ilticon. I did. I thought it was fine. Yeah, sorry. I can do that again. All right. Well, thank you, everybody, and I hope to see some of you in Vegas.

58:49I know a couple of people in the chat are going to be there also, so I hope to see you there. And stay tuned on what we have a show next week, I guess. All right. Thanks guys. See you.

From the publisher

Each week, the leading journalists in legal tech choose their top stories of the week to discuss with our other panelists.

 

This week's topics:

 

00:00 Introductions

(02:48) OpenAI Launches Legal-Specific Configuration of GPT-6 Astra, Its Latest LLM (Selected by Rhys Dipshan)

(20:25) 5 Things We Found Interesting From the 2026 ILTA Tech Survey (Selected by Rhys Dipshan)

(34:23) McCormack Goes to Clio (Selected by Bob Ambrogi)

(46:58) LSU Taking Legal Advice from ChatGPT (Selected by Joe Patrice)

(49:37) AI "Regulation" (Selected by Joe Patrice)

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