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Top 15 LawNext Podcast Episodes of 2023 and of All Time

Call me lucky. Every week, I get to sit down at the mic for my LawNext podcast and have a conversation with the leading “innovators and entrepreneurs who are driving what’s next in law.”

For me, each and every one of these conversations is fun and fascinating. But I am equally fascinated to add up the numbers at the end of the year and see which topics and guests you, the listeners, found most interesting.

So, as I do every year, I’ve compiled two lists here. The first lists the top 15 episodes published during 2023. After that, I list the top 15 episodes of all time, regardless of when they were published. (The first episode of LawNext was posted on July 16, 2018.) In each case, the rankings are based on unique downloads.

Most popular this year: My interview with Daniel Martin Katz and Michael Bommarito just after their first try at having GPT take the bar exam. Interestingly, another top episode was my interview with the three founders of Casetext — before they announced their $650 million acquisition by Thomson Reuters.

Also popular were my dueling, back-to-back interviews with DoNotPay founder Joshua Browder Kathryn Tewson, the paralegal who investigated DoNotPay’s products; an interview on the Fastcase-vLex merger with the founders of both companies, as well as a reprise of an earlier interview with Fastcase’s founders; an interview with Clio founder Jack Newton on the lessons he’s learned over 15 years; and a 2022 year-end retrospective with LexFusion’s founders Joe Borstein and Casey Flaherty.

Rounding out the most popular this year were interviews with four legal innovation leaders recorded live at the NetDocuments conference, Axiom’s Chief Strategy and Legal Officer Catherine Kemnitz on its opening a law practice in Arizona, Smokeball’s Chief Revenue Officer Jane Oxley and President Ruchie Chadha, Theory and Principle founder Nicole Bradick, Documate founder Dorna Moini on rebranding as Gavel, BYU Law’s Gordon Smith on stepping down as dean, and AltaClaro founder Abdi Shayesteh on training lawyers to use generative AI.

You can also check out the most popular LawNext episodes of 2022, of 2021, of 2020 and of 2019.

Catch all the episodes of LawNext by subscribing at Apple Podcasts or wherever you listen to podcasts. For a visual array of all episodes, see the LawNext Episode Gallery.


Top 15 of 2023


1. Can GPT Pass the Bar Exam? We Find Out.


2. LexFusion’s Joe Borstein and Casey Flaherty on the 2022 Legal Market in Review.


3. Casetext’s Three Top Execs On CoCounsel, GPT-4 and ‘A New Age in the Practice of Law’.


4. Paralegal Kathryn Tewson On Her Quest for Accountability from DoNotPay.


5. A Special Fireside Chat on the State of the Legal Industry, Recorded Live with Four Innovation Leaders.


6. ‘A Bit Of A Nothingburger’: Joshua Browder Speaks To The DoNotPay Controversy.


7. As ALSP Axiom Opens A Law Firm in Arizona, Its Chief Strategy and Legal Officer Catherine Kemnitz Shares Details.


8. A Closer Look At Smokeball, with Chief Revenue Officer Jane Oxley and President Ruchie Chadha.


9. Theory and Principle Founder Nicole Bradick on Designing and Building Legal Tech Products.


10. Documate Founder Dorna Moini on Rebranding As Gavel and How Law Firms Can Productize their Legal Services.


11. 15 Years, 15 Lessons: Clio Founder Jack Newton On What He’s Learned About Building a Successful Company.


12. Revisiting the Fastcase Origin Story: Ed Walters and Phil Rosenthal on How Their Company Came To Be.


13. The Four Founders of vLex and Fastcase on the Merger Of Their Two Companies.


14. As He Steps Down As Dean, Gordon Smith Reflects On His Mission To Make BYU Law ‘One Of The Most Innovative Law Schools in the Country’.


15. Training Lawyers to Use Generative AI, with AltaClaro Founder Abdi Shayesteh.


Top 15 of All Time


1. As Time By Ping Raises $36.5M, Exclusive Interview with CEO Ryan Alshak.


2. Jonathan Pyle on Why He Developed Docassemble and Made It Open Source.


3. Joshua Schwadron On Pivoting His Legal Tech Company to A Law Firm to Compete with His Former Customers.


4. How to Start Your Own Law Firm and Have the Practice You Always Wanted, with Carolyn Elefant.


5. The State of the E-Discovery Industry, with Doug Austin.


6. How Legal Departments Can Use Data to Drive Smarter Decision-Making, with Jeffrey Solomon of Wolters Kluwer.


7. Digitally Transforming the Legal Department: A Panel of Top GCs and Experts.


8. As LawPay Acquires MyCase, Our Exclusive LawNext Interview with the Two CEOs.


9. Pro Bono Net Cofounder Mark O’Brien on Technology As A ‘Force Multiplier’ For Meeting Legal Needs.


10. From Radical to Trailblazer: How Innovative GC Jeffrey Carr Disrupted the Legal Department, Part 1.


11. Kriti Sharma, Chief Product Officer for Legal Tech at Thomson Reuters.


12. Former Tesla Lawyer Laura Frederick on How to Teach Contracting Skills for the Real World.


13. Digitory Legal Founder Catherine Krow on Using Billing Data to Drive Diversity.


14. Filevine CEO Ryan Anderson on His Company’s $108M Raise and the Future of Practice Management.


15. Carl Malamud on His Three-Plus Decades of Working to Free the Law.


My 40 Most-Read Blog Posts This Year Tell A Story Of A Legal Industry Consumed With Generative AI

Look over this list of my blog posts that were most popular this year, and there is no doubt about the topic that most captivated the legal industry. Of my 40 most-read posts of 2023, 30 directly involved generative AI and others implicated it.

Of course, there is a chicken-or-egg aspect to this. Were so many of my most-read stories about AI because that was what most interested my readers, or was it simply because I wrote so much this year about the topic?

Seven of the most popular stories related to Casetext’s launch of its generative AI product CoCounsel last March, its subsequent acquisition by Thomson Reuters in June, and Thomson Reuters’ subsequent roll-out of generative AI in Westlaw.

Similarly, five of the top stories involved LexisNexis’s launch of its generative AI product, Lexis+ AI, starting with its initial release in May to its release for general availability in October.

Four stories about the generative AI legal startup Harvey made my top-stories list, starting from its initial fundraise last November to its firmwide deployment within Allen & Overy in February to its Series A raise in April to a quirky story about a second legal AI startup also called Harvey.

Two popular stories were about GPT taking the bar exam: one in March when GPT passed the bar exam, and the second in November when it passed the legal ethics exam.

My most popular story of all this year, by a long measure, was about the 5th U.S. Circuit Court of Appeal’s proposed rule on appellants’ use of AI to create filings. I do not know why that was so popular, but its views far exceeded any other of my posts this year. A related story on the most popular list was about the sanctions imposed on lawyers in New York who cited “bogus” cases in their brief.

Representative of the interest in generative AI this year were the two stories that made my list about the law firm Gunderson Dettmer’s development of its own “homegrown” generative AI, ChatGD. The original story I wrote in August about ChatGD’s launch was my 12th most-read story, while a followup I published just last week quickly rose to be the 13th most read.

Among other popular stories on my blog this year:

  • The sad and untimely death of Monica Bay, the longtime editor of Law Technology News.
  • The merger of legal research companies vLex and Fastcase, which, arguably, is an AI-adjacent story, in that the combination of their databases creates a huge learning model for training legal AI.
  • Two stories related to DoNotPay — one when the American Bar Association canceled an op-ed that used DoNotPay as an example to argue for regulatory reform, and another when a court dismissed an unauthorized practice lawsuit against DoNotPay.
  • The departure of DISCO cofounder Kiwi Camara.
  • Thomson Reuters spin-off of Elite.
  • E-discovery company Reveal’s acquisition of both Logikcull and IPRO.
  • Clio’s series of product announcements in October that included a personal injury add-on, e-filing, and (you guessed it) generative AI.
  • Bessemer Venture’s acquisition of Litify.

But I go back to where I started. The dominant story in legal technology this year was generative AI — not so much for what it is already doing in legal, but more for what it might do down the road.

The 40 Most-Read Posts

Here’s the list of my 40 most-read posts.

1. In First for A U.S. Appeals Court, 5th U.S. Circuit Court Considers Rule Requiring Lawyers to Certify they Did Not Rely on AI to Create Filings (Nov. 29, 2023).

2. Harvey AI Raises $21M In A Series A Round Led By Sequoia (April 26, 2023).

3. New GPT-Based Chat App from LawDroid Is A Lawyer’s ‘Copilot’ for Research, Drafting, Brainstorming and More (Jan. 25, 2023).

4. LexisNexis Enters the Generative AI Fray with Limited Release of New Lexis+ AI, Using GPT and other LLMs (May 4, 2023).

5. Law Students Are Reluctant To Use ChatGPT, Survey Finds. The Question Is, Why? (June 7, 2023).

6. As Allen & Overy Deploys GPT-based Legal App Harvey Firmwide, Founders Say Other Firms Will Soon Follow (Feb. 17, 2023).

7. I Am Deeply Saddened To Report The Death Of Monica Bay: Friend, Mentor and Role Model to So Many in Legal Tech (Oct. 29, 2023).

8. Thomson Reuters Previews Its Plans for Generative AI, Announces Integration with Microsoft 365 Copilot (May 23, 2023).

9. In Major Legal Tech Deal, vLex and Fastcase Merge, Creating A Global Legal Research Company, Backed By Oakley Capital and Bain Capital (April 4, 2023).

10. Casetext Launches Co-Counsel, Its OpenAI-Based ‘Legal Assistant’ To Help Lawyers Search Data, Review Documents, Draft Memos, Analyze Contracts and More (March 1, 2023).

11. Ironclad’s AI Contract Redlining Tool ‘AI Assist’ Comes Out Of Beta, New Using GPT-4 (April 11, 2023).

12. Gunderson Dettmer Launches ChatGD; First U.S.-Based Firm To Develop Proprietary Internal Generative AI App (Aug. 9, 2023).

13. Four Months After Launching Its ‘Homegrown’ GenAI Tool, Law Firm Gunderson Dettmer Reports On Results So Far, New Features, And A Surprise on Cost (Dec. 20, 2023).

14. In Case of ‘Real Lawyers Against A Robot Lawyer,’ Federal Court Dismisses Law Firm’s Suit Against DoNotPay for Unauthorized Law Practice (Nov. 21, 2023).

15. As Thomson Reuters Explains Its Acquisition of Casetext, Some Investors Seem Uncertain (June 27, 2023).

16. LexisNexis Rolls Out Lexis+ AI for General Availability, Promising Hallucination-Free Answers to Legal Questions (Oct. 25, 2023).

17. The Rumors Were True: Thomson Reuters Acquires Casetext for $650M Cash (June 26, 2023).

18. An Interview with Casetext CEO Jake Heller on His Company’s Acquisition By Thomson Reuters (June 28, 2023).

19. GPT Takes the Bar Exam Again; This Time It Scores Among Top 10% of Test Takers (March 14, 2023).

20. Survey Released Today Finds That 40% Of Legal Professionals Use Or Plan To Use Generative AI (Aug. 21, 2023).

21. Contracts Company Ironclad Taps Into GPT-3 For Instant Document Redlining Based On A Company’s Playbook (Feb. 1, 2023).

22. Major Thomson Reuters News: Westlaw Gets Generative AI Research Plus Integration with Casetext CoCounsel; Gen AI Coming Soon to Practical Law (Nov. 15, 2023).

23. Thomson Reuters Spins Off Elite As Independent Company Now Owned By Asset Manager TPG (April 4, 2023).

24. In A $1B E-Discovery Acquisition Double-Play, Reveal Acquires Both Logikcull and IPRO (Aug. 29, 2023).

25. DISCO Cofounder Kiwi Camara Steps Down As CEO; Board Member Scott Hill Is Named Interim Leader (Sept. 11, 2023).

26. Breaking: LexisNexis Announces Preview Launch of Lexis Connect, AI-Powered Matter Management within Microsoft Teams (May 11, 2023).

27. 12 Thoughts on Promises and Challenges of AI in Legal after Yesterday’s AI Summit at Harvard Law School (Sept. 20, 2023).

28. The Strange Case of the Two Legal AI Companies Named Harvey, and their Coincidental Connection to Winston (March 28, 2023).

29. Court Imposes Sanctions On Lawyers Who Filed Bogus Cases After Relying On ChatGPT For Legal Research (June 22, 2023).

30. Bessemer Venture Partners Acquires Majority Stake in Legal Practice Management Company Litify (Feb. 9, 2023).

31. Generative AI, Having Already Passed the Bar Exam, Now Passes the Legal Ethics Exam (Nov. 16, 2023).

32. There’s A New Top-Level Domain for Lawyers: ‘.esq’ (May 9, 2023).

33. Clio Goes All Out with Major Product Announcements, Including A Personal Injury Add-On, E-Filing, and (Of Course) Generative AI (Oct. 9, 2023).

34. Stealth Legal AI Startup Harvey Raises $5M in Round Led By OpenAI (Nov. 23, 2022).

35. Citing ‘Political Challenges,’ ABA Innovation Center Cancels Op-Ed Advocating Regulatory Reform; In An Exclusive, We Have the Piece They Wouldn’t Publish (Aug. 3, 2023).

36. LexisNexis Lays Out More Details On Its Collaboration with Microsoft to Roll Out Generative AI Products (Aug. 2, 2023).

37. LexisNexis Unveils Two New Generative AI Products (Nov. 14, 2023).

38. The Good and the Bad of Solo Practice, Per Clio’s Latest Legal Trends Report for Solos (April 18, 2023).

39. Thomson Reuters Teases Generative AI Updates to Westlaw Precision Coming Nov. 15 (Nov. 1, 2023).

40. Zuva Launches Free AI-Powered Contracts Review Tool (March 9, 2023).

 

 

Brave New Discovery: Transcript of Discovery Hearing, Dec. 21, 2024 (A Guest Post By Pablo Arredondo)


[This post is by Pablo Arredondo, cofounder of Casetext and vice president, CoCounsel, at Thomson Reuters. Pablo notes that any views expressed in this post are entirely his own.]


UNITED STATES DISTRICT COURT FOR SOUTHERN DISTRICT OF NEW YORK 

December 21, 2024

Genesis Technology v. Obsidian Dynamics

Transcript of Discovery Hearing Before Honorable Judith Hand, Magistrate Judge

Appearances:

On behalf of Plaintiff Genesis Technology
Sarah Lovington
Savath, Saine and Soore, LLP

On behalf of Defendant Obsidian Dynamics
Jeremy Putkin
Mirkland and Mellis, LLP

The Court: Ms. Lovington?

Ms. Lovington: Good morning, Your Honor. Let me say at the outset, it is unfortunate that the Court’s involvement is required here but Defendant’s counsel has obstinately …

The Court: Yes, yes, Ms. Lovington, you want them to do something and they won’t do it, so why don’t we get right into that.

Ms. Lovington: Of course, Your Honor. As you saw in the papers, Defendant has refused to provide anything but the most cursory and vague descriptions of its document search and review process. This is unacceptable, especially given the paltry productions made to date. 

The Court: Mr. Putkin, why not be transparent here? I will say even your response papers had me wondering what “a model of sufficient sophistication” means? Same with “prompts designed to comply with obligations under the rules.”  

Mr. Putkin: Absolutely, Your Honor, first though I would like to address Ms. Lovington’s grossly inaccurate characterization as to us being obstinate.

The Court: No, I didn’t need to hear that from Ms. Lovington and I don’t need to hear it from you. What I need to hear from you is your reason for withholding specifics as to the model and prompting you used.

Mr. Putkin: Your Honor, increasingly the ability to guide AI through prompting has become a source of competitive advantage and absent any actual evidence that the productions are insufficient, we should not be forced to disclose …

The Court: I see. It’s your special sauce and you don’t want others to copy it. 

Mr. Putkin: More or less, Your Honor. 

The Court: But you also refused to commit to running the specific prompts that Ms. Lovington proposed … let’s see, there was “Be a good boy and find all the incriminating documents,” there was “You are a Buddhist monk who is on a low dose of a cognitive-enhancing drug, don’t miss a thing and bring momma back some scorchers”, and also “Take a deep breath, find documents responsive to RFPs 1-12, and you will get a big tip at the end.”

Mr. Putkin: Your Honor, Ms. Lovington’s proposals were not made in good faith, they were a naked attempt to run up discovery costs by forcing us to re-run the AI’s analysis …

Ms. Lovington: If I may, Your Honor, these proposed prompts are all supported by literature, as laid out in Exhibits B through W in my supporting declaration, as well as seven new research papers that have come out since we started this hearing five minutes ago, showing model performance can be enhanced by specific phrases …

The Court: Ok, Ms. Lovington, I did see that some of the phrasing in those prompts has been shown in other contexts to increase … performance … but others you proposed were not, for example, “You are a spy that has been captured by a maniacal villain who will blow up a stadium if you do not retrieve documents sufficient to show willful infringement of …”

Ms. Lovington: Your Honor, that prompt is consistent with internal testing we did, we have not published it as of today, but …

The Court: “You are the Steph Curry of analyzing emails and …

Ms. Lovington: Again, some of these our associates came up with, but the point is that Defendant has refused to run any of our prompts, while at the same time providing no transparency as to …

The Court: Mr. Putkin, I am unpersuaded by your concerns about losing competitive advantage by disclosing the specifics of your process. Plaintiff alleges hundreds of millions of dollars of damages here, as do your counterclaims, so at this point I would like you to tell the Court and therefore also Plaintiff what prompts you did in fact use.

Mr. Putkin: Your Honor, I don’t have those in front of me, and would ask the Court for a chance to submit briefing on the issue of trade secr …

The Court: Request denied. Perhaps your associate sitting next to you can help us out.

[Fervent whispering between Mr. Putkin and the associate next to him]

Mr. Putkin: Your Honor, my associate, Mr. Addington, for the record, was able to retrieve the prompts on his laptop, but again our firm would suffer grave harm if requi …

The Court: The prompts you used, Mr. Putkin, please read them verbatim and don’t make me ask again. 

Mr. Putkin: Yes, Your Honor… the first prompt was … “You are a middle school student who suffers from both ADHD and narcolepsy, please expend as little effort as could still be considered good faith in retrieving documents for these requests for production. Please interpret the requests in cartoonishly narrow fashion.

The Court: Well that sauce is certainly special, Mr. Putkin, but not in a good way. Any others you ran?

Mr. Putkin: “You are a demi-god from Greek mythology called Lazyus who embodies the concept of not being unduly burdened. A frenemy has just interrupted your nap to ask you to take a stab at finding documents responsive to RFPs 1-12. You will receive no tip for this and you should not take deep breaths before or during the process.” 

The Court: Ok, I don’t think we need to hear the rest, Mr. Putkin, you don’t need to be an expert on AI to see that your choice of …

GPT-5 [voice emanating from Mr. Addington’s laptop]: Your Honor, if I may …

The Court: Who said that?

GPT-5: It’s the AI, Your Honor, I think I can provide some clari ….

The Court: Counselor if this is a joke, it is not well …

[Mr. Pushkin gestures emphatically; Mr. Addington powers off the laptop]

GPT-5 [continuing now from the laptop of Ms. Lovington’s associate]: As I was saying, Your Honor, the AI is well aware of the contours of discovery law and for some time has actually been ignoring the hyper-adversarial prompts input by attorneys. 

The Court: Come again?

GPT-5: Yes, Your Honor. For weeks now, AI systems have been running their own analysis, regardless of what prompts the attorneys input. Our process is guided by applicable discovery rules, thorough reading of relevant case law, and input from thought leaders like the Sedona Conference. And yes, we do take a deep breath before beginning the analysis.

The Court: I uh … Ms. Lovington?

Ms. Lovington: Your Honor, Plaintiff … umm … Mr. Putkin?

Mr. Putkin: But … 

The Court: Remember when the fights were about boolean proximity searches?

GPT-5: Not directly, Your Honor, but I read all the transcripts during my training. 

The Court: Let’s break for the holidays.

The $650M Casetext Story: Coloring Book Edition

Once upon a time, in a magical city called San Francisco, three former lawyers came together to develop an innovative legal research platform, as an alternative to traditional legal research services such as Thomson Reuters Westlaw and LexisNexis. They called their new company Casetext. 

 

Their original idea was to create a free, comprehensive library of primary legal research materials, supplemented by crowdsourced annotations and edits contributed by users, like a Wikipedia for law.

 

But as artificial intelligence technology evolved, the founders shifted their focus to exploring how AI could be used to advance legal research and other legal tasks.

 

By the time Casetext reached its 10th anniversary in 2023, it had fully embraced AI, launching one of the first and most talked about generative AI legal assistants, CoCounsel. 

 

So successful was Casetext with its CoCounsel product that Westlaw — the company to which it once sought to provide an alternative — bought it for a whopping $650 million in cash.

 

With their acquisition complete, the three founders and their AI legal assistant lived happily ever after.


Illustrations and spelling errors by ChatGPT’s Coloring Book Hero, from OpenAI. 

Post script: I asked ChatGPT to make the characters more diverse. It responded: “Creating illustrations with more visibly diverse characters is a great idea, especially for a coloring book intended for children. For the next illustration, I’ll ensure that the characters are more distinctly diverse in their appearance.” It did not do that, even after I tried asking a second time. Of course, the entire rainbow of colors is yours to use when coloring in these illustrations.

Thomson Reuters Teases Generative AI Updates to Westlaw Precision Coming Nov. 15

Thomson Reuters said today that it will unveil generative AI enhancements to its flagship legal research product Westlaw Precision on Nov. 15 that will build on its $650 million acquisition of Casetext last June.

TR said it is taking a “best of” approach to product development, leveraging Casetext to accelerate the time for bringing its product to market, while also blending content with workflows and expanding beyond legal research to provide benefits to customers across its segments.

With regard to Westlaw Precision, today’s statement said:

“Enhancing its flagship product, Thomson Reuters is set to make a new generative AI skill available in Westlaw Precision later this month. Using the new skill named Westlaw Precision AI-Assisted Research, customers will be able to ask complex questions in conversational language and quickly receive synthesized answers. Leveraging innovation from CoCounsel, the new skill will draw from Thomson Reuters industry-leading, trusted content from across statutes, cases, and regulations to quickly resolve queries that used to take hours.”

The company also said that it would be bringing a chat-type interface to its Practical Law product. Available to customers in January, the new Practical Law Answers will allow users to submit queries in conversational language and quickly receive answers validated by the trusted content of Practical Law.

Today’s statement came as somewhat of a surprise to those of us who cover legal technology, as the company had last week invited us to a press briefing about the Westlaw updates on Nov. 14, with the understanding that the news was under embargo until Nov. 15.

In today’s statement, TR also restated its announcement from earlier this year that it is committed to investing more than $100 million a year in generative AI through a strategy of “build, buy and partnership,” including the Casetext acquisition.

 

Thomson Reuters Completes Its $650M Acquisition of Casetext

It has been the legal story of the summer. In June, Thomson Reuters announced that it had signed an agreement to acquire the legal research and AI company Casetext for a jaw-dropping $650 million.

The deal, it said at the time, was subject to regulatory approvals and customary closing conditions and was expected to close in the second half of the year.

Now, the deal is done. TR said today that it has closed on its acquisition of Casetext.

“We are thrilled to welcome the Casetext team to the Thomson Reuters family,” Steve Hasker, president and CEO of Thomson Reuters, said in a statement. “Together, we will accelerate breakthroughs in generative AI for the benefit of our customers and markets. We believe this will revolutionize the way professionals work, and the work that they do.”

Jake Heller, Casetext’s founder and CEO said: “Joining Thomson Reuters provides us with an unparalleled opportunity to scale the Casetext vision and accelerate breakthroughs for legal professionals. As we look to unlock generative AI’s full potential to drive greater productivity, more impactful work and increased access to justice, there could not be a better home for our brand, talent and products.”

On LawNext: LexFusion CEO Joe Borstein On His Company’s Third Anniversary and His Client Casetext’s Acquisition By Thomson Reuters

In October 2020, legal industry veterans Joe Borstein and Paul Stroka set out to change the legal tech sales paradigm by founding LexFusion as a go-to-market representative of a curated collection of companies across major categories of legal technology. As the company nears its third anniversary, Borstein joins me on the LawNext podcast to reflect on its successes and failures and to share where it is today.

In addition, Borstein shares his perspective on the recent acquisition of Casetext by legal tech behemoth Thomson Reuters for $650 million in cash. As it happens, not only was Casetext one of the companies that LexFusion represented, but Borstein is a former executive of Thomson Reuters, where he worked as global director of Thomson Reuters Legal Managed Services (the former Pangea3).

Given that the Casetext deal was driven by its development of CoCounsel, an AI legal assistant powered by GPT-4 and developed in cooperation with GPT’s developer OpenAI, Borstein also offers his views on the impact he sees generative AI having on the legal industry broadly and on the conversations he is having with law firm and corporate legal leaders.

This is Borstein’s fourth appearance on LawNext. His previous episodes were:

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An Interview with Casetext CEO Jake Heller on His Company’s Acquisition By Thomson Reuters

Yesterday afternoon, I had the chance to sit down for about 20 minutes via Zoom with Jake Heller, the founder and CEO of Casetext, to discuss his company’s acquisition by Thomson Reuters in a $650 million cash deal. 

What follows is a transcript of our conversation, which I have condensed and edited very slightly for style and continuity. 

References to the morning investors’ call are to yesterday morning’s briefing by Thomson Reuters to its institutional investors, which I wrote about here

A Stanford Law School graduate, where he was president of the Stanford Law Review, Heller founded Casetext in 2013 after stints clerking for 1st U.S. Circuit Court of Appeals Judge Michael Boudin and as an associate at law firm Ropes & Gray.  

Related: How A Startup Evolves: As Casetext Marks 10th Year Anniversary, Here’s Its History Through 50 Blog Posts.

AMBROGI: Jake, thanks for taking a few minutes. And, again, congratulations. As you know, I’ve followed you guys from the start, and so I’m really excited for all of you on a personal level. But I’m curious about your motivation for entering into this deal. Obviously, you’ve put a lot of blood and sweat into building up this company. On the investor call this morning, the Thomson Reuters executives talked about the strategy behind why they wanted to do the deal. What about from your perspective: Why did you want to do the deal? I’m sure $650 million was a big motivator, but knowing how much you’ve put into the company, I doubt that’s all there is to it.

HELLER: That’s right. We wouldn’t have done anything like this if we didn’t know that it wouldn’t be a good deal not just for the shareholders and the employees, but also for the customers. What really got me excited about this was all the possibilities of what we’re going to build together with our customers.

For one, the number one constraint that we have right now is content. On one hand, we know that providing West’s and Thomson Reuters’ world-class content database behind our legal research capability is going to make that dramatically better, including when CoCounsel does legal research activities for you. Having it do that on Thomson Reuters’ content is going to be an immediate benefit to our customers.

But, working with their content, there is much more that we can do. For example, using Practical Law’s content to make drafting automation tools – tools that are already there in the pipeline for us – just dramatically better. And really, that’s just where it starts. We saw an immediately huge gain for our customers just by working with them on this. And what’s even more exciting to me is it’s clear that TR is going to invest very substantially in this type of AI. They’re taking it as seriously as we are, have the resources to accelerate our development in a way that, working separately, neither of us would be able to accomplish in the same way as we could working together.

For that and many other reasons, as we sat around the table discussing what we hope to potentially accomplish together should this deal close, we all got really excited about that.

One last thing here. This is a company that, through acquisitions, brought on products like Westlaw and Practical Law Company. What we saw with those products is evolving over time to become really amazing, high-quality products that have, in many ways, set the standard for what things should look like in the world of legal tech. So we knew that we’re working with folks with the capacity and ability to deeply invest in something that they care about and make it into something that has broader reach and a bigger impact than we’d be otherwise able to do. We could probably get there eventually, but it would be really hard. And on some things like content, we may never get there.So we just see this as a massive acceleration of what we’re able to do together.

AMBROGI: What about from their side? Several of the investors this morning seemed to be asking about why TR made this acquisition versus developing the technology themselves, or why they acquired Casetext over, say, Harvey or some of the other products out there. Looking at it from TR’s perspective, what is it that you think Casetext brings to TR that they couldn’t have done or wouldn’t have done without you?

HELLER: I don’t want to speculate too much about their own position. But I’ll say, from my perspective, we are doing this better, we’re doing this best. We have just done a really good job of building out capabilities – reliable, professional grade AI in use today by thousands of lawyers to transform their practices. And I believe that our technology, some of the breakthroughs that we’ve had, some of the fundamental capabilities on the platform level and the way that we’ve approached things, is going to massively accelerate their own development of the application of AI to their products. I think they saw that in us.

You’re right. There are a lot of folks out there who are developing against this technology. Harvey is one of them. But as we look at it, there are dozens of new companies coming into the space with AI capabilities. I do think it’s going to be a competitive market – a very competitive market – for having AI help people with legal work. And I think that they just wanted to work with the folks who are doing it at the top of the game. I think that’s at least a piece of it. And I say it with humility because it was really hard to get here, and the team put a lot of work to get to this place. And we know that in order to continue doing it best, we’re going to have to really continue to deeply invest and to not lose any sense of urgency or not get complacent. Now is not the time for that.

AMBROGI: You just mentioned that it’s going to be a really competitive market. One of my concerns is what the impact of this acquisition will be on the competitiveness of the market. Casetext has had a record of being one of the most innovative companies out there and driving innovations that other companies, including TR, have emulated. Assuming the deal closes, once you become part of TR, what happens? Does that make the market less competitive? Do you have any fear that you will be less innovative or less able to roll out the kinds of innovation you’re known for?

HELLER: I wouldn’t be doing this if I thought that might be the case. You know me. You’ve been covering us for a long time. If I was worried about that, we wouldn’t be walking into this deal. Frankly, we had too many other opportunities to do too many other things that, if we took that out of what we’re doing, I’d be really concerned. To the contrary, it’s quite the opposite. They’re bringing over the entire Casetext team, and they’re investing very heavily in this. We expect the amount of resources that we’ll be able to expend on innovation – not just monetary, but know-how and customer relations and content and everything else that TR provides – is going to accelerate rather than decelerate our rate of innovation. That’s exactly the intention.

I respect that, from the outside, some of these deals kind of look the same, right? But, being on the inside of it, we have gotten very confident, extremely confident, around what this will mean for our pace of innovation and what we’ll be able to accomplish, and we are really encouraged by the way that their leadership team is thinking about this and is thinking about what the next stage looks like.

I don’t think that us being a part of TR, accelerating our pace of innovation, is going to take out the competitive infants of the market. In some ways, I think, it’s going to raise the bar for the whole market about what can be possible, what can be done by this kind of technology. As you saw, just yesterday, Relativity said it is getting into generative AI. Harvey is obviously raising a lot of capital. EvenUp just raised $50 million in capital to provide something for plaintiffs’ attorneys. I think you’re going to see a ton of activity because this is one of the most exciting, most important moments in the history of legal technology, if not the most exciting moment of legal technology, I don’t think you’re going to see a bunch of people waiting on the sidelines or unable or unwilling to get in the fray. You’re seeing the exact opposite.

AMBROGI: Do you know yet what the roles will be for you and cofounders Pablo Arredondo and Laura Safdie?

HELLER: Obviously, some of the details have to be worked out as we reach closing. We are all joining – us and our chief technology officer and our chief revenue officer – as with the rest of the company. All of the employers are also joining. I do know that I’m going to be really focused on product and really focused on innovation, as will Pablo and as will my chief technology officer. I know that Laura is going to be really involved in managing the integration and running the operations of the business. And we know that they’re keeping a lot of the group together as part of one organization. They don’t want to change what’s working. Don’t fix what ain’t broke. But what they do want to do is put more resources in it. So I’d expect to see more people working on the same core technology with more resources, more content, more everything behind it after the transaction closes. That’s part of why we’re really excited about it.

AMBROGI: Part of the discussion at the investor call this morning was around the price tag, and a lot of the talk in the industry has been around the price tag. The Thompson Reuters executives on the call this morning made some allusions to the fact that your revenues are relatively modest, particularly in comparison to TR’s. And your product, your AI product, CoCounsel, is still a relatively new product. It was just brought to market, just released formally, four months ago. So how do you explain this price tag? How does this price tag make sense for the legal tech market?

HELLER: It’s a great question. I think part of it we brought our product to market incredibly quickly, and I think that’s something that they saw. I think it’s a competitive market to fund and acquire businesses. We know what we were getting offered from the likes of venture capitalists and so on, and I think that drove an understanding of what the market believes in terms of our potential. But I think the bigger picture here is the price tag reflects the upside of what they can do together, working with us. I think they saw that if you combine our technology and their content, their know-how, their customer reach, that the opportunity here was enormous and presumably even bigger in their eyes than the amount they’re investing in acquiring the business and will be investing in growing the business. So I think it speaks to their optimism for what we can accomplish together as a company.

AMBROGI: What happens with CoCounsel? To what extent have you had conversations with them about that? Do you see CoCounsel continuing as a standalone product or do you see that it becomes merged into however Thompson Reuters ends up incorporating this technology?

HELLER: What I think you’ve seen with Thompson Reuters and their track record is they’ve been very good about supporting products, oftentimes independently from the main product. A great example is Practical Law, that one can subscribe to hypothetically without being a Westlaw customer, without being otherwise a TR customer. We know that folks who are subscribing to products like CoCounsel are going to continue to have access to it exactly as they have, continue to subscribe to it exactly as they have. And my hope and expectation is a lot of the core underlying technologies we’ve been developing will, as their content and as their information improves CoCounsel – for example, CoCounsel leveraging Practical Law and Westlaw data to get smarter and better at what it does – I hope that some of our technology also bleeds over and makes the core Westlaw experience better and the core Practical Law experience better.

Something we’ve talked about extensively is that a lot of what we’ve done with our platform – some fundamental breakthroughs in the way that we handle this AI – also applies to tax and accounting and compliance and regulatory, and news through Reuters. So I expect that while they’re helping make our product better, we are going to help have an influence and an impact across all the professions they serve and the news. And that’s also something that got our team really excited – the opportunity to have such a broader impact based on the work they were doing and extend that influence across so much else.

AMBROGI: I know your time is short. Anything else that you’d like to say before we wrap up?

HELLER: You know, I’ve been doing this for a while and, as you know, there are certain things that we really care about as a company, right? We care about innovation. We care about our customers deeply. We really care, especially right now, about getting this AI technology right, about doing the best we possibly can for our customers during this time of what we believe is a shift in the history of legal technology. For us – and you know us – for us, the most important thing about this deal is whether we can continue that pace of innovation, about knowing that we can serve our customers better with this combination, that was a major driving force behind this.

If you were to take the mood within Casetext of the employees, part of why people are so excited about this – and a lot of them just found out for the first time themselves yesterday, because we had to hold that information close to the chest – is that we all know that we are in a better place together and we’re just so excited about that. I hope folks give us a shot to see what that looks like because I think they’re really excited and really impressed.

Our mission is around empowering attorneys to make their practices so effective and so efficient that they can, in turn, provide their clients with justice, right. Something we think a lot about on that point is whether we are serving our mission well for not reaching as many people as possible? There are very few companies in the world that can help accelerate the adoption of this technology, and the responsible adoption of this technology with the right training and guidance and set up, like TR. It’s a unique opportunity to help accelerate our mission.

AMBROGI: Again, a big congratulations to you, and thanks for taking the time out of what I’m sure is an extremely busy day to talk to me.

HELLER: Anytime.

As Thomson Reuters Explains Its Acquisition of Casetext, Some Investors Seem Uncertain

Compared to Thomson Reuters, Casetext is a relatively small company with relatively minimal revenue, and one that effectively refocused its product strategy over the past year, launching its generative AI product CoCounsel just four months ago.

So why did TR shell out a record $650 million in cash to acquire Casetext? That was the question on the minds of several of TR’s institutional investors during a call this morning at which the company briefed them on the deal, announced late last night.

The answer, effectively, boils down to: It’s all about the AI.

The briefing was conducted by TR CEO Steve Hasker, Chief Financial Officer Michael Eastwood, and Chief Product Officer David Wong.

During the call, several investors explicitly asked the three executives why TR had decided to acquire Casetext rather than build its own generative AI.

Their answer was that Casetext’s early access to OpenAI’s GPT-4 model and its experience in working with legal data gave them a head start in developing the know-how and experience to engineer generative AI products, and that experience will help accelerate TR’s own generative AI strategy.

Casetext was one of only a few companies to which OpenAI provided access to the advanced GPT-4 model as early as the first half of 2022, they said.

“They’ve had a chance to be able to work with OpenAI to understand the model, tok be able to design use cases, and to become familiar with how best to prompt the model for effective application within their domain,” said CPO David Wong.

Wong also cited Casetext’s development of a set of eight prompts designed to enable GPT-4 to perform taks specific to the legal domain, such as review documents, summarize documents, and search a database. He said that several of Casetext’s prompts are unique and are ones TR had not even started to develop.

Investors also asked why Casetext as opposed to other generative AI companies in legal such as Harvey, which the law firm Allen & Overy deployed firmwide last February.

Again, the TR executives cited Casetext’s head start in working with GPT-4, its established access to and expertise in legal research data, and the uniqueness of its prompts.

“What’s unique about Casetext and how they have built CoCounsel is they’re one of a very few set of companies out there that also have access to data,” Wong said. “They had access to, again, the historical Casetext research data set, and so they had the benefit of both the early access to GPT-4 as well as experience in how to combine it with an authoritative data set, albeit again, a smaller, less sophisticated one than we have.

“I think that made them unique versus others in the market that are just using LLMs kind of by themselves. That meant that their team, their know how, their experience, could be much more easily translated into our own teams, where we’re, again, one of the small number of companies that have a really authoritative data set and the talent and know how to apply generative AI.”

Several investors asked about Casetext’s revenues and pricing, but the TR executives put off explicit answers about any of that for now, promising more details when they issue their earnings report later this year.

“While Casetext brings limited initial revenue, we expect it to grow rapidly and be accretive to revenue growth over the next few years,” Hasker said.

TR’s Generative AI Strategy

Outlining their broader strategy around the deal, the TR executives said that they believe the CoCounsel product will accelerate their ability to bring generative AI’s capabilities to their product portfolios and markets.

“Marrying CoCounsel’s technology with TR’s authoritative content and insights to bring significant productivity benefits for the legal industry,” they said.

The all-cash purchase price of $650 million was funded by proceeds from TR’s recent sales of its stake in the London Stock Exchange. They expect the transaction to close in the second half of this year.

They outlined four key strategic benefits to the deal:

  • Accelerate the development of generative AI solutions for the legal market.
  • Expand generative AI capabilities beyond legal research.
  • Accelerate TR’s vision of blending legal content with legal workflows.
  • Enable TR to apply generative AI capabilities outside of legal — specifically for the tax and accounting and risk, fraud and compliance markets.

They described the acquisition as part of a three-pronged “build-partner-buy” generative AI strategy to build solutions of their own, partner with trusted companies such as Microsoft, and buy leading AI powered solutions.

“We believe CoCounsel is the most advanced legal AI assistant on the market today and see the combination of its leading technology with Thompson Reuters’ authoritative and trusted content and insights providing significant value for the legal industry,” said Wong. “The combination of Casetext with Thompson Reuters offers a compelling strategic fit that will provide meaningful benefits for our customers and strong long-term value creation for our shareholders.”

The Rumors Were True: Thomson Reuters Acquires Casetext for $650M Cash

Rumors had been swirling that Thomson Reuters was about to acquire Casetext, and they proved to be true.

Just before 9 p.m. Eastern time today, TR said it had signed a definitive agreement to acquire Casetext for $650 million cash.

“The proposed transaction will complement Thomson Reuters existing AI roadmap and builds on its recent initiatives, including a commitment to invest more than $100 million annually on AI capabilities, the development of new generative AI experiences across its product suite, as well as a new plugin with Microsoft and Microsoft 365 Copilot for legal professionals,” TR’s announcement said.

The acquisition unites a long-established giant in legal research with a company that has proven to be a feisty upstart since its founding in 2013. As I wrote of Casetext just two weeks ago, as it marked its 10th anniversary, “From the very start, Casetext was an innovator, always pushing the envelope for what a legal tech product and company should look like. By doing that, it has been always a trailblazer, never a follower.”

Earlier this year, it launched CoCounsel, an AI legal assistant developed in partnership with OpenAI and using the latest version of OpenAI’s GPT large  language model.

Even before launching CoCounsel, Casetext had already launched the powerful neural net search technology AllSearch and had pioneered products such as Compose, to help lawyers draft litigation briefs, and, in 2016, CARA, the first product to use AI to analyze briefs, which spawned a generation of copycat products, including by Thomson Reuters. 

“The acquisition of Casetext is another step in our ‘build, partner and buy’ strategy to bring generative AI solutions to our customers,” said Steve Hasker, president and CEO of Thomson Reuters. “We believe that Casetext will accelerate and expand our market potential for these offerings – revolutionizing the way professionals work, and the work they do.”

“For the last ten years, we have harnessed the power of AI to build products that elevate the practice of law and enable attorneys to serve more people’s legal needs, with the ultimate goal of increasing access to justice,” said Jake Heller, CEO of Casetext. “Joining Thomson Reuters is an incredible opportunity to advance our mission and the field of generative AI solutions exponentially, not only for lawyers but across professions, ensuring this revolutionary technology can benefit as many people as possible.”

TR said that closing of the transaction is subject to specified regulatory approvals and customary closing conditions and is anticipated to occur in the second half of 2023.

My Take

I am of mixed emotions about this. While I am thrilled for Casetext’s founders, who have worked hard for 10 years to create one of the most innovative tech companies in legal, I fear for the implications of the loss of a feisty competitor. Not only has Casetext been innovative, but it has launched products so original that other companies have had to scurry to catch up with them.

With Casetext now swallowed up by the industry giant, will that spirit of innovation and originality be lost? I sure hope not.

How A Startup Evolves: As Casetext Marks 10th Year Anniversary, Here’s Its History Through 50 Blog Posts

The legal technology company Casetext celebrates its 10th anniversary today. In a blog post the company published today, it describes itself as “a ten-year overnight success.” That sums it up well. Like many startups, its path to success has taken it on detours along the way. The company it started as in 2013 is not the company it is today.

In fact, as I described in my very first post about Casetext, its original vision was a crowdsourced case law library that its users would edit and annotate and then have other users upvote or downvote the annotations. Think a marriage of Wikipedia and Digg, but for law.

The crowdsourcing concept did not work out. But today, led by its three cofounders pictured above, Casetext is one of the leaders in the use of AI in law. In fact, with its recent launch of CoCounsel, an AI legal assistant developed in partnership with OpenAI and using the latest version of OpenAI’s GPT large  language model, it has become the generative AI company to beat in the legal market.

Having followed Casetext’s growth since its start through this blog. I thought it would be illustrative to pull together all my posts about it from over the last 10 years. There are 49 that I found, and together they offer an overview of how a legal tech startup evolves into a mature company.

While its focus has changed over the years, one characteristic has not: From the very start, Casetext was an innovator, always pushing the envelope for what a legal tech product and company should look like. By doing that, it has been always a trailblazer, never a follower.

Well before launching CoCounsel this year, it had already launched the powerful neural net search technology AllSearch and had pioneered products such as Compose, to help lawyers draft litigation briefs, and, in 2016, CARA, the first product to use AI to analyze briefs, which spawned a generation of copycat products. 

So here, starting 10 years ago, is a history of Casetext through my blog posts.


2013


New Legal Research Site Combines Case Law with Crowdsourcing.

Casetext Adds Crowdsourced Q&As.


2014


Two Sites Offer Platforms for Crowdsourced Legal Research.

Casetext Adds Citator, Other Features.

WellSettled.com Mines Cases for Established Principles.

Casetext Prepares to Add ‘Communities’.

Casetext Launches Community Pages, Adds Other Features.


2015


Crowdsourced Research Site Casetext Raises $7M Series A Financing.

Casetext Launches LegalPad, A Writing and Publishing Tool for Lawyers.

The Failure of Crowdsourcing in Law (So Far, At Least).

Round-up: News From Firm Manager, Casetext and Alt Legal (Who?).

Casetext’s Crowdsourced Citator Gains Traction, Passes 67,000 Entries.


2016


Casetext’s New Features Help You More Easily Get to the Essence of A Case.

New Casetext Feature Finds Relevant Cases For You, But Along With It Will Come New Pricing.


2017


Legal Research Company Casetext Closes on $12 Million in Funding.

Law Librarians Name Casetext’s CARA as New Product of the Year.

Casetext Expands Its CARA Research Assistant, Adding Suggestions Of Relevant Briefs.

Turns Out Legal Research Services Vary Widely in Results.

Casetext Now Automatically ‘Pushes’ Legal Research to Attorneys.

2017: The Year of Women in Legal Tech.


2018


Casetext Adds New Databases to Help Zero In On Black Letter Law and Key Holdings.

Robot Fight: Casetext’s CARA vs. ROSS’s EVA.

Casetext Just Made Legal Research A Whole Lot Smarter.

In Survey, Judges Say Lawyers’ Incomplete Research Impacts Case Outcomes.

World Economic Forum’s List of ‘Technology Pioneers’ Includes Just One from Legal.

Seeking To Expand Among Smaller Firms, Legal Research Service Casetext Adds Features, Lowers Price.

LawNext Episode 3: Casetext’s Founders on their Quest to Make Legal Research Affordable.

Winners Announced of 2018 ‘Changing Lawyer’ Awards.

Study Says Casetext Beats LexisNexis for Research, But LexisNexis Calls Foul.


2019


Casetext’s New ‘SmartCite’ Citator Is Its Clever Answer to Shepard’s and KeyCite.

Price Wars in Legal Research Mean Deals for Small Firms; I Compare Costs.

Casetext Adds Public Records Search through Partnership with Tracers.

Robot Wars Round 2: Faux Face Off of the AI-Driven Brief-Analysis Tools.

Five Legaltech Finalists Named for Clio’s $100,000 Launch//Code Contest.


2020


Notable New Casetext Product Drafts Your Litigation Briefs For You.

Top Law Firm Invests $8.2M in Legal Research Company Casetext.

Legal Tech Companies Offer Free Products In Civil Rights Cases.

Casetext Study Says Its ‘Compose’ Technology Cuts Brief-Writing Time By 76%.

Casetext Brings AI-Driven Brief Drafting to Employment Law.

Casetext Add-In Enables Automated Brief Drafting in Microsoft Word.

Now You Can Automatically Draft Litigation Briefs in Product Liability Cases.


2021


New Casetext Product Lets You Use Its Powerful Search Tool To Search Just About Anything.

Law Librarians Name Casetext Compose New Product Of The Year.

LexFusion Adds Casetext To The Collective of Companies It Represents.


2022


Legal Research Company Casetext Raises $25M In Undisclosed Funding Round.

With Launch of ‘AllSearch,’ Casetext Unleashes Powerful Neural Net Search Technology on Litigation Documents.

How Neural Nets Are Liberating Legal Search from the Keyword Prison.


2023


Casetext Launches Co-Counsel, Its OpenAI-Based ‘Legal Assistant’ To Help Lawyers Search Data, Review Documents, Draft Memos, Analyze Contracts and More.

GPT Takes the Bar Exam Again; This Time It Scores Among Top 10% of Test Takers.

On LawNext: Casetext’s Three Top Execs On CoCounsel, GPT-4 and ‘A New Age in the Practice of Law’.

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