Jean O’Grady shares her journey from academic reference librarian to Director of Research Services at one of the world’s largest firms. Find out what it was like to transition from a world without the internet (or even Post-Its) to one increasingly focused on innovation, and learn how law librarians, millennials, and AI will shape the future of law. 

Episode 1: Jean O'Grady

Before joining Casetext to focus on legal tech full-time, Anand practiced law for six years, first as a prosecutor and then as a litigator at a large firm. Know someone shaping the future of law? Reach out to to recommend a guest.

Everything today's modern lawyer needs to know about the future of legal practice. 

The Modern Lawyer podcast is sponsored by Casetext. To learn more about how Casetext's CARA A.I. technology is shaping the future of legal research, visit and see for yourself with a complimentary trial, or request a personalized demo.

Hosted by Anand Upadhye  Attorney & VP of Business Development, Casetext

When Jeff Rovner started working in KM, it was still “this thing that had no name.” Now, KM is at the forefront of some of the most fundamental issues in legal innovation, including Jeff’s own “white whale” of legal tech adoption. Anand talks with Jeff about the evolution of KM, what law firms can learn from the consulting world, and how adoption of legal tech will impact attorneys’ workflows, law firm business models, and more.

Episode 2: The "White Whale" of Legal Tech Adoption with Jeff Rovner

When many of us hear “blockchain,” we think of Bitcoin. But Judy Rinearson, partner at K&L Gates, wants attorneys to know: “The blockchain is not just cryptocurrencies. It’s a very intriguing and powerful technology that a lot of applications can run on.” On this episode of The Modern Lawyer, find out how applications of blockchain could soon change the way attorneys work. As Judy says, “Your clients are going to want you to know about the blockchain.” 

Episode 3: What Your Clients Will Want You to Know About Blockchain

When Scott Rechtschaffen thinks “there has to be a better way,” he creates that better way. As a shareholder and later CKO at Littler, Scott has implemented outside-the-box solutions to a number of long-standing problems in legal practice. Find out how he eliminated the annoyance of firmwide RFI emails, made training on workplace regulations actually fun, and more.

Episode 4: Old Problems, New Solutions

Jason Barnwell, Assistant General Counsel at Microsoft, explains why he tries to structure his relationships with outside counsel as partnerships rather than a supplier or vendor relationship, and the signals he looks for that a firm will be a good partner to him. You’ll also find out why Jason believes “The billable hour is a shackle on innovation and efficiency,” and what Microsoft is moving toward to replace it.

Episode 5: What Your Clients Are Thinking

Evan Shenkman, Ogletree Deakins’ Director of Knowledge Management Counsel and Research, describes how his experiences practicing law and building Ogletree’s KM department led him to the “holy grail” of legal technology: a system that can automatically kick off a chain of events involving both external vendors and internal systems whenever a motion is filed.

Episode 6: The Holy Grail of Legal Tech

As the Associate GC leading the litigation group at Macy’s, Betty Tierney and her team actually handle much of the company’s litigation themselves -- and she’s using that experience to guide her expectations when she works with outside counsel. Learn more about Macy’s unique approach to litigation, find out why Betty believes we’re going to see an increase in alternative fee arrangements over the next 10 years, and more.

Episode 7: Start-to-Finish Litigation

Frances McDormand ended her Oscars acceptance speech with two words: “inclusion rider.” Attorney Kalpana Kotagal, who actually wrote the inclusion rider, explains what it is, how it came about, and why it will drive diversity and inclusion in Hollywood and beyond.

Episode 8: The Inclusion Rider

Carolyn Elefant, solo attorney and author of the popular blog MyShingle, shares her predictions for how solo practice will change in the next 20 years, including new technologies and business models that are already gaining popularity among solo practitioners.

Episode 9: Is Small Law the Future?

Some estimates show that over 65% of legal needs in the United States are not met because most people simply cannot afford attorneys. Pro bono work can help bridge that gap, but as attorneys who have worked on pro bono cases know, it's often difficult to find and manage pro bono cases. That's what inspired Felicity Conrad to start Paladin, a platform that helps companies and law firms manage their pro bono work.  Join us for Anand's conversation with Felicity about problems in the way the legal industry does pro bono work, how technology can be leveraged to fix it, and the access to justice gap that Paladin is helping fill.

Episode 10: Innovating Pro Bono

Scott Bailey is the Global Director of Research Services at Squire Patton Boggs. He’s seen decades of law firm transition, including acquisitions, rapid growth and restructuring.  He’s a specialist in not just  identifying technology that can help his firm’s attorneys, but also bringing it into his firm across practice groups and stakeholders.  He comes to us today with a radical, industry shaking idea: have people sit down and talk.  Sometimes, it's the little things that can change an industry.

Episode 11: Stop, Collaborate, and Listen

In this episode Anand is joined by Joshua Browder, a software engineer and the Founder of DoNotPay, a robot lawyer startup that helps customers fight parking tickets and obtain refunds from airlines. DoNotPay has saved their customers an estimated $15M in parking fines alone. Time Magazine proclaimed DoNotPay as the “Hero the World Needs,” and the BBC nicknamed it the “Robin Hood of the internet.” They talk about chatbots tailored to specific legal problems, the challenges in creating robot lawyers, and how technology can address exploitative industries in pro-consumer ways.

Episode 12: The Chatbot that Saved 15 Million Dollars

In this episode we take a look at what is happening in an entirely distinct legaltech ecosystem by taking a trip to Brazil.  We see some of the same trends in Brazil, alongside some fascinating differences.  Our guests are Bruno Barata, Evy Marques, and Bruno Feigelson, all preeminent figures in the Brazilian Legal Tech community

Episode 13: Revolução! A discussion of Brazil's Legal Tech Boom

Today’s guest is Jordan Grotzinger, a shareholder and Co-Chair of the Los Angeles Litigation Practice at Greenberg Traurig.  Jordan is a business litigator and trial attorney who has experience in entertainment law and intellectual property.  Lately, he has spent an increasing amount of time driving innovation and modernization at the firm.  We were honored to host Jordan in our office at Casetext in San Francisco to talk about how attorneys can incorporate technology into their practice at large firms, what trends he is seeing in litigation, and what an “innovation narrative” means at a large firm.  

Episode 14: The Innovation Narrative

Matthew Stubenberg is an attorney entrepreneur who is now the associate director of Legal Technology at Harvard Law School.   Matthew has  created notable and useful technology based on pain points he experienced as a practitioner in Baltimore, Maryland.  So far he has created the NotGuilty App and MD Expungement, two tools that have earned thousands of users.  We speak with Matt about what it was like creating apps specifically for lawyers, how he spots legal processes that can be easily automated, and what role he thinks technology and coders in particular are going to play in the practice of law.

Episode 15: Legal Tech from Scratch

Today you’ll hear an interview with Beatrice Seravello, who was the chief strategy officer at Blank Rome and Kaye Scholer, and is now a senior executive at Arnold Porter.  As a chief strategy officer, Bea had oversight over all revenue-generating activities, leading strategy, business development, marketing and practice management for the firm, client development and retention strategies, pricing, and public relations.  At Arnold & Porter she is working on the ongoing project of ensuring that the Arnold & Porter and Kaye Scholer merger goes smoothly, both operationally and culturally.

Episode 17: Culture, Mergers, and Metrics

Today’s guest is Bryon Bratcher, the Managing Director of Gravity Stack, a wholly owned subsidiary of AmLaw 50 law firm Reed Smith.  Gravity Stack is a revenue-generating company within the firm that builds products and offers up services for law firms and other businesses.    We speak with Bryon about his journey from the head of the Reed Smith client technology solutions group, which was renamed and spun out as Gravity Stack.  Bryon talks to us about the future of the industry, including the threats from the Big Four, consolidation among solutions providers, and the future of revenue generating solutions providers owned entirely by law firms.  

Episode 16: Gravity Stack: Innovation in the AmLaw 50