Jean O’Grady shares her journey from an 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.

Season 1 Ep. 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.

Season 1 Ep. 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.”

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 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.

Season 1 Ep. 12: The Chatbot that Saved 15 Million Dollars

In this episode, we take a look at what is happening in an entirely distinct legal tech 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

Season 1 Ep. 13: Revolução! A discussion of Brazil's Legal Tech Boom

Our 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.  

Season 1 Ep. 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.

Season 1 Ep. 15: Legal Tech from Scratch

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.

Season 1 Ep. 17: Culture, Mergers, and Metrics

Our 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.  

Season 1 Ep. 16: Gravity Stack: Innovation in the AmLaw 50

Season 2 Ep. 1: The Wizard

Our guest, Oz Benamram, is the Chief Knowledge Officer at White and Case, where he has led their KM program for over 10 years.  Oz is a leader in the field and his ideas on technology, law firm economics, and information management are often years ahead of his peers.

Season 2 Ep. 2: The Millennial Episode

Today on The Modern Lawyer we speak with JP Box.  He's a lawyer, entrepreneur, author, and millennial. After a career in AmLaw 100 firms, JP left law practice dissatisfied with his experience.  After changing his career, he just couldn’t kick the feeling that there was some shared experience causing many lawyers of his generation to leave the law.  He decided to explore this and through years of research and discussion, he became an expert in showing law firms how to get the most productivity out of their millennial attorneys.  He’s concluded that there are clear, simple steps law firms can take to leverage their younger associates in ways that inspire them to do the great quality work expected of them.

Season 2 Ep. 3: "Law is Divinity with More Money at Stake"

Augie Rakow is the co-founder and managing partner of Atrium LLP, a law firm that uses modern technology to provide startups fast, transparent, and predictable legal services. Augie co-founded Atrium in 2017 with Justin Kan, who built and sold the popular video game streaming platform Twitch to Amazon for close to a billion dollars.  Before founding Atrium, Augie was a corporate partner at Orrick focusing on startups.  In this episode, we discuss how Atrium plans to change the legal industry, Augie’s view on how legal services ideally should be delivered, and the similarities between his studies at Harvard Divinity School and law practice.

Season 2 Ep. 4: Lessons from the Big 4

Today we are joined by Vishal Agnihotri, the Chief Knowledge Officer of Hinshaw & Culbertson, an AmLaw 200 law firm.  Vishal has a background as an executive at KPMG and Ernst & Young.  In this episode, we talk about the differences between two big areas of professional services, BigLaw and the Big 4 accounting firms.  Vishal observes a few different lessons that large law firms can learn from the Big 4, in addition to certain key roles the Big 4 will have a hard time replacing.  She also shares her thoughts on the ‘unbundling’ of legal services, and how automation will affect the future of law firms providing value to clients.

Season 2 Ep. 5: Answering the "So What?" Question

Today we share our conversation with the Chief Marketing Officer of Winston Strawn, Howard Kravitz.  He works us through the past, present, and future of the law firm marketing pitch, and how it is different from the consulting world, and how often marketers at a law firm have many more audiences than just a potential client.

Season 2 Ep. 6: Inside the Greenberg Innovation Lab

Marlene Gebauer, the Director of Strategic Legal Insights at Greenberg Traurig joins us on the podcast today. In this episode, Marlene shares how she ended up in her unique role at Greenberg and we discuss how she developed their 'innovation lab'.  We get to hear about her passion for client collaboration, and what AmLaw executives are looking for in new technology tools.

Season 2 Ep. 7: The Startup Within Wilson

Today we talk to Kimball Parker, President of SixFifty, the technology subsidiary of top technology law firm Wilson Sonsini Goodrich & Rosati.  In his role at the helm of SixFifty, he is able to create and provide solutions with minimal attorney time spent.  We discuss collaborations with legal design labs at law schools and how they can contribute to addressing the severe gap between the supply of attorney time and the immense need for legal services.  We hope you enjoy our conversation.

Season 2 Ep. 8: Fixing What You Didn't Know Was Broken

What is a Chief Innovation Officer?  I ask this question to Ali Shahidi, the Chief Innovation and Client Solutions Officer at AmLaw 100 law firm Sheppard Mullin.  Ali is an experienced and trusted innovation expert and technologist.  He has decades of experience in legal.  Combined that with his engineering background, he has world-class perspective on where the industry is going with respect to technology and automation. In this episode, we talk about what he does in his role, what problems he is looking to solve for his firm, and where law firms have gone wrong in the past.  I hope you enjoy our conversation.

Season 2 Ep. 9: The Indiana Jones Aspect

Today we're joined by Charles Frey, the Director of Library at elite law firm, Munge Tolles & Olson. In this episode, we talk about the evolution of the librarian function in law firms, assisted my metaphors randing from Indiana Jones, to chicken farming, and the library of Alexandria. Charlie talks about how librarians are increasingly expected to be experts, not just in retrieving information, but in evaluating new technologies and their use cases. We hope you enjoy our conversation.

Season 2 Ep. 10: The Man-Shaped Woman Attorney

Today we are sharing our conversation with Christina Blacklaws, the President of The Law Society of England and Wales, (the equivalent of our American Bar Association). Throughout her career, Christina has been a champion for gender equality in law, alternative fee arrangements, and awareness of mental health issues in law.  In our interview today, we discuss when and why women drop out of the profession, the impact of millennials in the work-place, and what she means by the concept of the “man-shaped woman” attorney.

Season 2 Ep. 11: The A.I. Arms Race

In this episode, we’re joined by Alex Lakatos, a litigation partner at Mayer Brown in Washington, DC. Alex is an example of a successful attorney at a thriving firm who is pushing himself to become an expert in the brand new area of artificial intelligence in financial services, lending, and credit. Alex organizes and speaks on AI in financial services symposia and events and discusses regulation of new AI technologies, AI-bias and the liability flowing from it, and how attorneys will interact with and shape AI in the near future

Season 2 Ep. 11: The Next Generation GC

This episode's guest is Bradley Gayton, the General Counsel and Chief Administrative Officer of Ford Motor Company, ranked #12 in the Fortune 500.  Bradley embodies the new generation of GCs.  He’s up to speed on new technology including AI and machine learning.  He’s interested in changing the business model in law.  He’s curious and interested in the massive changes we are all witnessing in the legal industry. In this episode, Bradley shares his thoughts on outside counsel as “part of the family”, viewing a case from the perspective of business from cradle to grave, and promoting diversity not just at Ford but in the legal industry as a whole.

Season 2 Ep. 12: The Small Firm Guide to Marketing

On today’s episode of the Modern Lawyer Podcast, we speak with Karin Conroy, Legal Marketing Consultant and founder of Conroy Creative Counsel. In our conversation, we talk about marketing strategies for small and mid-size law firm attorneys. Karin provides us with guidance on how to create a prospective-client-focused website, aligning website visuals with each firm’s ideal client, and the demands of the modern prospective client operating in a world of limitless attorney options.

Season 2 Ep. 13: The Modern Law Student

On today’s episode of the Modern Lawyer Podcast, I had the opportunity to talk to University of Dayton School of Law dean Andrew Strauss.  The Law School is examining new ways to use online tools to make a legal education accessible to more students. In this episode, we hear Dean Strauss’s opinions on how on-demand online education can sometimes more effectively educate the modern law student than traditional classes, the challenges facing law schools today, and the struggle inherent in balancing the traditions of legal academia with the demands of the new economy. 

Season 2 Ep. 14: The 2 a.m. Idea

Today we share our conversation with Haley Altman, founder and CEO of Doxly, which was recently acquired. Haley tells her story from the point of view of a former big law partner specializing in corporate transactions. In that senior role, she personally felt a pain point and looked to the market for a solution. Finding none, she founded Doxly, a company that manages corporate legal transactions. Recently, Doxly was acquired and integrated into document life cycle powerhouse Litera Microsystems. In this episode, Haley takes us through the conception, growth, and sale of her company, including all of the failures and triumphs along the way.

Season 2 Ep. 15: Indicators and Intuition

Today we share our conversation with Evan Parker, a Ph.D statistics expert and founder of Parker Analytics. Evan is ushering in a new era of data-driven decision-making for law firms by working with them to collect, assess, and evaluate their data, optimizing how they do business.  He uses data to help them discover problematic trends on recruitment, diversity, and efficiency, then identify their solutions.  He recently discussed one of these trends on Malcolm Gladwell’s podcast, Revisionist History.  In this episode, Evan shares some surprising insights he has unearthed through looking at firm data, like how a good grade in torts is a better predictor of success than a good grade in contracts, why a top tier law degree does not predict greater success at a law firm than a mid-tier law degree, and the key factors causing certain demographic groups at law firms to fall behind, and others to succeed.  

Season 2 Ep. 16: It's Not All Perry Mason

We're honored to share our conversation with David Wilkins, a Law Professor at Harvard Law School and the Faculty Director of the Center on The Legal Profession.  Anand recently had the opportunity to present to Professor Wilkins’ class at HLS, "The Legal Profession," where he shared his thoughts on technology’s impact on the future of legal jobs. Afterwards, he had the chance to sit down with Professor Wilkins to talk about how Richard Nixon affected his legal career, three key forces affecting the legal industry, and how he educates students on the realities of legal practice.  As it turns out, it’s not as glamorous as Perry Mason.