How I Lawyer Podcast with Jonah Perlin

Jonah Perlin
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Aug 8, 2025 โ€ข 44min

#148: C.J. Mahoney - Microsoft General Counsel, Former Deputy US Trade Representative, & Law Firm Partner

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is C.J. Mahoney, the Corporate Vice President and General Counsel at Microsoft. Before joining Microsoft, C.J. served as the Deputy United States Trade Representative (a position to which he was unanimously confirmed) and was previously a partner at Williams & Connolly. He started his career as a law clerk for Associate Justice Anthony Kennedy after graduating from Yale Law School where he was Editor-in-Chief of the Yale Law Journal and attending Harvard University. C.J. was also one of Jonah'sfirst legal supervisors when he was a summer associate at Williams & Connolly 15 years ago.In this episode, C.J. shares valuable insights about the legal profession including:๐Ÿ™๏ธ๐Ÿงฉ How growing up in a small Kansas town where lawyers were well-respected influenced his decision to pursue law as a career path [1:59]๐ŸŽ“โš–๏ธ How his journey through Yale Law School and prestigious clerkships ultimately led him to realize he wanted to learn how to try cases rather than focus solely on appellate work [3:46]๐Ÿ”„๐ŸŒŸ How his career path wasn't as linear as it might appear on LinkedIn, but rather involved being open to new opportunities and distinguishing himself from other talented lawyers [6:48]๐Ÿ“๐Ÿ’ผ How his litigation skills proved surprisingly transferable when he moved to trade negotiations, particularly in synthesizing complex information and cross-examining experts [14:19]๐Ÿง ๐Ÿ“Š How the ability to take complex facts and make them understandable is a superpower that has served him well across different roles [18:13]โœ๏ธ๐Ÿ” How writing things down and putting concepts in your own words is crucial for learning new areas and sharpening your thinking [18:44]โš–๏ธ๐Ÿ’ป How his perspective on litigation changed dramatically once he moved in-house and saw firsthand the burden it places on businesses [24:52]๐Ÿค๐Ÿ’ฏ How building trust is the most important aspect of managing people, particularly in creating an environment where people feel comfortable bringing bad news [27:12]๐ŸŒ๐Ÿ”ฎ How the intersection of AI advancement and political polarization creates unique challenges and opportunities for lawyers in the technology sector [34:11]โณ๐Ÿ† How sticking it out through hard times at a law firm and building a strong foundation was one of the best career decisions he made [41:06]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.
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Aug 1, 2025 โ€ข 49min

#147: William Treanor - Former Georgetown Law Dean

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is William (Bill) Treanor, who recently stepped down as Dean of Georgetown University Law Center after serving for 15 years. Before Georgetown, Bill was a professor and later Dean at Fordham Law School for 20 years. His legal career began as a law clerk to Judge James L. Oakes of the U.S. Court of Appeals for the Second Circuit and as associate counsel during the Iran-Contra Investigations. From 1998 to 2001, he served as Deputy Assistant Attorney General for the Office of Legal Counsel. Bill holds degrees from Yale University, Yale Law School, and a PhD in history from Harvard University.In this episode, Bill shares valuable insights about the legal profession including:๐ŸŽ“๐Ÿ”„ How a pivotal lunch conversation with Harvard professor Henry Louis Gates Jr. changed his career trajectory and led him to pursue both a JD and PhD to maximize his impact on future generations [03:00]๐Ÿ‘จโ€โš–๏ธ๐Ÿ”Ž How his experience working on the Iran-Contra investigation provided invaluable trial experience and showed him the importance of thinking on your feet in high-pressure situations [09:00]โš–๏ธ๐Ÿ‘จโ€๐Ÿซ How he unexpectedly transitioned from government service to academia when Fordham Law offered him a tenure-track position rather than the visiting role he initially sought [19:00]๐Ÿ“š๐Ÿ›๏ธ How his early teaching experience involved staying just one week ahead of his students in property law courses โ€“ demonstrating the importance of adaptability in legal education [21:00]๐ŸŒŸ๐Ÿข How his decision to pursue a deanship was motivated by a desire for more tangible impact and the opportunity to work with teams to build institutions [24:00]๐ŸŽฏ๐Ÿ”„ How serendipity and a handful of phone calls played crucial roles in his career transitions, including his move from Fordham to Georgetown [32:00]๐Ÿ’ฐ๐ŸŽ“ How his commitment to expanding access to legal education was inspired by his family history and led to doubling financial aid and creating opportunity scholarships at Georgetown [35:00]๐Ÿงฉ๐Ÿ” How the RISE program has transformed outcomes for students from backgrounds without exposure to law, with many becoming Law Journal editors and Student Bar Association presidents [36:00]โฑ๏ธ๐Ÿ”‘ How the average law school dean tenure of four years is insufficient to make meaningful change, and why he advocates for longer-term commitments to leadership positions [41:00]๐ŸŒฑ๐Ÿ’ผ How new lawyers should remain optimistic, nimble, and hardworking while building and maintaining strong personal networks that will support both career advancement and personal satisfaction [45:00]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.
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Jul 24, 2025 โ€ข 46min

#137: Adrienne Prentice - Tech Attorney Turned Founder & Lawyer Trainer

Adrienne Prentice, CEO and Founder of Keep Company, shares her journey from labor relations to corporate law. She discusses the importance of mentorship and strategic relationships, revealing how her career was shaped by meaningful connections rather than just subject matter. Adrienne reflects on unexpected opportunities that arose during the 2008 recession and emphasizes the critical role of sponsors in career advancement. With insights on balancing legal careers and parenthood, she advocates for authenticity and open-mindedness in career paths.
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May 23, 2025 โ€ข 39min

#146: Christopher Stephens - World Bank General Counsel

Welcome back to another episode of the โ How I Lawyer Podcastโ , where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is Christopher Stephensโ , the Senior Vice President and General Counsel of the World Bank Group, a role he has held since 2022. Before joining the World Bank Group, Chris served as General Counsel of the International Finance Corporation (the private sector arm of the World Bank) and General Counsel of the Asian Development Bank. Earlier in his career, he was Managing Partner for Asia and a member of the management committee at Orrick, Herrington & Sutcliffe, where he was based in Hong Kong. He is a graduate of Colgate University and New York Law School.In this episode, Christopher Stephens shares valuable insights about the legal profession including:๐Ÿข๐Ÿ’ผ How his desire to avoid the repetitive nature of advanced microeconomics led him to pursue law as a career that would provide variety in clients and challenges [1:38]๐Ÿ“๐Ÿ”„ How his initial "two-year plan" to work in Big Law before joining his father's small firm evolved into a much longer career path as he got caught up in the partnership track [3:46]๐Ÿ“Š๐Ÿ’ฐ How the 1980s "decade of greed" created a frenzy of transactional work with leveraged buyouts, management buyouts, and private equity deals that shaped his early career [5:27]๐ŸŒ๐Ÿ“ˆ How the American legal market's focus on profits per partner, which increased partner mobility [7:10]๐ŸŒ๐Ÿ’ฑ How the 1997 Asian currency crisis forced him to reinvent himself as a China Investment Lawyer just six months after arriving in Hong Kong [11:42]๐Ÿฆโš–๏ธ How moving from a law firm to an in-house position at the Asian Development Bank represented a major shift from a business where law is the product to one where legal is a support function [19:21]๐ŸŒ‰๐Ÿค How the public sector mindset differs from private practice, with a focus on outcomes like poverty elimination rather than profit [23:43]๐ŸŽ“๐Ÿ“š How law students should take challenging courses like tax, environmental law, accounting, and international law that are difficult to learn after graduation [26:45]๐Ÿง ๐Ÿ” How critical thinking is the most important skill for young lawyers, who should question conclusions rather than accepting them at face value [34:30]๐Ÿ›ฃ๏ธ๐Ÿ”„ How being open to change and adapting plans can lead to better opportunities and more enriching professional experiences [37:36]This episode is sponsored, edited, and engineered by โ โ LawPods, a professional podcast production company for busy attorneysโ โ .
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May 9, 2025 โ€ข 49min

#145: Panel Opinion - What Law Students Need to Know to Land a Summer Job

In today's special episode of How I Lawyer Panel Opinion, I am happy to share the recording of an event co-hosted by two longtime friends of How I Lawyer: The Legal Mentor Network and Summer Associate Hub. This conversation about finding a summer job (pre-OCI, OCI and beyond) features:Albert Tawil (Founder and CEO of Summer Associate Hub)Ashley Alford (Manager of Early Careers and Legal Recruitment - Americas at White & Case)Douglas Saphire (Recruitment and Employer Outreach, BC Law)Lauren Tapper (Chief Talent Officer at Kramer Levin)I think the conversation is particularly valuable for current law students but may also be of significant interest to lawyers at every stage of their career.
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May 2, 2025 โ€ข 39min

#144: Sophia Lin Lakin - ACLU Voting Rights Project Director

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is Sophia Lin Lakin, the Director of the Voting Rights Project at the American Civil Liberties Union (ACLU), where she directs and supervises the ACLU's voting rights litigation strategy nationwide. Before joining the ACLU, Sophia clerked for Judge Raymond J. Lohier Jr. of the U.S. Court of Appeals for the Second Circuit and Judge Carol Amon of the U.S. District Court for the Eastern District of New York. She is a graduate of Stanford Law School, where she also received her MS in Management Science and Engineering, and holds a BA in Political Science.In this episode, Sophia shares valuable insights about the legal profession including:๐ŸŽ“๐Ÿ”„ How her academic journey through political science, management science, and engineering prepared her for a career focused on security and human rights before she discovered law [2:35]๐Ÿฅ๐Ÿ’ช How her experience with a serious health condition shaped her desire to become an advocate for the public interest [6:08]๐Ÿ”„๐Ÿ—ณ๏ธ How serendipity led her to voting rights work when Professor Pam Karlin suggested an internship at the NAACP Legal Defense Fund during an extra summer [7:52]โš–๏ธ๐Ÿ” How the Supreme Court's Shelby County v. Holder decision created a sea change in voting rights work just as she was entering the field [11:10]๐Ÿš€๐Ÿ’ผ How her early career involved being thrown into challenging litigation tasks with minimal preparationโ€”taking depositions, handling expert witnesses, and defending clients just months into her fellowship [12:36]๐Ÿง ๐Ÿ‘ How she advises junior lawyers to "take a shot" and try to figure things out themselves first to build confidence and judgment [14:49]๐Ÿ“œ๐Ÿ”„ How voting rights litigation has evolved from focusing on voter ID and early voting restrictions to exploring new legal avenues including First Amendment protections, disability rights law, and state courts [16:37]๐ŸŒŽ๐Ÿšซ How election subversion and anti-immigrant rhetoric present serious concerns for voting rights in the current political climate [19:34]๐Ÿข๐Ÿ”„ How law firm experience can be valuable for public interest careers by providing litigation skills that small organizations can't easily teach [28:00]๐Ÿฅ๐Ÿ’ฌ How being open and honest about her health condition throughout her education and career has been valuable, emphasizing that everyone deserves accommodations to perform at their best [33:28]๐ŸŽฏ๐Ÿง  How staying true to your goals despite law school distractions and maintaining confidence in your own path is crucial for success [36:46]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.
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Apr 18, 2025 โ€ข 43min

#143: Woodrow Hartzog - Law Professor and Privacy & Technology Law Expert

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is Professor Woodrow Hartzog, an internationally recognized expert in privacy and technology law whose work has been published in numerous top journals and books. Before becoming a law professor, Woodrow followed a nontraditional path that included earning his JD/MBA from Samford University, practicing at the regional law firm Burr and Forman, earning an LLM from George Washington University Law School, working as a trademark attorney at the US Patent and Trademark Office, and ultimately earning a PhD in mass communications from the University of North Carolina at Chapel Hill.In this episode, Professor Hartzog shares valuable insights about privacy, technology law, and career development including:๐ŸŒโš–๏ธ How his undergraduate journalism class sparked his interest in technology law when his professor admitted "nobody knows what the law of the Internet's going to be" [3:24]๐ŸŽต๐Ÿ’ฟ How writing about Napster for his college newspaper and receiving feedback about copyright infringement further pushed him toward law school [4:11]๐Ÿ”๐Ÿ“ฑ How the events of September 11, 2001 and the subsequent USA Patriot Act made him think seriously about privacy issues for the first time [5:04]๐Ÿ“šโœ๏ธ How he discovered his passion for academia when he realized he was writing law review articles about privacy "for fun" while working as a trademark attorney [11:29]๐ŸŽ“๐Ÿ”„ How his mentor Dan Solove told him being a "privacy attorney" wasn't yet a real career path in the early 2000sโ€”a reality that has dramatically changed [10:26]๐ŸŒŠ๐Ÿšฃ How sometimes you need to "feel where the river is taking you" in your career while still making intentional choices [13:16]๐ŸŽฏ๐Ÿ’ญ How the most important writing advice he received was that readers will only remember one thing from anything you writeโ€”so make that one thing count [32:51]๐Ÿ“๐Ÿง  How his writing process often starts with "white hot rage" about something wrong that needs fixing, then breaking complex concepts into simpler parts [32:21]๐Ÿ”‘๐Ÿšช How reaching out to professors and mentors is crucial for successโ€”"people are kind and want you to succeed" [40:18]โ“๐Ÿง  How asking questions, even when afraid of looking foolish, is essential because "real wisdom is understanding what you don't know" [41:31]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.
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Mar 28, 2025 โ€ข 40min

#142: LIVE Episode at Stetson Law with Howard Williams - Public Defender

This episode was recorded LIVE at Stetson University College of Law as part of the school's landmark campus to career program! Special thanks to Stetson for inviting me to do this episode on their beautiful campus.Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is Howard Williams, an Assistant Federal Public Defender for the District of Florida. Before his current role, Howard served as a public defender in the Sixth Judicial Circuit in Florida and worked in private practice. He holds degrees from Northwood University and Stetson University College of Law. In this episode, Howard shares valuable insights about the legal profession including:๐Ÿง ๐Ÿ’ผ How his pre-law background in business management, including managing UAW facilities and sports stadiums, helped him develop people management skills that serve him well as an attorney [3:13]๐Ÿ”„โš–๏ธ How transitioning from business (which is results-based) to law (where "the why matters") required a significant mental shift in his approach to problem-solving [4:00]๐Ÿค๐Ÿ™ How public defense is fundamentally about helping people through the worst situations of their lives, often when the deck is stacked against them [7:13]๐Ÿ•ต๏ธโ€โ™‚๏ธ๐Ÿ” How federal cases differ from state cases because federal prosecutors typically build cases for months or years before making arrests, while state cases are often more reactionary [8:28]๐Ÿ—ฃ๏ธ๐Ÿ‘ฅ How his background helps him translate legal concepts into everyday language for his clients, making complex legal situations understandable [9:55]๐Ÿฅ๐Ÿ”ช How state court work is like being an "ER doctor" (fast-paced triage) while federal court work is like being a "surgeon" (methodical, precise, and slower-paced) [14:20]๐Ÿ“โšก How depositions are a critical tool in state court practice that he misses in federal court, as they allow attorneys to lock in witness testimony and discover case weaknesses [18:29]๐Ÿ”Žโš–๏ธ How facts are the foundation of legal practice, with juries ultimately deciding what the facts are based on witness testimony [23:04]๐Ÿ›ฃ๏ธ๐Ÿ”„ How career paths often involve unexpected turns, including jobs not received that ultimately proved beneficial for his professional development [25:12]โฐ๐Ÿ‘ถ How balancing the demands of criminal defense work with personal life requires being fully present in whatever you're doing, whether work or family time [32:17]๐Ÿ”๐Ÿ’ฏ How self-reflection and knowing what truly makes you happy is essential for long-term career satisfaction in the legal profession [35:01]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.
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Mar 7, 2025 โ€ข 53min

#141: Kyle Robisch - Big Law Litigator Turned Flex Legal Talent Leader

In this conversation, Kyle Robisch, a Partner at Latitude Legal and former litigation partner, shares how high school debate shaped his career in law. He discusses the critical decision of selecting the University of Florida for financial flexibility, and the invaluable lessons gained while clerking for a federal judge. Kyle reflects on his move from DC to Florida, which he initially saw as a downgrade but ultimately broadened his practice. He emphasizes the evolving landscape of legal careers, the significance of work-life balance, and the courage to pivot towards fulfilling roles.
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Feb 21, 2025 โ€ข 55min

#140: Mike G. Silver - Consumer Finance Lawyer, Ex-CFPB Lawyer

Welcome back to another episode of the How I Lawyer Podcast, where Professor Jonah Perlin interviews lawyers about what they do, why they do it, and how they do it well.Today's guest is Mike G. Silver, a Partner at Husch Blackwell's DC office specializing in consumer financial services law. Before joining Husch Blackwell, Mike spent 12 years at the Consumer Financial Protection Bureau (CFPB) and 7 years as an associate at Pillsbury. Mike earned his degrees from the University of Pennsylvania (where he served as student body president) and George Washington University Law School (where he was active on Law Review and Moot Court Board). Prior to law school, Mike worked as a legislative assistant at the Religious Action Center.At this moment, the CFPB's future is very much in question but Mike's story remains an important one about how government works and where his industry may go in the future. In this episode, Mike shares other valuable insights about the legal profession including:๐ŸŽ“๐Ÿ’ผ How his path to law wasn't predetermined, but emerged from his interests in history, government, and politics [3:18]๐Ÿ“šโš–๏ธ How being active in various law school activities and internships enhanced his legal education experience [5:01]๐Ÿข๐Ÿ’ซ How his initial real estate practice at Pillsbury evolved unexpectedly from litigation aspirations [11:18]๐Ÿ›๏ธ๐Ÿ”„ How joining the newly-created CFPB in 2011 allowed him to help build regulatory frameworks from the ground up [17:51]๐Ÿ‘ฅ๐Ÿ“Š How being a civil servant requires adapting to changing administrations while maintaining institutional expertise [33:46]๐Ÿ’ผ๐ŸŽฏ How transitioning to private practice requires developing marketing skills and building a business plan [40:25]๐Ÿ“‹๐Ÿ’ก How consumer financial services law involves navigating complex regulations governing personal financial transactions [46:08]๐Ÿ”„๐ŸŒŸ How career pivots require recognizing transferable skills and maintaining a growth mindset [50:26]This episode is sponsored, edited, and engineered by LawPods, a professional podcast production company for busy attorneys.

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