Jaimie Nawaday is a former federal prosecutor and current white-collar defense and government investigations litigator. In this episode, she reflects on the skills and insights she brought from her time as a prosecutor, switching sides, and how real-world experience shapes confidence in the courtroom and at the negotiating table. Jamie also offers candid thoughts on the drinking culture within the legal profession and the personal decision she made to step away and speak out. She is a partner and head of her firm’s Government Enforcement and Internal Investigations practice and a graduate of Cornell Law School.

This episode is hosted by Kyle McEntee.

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In this episode, Ezra Lintner (they/she), a legal aid lawyer in San Francisco, discusses defending evicted tenants in a city on the forefront of a civil right to counsel. The conversation highlights the high-stakes reality of eviction defense work, the nuances of habitability, and the emotional challenge of helping clients through a fundamentally disruptive experience. Ezra also reflects on the personal toll of their work, the value of strong support networks, and how the work has only deepened their commitment to housing justice. This episode offers an unflinching look at what it means to defend the right to stay housed in one of the country’s most expensive cities. Ezra Lintner is a graduate of DePaul University College of Law.

This episode is hosted by Kyle McEntee.

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Mergers, acquisitions, hostile takeovers...if you've ever watched television lawyers arguing on the big screen, you’ll know these terms. For transactional lawyer Stephanie Hurst, these words are part of her daily diction. As an income partner at Mayer Brown, Stephanie has been negotiating cross-border transactions for years. In this episode, she highlights the complexities of structuring deals, the role of an M&A lawyer on a larger expert team, and her development from a junior lawyer into a partner. She also talks about the realities of finding balance as a Biglaw attorney managing matters on tight deadlines. Stephanie is a graduate of the University of Southern California School of Law.

This episode is hosted by Katya Valasek.

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Samm Tillotson is a commercial litigator at an elite law firm, where she spends a lot of time defending class action lawsuits for insurance clients. While she doesn't go to trial often, she spends a lot of time in court, preparing for court, and negotiating. Despite the firm's size, Samm's cases are leanly staffed, which means she works a case from beginning to end. She talks a bit about her love of discovery, work-life balance, and partnership. Samm is a graduate of the University of Denver Sturm College of Law.

This episode is hosted by Katya Valasek.

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For Katie King, investigations have always been at the center of her work. As a federal prosecutor turned Title IX and institutional equity expert, she’s spent her legal career tasked with piecing together the truth. Katie now serves as a senior administrator at Cornell University – a job that does not require a law degree or license. In this episode, Katie shares her journey into the world of civil rights law, from handling Title IX cases to overseeing compliance in areas like discrimination and employee accommodations. Katie talks about the need for constant learning and the challenges of navigating an emotional workload. Katie is a graduate of New York University School of Law.

This episode is hosted by Katya Valasek.

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Tijana Brien, a partner at the elite law firm Cooley, specializes in high-stakes securities litigation. In this episode, she unpacks the complexities of defending major corporations, discussing the importance of motions to dismiss, investigation, and focusing on the elements of a case. She shares how she navigates the challenge of translating complex technological concepts—like encryption—into accessible arguments that judges can readily comprehend, drawing from her experience representing companies such as Zoom. TIjana also reflects on how her role has evolved from detailed casework as an associate to more big-picture strategy as a partner, although she still spends more time in the weeds than more senior partners. She talks about managing the pressures of biglaw and the importance of teamwork in a high-stakes environment. Tijana is a graduate of Santa Clara University School of Law.

This episode is hosted by Kyle McEntee.

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As a “dirt lawyer,” Don Pinto’s cases typically involve one party that wants to do something in real estate, and another party trying to stop it. Whether coastal erosion or view obstruction with residential homeowners, or developers seeking to build new commercial or residential property, disputes end up in court if he can’t help his clients come to terms sooner. Each day on the job looks different, from delving into historical records for title disputes to navigating complex cases involving difficult expert witness and judges who cannot help get into the weeds on a very specialized area of law. Don also talks about how the business of real estate law has changed as land values increase, and the unexpected downsides of transparency in law firm compensation—where open financials can breed tension and rivalry among colleagues. Don is a graduate of Suffolk University Law School.

This episode is hosted by Kyle McEntee.

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Lynette Paczkowski is a litigator at heart, and her career journey has taken her to the world of probate litigation. When a will is contested, the legal battle is rarely just about money—it’s about trust, family dynamics, and sometimes the question of whether someone "pulled a fast one." In this episode, Lynette walks us through the complexities of her practice, from uncovering undue influence to determining if a codicil is legally valid. We explore how lawyers strategize, what makes a case worth fighting, and why these disputes can be so emotionally charged. As a partner on the domestic relations team at her mid-sized general practice firm, she also provides helpful insights about the business operations of her firm and its internal dynamics. Lynette is a graduate of Boston College Law School.

This episode is hosted by Katya Valasek.

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