Before becoming a judge, Alex Manning served in the military, worked undercover as a cop, and defended people in complex criminal cases. She was also a key spokesperson advocating against the military’s “Don’t Ask, Don’t Tell” policy. In this episode, Judge Manning talks about what drew her from law enforcement to the law, the challenges of presiding over a courtroom, and the mental and emotional toll of making high-stakes decisions as a day job. She talks about how her investigative experience informs her judge-instincts and gets real about the mental health challenges judges face. Judge Manning is a graduate of Vermont Law and Graduate School.

This episode is hosted by Kyle McEntee.

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Today, Venetia Mayhew is one of Oregon’s most well-known clemency and post-conviction lawyers, but her path to the law was anything but typical. She started college at 39 and law school at 43. Her prior experience? Working in film, catering, and truck driving. In this episode, she explains how her unconventional path shaped her work as a criminal defense attorney. She reflects on years spent leading clemency efforts at a law clinic and what it’s meant to her to help clients receive a second chance. Now in private practice, she works on complex criminal cases after her clients are already incarcerated. As she puts it, it’s a field where “you get a lot of losses, but the wins are just very, very sweet.” Venetia is a graduate of Lewis and Clarke Law School.

This episode is hosted by Katya Valasek.

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Alexis Taitel, a commercial litigator and fourth-year associate at a large firm, spent her first two years after law school clerking in federal district court. She explains what a federal clerkship really involves and how that experience helped her launch a litigation career in private practice. Alexis offers a window into her work on breach of contract cases as a mid-level associate, from pre-litigation strategy and writing compelling motions to learning how to advocate effectively from behind the scenes. She shares her love for legal writing and research, comparing research to a scavenger hunt and writing to storytelling. Alexis also reflects on the steep learning curve and pressures of the billable hour, the mentorship she’s received, and how the reality of being a lawyer differs from what she once imagined. Alexis is a graduate of the University of Nevada-Las Vegas, William S. Boyd School of Law.

This episode is hosted by Kyle McEntee.

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Eric Bernheim works at the intersection of real estate transactions and land use law—two areas that are often siloed but deeply interconnected in his practice. We focus on his commercial real estate practice, highlighting how he supports restaurant clients through lease negotiations, why standardized provisions matter for growth and sale, and how seemingly small terms can affect a company’s long-term strategy. Eric also discusses how he built his leasing practice by working closely with clients over time, how he navigates common points of friction arise with landlords, and what led him and two colleagues to leave a larger firm and start their own during the pandemic. Eric is a graduate of Roger Williams School of Law.

This episode is hosted by Katya Valasek.

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What really draws people to become lawyers? In this special bonus episode, we draw on previously unpublished clips with recent guests. You'll hear from lawyers inspired by family members in the profession, those who found their calling through student government or workplace experiences, and others who were motivated by iconic legal dramas like Legally Blonde and A Few Good Men.

But inspiration is just the beginning. Our guests also reveal what pop culture gets dramatically wrong about legal practice. Spoiler alert: it's far less glamorous and much more tedious than TV suggests. From the reality of billable hours to the emotional weight of client relationships, these lawyers share what truly surprised them when they first started practicing.

Featured voices include:

• Adam Deutsch, personal injury lawyer following in his father's footsteps
• Tijana Brien, securities litigator who promised her refugee father she'd become the lawyer he never got to be
• Samm Tillotson, commercial litigator inspired by her student government experience
• Katie King, who discovered her legal calling through workplace advocacy
• Ezra Lintner, legal aid lawyer using law as a tool for their community service
• And many more sharing their honest takes on expectation vs. reality

This episode is hosted by Kyle McEntee.

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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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