Have you ever felt you had to become someone else to fit in as a lawyer?

In this selected replay from an earlier episode of That One Lawyer Podcast, Neal Goldstein revisits his conversation with corporate lawyer Lani Medina about the pressure to fit a professional mold and the strengths that pressure can cause you to overlook.

Lani, a Puerto Rican attorney raised in the Bronx and the first lawyer in her family, recalls feeling out of place at Columbia. She talks about being an introvert in an extroverted world, learning to value her ability to listen, and making herself visible so younger lawyers can see another version of what a corporate attorney can look like.

Their conversation explores client trust, bringing a human touch to corporate law, and handling difficult people with kindness and professionalism. Lani also shares why she speaks openly about OCD and anxiety, despite uncertainty about how those disclosures will be received.

They close by discussing whether lawyers can embrace artificial intelligence while preserving their authenticity, judgment, and responsibility to clients.

Follow or subscribe to That One Lawyer Podcast for more honest conversations about the human side of being a lawyer.

In Part 2 of Neal Goldstein's conversation with Brian Cuban, the focus turns to the lawyer Brian became while his personal life was unraveling.

Brian speaks candidly about his years practicing personal injury law and why he has described himself as an "ambulance chaser." He and Neal discuss the referral relationships, chiropractors, settlements and ethical questions surrounding that period of his career, without pretending the past was cleaner than it was.

Their conversation also explores addiction and mental health in the legal profession, the role of lawyers assistance programs, and the complicated reality of lawyers who may continue functioning professionally while struggling privately.

Brian also discusses his transition into writing and his novel The Ambulance Chaser, which draws from a professional world he experienced firsthand.

The conversation ultimately returns to connection, recovery and what it means to show up for another lawyer who may be struggling. Brian closes with a deeply personal story about a lawyer he knew and what he wishes he could say to him today.

Follow or subscribe to That One Lawyer Podcast for conversations about the people, relationships and experiences behind the practice of law.

Brian Cuban - https://briancuban.com/

Brian Cuban - LI - https://www.linkedin.com/in/briancuban/

Neal Goldstein - YT - https://www.youtube.com/@ThatOneLawyerPod

Neal Goldstein - LI - https://www.linkedin.com/in/nealagoldsteinlaw/?isSelfProfile=true

Brian Cuban's story did not begin with recovery, writing, or being Mark Cuban's brother. It began with a kid in Pittsburgh struggling with shame, bullying, body image, and an overwhelming desire to belong.

In Part One of this two-part conversation, Brian talks about the childhood experiences that shaped his identity, the loneliness he carried to Penn State, the eating disorder and drinking that followed him into law school, and why he became a lawyer even though he never really wanted to practice law.

Brian also recounts one of the darkest moments of his addiction and the role his brothers, Jeff and Mark, played when his life was in danger.

This is a conversation about the things people carry with them long before anyone else can see the consequences, and about the family connections that can matter when everything else begins to disappear.

Follow or subscribe to That One Lawyer Podcast so you don't miss Part Two of Neal Goldstein's conversation with Brian Cuban.