Kristyan Gilmore is an attorney, professor, consultant, and founder of To Be Free, a business advisory company focused on helping entrepreneurs align their work with their values. In this episode, Kristyan shares how the 2008 financial crisis reshaped her legal career, why she believes lawyers should “find their voice,” and how she built a life centered on freedom, teaching, and creative entrepreneurship.

Elaine Lee is a lawyer, travel journalist, and author of Go Girl: The Black Woman’s Book of Travel and Adventure. In this episode, Elaine shares how she built a legal career rooted in civil rights work, how a trip to Paris changed the trajectory of her life, and how she designed a lifestyle that allows her to travel the world while still using her law degree.

Anne Marie Engel is a lawyer, fractional general counsel, and self-described accountability architect. In this episode, Anne Marie shares how her 30-year legal career led her to rethink the role of lawyers in business, why accountability and fiduciary duty are being lost in the profession, and how she now helps companies prevent problems before they start.

Sean Olson is a trial lawyer and founder of Olson Law Firm in Colorado. In this episode, Sean shares how he transitioned from journalism into law, built a personal injury firm from a solo practice into a growing team, and why he still makes time for the courtroom even as a CEO.

Caroline Vickers is an attorney, entrepreneur, and founder of Bar Prep Champs, where she coaches first time and repeat bar takers to pass the exam with strategy and confidence. In this episode, Caroline shares how her own law school experience shaped her career, why mindset is the missing piece in bar prep, and how she built a business helping lawyers overcome shame and finally pass.

Aman Costigan is a former law firm partner, life strategist, yoga teacher, podcaster, and financial independence advocate. In this episode, Aman shares why she left the law from a place of happiness and completion, how she and her husband planned their exits strategically, and why financial literacy is the key to career freedom.

Victoria Inoyo is the Director of Advising at Juris Education, an edtech platform advising students toward careers in law, and a lawyer working in business affairs and creative marketing at Apple. In this episode, Victoria shares how she navigated law school as a first generation American, why she chose the creative side of the legal industry, and how she now helps aspiring lawyers “take the elevator” instead of the stairs through the admissions process.

SeNita McRae is a legal operations professional with a background in broadcast journalism, public administration, and law. In this episode, SeNita shares how she built a thriving career in eDiscovery and legal operations, why passing the bar was not required for her success, and how every degree she earned eventually fit together.

John Lopez is the Legal Director of the Youth Sentencing and Reentry Project, where he supports children charged as adults across Pennsylvania. In this episode, John shares how combining law and social work allowed him to practice in alignment with his values, and why treating people as people is central to meaningful legal advocacy.

Kyla Denanyoh interviews Akshay Verma, Chief Operating Officer at SpotDraft and a former environmental lawyer whose career spans law firms, legal operations, and executive leadership in tech. In this episode, Akshay shares what it felt like to leave firm life, take a financial risk for his family, and build a career that better aligned with how he wanted to live and work.

Kyla Denanyoh interviews Sergio Gregorio is a lawyer, podcast host, and creative who’s redefining what it means to have a legal career. In this conversation, he shares how growing up in Brooklyn, studying journalism, and working in federal service shaped his storytelling instincts, and why today’s lawyers must balance visibility, authenticity, and creativity in the digital world.

Kyla Denanyoh interviews Rob Levine and discussed how case managers can transform your law firm’s operations. Attorney Rob Levine shares three ways case managers improve workflow, client experience, and firm scalability.

Rhonda Coleman Wandel is a commercial attorney, podcast host, and founder of RCW Strategies LLC, a legal consulting firm serving visionary companies and legal teams. In this episode, she shares her bold transition from education to law, her path through in-house legal roles, and why she recently stepped into entrepreneurship after years at companies like Accenture and Google. From Memphis to Chicago, single motherhood to legal leadership, Rhonda’s story is about clarity, cour

Keith Shannon is a former lawyer, legal educator, and lifelong theater fan. Kara Shannon is his daughter and creative collaborator. In this episode, Kyla speaks with the father-daughter duo about their journey from legal careers and musical soundtracks to launching Fourth Row Center, a podcast celebrating Broadway and family bonds. Their story is a heartfelt reminder that success can look like connection, creativity, and choosing joy on your own terms.

Dr. Rhonda Glover Reese is a certified career and leadership coach with 34 years of FBI experience under her belt. From counterintelligence to white collar crime, her federal career was vast and dynamic. In this powerful episode, Dr. Rhonda shares how her dream of working for the FBI led to a fulfilling career in public service and how her new chapter as a coach helps others step into their purpose with confidence.

Lem Garcia is a personal injury attorney and the founder of Lem Garcia Law in California. In this episode, Lem shares how he went from answering Craigslist job ads to running a 20-person law firm. With humility, insight, and honesty, Lem walks us through what it takes to start a firm from nothing and why self-belief and strategic thinking are key to long-term success.

Vernon Thomas is a military attorney, community servant, and judicial candidate for the 19th Judicial District Court in Baton Rouge. In this heartfelt conversation, Vernon and Kyla reflect on his legal journey—from public defender and prosecutor to staff attorney and JAG officer—and how each role shaped his approach to justice. With lessons from his father, mentorship from respected judges, and deep Southern roots, Vernon is driven by more than ambition—he’s driven by service

Danielle Lyn is a practicing attorney, coach, speaker, and podcast host who is boldly redefining what career success looks like. In this honest and energizing episode, Danielle shares her transition from corporate law to a more aligned life of coaching and creating content that empowers others. Whether you’re a law student feeling boxed in or a mid-career professional exploring a pivot, this episode is a must-listen.

Alex Mitchell, owner of Cumberland Law Group, shares his journey from law school to building a thriving multi-state law firm specializing in tax defense, criminal defense, and personal injury. In this episode, Alex reveals how strategic networking and authentic connections have propelled his career, offering practical advice for young lawyers and law students looking to grow their legal careers.

Jon Groth, a personal injury attorney and managing partner of Groth Law Firm in Milwaukee, Wisconsin, shares his journey from law school to running a successful practice with a diverse range of cases, including car accidents and vaccine injuries. In this episode, Jon emphasizes the importance of continuous learning and effective communication in the legal profession, while also discussing the unique challenges and rewards of managing a law firm.