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.

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.

Kyla Denanyoh, founder and host of You Are a Lawyer, steps into the guest seat in this special episode as she is interviewed by her former law school classmate Vernon Thomas. Together, they unpack a question many lawyers quietly ask: how valuable is a law degree, really? Kyla reflects on her own journey, the evolution of the podcast, and why she believes the JD is more expansive than most people realize.

Kyle Sherman is a trial specialist, civil plaintiff’s attorney, and founder of Trial Structure. In this episode, Kyle shares why law school was the hardest season of his life, how Jerry Spence Trial College reshaped his confidence, and why he believes jury work is about persuasion, not convincing.

Kyla Denanyoh, founder and host of You Are a Lawyer, steps into the guest seat in this special episode as she is interviewed by her former law school classmate Vernon Thomas. Together, they unpack a question many lawyers quietly ask: how valuable is a law degree, really? Kyla reflects on her own journey, the evolution of the podcast, and why she believes the JD is more expansive than most people realize.

Francesca Chang is a lawyer, former travel blogger, and entrepreneur who sued the U.S. Department of Education to discharge nearly $260,000 in student loan debt. In this episode, Francesca shares what it was like to declare bankruptcy, represent herself pro se, and fight for relief in a system with a historic 0.1 percent success rate.

Casey Berman is the founder of Leave Law Behind and a former in-house lawyer who helps attorneys transition into careers that better align with their skills, values, and lives. In this episode, Casey shares how he left traditional legal practice, built a remote business from Hawaii, and helps lawyers rethink identity, risk, and what fulfillment can look like after law.

Stephen Candelmo is a corporate lawyer turned tech founder who has spent nearly thirty years advising emerging companies and building his own ventures. In this episode, he explains how a recession, a machine learning experiment, and a desire for fairness inspired him to create Paralex, a legal platform that delivers fixed-fee, AI-powered legal services for small businesses and startups. He also shares why he believes the legal profession is on the edge of a major transformati

Kyla Denanyoh interviews Daria Levina is a lawyer, academic, and business owner whose path spans Russia, the United States, Italy, and now Berlin. With two law degrees, a PhD in law, and a thriving admissions-advising business, Daria brings a global perspective to legal education and career design. In this episode, she shares what makes a PhD different from a JD, how stand-up comedy transformed her thinking, and why she believes education should be accessible to everyone.

Kyla Denanyoh interviews Edward Cohn is a criminal defense attorney who has spent 23 years running his own solo practice across three states. In this episode, he shares why opening his own firm right out of law school gave him the freedom he always wanted, how a background in music shaped his confidence and creativity, and why some lawyers thrive when they build their practice on their own terms.

Kyla Denanyoh interviews Anne Hamer is a top-rated family lawyer based in Nashville, Tennessee, whose path to success was anything but traditional. After years in corporate and plaintiff work, and even a decade as a stay-at-home mom, Anne returned to the courtroom with a new sense of purpose. In this episode, she shares how to change your legal career at any age, how her own divorce reshaped her understanding of family law, and why it’s never too late to find work you love.

Kyla Denanyoh interviews Chelsea Jones is the founder of Chelsea Anne Media, a social media marketing agency that helps lawyers build personal brands that feel genuine, not forced. In this episode, she shares how one Upwork client turned into a thriving niche, why Instagram remains the most powerful platform for lawyers, and how authenticity can turn online visibility into real relationships.

Kyla Denanyoh interviews Stephen Weisberg is a Detroit-based tax attorney who helps individuals and business owners resolve IRS controversies and tax-debt issues. In this episode, he shares how the 2008 recession launched him from corporate bankruptcy work into tax law, why most people wait too long to seek help, and what every lawyer (and taxpayer) should know before they get that letter from the IRS.

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.

Laura Terrell is an executive coach, general counsel, and former special assistant to the president who has built a career across government, private practice, and nonprofit leadership. In this episode, she shares how coaching helps lawyers advocate for themselves, embrace career pivots, and find clarity in uncertain times.

Kyla Denanyoh interviews Daniel Rosenberg is a seasoned trial lawyer and the co-founder of a thriving civil litigation firm. With roots in criminal defense and a career built in courtrooms, Daniel shares how he went from retail entrepreneur to legal leader and why flexibility, grit, and courtroom instinct are the skills that drive his success. This episode is all about staying ready, even when your office is your car.