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.
Lawyer and podcaster Sergio Gregorio explores how legal professionals can embrace creativity and authenticity while navigating visibility in the modern digital age.
Born and raised in Brooklyn to Guatemalan parents, Sergio Gregorio grew up surrounded by resilience, resourcefulness, and a deep appreciation for hard work. As a child, he dreamed of driving New York City trains, until his sister offhandedly suggested that lawyers “made more money,” setting him on an unexpected path toward law. That spark led him to a magnet high-school programme for aspiring attorneys, where teachers who practised law inspired him to imagine a life of purpose and influence.
“There was nothing in me that suggested this is the way I should go, but I decided to follow the money," shares Sergio Gregorio on You Are A Lawyer.
After earning his undergraduate degree in English and Broadcast Journalism at Syracuse University, Sergio pursued law at Howard University, graduating in 2001. Although his education prepared him for traditional legal practice, his creative instincts never faded. Today he channels both his legal acumen and his storytelling flair through his podcast Frolic & Detour—a title borrowed from a torts concept that perfectly mirrors his own professional path: a deliberate deviation toward the unexpected.
It wasn’t family pressure or generational expectation that influenced Sergio’s decision to attend law school. His parents, immigrants from Guatemala, encouraged him to choose freely, an uncommon liberty in many first-generation families. Yet he still sought what he saw as the “safe” route. Law school felt like a dependable next step for a young man uncertain about how to turn his journalism ambitions into a career.
“As crazy and unpredictable as law school can be, it’s still relatively safe," explains Sergio Gregorio on Episode 216 of You Are a Lawyer, “You go to school, you study hard, you get the degree.”
At Howard Law, he discovered a new form of storytelling, one built on advocacy and precision. Still, he recognised early that the law’s structured nature didn’t leave much room for creative expression. The challenge became how to merge his legal expertise with his natural curiosity about people, culture, and media—a challenge that would ultimately shape his unconventional career.
After more than fifteen years as a federal attorney, Sergio Gregorio has built a steady career writing disability decisions and analysing complex medical evidence. The work satisfies his love of logic and service, but he also acknowledges how the profession, and his relationship to it, has evolved. The early years felt like a dream job: intellectually stimulating, purposeful, and calm. Over time, though, he felt the pull to create something more personal.
“You can’t be a public person with a private profile," shared Sergio Gregorio on Episode 216 of You Are a Lawyer.
That advice resonated. Through Frolic & Detour and his growing YouTube presence, Sergio is learning how to reconcile his introverted nature with the demands of visibility. He encourages other lawyers to cultivate authenticity online—sharing selectively but honestly, ensuring that their professional persona aligns with who they truly are. For Sergio, being visible isn’t about self-promotion; it’s about owning your narrative before someone else defines it for you.
Sergio’s podcast, Frolic & Detour, showcases the multifaceted lives of lawyers who have stepped outside conventional career paths. Through conversations that blend humour, culture, and creativity, he invites listeners to see law as a foundation, not a limitation. He’s also expanding his creative portfolio with food-review videos, blending his love of storytelling with his natural curiosity about everyday pleasures.
“People don’t really get to see the silly side,” Sergio Gregorio admits in Episode 216 of You Are a Lawyer, “The podcast can feel serious, but there’s more to me than that.”
By bringing humanity into his work, Sergio embodies the podcast’s core philosophy: lawyers are people first. Thinkers, creators, and dreamers who deserve space to explore beyond the billable hour. His story is a reminder that embracing detours can lead to the most authentic destinations.
Sergio is licensed to practice in New York and the District of Columbia
This episode is produced by Skip The Boring Stuff, a podcast strategy company for business owners and creatives.
