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 SIDE HUSTLES

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.

Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania? 

You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers. 

Visit YSRP.org to support this cause. Thank you.