Behind the Hustle

9/11 Was Her Wake-Up Call: Joanna Briley’s Journey to Comedy

Joanna M. Briley shares her journey from being a stand-up comedian to her experiences growing up and finding humor in difficult situations. She discusses her transition from Brooklyn to Connecticut, her struggles with learning, and the impact of vulnerability in her comedy. She also highlights the importance of finding purpose and healing through laughter. Joanna M. Briley shares her journey in comedy, from finding her passion to creating a supportive community for Black women in comedy. She discusses the challenges, sacrifices, and pivotal moments that shaped her career and the importance of safe spaces in the comedy industry. Joanna M. Briley shares her journey as a comedy festival creator, her personal experiences, and the impact of her work on the comedy community. She discusses the importance of self-worth and vulnerability, as well as the challenges and triumphs of her career. The conversation also delves into the significance of Black women in comedy Laff Fest, a comedy festival she founded in 2020 to celebrate and support women in comedy.  That’s a wrap on today’s hustle! If you loved it (or even if you didn’t), hit subscribe, leave a review, and follow me on Instagram @thebehindthehustle for more behind-the-scenes stories and weekly “I Dare You” challenges.

Beyond No: How Relationships Drive Business Development

In this episode, I sit down with Tara Gilbert, Director of Economic Viability, to talk all things business development and relationship-building. We dig into what it really takes to build trust with clients—and, just as importantly, how to maintain those relationships over time. Tara shares her journey from Finance in Corporate America to the nonprofit sector and what prompted that shift. We unpack the realities of business development in nonprofit versus corporate environments, including the resilience required in sales and relationship-driven work. We also explore the power of the word no—when to say it, why we fear hearing it, and how learning to navigate rejection can actually strengthen trust and lead to better outcomes. This conversation is an honest, practical look at persistence, purpose, and building relationships that last.  That’s a wrap on today’s hustle! If you loved it (or even if you didn’t), hit subscribe, leave a review, and follow me on Instagram @thebehindthehustle for more behind-the-scenes stories and weekly “I Dare You” challenges.

From Law to Laughter: Legally Funny with Moonie Desvarieux

From Law to Laughter is the raw, heartfelt, and unapologetically honest journey of Moonie Desvarieaux—a woman who did everything “right” until she finally chose what was true. Raised by a determined single mother with sky-high expectations, Moonie grew up with a very clear message: you have three options in life — become a lawyer, become a doctor, or become a failure. So she pushed, studied, excelled—and became a lawyer. On paper, it was everything she was supposed to want. But inside, another calling was growing louder: a vibrant, creative, laughter-filled life she could no longer ignore. And now, standing at the edge of a major transition, Moonie is preparing to honor that calling fully—planning to step away from law and take a deep dive into entertainment full-time. This episode explores the moments that shaped her—childhood pressures, family sacrifice, cultural expectations, and the powerful rediscovery of her own voice. Moonie opens up about the fears she faces, how she actively works to overcome them, and the deep personal development journey she’s committed to as she builds a future rooted in authenticity and purpose.  That’s a wrap on today’s hustle! If you loved it (or even if you didn’t), hit subscribe, leave a review, and follow me on Instagram @thebehindthehustle for more behind-the-scenes stories and weekly “I Dare You” challenges.

From Prison to Purpose: The Tyquan Morris Story

Tyquan Morris’ story is one of survival, struggle, and transformation. Growing up in the Bronx surrounded by gangs, he was labeled “the enforcer” by the feds — living a life most wouldn’t survive. In this live, unfiltered conversation recorded in front of an audience, Tyquan breaks down life before prison, what it was like serving time in some of the toughest facilities in the country — including the infamous “Bloody Pollack” — and the moment he decided enough was enough. Tyquan shares how changing his mindset behind the wall led him to rebuild his life on the outside, write his book “If I Can, So Can You,” and give back through his work with STRIVE, a nonprofit organization in East Harlem that helped guide and support his transformation. This episode is about pain, growth, and redemption — a real reminder that no matter where you start, you can always change the direction of your life.  That’s a wrap on today’s hustle! If you loved it (or even if you didn’t), hit subscribe, leave a review, and follow me on Instagram @thebehindthehustle for more behind-the-scenes stories and weekly “I Dare You” challenges.

Why I Started Behind the Hustle

In this very first episode of Behind the Hustle, host Jill Plair pulls back the curtain on why she created this show — and what you can expect in the episodes ahead. This isn’t about picture-perfect success stories. It’s about the real, messy, behind-the-scenes journeys of people chasing purpose, pivoting careers, and building something from the ground up. Jill shares her own path as a recruiter-turned-career coach, what draws her to human stories, and why she believes the struggles, doubts, and small wins are what make success truly meaningful. If you’re ready to embrace your own journey and hear honest conversations from people still in the grind (and those who’ve made it to the other side), you’re in the right place.  That’s a wrap on today’s hustle! If you loved it (or even if you didn’t), hit subscribe, leave a review, and follow me on Instagram @thebehindthehustle for more behind-the-scenes stories and weekly “I Dare You” challenges.