Next-Gen Leaders: Reilly Berk & Christine Schindler on Breaking the Mold
Release Date: 06/18/2025
Prosper Brief
In this insightful episode of The Prosper Brief, host Kim DeCarolis sits down with Rob Lynch, CEO of Shake Shack, to discuss his leadership journey—from Procter & Gamble to Taco Bell, Papa John’s, Arby’s, and now the helm of one of the most beloved fast casual brands in the world. Rob shares how he leads through change, builds team-first culture, and stays rooted in purpose while delivering performance. This episode is full of wisdom on scaling without losing soul, building trust after transition, and innovating by returning to what matters most: the guest. Attend Prosper Forum The...
info_outlineProsper Brief
In this heartfelt and insightful episode of The Prosper Brief, host Jeremiah Wynn sits down with Cynthia Zhang, SVP of Global Marketing & Product Strategy at Henny Penny. Together, they explore the often misunderstood concept of empathy in leadership, distinguishing it from sympathy and diving into how empathetic leadership can transform teams, workplaces, and lives. Cynthia shares powerful personal stories from her upbringing in China and her early career, highlighting how real empathy builds trust, fosters innovation, and enhances mental well-being. If you’re a leader, team member, or...
info_outlineProsper Brief
In this powerful episode of The Prosper Brief, host Jeremiah Wynn is joined by Richard Weintraub, Head of North & Latin America Global Family Office Group at Citi, and Grace Zuncic, Managing Director at Manna Tree Partners, for a deeply human conversation about leadership, connection, and culture. Through personal stories of grief, growth, and legacy, they explore how cultivating a family-like culture at work isn’t just a feel-good concept—it’s a high-performance strategy. If you lead people, this episode will reshape how you think about trust, loyalty, and what it means to truly...
info_outlineProsper Brief
In this episode of The Prosper Brief, host Jeremiah Wynn sits down with Sean Tresvant, CEO of Taco Bell and Chief Consumer Officer at Yum! Brands, to talk about leadership, branding, and building global consumer trust. Sean shares his path from working at Campbell’s and Sports Illustrated to leading iconic brands like Jordan and now Taco Bell, highlighting the key lessons that shaped his approach to leadership. Listeners get an inside look at what it means to lead with humility, emotional intelligence, and a strong understanding of consumer behavior. Sean unpacks the power of brand...
info_outlineProsper Brief
In this power-packed episode of The Prosper Brief, host Jeremiah Wynn sits down with Jim Bitticks, President & COO of Dave’s Hot Chicken. From flipping fries in his teens to building billion-dollar brands, Jim shares the behind-the-scenes grit and golden lessons from his journey in the fast food and franchise industry. They dive into what it takes to scale operations, why people matter more than anything, and how spicy chicken changed his life (literally). It’s an inspiring, hilarious, and deeply insightful look into how loyalty, leadership, and risk-taking can lead to massive success....
info_outlineProsper Brief
In this soul-stirring episode of The Prosper Brief, host Jeremiah Wynn sits down with Derek Gaskins, Chief Guest Experience Officer at BP. More than a business conversation, this is a masterclass on emotional intelligence, self-awareness, leadership, and legacy. From his Southeast D.C. roots to executive leadership, Derek shares how knowing yourself unlocks your power to inspire others. The duo dives into the science of temperament, leading high performers, and how excellence and discomfort are vital to growth.
info_outlineProsper Brief
In this heartfelt and inspiring episode of The Prosper Brief, host Kim DeCarolis sits down with Alexandra Brown, a rising leader at Toast, Inc., to reflect on her experience at the Prosper Forum. From stepping into her new management role to building community in tech sales, Alexandra opens up about what it means to grow, lead authentically, and support the next generation of industry talent. With candid moments, leadership insights, and a dose of mentorship magic, this episode will leave you motivated to take your own leap forward. Subscribe, share, and send this episode to a leader or rising...
info_outlineProsper Brief
In this episode of The Prosper Brief, host Anthony Zaller sits down with Kirk Grogan, COO and Co-Founder of TipHaus, to unpack the complex, evolving world of tip management in the hospitality industry. From automating compliance across 37+ states to processing over $5 billion in tips annually, TipHaus is revolutionizing how restaurants handle payouts, avoid legal pitfalls, and retain staff in a cashless world. Kirk shares his journey from Chili’s host to hospitality tech founder, offering practical wisdom and deep insight on labor, compliance, digital...
info_outlineProsper Brief
In this future-forward episode of The Prosper Brief, host Jeremiah Wynn is joined by Sho Shafiei of DSA Signage and Eli Chmouni of NEON to explore how signage, AI, and smart guest experiences are evolving the hospitality space. From transforming static menu boards to launching AI-powered drive-thru voice solutions, these two innovators break down what’s next for restaurants and retail. It’s a conversation packed with tech, teamwork, and how to turn operational headaches into streamlined success.
info_outlineProsper Brief
In this powerful episode of The Prosper Brief, Dr. James Pogue delivers a masterclass on leading through disruption with clarity, compassion, and courage. Tackling everything from emotional intelligence to the fragility of organizational culture in the age of viral social media, Dr. Pogue brings unmatched insight into how leaders can not only survive turbulent moments, but grow through them. With practical frameworks, real-world examples, and a human touch, this conversation is a must-listen for current and emerging leaders navigating today's increasingly complex and emotionally charged work...
info_outlineEpisode Summary
In this dynamic episode of The Prosper Brief, host Justine Jobe sits down with two powerhouse leaders—Reilly Berk, CEO of Berk Enterprises, and Christine Schindler, co-founder and CEO of PathSpot—to talk next-gen leadership, hustle, and redefining what the C-suite looks like today. Reilly shares her experience leading her family’s fourth-generation business with a bold, fresh perspective, while Christine details her journey from engineering student to health tech innovator. Together, they explore the reality of leading as young women in male-dominated industries, the weight of urgency, and the power of showing up as your full, authentic self.
Call to Action
If you know a rising leader who needs encouragement to own their voice and step into their next role—share this episode. Then subscribe to The Prosper Brief and leave a review to help us keep amplifying stories that matter.
5 Key Takeaways
- Young Leaders Are Rewriting the Playbook – Reilly and Christine prove age isn't a limitation—it's often an advantage.
- 2. Urgency Is a Superpower – Acting fast and thinking ahead are crucial when you're building something that matters.
- 3. Authenticity is Leadership – Being your real self, especially in high-pressure environments, fosters deeper trust and stronger teams.
- 4. Legacy Doesn’t Mean Limits – Reilly is building on her family’s history while forging a new, modern path forward.
- 5. Start in the Scrappy Phase – Christine reminds us that prototypes, late nights, and trial-and-error are where greatness is born.
📍 Join us at Accelerate → https://prosperaccelerate.com Let’s close the gap between where you are and where you could be—one inch at a time.