Prosper Brief

In this deeply personal and energizing episode of The Prosper Brief, host Jeremiah Wynn sits down with Meredith James, EVP of Business Development at Prosper, and her longtime friend and business ally Jigar "JP" Patel, VP and Co-Founder of SAASTA (Strategic Alliance of Affiliated Stores of America). What began as a grassroots solution for small operators has grown into a 5,200+ member network advo...

In this episode of The Prosper Brief , Jeremiah Wynn sits down with Chris Hellmann, a seasoned executive retiring as Chief Commercial Officer at RTI, after a remarkable career spanning nearly 30 years with Coca-Cola and beyond. Chris shares powerful insights on navigating rejection, building a career through diverse experiences, and leading with authenticity in an ever-changing world. From pivotal...

In this energizing episode of The Prosper Brief , host Anthony Zaller sits down with Ray Johnson, former divisional VP at Cracker Barrel and founder of ReCee's Leadership Consulting Group. With over 35 years in hospitality operations, Ray shares the powerful lessons he's now bringing to franchisees and operators nationwide. From mastering the five core foundations of service to avoiding common ear...

In this flavor-packed episode of The Prosper Brief, host Jeremiah Wynn chats with Briana Jurado, the vibrant and visionary VP of Beverage Program at Botrista—a company shaking up the craft beverage world with automation. As a newly announced 2025 Prosper Accelerator, Briana shares her inspiring journey from Coca-Cola to leading beverage innovation, flavor development, and brand collaboration at Bo...

In this inspiring episode of The Prosper Brief, host Kim DeCarolis is joined by Wade Allen, President of Win Brands, the company behind Costa Vida Fresh Mexican Grill and FatCats Entertainment. With a background that spans tech, marketing, and innovation leadership at Brinker International, Wade brings a modern, multidimensional view of what it takes to lead companies that prioritize people, perfo...

Recorded live at the Prosper Forum at the Ritz-Carlton, Amelia Island, this episode features Shannon Iverson, 2025 Prosper Accelerator. Shannon shares her powerful story of resilience—growing up in Southern California in a widowed household, caring for her partially paralyzed mother at just eight years old, and starting her QSR journey at 14. From teaching to chemical manufacturing to boldly stepp...

In this heartfelt and energizing episode of The Prosper Brief, host Jeremiah Wynn is joined by three dynamic leaders using business to change lives: Christine Conroy of Greyston Bakery, Phillip Scotton, President & CEO of Primo Partners, and Ray Sawyer, Chief Innovation Officer. Together, they unpack what it truly means to build with purpose—creating second chances, scaling community impact, and r...

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 perfor...

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 person...

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 cul...

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...

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 a...

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 di...

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...

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 staf...

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 conv...

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...

In this powerful episode of  The Prosper Brief , host  Jeremiah Wynn  sits down with  Jeffrey Kiesel , CEO of  Restaurant Technologies, Inc. , to dive into 20 years of transformational leadership, cultural innovation, and scaling a company from 12,000 to over 50,000 customers. Jeff shares how his focus on values, trust, and talent development helped shape one of America's best workplaces. From ope...

In this forward-thinking episode of The Prosper Brief, host Anthony Zaller sits down with serial entrepreneur and Squeez CEO Chris Ogboke to unpack how a personal pain point sparked a tech solution that's disrupting the hospitality industry. Chris shares the journey behind Squeez, a platform turning empty restaurant tables into revenue by digitizing last-minute VIP access: the modern $50 handshake...

In this heartfelt and insightful episode of The Prosper Brief, host Jeremiah Wynn sits down with Hattie Hill, renowned business leader, inclusion advocate, and board member at Prosper, to explore her remarkable journey from humble beginnings on an Arkansas farm to building a 35-year career transforming corporate culture. Hattie shares lessons learned from mentors like Herb Kelleher of Southwest Ai...

In this episode of The Prosper Brief, we sit down with Lois Alexis-Collins, a powerhouse HR executive at Chipotle Mexican Grill, to explore how breaking free from silos, leading with empathy, and getting uncomfortable can be the key to unlocking real career growth. Lois shares her journey from the frontlines to the C-suite, offering actionable insights on cross-functional leadership, talent develo...

What does it take to revive a legendary brand and lead with heart through crisis? In this episode of The Prosper Brief, Reilly Berk, Prosper Accelerator and CEO of Berk Enterprises, sits down with David McKillips, the visionary CEO behind the transformation of Chuck E. Cheese. David shares his journey of stepping into leadership just weeks before a global shutdown, navigating bankruptcy, and leadi...

In this rich, thought-provoking episode of The Prosper Brief, host Jeremiah sits down with Ryan Berman, founder of Courageous, corporate fear fighter, speaker, and author, to explore the intersection of purpose, fear, leadership, and courageous decision-making. The conversation flows from personal stories to leadership insights, diving deep into the true meaning of courage in business and life.

In this powerful episode of The Prosper Brief, host Jeremiah Wynn welcomes back Dan Simons, co-founder of Founding Farmers Restaurant Group, for a deeply personal and transformative conversation about the true meaning of loyalty in leadership. Dan shares real stories of failure, hard choices, and lessons learned from decades in hospitality. He explores how transparency, vulnerability, and a commit...

In this deeply personal and energizing episode of The Prosper Brief, host Jeremiah sits down with communications leader Stacie Barrett to unpack the power of personal branding—not as a marketing tactic, but as an act of self-awareness, alignment, and integrity. From navigating code-switching and cultural identity in corporate spaces to embracing vulnerability and values on social media, this conve...