Matt is joined by Shawn Kanungo, who shares his perspective on why AI is one of the most transformative technologies of our time and how it will reshape every industry. He explains that success in an AI-driven world isn’t about prompt engineering, but about creativity, context, and the ability to generate ideas that AI can execute. Shawn breaks down how individuals at every stage of their career should approach AI—encouraging younger professionals to build skills with the tools, while urging experienced professionals to pair their deep industry knowledge with AI as a “technical co-founder.” He emphasizes that the real opportunity lies in reimagining work, designing around human strengths, and becoming more adaptable in a world where change is constant. Ultimately, he highlights that those who lean into uncertainty, experiment, and build a muscle around AI will thrive, while those who resist it risk being left behind in a rapidly evolving landscape.

Matt is joined by Rod Strata Jr., who shares his journey from cold-calling medical supplies and college recruiting to leading benefits strategy at GDK. He explains how those early experiences built resilience and shaped his approach to helping employers navigate the complexities of healthcare. Rod breaks down why transparency and access to data are critical in a system where prices can vary dramatically for the same service, and how tools that guide employees to lower-cost, higher-value care can make a meaningful difference. He also highlights how innovative strategies like specialty drug sourcing, cost containment, and the right vendor partnerships help flatten rising healthcare costs while improving the member experience.

Matt is joined by Eric O’Brien, who shares his journey from aspiring professional lacrosse player to founding Mosaic Employee Benefits after recognizing the disruption coming with the Affordable Care Act. Drawing on his experience as an athlete, Eric explains how resilience, discipline, and a competitive mindset shaped his approach to building a business and serving clients. He breaks down how education and employee engagement are key to lowering healthcare costs, helping companies move beyond the traditional “use your card and pay the bill” mindset toward more informed, cost-conscious decisions. Eric emphasizes that in a complex and rapidly evolving benefits landscape, success comes from cutting through noise, focusing on the right partners, and leading with transparency, trust, and genuine care for clients and their employees.

Matt is joined by Buzz Hannum and Tonya Crawford, who share their journeys into the insurance and healthcare space and how they came together at Crumdale Specialty. Buzz started on the broker side, developing a focus on risk management and alternative financing, while Tonya transitioned from a clinical healthcare role into the business side, keeping patient outcomes at the center of her work. Together, they explain how Crumdale’s approach differs from traditional models by guiding employers through a phased transition from fully insured plans to captive solutions, using data, cost containment strategies, and integrated services to reduce costs and improve outcomes. They also highlight the importance of alignment, transparency, and partnership with brokers—positioning Crumdale as a true extension of their teams in an increasingly complex and fragmented healthcare market.

Matt is joined by Ahmed Marmoush, who shares his journey from growing up in a family of pharmacists to building a healthcare technology company aimed at fixing inefficiencies in the U.S. system. After working across New Zealand, Australia, the UK, and eventually the U.S., he became frustrated by the lack of transparency and high costs in American healthcare, sparking the idea for Handl Health. The company initially focused on empowering consumers but quickly shifted upstream to influence employers and health plan design, using data to drive better outcomes and lower costs. Ahmed explains how pricing transparency, provider quality insights, and real-time plan monitoring form the foundation of their platform, with a long-term vision of fully personalized healthcare plans powered by data and AI.

Matthew Naylor interviews Joe Hessling, CFO of Parcels, about his career in finance and the challenges of managing healthcare costs for a growing, people-focused business. Joe shares how years in the fully insured market led to frustration with rising costs, lack of transparency, and limited control over decision-making.

He explains how transitioning to a level-funded model and eventually into a captive provided greater visibility, predictability, and access to data, allowing Parcels to better manage risk and support employees. For the first time in years, the company was able to maintain stable costs without shifting the burden to employees.

Joe emphasizes that the biggest impact has been improved transparency, stronger partnerships, and a more proactive approach to healthcare management, giving him confidence in long-term planning and a better overall experience for both the company and its employees.

Matthew Naylor interviews Ryan Hanratty of Swingle Collins, who shares how his path from professional golf into employee benefits shaped his work ethic and approach to business. He explains how resilience, discipline, and learning from failure translated directly into building and growing a successful benefits practice.

Ryan discusses how his firm focuses on educating employers about alternatives to traditional healthcare models, using data-driven strategies and creative solutions to reduce costs and improve outcomes. He emphasizes the importance of personalized approaches, especially in areas like pharmacy benefits, where better sourcing and awareness can significantly impact both employers and employees.

He also highlights the importance of culture and leadership, describing a family-oriented company environment and a philosophy centered on putting others first. For Ryan, long-term success in both business and life comes from serving others, continuously improving, and staying committed to making a meaningful impact.

Matthew Naylor interviews Don Gasparro, who shares his journey from aspiring teacher to actuary and eventually to building and scaling a major stop loss insurance business. After early roles at Aetna and in consulting, Don co-founded Apex Management Group, which grew through its data-driven approach before being acquired by Gallagher. Don explains how thinking creatively, developing new structures like captives, and solving real employer problems helped reshape the market.

The conversation also explores the future of captives, emphasizing that success depends less on the financial vehicle itself and more on actively managing risk, educating employers, and aligning incentives. Don highlights that the next phase of the industry will be driven by organizations that combine deep expertise with integrated solutions to truly control costs and improve outcomes.