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.