Matt Naylor sits down with Chris Wilson, President of Healthcare Highways, to discuss his journey from entrepreneur and benefits advisor to leading one of the healthcare industry's most innovative network organizations. Chris shares how lessons learned from building and selling his own brokerage firm shaped his approach to healthcare, why transparency and alignment are critical to fixing rising healthcare costs, and how Healthcare Highways is helping employers, providers, and members achieve better outcomes through smarter network design. The conversation explores the challenges facing the healthcare system today, the role employers play in driving change, and Chris's vision for a more transparent and accountable healthcare future.

Matt Naylor sits down with Rob Adams, CFO of Crumdale Specialty, to trace the arc of a career built on persistence, differentiation, and calculated risk. Rob opens up about his early inflection points—switching from public school to all-boys Malvern Prep (which turned his grades around), fighting the administration for the right to recruit with Big 4 accounting firms as an econ major, and the frustration of watching entrepreneurs reap equity rewards while his firm could only collect fees. That frustration sparked his pivot from service provider to principal, leading him to an MBA at the University of Michigan—and a tough choice between grad school and a budding romance that ultimately shaped his path. From Ernst & Young to the music industry to the CFO seat, Rob shares how grit, diverse experience, and knowing when to zig while others zag built the career he has today.

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.