Dearborn Labs Launches “Context Window” Podcast Exploring the Real Stories Behind AI Adoption in Insurance
Context Window: AI, Insurance & The Humans Behind It” premieres June 25, spotlighting the real-world challenges, lessons and breakthroughs of deploying AI in insurance and the people reshaping the industry
CHICAGO, June 25, 2026 — Dearborn Labs, a forward-deployed AI firm focused exclusively on insurance, today announced the launch of Context Window: AI, Insurance & The Humans Behind It, a new podcast hosted by Dearborn Labs Co-founder and CEO Kyle Nakatsuji.
The show launches June 25 on Apple Podcasts, Spotify and YouTube with insurance technology entrepreneur and Reserv Co-Founder and CEO CJ Przybyl as its inaugural guest.
At a time when nearly every insurance organization is discussing AI, Context Window focuses on the stories from people actually deploying it. Each episode features candid conversations with founders, operators, investors and industry leaders who are navigating the opportunities, challenges and tradeoffs of bringing AI into one of the world’s most complex industries.
Rather than focusing on headlines, product launches or conference talking points, the podcast explores the personal journeys, leadership lessons and real-world decisions shaping insurance’s next chapter.
“We’re not doing a five-minute version of anyone’s bio,” said Nakatsuji. “I want to bring on leaders, CEOs, operators, builders and investors who have real experiences to share. We’ll spend time understanding where they came from, what shaped them, the decisions they’ve made and the lessons they’ve learned.”
The show dives into AI and insurance, focusing on what’s working, what’s over-hyped and where they see the industry heading. Episodes wrap up with questions that reveal how people think: the books that changed them, the advice they carry and how they navigate uncertainty.
Nakatsuji brings a unique perspective to the host’s chair. As Co-founder and CEO of Clearcover, he has spent the past decade building one of the most automated insurance operations in the United States. Over 90% of claims intake runs through AI agents, 93% of policies are bound digitally and claims handling operates at three times the efficiency of traditional carriers.
Earlier this year, he launched Dearborn Labs to help carriers and MGAs apply those same lessons and capabilities to their own AI transformations. Prior to founding Clearcover, Nakatsuji led insurtech investments at American Family Ventures.
Inaugural Guest: CJ Przybyl, Co-Founder & CEO, Reserv
The debut episode features CJ Przybyl, co-founder and CEO of Reserv, the AI-powered third-party administrator transforming claims management for insurers, MGAs and self-insured organizations. A second-time insurtech founder, Przybyl has grown Reserv into a trusted claims partner for more than 100 clients in just four years by combining human expertise with AI-enabled operations. He also serves as an adjunct professor of entrepreneurship at the University of Chicago Booth School of Business.
In the episode, Przybyl discusses his journey from first-time founder to building Reserv, lessons learned scaling a modern claims organization, and why successful AI adoption depends as much on people and process as it does on technology.
“Insurance is ultimately a people business,” said Przybyl. “AI can create tremendous leverage, but the companies that win will be the ones that thoughtfully combine technology with human expertise. I enjoyed the opportunity to talk with Kyle about what we’ve learned building Reserv and where we believe the industry is headed.”
Context Window: AI, Insurance & The Humans Behind It is available on Apple Podcasts, Spotify and YouTube.
Insurance leaders interested in being considered for future episodes, please contact [email protected].
About Dearborn Labs
Founded in 2026 as part of the Clearcover holding company, Dearborn Labs is a forward-deployed AI firm focused exclusively on insurance. The concierge practice is powered by the proprietary technology stack, data infrastructure and leadership team that built Clearcover, Inc. and its multiple licensed insurance carriers into a nationally recognized digital insurer.