Profiles in Risk

Insurance Nerds
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Mar 16, 2026 • 54min

Kyle Nakatsuji, Founder & CEO at ClearCover & Dearborn Labs - PIR Ep. 794

Tony chats with Kyle Nakatsuji, Founder & CEO at ClearCover & Dearborn Labs. Kyle started ClearCover a decade ago, and still runs it. Now he has also founded Dearborn a forward-deployed technology and AI firm focused exclusively on insurance. This new concierge practice is powered by the proprietary technology stack, data infrastructure and the leadership team that built Clearcover and its multiple licensed insurance carriers into a nationally recognized digital insurer. An absolutely fascinating conversation you simply can't miss!Kyle Nakatsuji: https://www.linkedin.com/in/kylenakatsuji/Old Episode about ClearCover: https://youtu.be/2u1x2GAXVSY?si=Jr_70LbeIQMQOQe8ClearCover: https://clearcover.com/Dearborn Labs: https://dearbornlabs.com/Video Version: https://youtu.be/aX48qP2Tio0
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Mar 12, 2026 • 43min

Jeffrey Glusman, Founder & CEO and David Ratner, Chief Investment Officer at BDIC - PIR Ep. 793

Tony chats with Jeffrey Glusman, Founder & CEO and David Ratner, Chief Investment Officer at Blockchain Deposit Insurance Corporation (BDIC). BDIC  is building the FDIC equivalent for crypto! No other player is working on offering deposit insurance for the 99% of people who are interested in crypto but can't afford the possibility of losing their money. A fascinating conversation!
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Mar 9, 2026 • 35min

Craig Caryl, Founder & CEO at InsureMep - PIR Ep. 792

Tony chats with Craig Caryl, Founder & CEO at InsureMep, they are a tech enabled MGA that created software that tracks electrical, mechanical and plumbing of large electrical facilities to track risk and prevent losses. This was a fantastic conversation you should not miss!Craig Caryl: https://www.linkedin.com/in/craig-caryl/InsureMEP: https://www.insuremep.com/Video Version: https://youtu.be/Ljxf9KrJaNk
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Mar 4, 2026 • 30min

Grace McNamara, Chief Strategy Officer at Elfie - PIR Ep. 791

Tony chats with Grace McNamara, Chief Strategy Officer at Elfie, they are the health superapp that brings all your health apps into one place with one seamless experience and give you better insights. A fascinating episode!Grace McNamara: https://www.linkedin.com/in/grace-mcnamara-irelandlondonnewyork/Elfie: https://www.elfie.co/Video Version: https://youtu.be/t5VyIRBKE5A
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Mar 2, 2026 • 30min

Chris Casaleggio, Claims Author - PIR Ep. 790

Tony chats with Chris Casaleggio, Regional Director NE at MC Consultans, Forensic Expert, and Claims Author. Chris has written six books about the claims trade! Today we chat about his latest book: "Claims Crossroads: Fresh Starts, Smart Pivors & New Paths for Adjusters". The entire series is fantastic, but this latest entry is so important. What happens when a claims adjusters decides they need to seek a different direction? Don't leave the industry, there are many ways to make the most of your claims background and Chris can help you find the way!Chris Casaleggio: https://www.linkedin.com/in/casaleggio/Claims Crosswords: https://amzn.to/4l1sUhv
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Feb 26, 2026 • 47min

Kristina Fahl, Founder & CEO at Shuttlebee - PIR Ep. 789

Tony chats with Kristina Fahl, Founder & CEO at Shuttlebee, 54% of K-12 students in the US don't have traditional school bus service. Kristina set out to solve this issue with a network of highly vetted micro-entrepreneurs and found that insurance was the main stumbling block her partners faced. This is the story of how she's solving that problem. A fascinating episode you cannot miss!Kristina Fahl: https://www.linkedin.com/in/kristinagfahl/ShuttleBee: https://getshuttlebee.com/Video Version: https://youtu.be/jkbdAMbZOvo
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Feb 23, 2026 • 34min

Serge Salager, CEO at Visualping - PIR Ep. 788

Tony chats with Serge Salager, CEO at Visualping, a simple idea that's incredibly useful. Be notified when an important change happens online. Sounds simple, but the insurance underwriting implications are massive. Don't miss this one!Serge Salager: https://www.linkedin.com/in/sergesalager/Visualping: https://visualping.io/
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Feb 17, 2026 • 56min

Kelly Donahue-Piro, Agency Performance Partners - PIR 787

Tony chats with Kelly Donahue-Piro at Agency Performance Partners, they are the BFF every independent agency owner needs, regardless of the size of your agency. If you're not loving the way your agency is running, think you might need to update your processes or your systems, you owe it to yourself to chat with Kelly and her team. They can help in many ways from deep in-person consulting and training to affordable access to the most in-depth and comprehensive online school on how to run every aspect of a modern insurance agency.Kelly Donahue-Piro: https://www.linkedin.com/in/kellydonahuepiro/Agency Performance Partners: https://www.agencyperformancepartners.com/Video Version: https://youtu.be/2IuIyPYFk2A
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Feb 12, 2026 • 32min

David Stafford, Co-Founder and COO at Substance - PIR Ep. 786

Tony chats with David Stafford, Co-Founder and COO at Substance, they are a budding insurtech, currently in pre-seed funding round, that is building an An MGA that is powered by AI and robotics to completely change the risk evaluation and loss prevention process focused in warehouse and supply chain space. Their technology will have applicability to warehouses, manufacturing, and the fast growing space of data centers. They completely turn the model upside down with proprietary products starting in property. Instead of a loss control inspection they create a deep digital twin of the facility to 2 mm of precision using video, sensors and lidar. Once the policy is written they leave behind the robot to continuously scan the facility in case something changes, think of it like an industrial roomba, and his name is FELIX. An incredible conversation you wouldn't miss! #Insurance #insurtech David Stafford: https://www.linkedin.com/in/david-stafford-b842048/Substance: https://substance-corp.com/Video Version: https://youtu.be/ICfUpKMSHQs
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Feb 10, 2026 • 17min

Nicolas Christiaen, Co-Founder & CEO at Donna - PIR Ep. 785

Tony chats with Nicolas Christiaen, Co-Founder andCEO at Donna, this is an update episode. Nicolas first appeared in PIR Ep. 693. Donna is an amazing AI assistant for sales teams and she just keeps getting better. Whether you're in sales or run a sales team you shouldn't miss this episode!Nicolas Christiaen: https://www.linkedin.com/in/nicolaschristiaen/Donna: https://www.askdonna.com

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