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Building Tomorrow's Insurer

Building Tomorrow's Insurer

By: Nigel Fellowes-Freeman
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Hosted by Kanopi’s Founder and CEO Nigel Fellowes-Freeman, 'Building Tomorrow's Insurer' slices through the complex insurtech landscape. Simple, clear, and forward-thinking – this podcast is your guide to understanding how technology is rewriting the rules of insurance. Each episode brings together industry leaders, innovators, and disruptors for in-depth conversations on how emerging technologies are reshaping the landscape of insurance. Follow us on LinkedIn: https://www.linkedin.com/company/kanopicover/ Follow our YouTube channel: https://www.youtube.com/channel/UC7bBpTJEoJ-oaVm5xaMCigg2026 Nigel Fellowes-Freeman Politics & Government
Episodes
  • Ep. 49 | How Agentic AI Will Rebuild Insurance Operations with Kyle Nakatsuji, Founder of ClearCover
    Jun 10 2026

    Most insurers are asking how to add AI to existing workflows.

    Kyle Nakatsuji thinks that's the wrong question.

    In this episode of Building Tomorrow's Insurer, Nigel Fellowes-Freeman sits down with the founder of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated.

    After spending a decade building one of the world's best-known tech-native insurers, Kyle believes Agentic AI is forcing the industry to rethink everything from claims and underwriting to operating models and core systems.

    Together they discuss:

    • Why even modern insurers may need rebuilding for the AI era
    • The difference between automation and agentic systems
    • Why many AI initiatives stall between pilot and production
    • The future of headless insurance platforms
    • How AI changes the economics of underwriting and claims operations
    • Whether insurers should build proprietary AI workflows or rely on vendors
    • Why context, judgement and human relationships still matter
    • The future of embedded insurance in an AI-native world

    If you're a CEO, CIO, COO, Chief Claims Officer or transformation leader trying to understand what insurance operations could look like over the next five years, this conversation provides a practical look at what's changing now.

    Topics:
    Agentic AI in insurance, insurance digital transformation, AI claims automation, insurance operations, insurtech innovation, embedded insurance, AI underwriting, future of insurance technology, Clearcover, Dearborn Labs.

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    46 mins
  • Ep 27 | Building Tomorrow’s Insurer | Why the Insurance Industry is Missing the Point on Media, Tech, and Customer Connection with Ian White
    Mar 3 2025

    Is the insurance industry stuck in its old ways? In an era where digital media drives brand loyalty and tech reshapes customer expectations, insurance companies might be missing out on huge opportunities. Featured in Feedspot's Top 10 Insurance Podcasts, Kanopi’s Building Tomorrow’s Insurer brings you insights from leaders who are redefining insurance.


    In this episode, host and Kanopi CEO Nigel Fellowes-Freeman speaks with Ian White, the force behind Turbo Ventures and MGA Labs. Ian’s decades of experience in insurance and media give him a unique perspective on why insurers need to radically rethink how they connect with customers.


    Tune in as Ian challenges traditional approaches and shares eye-opening insights on:

    • Why the insurance industry needs media as much as it needs tech
    • How legacy mindsets could be losing insurers a digital-savvy customer base
    • The untapped potential of AI and content to rebuild trust in insurance
    • The insurtech trends no one’s talking about—but should be

    For insurance leaders ready to break out of the status quo, this episode offers fresh takes that just might redefine your approach. Don’t miss this discussion with Ian White as he calls out what’s missing—and what’s possible—in the future of insurance.

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    47 mins
  • Ep 24 | Building Tomorrow’s Insurer | Redefining Insurance with Authenticity, AI, and Storytelling with Jeff Shi
    Jan 14 2025

    What does it take to revolutionize the insurance industry while staying grounded in authenticity and purpose? In this episode of Building Tomorrow’s Insurer, host and Kanopi CEO Nigel Fellowes-Freeman sits down with Jeff Shi, founder of Insurtechs.io and a top 50 InsurTech influencer.

    Jeff shares his inspiring journey from building a car performance shop in his early days to founding J&J Insurance, where he grew a scratch agency to $27 million in premiums. He brings a wealth of insights on innovation, customer-centric strategies, and the critical role of storytelling in creating trust and brand value in the insurance sector.

    Tune in to explore:

    • The power of grit and entrepreneurial spirit in building a successful insurance agency
    • How storytelling and authenticity are shaping the future of insurance
    • The role of AI and technology in redefining customer experience and distribution channels
    • Lessons from industry challenges, including managing risks in a rapidly changing environment

    This episode is packed with actionable insights and forward-thinking perspectives for anyone navigating the evolving insurance landscape.

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    45 mins
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