InsurTech Geek Podcast

JBKnowledge

A bi-weekly interview series highlighting the technology that is shaping the future of insurance and exploring how industry leaders are leveraging technology to grow their businesses.

  1. Reimagining Risk in the Age of AI | Amir Kabir | InsurTech Geek Ep. 176

    4 HR AGO

    Reimagining Risk in the Age of AI | Amir Kabir | InsurTech Geek Ep. 176

    Amir Kabir, Founding & Managing Partner at Overlook Ventures, joins hosts James Benham and Rob Galbraith to reimagine risk in the age of AI — what the last decade of insurtech got wrong, where the next wave of opportunity actually lives, and why "liability is getting weird" is an understatement. Amir spent the first chapter of his career in Germany, building enterprise software at a Karlsruhe startup that was eventually acquired by a Silicon Valley company. In 2013 he immigrated to the US for an MBA at Georgetown, became the third person on the founding team at Munich Re Ventures, and helped grow that fund from $50M to over $1B. He later served as General Partner at AV8 Ventures leading the financial services practice before launching Overlook Ventures to invest full-time at the intersection of risk and frontier technology. In this episode: • Why the early insurtech era mistook insurance for a scalable SaaS business • "Insurance is a get-rich-slowly business" — and what that means for exit math • The Overlook thesis: investing in the infrastructure of risk across every tech cycle • Where AI is real in insurance today (claims, underwriting data extraction) — and where regulation still slows it down • The emerging risk categories that don't fit today's policy structures: autonomous systems, longevity, and reputational narrative risk Key Quotes: "Insurance is a get-rich-slowly business." "Technology moves in cycles. Risk always evolves through them." "Liability is getting weird." "Try to find a problem before you find a solution." "A brand can be destroyed in 48 hours by a viral moment." 🔗 Connect: Amir Kabir: https://www.linkedin.com/in/amirkabir/ Overlook Ventures: https://www.overlook.vc | https://www.linkedin.com/company/overlookvc/ 👤 Hosts: James Benham: https://www.linkedin.com/in/jbenham Rob Galbraith: https://www.linkedin.com/in/rob-galbraith/ 🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software. Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/ 📌 Find InsurTech Geek: LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/ Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

    35 min
  2. Technology Leadership, AI Adoption and the Future of Mutual Insurance

    10 APR

    Technology Leadership, AI Adoption and the Future of Mutual Insurance

    Vineet Bansal, Chief Information and Technology Officer at The Mutual Group, joins hosts James Benham and Rob Galbraith to explore how technology leadership, disciplined AI adoption, and a shared operating model are shaping the future of mutual insurance — from inside a two-year-old, Bain Capital-backed startup built to help community-based carriers compete and grow.Vineet brings over 20 years of financial services and insurance technology experience to the role — from engineering roots in Nagpur, India, to nearly two decades at Fidelity Investments across ten different business lines, to building a greenfield digital platform as CTO at IptiQ by Swiss Re. Now at The Mutual Group, he's architecting a shared technology and operations platform designed to scale across multiple member companies — starting with GuideOne Insurance in Des Moines, Iowa.In this episode:Why insurance is a deliberately risk-managed industry — and what that means for responsible AI adoptionHow The Mutual Group is building a multi-tenant platform to help smaller mutual carriers access enterprise-level capabilitiesWhy clean data, API-driven ecosystems, and strong governance are the real foundation for AI success — not the tools themselvesWhat it means to hold the combined CIO and CTO role — and how Vineet divides his focus across operations, applications, strategy, and multi-member platformThe shift toward hyper-personalized insurance: policies sold by the hour, by the day, or only when the risk event is happeningKey Quotes:"The winners will be the ones with the strongest foundation.""Insurance sits at the intersection of risk, regulation, economics, and human behavior.""AI won't solve your data issues. It's garbage in, garbage out.""There's no easy answer. It takes meticulous planning and thoughtful execution.""We may have insurance products sold by the hour, by the day."🔗 Connect:Vineet Bansal: https://www.linkedin.com/in/vineet-bansal/The Mutual Group: https://www.themutualgroup.com/ | https://www.linkedin.com/company/the-mutual-group/👤 Hosts:James Benham: https://www.linkedin.com/in/jbenhamRob Galbraith: https://www.linkedin.com/in/rob-galbraith/🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

    36 min
  3. Leading Transformation Through Systems, Strategy, and People

    12 MAR

    Leading Transformation Through Systems, Strategy, and People

    Holly O'Dell, President & CEO of Montana State Fund, joins host James Benham to discuss how systems thinking, people-first leadership, and strategic clarity are transforming workers' compensation — from inside a mission-driven organization that competes and wins in a fully open market. Holly brings a rare combination of credentials to the role: a BSN from Oregon Health & Science University, a JD from Lewis & Clark College, and an MBA from the Wharton School. Before joining Montana State Fund in 2022, she spent nearly 17 years at SAIF Corporation in Oregon, rising from trial attorney to VP of Strategy, Government Relations, Legal, and Procurement. Montana State Fund covers more than 60% of Montana's workers' comp market — in a fully competitive environment where they earn every dollar.In this episode:- Why risk tolerance is the real foundation of innovation — and how to build it before anything else- How Montana State Fund reduced 27,000 annual policy cancellations by two-thirds — without a single new technology- The people-first shift that brought claims turnover from 40% down to 4.5%- Building a culture where frontline employees have genuine FOMO about AI and innovation projects- What it means to be strategic in an industry full of shiny objects- The world's first workers' comp regulatory sandbox — and what it could unlock Key Quotes: "I'm not into norming. I'm into storming." "Risk is an opportunity for gain or for a loss." "Nonprofit is not a business model." "Strategy is an integrated set of choices." "This is an industry worth hanging out in." Timestamps:07:53 — The 20-sided dice: why insurance attracts multi-disciplinary thinkers 15:12 — "I'm not into norming. I'm into storming." — Holly's leadership philosophy 19:30 — Cancel cancellations: solving a 27,000-policy problem without technology 23:57 — From 40% turnover to 4.5% — the people transformation at Montana State Fund 27:04 — The FOMO effect: building a culture where everyone wants in on AI35:51 — Firefighter training injuries reduced from 50% to zero — the predict-and-prevent model in action 🔗 Connect:Holly O'Dell: https://www.linkedin.com/in/holly-o-dell-26228452 Montana State Fund: https://www.montanastatefund.com/ | https://www.linkedin.com/company/montana-state-fund/👤 Host:James Benham: https://www.linkedin.com/in/jbenham 🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/ 📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

    39 min
  4. Adapting Commercial Auto Insurance to Platform-Based Work

    27 FEB

    Adapting Commercial Auto Insurance to Platform-Based Work

    Dan Bratshpis, CEO and Co-founder of INSHUR, joins host Rob Galbraith to discuss how commercial auto insurance is being reimagined for the platform economy — and why traditional products are failing the drivers powering the gig economy. Dan built INSHUR from a two-person MGA startup into a 200-person global company operating across the US and UK, with embedded insurance partnerships with platforms like Uber, Amazon, and DoorDash. His approach: build coverage that works with how people actually live and work, not how insurers traditionally categorize risk. In this episode: Why traditional commercial auto products fall short for gig and platform workersHow INSHUR embeds insurance directly into platform onboarding — and what that data advantage means for underwritingThe usage-based wallet model: pay-per-ride, pay-per-delivery, pay-per-minuteHow COVID wiped out rideshare demand overnight — and became the pivot that launched INSHUR's delivery insuranceWhy INSHUR built Komodo Claims from scratch instead of outsourcing to TPAsWhat autonomous vehicles mean for frequency, severity, and the future of commercial auto insuranceKey Quotes: "What doesn't kill you makes you stronger.""Technology is an enabler to do things differently, do things better.""Claims is kind of at the heart of insurance.""These things don't get into accidents nearly as much as humans do." — on autonomous vehicles"Insurance is a really big part of protecting this new economy."Timestamps: 09:05 — The wedding night pitch that launched Columbia Pacific Finance (placeholder — update with actual)10:55 — From Wall Street to rideshare insurance (placeholder — update with actual)19:13 — The COVID cliff: how INSHUR pivoted to delivery insurance overnight23:49 — Building Komodo Claims: why INSHUR owns its claims infrastructure26:22 — Autonomous vehicles and the frequency drop coming for commercial auto🔗 Connect: Dan Bratshpis: https://www.linkedin.com/in/dan-bratshpis/ INSHUR: https://inshur.com/ | https://www.linkedin.com/company/inshur/ 👥 Host: Rob Galbraith: https://www.linkedin.com/in/robgalbraith1/ 🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp. Visit 👉 https://terra.insure 📲 Find InsurTech Geek: LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/ Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

    35 min

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A bi-weekly interview series highlighting the technology that is shaping the future of insurance and exploring how industry leaders are leveraging technology to grow their businesses.

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