The Future of Insurance Podcast – Simon Wilson CEO, Markel Insurance Season 9, Episode 1, August 11, 2026 Episode Details Season 9 of The Future of Insurance opens with a conversation about what happens when a $10 billion specialty insurer decides its own scale isn’t a reason to move slowly. Bryan Falchuk talks with Simon […]
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The Future of Insurance Podcast – Kyle Nakatsuji Founder & CEO of Dearborn Labs and Clearcover Season 8, Episode 18, April 7, 2026 Episode Details Kyle Nakatsuji is the Founder and CEO of Dearborn Labs and Clearcover. He joined the show during Season 1 to talk about Clearcover (which is the subject of one of
The Future of Insurance Podcast – Wayne Slavin Co-Founder & CEO, SURE Season 8, Episode 15, February 17, 2026 Episode Details Wayne Slavin is the CEO and Co-Founder of Sure, a VC backed insurtech startup. Prior to Sure he was the VP of Product Management at Tapingo, TechCrunch’s Most Innovative Company of 2013. His other
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The Future of Insurance Podcast – Peter Settel CEO, Bold Penguin Season 8, Episode 2, October 28, 2025 Episode Details Peter Settel, CEO of Bold Penguin, is a business and technology leader with a proven track record of leading technology-led growth companies across the insurance sector. Prior to Bold Penguin, Settel was the Enterprise Chief Strategy
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The Future of Insurance Podcast – Alex Timm Co-Founder & CEO, Root Insurance Season 8, Episode 1, October 21, 2025 Episode Details With a vision of completely transforming the car insurance industry, Alex founded Root in 2015 on the principle that rates should be based primarily on driving behaviors, not demographics. As Founder and Chief
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The Future of Insurance Podcast – Rick McCathron CEO, Hippo Insurance – LIVE from ITI NYC 2025 Season 7, Episode 17, June 24, 2025 Episode Details Over the last decade, the insurtech landscape has rapidly evolved, transitioning from a space dominated by startups innovating at the fringes to becoming a thriving industry amassing huge investment and
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The Future of Insurance Podcast – Andrew Horton Group CEO, QBE Insurance Group Season 7, Episode 1, March 4, 2025 Episode Details Andrew joined QBE as Group Chief Executive Officer in September 2021. With a strong focus on bringing the enterprise together, Andrew has driven performance consistency and progress towards QBE’s vision to become the
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The Future of Insurance Podcast – Mark Holweger President & CEO, Legal & General America – Recorded Live at ITC Vegas 2024 Season 6, Episode 20, December 3, 2024 Episode Details Mark Holweger is President and CEO of Legal & General America’s insurance division, which includes operating companies Banner Life Insurance Company and William Penn Life
The Future of Insurance Podcast – Wesley Pergament Co-Founder & CEO, Sola – Recorded Live at ITC Vegas 2024 Season 6, Episode 18, November 12, 2024 Episode Details Wesley is CEO and Co-Founder of Sola Insurance based in Atlanta, GA. Wesley comes from a tech background and jumped into the insurance industry at a flood insurance
The Future of Insurance Podcast – Rick McCathron President & CEO, Hippo Insurance Season 6, Episode 5, July 2, 2024 Guest Bio Richard McCathron is CEO and President of Hippo Insurance and has served as a member of the Board of Directors since February 2017. Prior to Hippo, Rick held senior executive positions at various
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