In this special 100th episode of the Insuring Cyber podcast, tune into an exclusive interview with the three cofounders of InsurTech Cowbell— CEO Jack Kudale, Chief Operating Officer Trent Cooksley , and Chief Product Officer Rajeev Gupta. Together, they share Cowbell’s startup origins and its mission to revolutionize cyber insurance for small and medium-sized enterprises, as well as the personal journeys that inspired them to tackle the complexities of the cyber insurance field. From Kudale’s farm roots and vision for cross-industry innovation to Cooksley’s expertise in insurance technology and Gupta’s technical focus on risk quantification, the trio shares insights on how Cowbell leverages advanced data and AI to redefine cyber underwriting. Alongside celebrating Cowbell’s five-year anniversary, this episode explores how their shared vision is empowering SMEs to address cyber risks and how other startup leaders can thrive in the cyber risk space. To sign up or apply to be a speaker for our InsurTech Summit 2025, visit theinsurtechsummit.com! The post EP. 100: More Cowbell, More Resilience: How the Five-Year-Old Cyber InsurTech is Empowering Small Businesses appeared first on Insurance Journal TV.