Cowbell’s Founder and CEO, Jack Kudale, shares his inspiring journey from growing up on a small farm to leading a cybersecurity insurance revolution, transforming risk management for small businesses.

This excerpt highlights the following:

Bridging Cybersecurity & Insurance – How Cowbell is pioneering innovation on the “right of the boom” by combining cybersecurity with tailored insurance solutions.

To watch the full 100th Episode of the Insuring Cyber Podcast, click here!

To register for this year’s InsurTech Summit visit: https://theinsurtechsummit.com/

#CyberInsurance #InsurTech #SmallBusinessSecurity

The post From Farm to Cybersecurity: How Cowbell is Innovating Cyber Insurance appeared first on Insurance Journal TV.

Join Golfertainment George, Patrick Wraight, and Kevin Amrhein as they tee off on Florida Man insurance fraud, bizarre cold-weather lizard claims, and the potential return of 1920s golf fashion! Plus a look at some Oscar show fashion!

Florida Man Strikes Again – A wild tale of insurance fraud, fake death certificates, and a $6M scheme gone wrong.

Falling Iguanas & Insurance Claims – When Florida temps drop, so do frozen lizards—what’s the risk, and who pays?

Should Knickers & Tweed Make a Comeback? – The case for reviving classic 1920s golf fashion on the modern course.

Not yet a member of the academy? Join Today!

#FloridaMan #InsuranceFraud #FallingIguanas

The post EP. 10: Insurance, Frozen Lizards, and Golf Fashion! appeared first on Insurance Journal TV.

Here’s a chance to meet a driven, dynamic leader in Omari Aarons-Martin, who oversees the National African American Insurance Association. Omari outlines the history of NAAIA, founded by an independent agent 28 years ago. With 2,700 members and 24 chapters nationwide, NAAIA represents every industry sector and is dedicated to members’ professional development and empowerment. Your On Point host naturally asks the honest (if cringeworthy) questions you’ve come to expect on race and racial issues. And Omari deftly educates! Diversity means different things to different people, he says. Thus, he encourages insurance organizations to be specific about any talent gaps. “Give yourself permission to say, for example, ‘We want blacks and African Americans.’ We have been unwilling as a society to do that. It makes us uncomfortable. It pits people of color groups against each other.” He advises, “Start with the group you have the largest gap in,” and never stop paying attention so that your organization is future-ready to serve the customer.

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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.

When we started our “bimonthly trip into the intersection of two industries that couldn’t be more different,” we were in the grips of a pandemic and cannabis legalization was sweeping states across the country. Episode 1 aired in May 2020 with a few industry experts talking about how the industry would weather the pandemic and an eventual return to normalcy. Four years later and the industry is still kicking—though federal legalization is probably about as far away now as it was then. One of our first podcast guests was Morgan Fox, who is now the political director NORML. To mark 100 episodes, we asked him on again to talk about what the cannabis industry will look like in the year ahead with the new administration, and what may lie beyond.

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Property losses and coverage woes are all over the national news: fires, hurricanes, tornadoes, floods. As a result, new home buyers are fearful of the risks and costs of owning property. On this recording, we hear key findings from consumer research on home ownership from Kimberly Burdi-Dumas with DocuSketch. The insurance industry has an opportunity to educate Generation Z on home protections, the research  suggests.  DocuSketch provides accurate, consistent views of property losses to eliminate claim disputes. Kimberly says was “born and bred in insurance. My parents started a restoration company back in the 1980s before restoration was even a thing. We were called ‘carpet cleaners.’ I remember mixing chemicals. Two scoops of green and one scoop of blue. Sketch on graph paper. Wear boots and walk losses. Haul hoses and lug equipment.”

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The Insuring Cannabis Podcast launched at a time of uncertainty — pandemic lockdowns, shifting regulations, and a rapidly growing cannabis industry. Now, 100 episodes later, we’re still here, still talking, and still looking ahead!

For this milestone episode on Feb. 20th, we’re bringing back one of our early episode guests: Morgan Fox, Political Director at NORML, to discuss what the future holds for cannabis policy in 2025 and beyond.

Tune in Thursday, February 20th as we reflect on where we’ve been—and where we’re headed.

#Podcast100 #StillLookingAhead

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On this installment, we check in with Luke Bills, president of independent agent distribution for Liberty Mutual’s U.S. retail markets. Luke outlines challenges for agents, including consolidation and pricing. Agents have had to deal with suffocating rate increases in recent years—“there was nowhere to hide from that,” Luke says. While auto rates are stabilizing, property is another story: “I don’t see a soft market coming,” he adds. Looking down the road, he says he is “very bullish on the IA channel. This [hard] market has shown the value of the independent agent.” With homeowners having to manage more risk and costly assets, and as insurance coverages “gets more expensive and availability gets more challenging, consumers need to have choice and expert guidance. That’s what independent agents do.” Captive agent models, too, “are moving toward finding choice,” he adds.

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Join Elizabeth Blosfield, Allen Laman, and Ezra Amacher as they recap the top 10 episodes of the Insuring Cyber podcast, highlight industry-shaping conversations, and share exciting news about their 100th episode milestone.

Don’s miss the Insuring Cyber Podcast’s 100th episode on February 26th!

#InsuranceInnovation #AIRegulation #CyberRisk

The post Top Podcast Moments: Insights, AI Regulation, and What’s Next for Insurance Innovation appeared first on Insurance Journal TV.

Mark your calendars! On February 26th, the Insuring Cyber Podcast hits a major milestone with its 100th episode, and we’re celebrating in style!

Join us for an exclusive interview with the visionary cofounders of InsurTech Cowbell: CEO Jack Kudale, COO Trent Cooksley, and CPO Rajeev Gupta. They’ll take you behind the scenes of Cowbell’s remarkable journey—from its startup roots to becoming a trailblazer in cyber insurance for small and medium-sized businesses.

Hear firsthand about:

As Cowbell celebrates its fifth anniversary, this episode is packed with insights, inspiration, and actionable takeaways you won’t want to miss on February 26th!

PLUS: To thank our incredible viewers, we’re celebrating the 100th episode with a giveaway! Three lucky winners will get the chance to snag an Academy of Insurance prize-bundle worth over $500! Watch episode 100 to find out how to win!

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