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. A Founder’s Journey – Jack’s transition from engineering to insurtech leadership, driven by d...
Mar 05, 2025•3 min
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 ...
Mar 04, 2025•38 min
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....
Mar 03, 2025•39 min
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 f...
Feb 26, 2025•51 min
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...
Feb 20, 2025•19 min
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...
Feb 17, 2025•33 min
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...
Feb 07, 2025•19 sec
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 c...
Feb 03, 2025•41 min
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. Celebrating Success : Over 63,000 downloads since 2020 and 100 episodes of industry-leading insights—thank you to all our listeners and contributors. Key Conversations : Revisit top discussions, including Carolyn Rosenberg and Anthony Crawford’s take on evolving AI regulation...
Jan 28, 2025•4 min
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: – How Cowbell...
Jan 23, 2025•25 sec
Join Carrier Management Deputy Editor and host of The Insuring Cyber Podcast, Elizabeth Blosfield, Wells Media Content Editor Allen Laman, and Insurance Journal’s Midwest and South Central Editor Ezra Amacher for a special episode of The Insuring Cyber Podcast that explores the most viewed episodes of 2024 to start the year. Check it out! To sign up or apply to be a speaker for our InsurTech Summit 2025, visit theinsurtechsummit.com ! The post EP. 99: 2024’s Top Cyber Insurance Insights Wrapped ...
Jan 22, 2025•30 min
Who remembers when you’d never think to “bring your whole self to work?” Boomers do! But today’s workplace is vastly different. Bosses need to watch for signs of employees’ mental health issues. On this recording, we hear from Travelers’ Joan Woodward, who highlights key findings of a new study on the pervasiveness of mental health in the workplace. Joan oversees the Travelers Institute, a public policy platform within the carrier to educate the public about all things insurance. Joan provides a...
Jan 20, 2025•30 min
Insuring cannabis is far from a straightforward endeavor, so one would expect cannabis insurance claims to be a complex subject. One would be correct. Corey Tobin, a director with Symphony Grow, has seen some interesting—and big—claims. Tobin is also formerly a licensed cannabis operator. We spoke to Tobin about cannabis insurance claims for our latest podcast. The post 99: Cannabis Insurance Claims – Insight from a Producer and Former Operator appeared first on Insurance Journal TV ....
Jan 16, 2025•11 min
Replay Insurance Journal’s Emergency Podcast discussion, hosted on X, covering the Los Angeles Wildfires and it’s impact on insurance. Join Patrick Wraight, Director of the Academy of Insurance, Ezra Amacher, the Midwest/South Central Editor of Insurance Journal, and George Jack, Customer Success Manager of the Academy of Insurance as they talk about recent events and how the industry is responding. Read some of the articles discussed in the event: Insured Losses From Los Angeles Wildfires Risin...
Jan 14, 2025•35 min
Insurtechs and online MGAs increasingly will be folded into tech-enabled carriers and marketplaces. That’s the prediction of Bryan Davis, who leads VIU, HUB’s online insurance platform for consumers and business partners. Most insurtechs aren’t profitable, he says. On this recording, Bryan outlines the underlying reasons why the pressure is on insurtechs, such as more expensive investment capital and incomplete end-to-end technology. He also challenges agents and brokers to focus on sales and le...
Jan 06, 2025•38 min
Explore the hilariously absurd world of Santa-related insurance claims, from magical animal damages to holiday endorsements we wish existed, in this Golfertainment episode! Join George Jack , Patrick Wraight, and Kevin Amrherin for a holly jolly discussion on holiday-related insurance quirks and risks! Holiday topics include: -Cybersecurity & Holiday Foods: Krispy Kreme’s online hack highlights a rising trend. Will cybersecurity premiums spike for companies? And should you think twice about ...
Dec 18, 2024•39 min
As we wrap up another eventful and informative year of “On Point” episodes, your host Peter van Aartrijk details the front-seat view he had of Hurricane Helene as it came ashore in St. Petersburg, Fla. Disasters are macabre events to watch from afar. But up close? In a word, surreal. Peter, his family and neighbors experienced what many Americans have witnessed amid fires, earthquakes, floods and convective storms. Put simply: The impact is devasting financially and emotionally. Moreover, Helene...
Dec 09, 2024•32 min
Cannabis beverages are a $1 billion and growing market, with some estimates calling for a $100 billion or larger market in the next decade. They are popular, but these infused drinks pose interesting opportunities and risks for insurers. For our latest podcast we spoke with Lee Woodruff, vice president of the cannabis practice for Jencap, and Beth Medvedev, vice president of underwriting for Hudson Insurance Group. The post 98: Cannabis Beverages Are Popular but Pose Interesting Risks for Insure...
Dec 05, 2024•19 min
On this episode of The Insuring Cyber Podcast, Coterie Insurance Founder and CEO David McFarland discussed Coterie’s October announcement that the InsurTech is now offering cyber insurance on its platform through a new partnership with Berkley Re Solutions and TransUnion. He discussed how this fits into the company’s growth strategy for next year, and the company’s focus on the small business space – particularly micro small businesses, which he described as mom and pop shops with sometimes just...
Nov 27, 2024•12 min
Listen in as insurance carrier veteran Jamie Luce, who recently founded a startup, says parametric products are an “untapped” pathway to unleash more value for customers, agents, insurers and reinsurers. His firm, AIR Parametric, provides commercial customers with financial protection to mitigate the short-and long-term revenue shortfalls and expense overruns of unanticipated, extreme weather events. (Think heat spells, cold snaps, excess rainfall.) These weather events typically don’t cause phy...
Nov 25, 2024•40 min
