In this episode of CHATTINN CYBER, Marc Schein interviews Trent Cooksley, the co-founder and CEO of Cowbell Cyber about his journey into cybersecurity and how he founded one of the most successful cyber insurance companies to date.
Starting his career as a bond trader on the Chicago Board of Trade, Trent quickly realized that he wasn’t cut out for that type of work and decided to learn the ropes of becoming an entrepreneur. After serving Markel Corporation in a variety of different roles for a decade and gaining experience in international insurance business, property lines, professional lines, and acquisitions, Trent decided to build his own company, something he had been putting off for some time. He watched what was happening in the insurtech space and found an opportunity in cyberspace, and ventured in.
Trent developed proprietary technology that allowed his newly formed company to evaluate the cybersecurity health and hygiene of every business in the United States, which gave it an opportunity to really understand risks when they come in at a much more granular and better level.
Aside from his journey, Trent also talks about the biggest challenge facing the cyber insurance industry: the rapid and continuous evolution of cyber risks, which requires companies to be proactive and reactive at a rapid pace. He shares that this uncertainty also presents opportunities for those who put themselves in a position to take advantage of them. Cowbell, his company, is working towards finding a long-term solution for their policyholders by continuing to be experts in the space and how they’re modeling the risk and understanding the risk.
Listen to this episode to learn more.
“One of the little things that we do that I think accentuates our culture, we have a really transparent organization. So we like to be transparent. We encourage resiliency, urgency and empowerment.”
“We’re continually evaluating the cybersecurity health and hygiene of every business in the United States, the entire market. And that gives us an opportunity to really understand risks when they come in, at a much more granular and better level.”
[01:43] Trent’s business milestones
[03:42] Challenges with the rapid growth of Trent’s company.
[06:25] Deep market penetration in the cyber insurance marketplace.
[08:14] Taking a cross-disciplinary approach.
[10:18] Understanding risks at a more granular and better level.
[12:39] How it looks like being the CEO of Cowbell Cyber for a day and the process behind it.
Connect with Trent: