Jack Kudale is Founder and CEO at Cowbell Cyber with over two decades of business executive experience. Previous senior roles include COO at Cavirin, CEO at Lacework, both cloud security startups; SnapLogic, a leader in hybrid cloud integration; and CA Technologies, where Jack led DevOps sales for the Fortune 500 leader. With deep operational experience in the DevOps, Cybersecurity, IT Ops, & Big Data spaces, Jack leads Cowbell to execute on its vision of bridging the cyber insurability gap. Jack also serves as a governing board member of Brighter Children, a non-profit organization. In this episode, we discuss the importance of cyber insurance, risk management, the difference between cyber insurance vs other insurance products, the risks COVID-19 pose to small businesses, right-sizing cyber insurance policies, industries that are targets for attackers, and so much more. Where you can find Jack:LinkedInTwitterCowbell Cyber Blog


#092 – Jack Kudale: You Gotta Have More Cowbell

There is “no one way” to start and stay in the field of cyber security. Whether you are involved from the military, law enforcement, consulting, or IT services, it doesn’t matter. I have had countless discussions for years with other professionals online, at conferences, or over drinks, which have changed the way I think about cyber security. That is where this podcast comes in. What if I can capture those moments and frank discussions? I want to share the stories from other cyber security leaders and influencers so everyone can learn from their respective journeys and challenges. Why did they take the path they did? Who were their mentors? How did they tackle some of their biggest career challenges? By hearing how the industry leaders and influencers got to where they are and how they overcame some of the problems they faced, I hope to shed light on the path for other professionals. I will discover what motivates them, explore their journey in cyber security, and discuss where they think the industry is going.

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This is the 5th part of the podcast's return after a brief hiatus. 

Daniel Ayala continues his interview of me. In this fifth part, we will discuss the start-up resources we provided in our Hang Out A Shingle presentation, what I am doing with Accel Consulting, selling to CISOs, tips to avoid when presenting cyber services, the selling to CISOs Master Class we are developing, and so much more!

#127 – Douglas Brush (Part 5): Analysis Paralysis

This is the 4th part of the podcast's return after a brief hiatus.  Daniel Ayala continues his interview of me. In this fourth part, we will discuss my first forensic litigation case, the importance of data governance, the myth of cyber, why I am tired of cybersecurity conferences, and so much more!

#126 – Douglas Brush (Part 4): Dollars and Cents, Not Bytes

This is the 3rd part of the podcast's return after a brief hiatus.  Daniel Ayala continues his interview of me. In this third part, we will discuss what I am doing as a Special Master and Court Appointed Neutral, the reasons I think there will be a continued convergence of legal, cybersecurity, and data privacy, why I decided to start another consulting firm, data valuation, and so much more!

#125 – Douglas Brush (Part 3): What is a Special Master?

This is the 2nd part of the return of the podcast after a brief hiatus. Daniel Ayala continues his interview of me. In this second part, we will discuss how I got started in the industry, defining moments of my career, my first computer, early entrepreneurship, characteristics I look for in professionals, the toxic cybersecurity gatekeeping, and so much more!

#124 – Douglas Brush (Part 2): Words of Advice

After a hiatus, the Cyber Security Interviews podcast is back! A lot has happened in my life over the past 18 months. I have endured death, despair, divorce, and car theft, to name a few traumatic events that made me take a break from several endeavors. However, it has allowed me to reprioritize many things to understand where I am now and where I want to go. This is the first of several episodes where Daniel Ayala interviews me. In this first part, we will cover mental resiliency, the importance of taking time off, how to be your best, and so much more!

#092 – Jack Kudale: You Gotta Have More Cowbell

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