Chattinn Cyber Marc Schein

Summary



In this episode Marc Schein is chattin’ with Kevin Sherry, the founder of DarkWeb IQ, a pioneering offensive cybercrime prevention firm. Kevin shares his unconventional journey from a hedge fund trader and entrepreneur to a leader in the cyber insurance industry, eventually leading to the inception of DarkWeb IQ. Kevin's entrepreneurial spirit and proactive approach to spotting opportunities in the evolving insurance landscape laid the foundation for his innovative venture.

Kevin details the origins of DarkWeb IQ, emphasizing his belief in the necessity for a new approach to cybersecurity. In 2020, amid the chaos of the pandemic, the cyber insurance market faced unprecedented challenges due to a surge in ransomware attacks. As market panic ensued, Kevin, leading a team at Everest, realized the need for a radical solution to protect against mounting losses. His sleepless nights and relentless pursuit of answers culminated in the idea of infiltrating and disrupting the cybercriminal supply chain, a concept that formed the core of DarkWeb IQ’s mission.



DarkWeb IQ’s approach diverges from traditional defensive security measures. Instead of merely implementing preventive controls, the firm actively engages with the criminal underground to disrupt cybercrime operations. Kevin recounts how the cybercriminal ecosystem, similar to a supply chain, can be infiltrated and dismantled by targeting its vulnerable links. Despite initial assumptions that such methods were already in use, Kevin was surprised to find significant gaps in the existing threat intelligence efforts, paving the way for DarkWeb IQ’s unique offensive strategy.



Kevin's firm has intercepted over 800 attacks in two years, employing various methods from direct interventions to collaborations with vendors and government agencies. These interventions range from alerting companies about immediate threats to helping software vendors secure their tools against misuse. Kevin explains how his team's efforts not only protect individual clients but also contribute to broader societal benefits, such as safeguarding critical infrastructure like hospitals and water treatment facilities.



Reflecting on lessons learned, Kevin highlights the importance of focusing on the basics of cybersecurity. Many attacks exploit simple vulnerabilities, often overlooked despite significant investments in security tools. He advocates for a pragmatic approach where companies prioritize understanding and addressing the most common attack vectors rather than being overwhelmed by compliance checklists. Kevin also stresses the value of proactive vulnerability scanning for insurers, while cautioning against the pitfalls of alert fatigue caused by overemphasis on less critical vulnerabilities.



As the conversation concludes, Kevin expresses his pride in the public-private partnership model that DarkWeb IQ embodies, working closely with law enforcement and the insurance industry to create impactful solutions. He reflects on his journey and the collaborative spirit of their mission, looking forward to continued innovation and progress in the fight against cybercrime.



Key Takeaways



Kevin Sherry started DarkWeb IQ due to his frustration with the rise in ransomware attacks and wanted to find an innovative way to combat cybercrime.

DarkWeb IQ works to infiltrate the cybercriminal ecosystem and supply chain to gain visibility into potential attacks. They intercept attacks and work with law enforcement to build cases against criminals.

DarkWeb IQ has directly intercepted over 800 attacks in their 2 years of existence by infiltrating criminal operations.

Most cyber attacks utilize basic methods, even though security has become very complicated. Focusing on how real-world attacks occur can improve security programs.

Proactive vulnerability scanning by insurers provides value,

Summary



In this episode of Chattinn Cyber, Marc Schein sits down to chat with Paul Dowding, co-founder and head of design at L4S Corporation, focusing on blockchain technology and its real-world applications. Paul, an authority on digital assets, begins by demystifying blockchain for novices, describing it as a distributed ledger system that eliminates reliance on central authorities for transaction validation. He explains the intricate process of trust-building within blockchain through mathematical hashing, emphasizing its potential to revolutionize peer-to-peer transactions and reduce errors.



The dialogue delves into Paul's journey into blockchain, revealing his unique background in operational infrastructure and encryption. He recounts how his expertise in engineering and global banking operations converged, leading him to explore blockchain's capabilities and limitations. Paul's insights shed light on the challenges faced by early blockchain solutions and the development of Tapestry X, a distributed ledger designed to meet scalability, interoperability, and real-time processing needs.



Marc and Paul explore the intersection of blockchain with AI, highlighting opportunities for algorithmic inference and auditable record-keeping within blockchain networks. They envision a future where blockchain simplifies transactions to the extent of communication protocols, ushering in an era of seamless peer-to-peer interactions. Paul underscores the potential of blockchain in diverse sectors like capital markets, supply chain management, healthcare, and identity verification, showcasing the versatility and adaptability of L4S Corporation's offerings.



The conversation concludes with Paul extending an invitation for further engagement through LinkedIn and TapestryX.com, emphasizing the accessibility of blockchain technology for businesses and individuals alike. His closing remarks underscore the transformative nature of blockchain as a process engineering and operational control innovation, urging listeners to perceive it beyond mere technological novelty. The dialogue encapsulates the profound impact of blockchain on transactional efficiency, trust-building, and future digital economies, setting the stage for continued exploration and innovation in this dynamic field.



Key Takeaways



Blockchain is a distributed ledger technology that allows peer-to-peer transactions without a central authority. It uses cryptographic hashing to ensure data integrity.

Blockchain has the potential to simplify transactions, reduce errors, and enable near real-time settlement. It could be as transformative as the internet protocol.

Paul got involved with blockchain in 2014-2015 when enterprises were starting to explore it. He saw limitations in early solutions which led to developing Tapestry.

There are opportunities to use blockchain to track what data AI bots have absorbed, creating an auditable record. AI could also potentially help drive what gets recorded on a blockchain.

Tapestry is a configurable, scalable blockchain solution focused on accounting to enable real-time transactions. It is industry-agnostic and can be used for supply chain, healthcare, voting, and more.



Key Quotes



[00:03:10] "So there's a mathematical way to give your own ledger so that you can trust other people based on what you see, not what they present to you. And then there's a method of agreeing it across the ledger. And so this allows, rather than you transacting through central authorities, what bitcoin really showed the world was you could transact peer-to-peer, or b-to-b, without that central authority, which then means you can settle in hours, minutes, or not seconds."

[00:06:15] "The […] origination of what became Tapestry X was going back to the basics and saying, okay, let's take the blockchain concepts,

Tech-related business insurance is evolving fast and Anthony Dolce, our guest on this episode of Chattinn Cyber, is a thought leader at the forefront. As head of Professional Liability & Cyber Underwriting at The Hartford, he brings 25 years of industry expertise to the myriad issues shaping policy development and recommended coverages for businesses – whether tech giants or third-party users of technology. Anthony explains the differences between Cyber and Tech Errors & Omissions (E&O) policies – as well as who needs which and in what combination. He also highlights for Host March Schein, National Co-Chair of the Cyber Center for Excellence, the confluence of factors that make tech companies such attractive targets for threat actors. You’ll learn about the most common – and damaging – cyber liabilities out there; things like network attacks, ransom ware assaults, data breaches, business interruption, data restoration costs and third-party vulnerabilities. And don’t miss our guest’s comprehensive list of best practices to control risk for companies of all kinds, whatever their core business. “Nothing’s a silver bullet, but you can help mitigate potential exposure,” says Anthony, whose Connecticut-based career began in claims before migrating to underwriting. Find out what differentiates The Hartford’s Tech E&O and Cyber insurance solutions and how their team of experts guarantee insureds the best possible outcomes when privacy breaches, data hacks or other negative events occur. (Hint: specialized expertise and preparedness are key!)



Key Takeaways:



Why taking a leap and moving to the business side at The Hartford was one of those pivotal choices that changed the course of Anthony’s career – and all too the good!

From claims to underwriting: How Anthony made the jump and why it has shifted his focus.

About the collaborative, social elements that define much of the underwriter’s process and goals.

What’s a Cyber Policy? If you’re doing business of any kind on the internet, then you probably need some form of coverage.

What’s a Tech E&O Policy? If you providing a tech service of some kind, then you probably need some form of coverage.

At the intersection: A look at insurance policies that simultaneously cover exposures in the realms of both Cyber and Tech C&E exposure.

About the evolution of Tech E&O + Cyber and coverages required in an internet economy full of data transmittal, management and risk exposures.

Why large technology companies are such high-value targets for threat actors eager to double-dip by accessing downstream secondary client information.

How The Hartford differentiates itself as an established carrier with a wide array of solutions for any business eventuality:



Stand-alone Tech E&O coverage.

Tech E&O coverage + cyber coverage.

A wide variety of mix-and-match options.

Specialized tech expertise to ensure optimal insurance outcomes.





About potential cyber liabilities unique to technology firms:



Network cyber-attacks.

Ransom ware attacks.

Data breaches (and related extortion).

Business interruption.

Data restoration costs.

Professional/product exposure due to third-party contractual, regulatory or subrogation issues.





Supply chain and systemic risk: A closer look at the variety of vulnerabilities passed down to companies impacted by global industry events.

Recommended best practices to note:



Perform regular software composition analyses.

Deploy tools to track vulnerabilities.

Undertake regular code reviews, including both static and dynamic scans.

Implement regular in-house or third-party security and resiliency testing.

Develop a solid IRP (Incident Response Plan).

Our guest on this episode of Chatting Cyber is at the forefront of Insurtech innovation, deploying new approaches to cyber underwriting (with a ripple effect on traditional insurance). Peter Hedberg, VP for Cyber Underwriting at Corvus Insurance, shares with Host Marc Schein the many ways tech-enabled strategies are transforming the landscape. Says our guest: Heightened engagement among both cyber insurance brokers and policy-holders is yielding a “virtuous cycle” of better bottom-line results! Find out how brokers can help foster alignment and build trust between insurance policy purchasers (often CFOs) and their IT executives (often CIOs, CTOs). You’ll also learn how Corvus offers financial incentives to those who proactively undertake risk self-assessments to reduce liability – a major plus for all concerned. Peter also underscores why it’s so important to put in place a solid three-legged stool: Application, Exposure, Technology. When these elements are in sync, he explains, vulnerability is minimized to everyone’s benefit. Find out where cyber insurers are with developments related to third-party and systemic risk (works in progress!) and how a Minneapolis-born guy who originally got licensed as a traditional insurance broker became one of the most well-respected cyber specialists out there. “The feedback we’re getting from policy-holders is that we are creating an eco-system and environment that is improving their stance,” says Peter. “And I’m just really happy that as an Insurtech I can point to those numbers and that value.”



Key Takeaways:



 



Check your complementary skill sets. You may be positioned for a niche specialty!

How does Insurtech differ from traditional insurance? The focus is on driving down losses through technology-enabled underwriting.

The Three-Legged Stool of Underwriting: Application, Exposure and Technology.

Putting the right underwriting elements together creates a profitable “virtuous cycle.”

Insurtech adds value by generating tech-enabled approaches that drive down losses.

Corvus Differentiator: It incents policy-holders to engage with proactive risk assessment.

How can brokers help?



By proselytizing the idea of cyber policy-holder engagement.

By fostering alignment between the insured’s buyer (typically a CFO) and their IT leadership (typically a CIO or CTO).





Third-party wrongful collection of information has surged but ramifications are still actuarially unclear and still being litigated.

Assessing systemic risk requires nuance and working through unknown liabilities.

On the horizon for 2024? More frontlines information about how well policy-holder controls are working to control risk.



Key Quotes:

“When cyber (insurance) slowly became more of a mainstream product offering they just pointed to me and said: You’re the cyber guy!” - Peter (02:10)

“The value proposition with Insurtech is just so fundamentally different from insurance.” - Peter (04:20)

“Insurtech is leveraging technology to create a better policy-holder experience, better value and more profit left over at the end of the year.” – Peter (05:24)

“Insurtechs have proven that they can grow really fast, but that doesn’t mean they can make money.” - Peter (05:49)

“Engagement brings dividends to you as a policy-holder. It makes you a safer policy-holder.” – Peter (09:15)

“We in the cyber market really demanded much better controls on our policy-holders over the last couple of years and a lot of that has been delivered to us.” - Peter (14:25)

“The feedback we’re getting from policy-holders is that we are creating an eco-system and environment that is improving their stance. And I’m just really happy that as an Insurtech I can point to those numbers and that value.” - Peter (15:58)

In this episode of CHATTINN CYBER, Marc Schein interviews Justin Daniels, an equity partner at Baker Donelson, an AM law 60 firm. Justin worked as a corporate M&A attorney and started doing technology work, before eventually narrowing down to cybersecurity. In today’s episode, he talks about cybersecurity in M&A transactions, explaining in depth his three-layer cake approach to cybersecurity in M&A and the importance of cybersecurity and privacy in all aspects of technology, from individual to business transactions.



Justin begins by discussing the importance of cybersecurity and privacy for individuals and businesses, particularly in the context of smart contracts and digital wallets used in the crypto space. He emphasizes the need for individuals to shift their mindset and make intelligent choices about sharing their data. He also suggests that individuals take advantage of privacy and security settings on their phones and consider multi-factor authentication.



He then shifts to cybersecurity in M&A transactions. Justin explains his "three-layer cake" approach to cybersecurity in M&A, which includes asking the right questions, having proper representations and warranties in the purchase agreement, and not integrating the target's network too quickly after the acquisition. He also discusses liability caps and super caps in technology contract negotiations.



Overall, this conversation stresses the importance and relevance of cybersecurity in all technology business transactions today.



 



Highlights:



 



“You have to have a certain period where cybersecurity lasts after the closing. In fact, I make it a fundamental rep where it could last through the statute of limitations, it can get negotiated.”



 



“Once you own a network, you can send in your security people and try to find any intrusions. And if you can do that, while the network is isolated, that doesn't give the threat actor the opportunity to move laterally onto your network and probably cause a lot more damage.”



 



Time-Stamps:



 



[01:06] Justin’s journey into cybersecurity



[03:17] The importance of smart contracts and digital wallets.



[05:12] How businesses and individuals can manage privacy and security concerns.



[07:33] The pros and cons of using private browsers



[09:35] How important is cybersecurity in M&A?



[11:27] The three-step approach to cyber security.



[13:43] Liability caps helpful in M&A negotiations



[15:17] About Justin's book, Data Reimagined, and how to connect with him online



 



Connect with Justin:



 



LinkedIn: https://www.iansresearch.com/our-faculty/faculty/detail/justin-daniels



 



 



 



 



 

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.



 



Highlights:



 



“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.”



 



Time-Stamps:



 



[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:



 



LinkedIn: https://cowbell.insure/team/