During incident response, what separates good from great counsel is bedside manner.

In this episode, host Anthony Hess sits down with Josh Mooney, Partner and US Head of Cyber and Data Privacy at Kennedys Law, for a candid look at effective cyber response leadership.

Josh explains why empathy and communication are as critical as legal precision when guiding clients through chaos. He also shares how US courts are reshaping ransomware incentives, why data governance failures attract OCR scrutiny, and how privacy law is edging toward a fifth fundamental right, namely the right not to be tracked.

From the psychology of crisis response to courtroom strategy and compliance realities, Josh reveals how the next decade of cyber risk will test not only systems, but the people behind them.

You’ll learn:

1. Why empathy and trust are strategic tools in breach response
2. How US court rulings are driving ransom payment dilemmas
3. What OCR investigations reveal about weak governance
4. Why data inventory discipline determines breach outcomes
5. How privacy law may soon expand to include a “right not to be tracked”

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Get in touch with Josh Mooney on LinkedIn: https://www.linkedin.com/in/joshua-mooney-cybersecurity/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

Telemetry is changing the underwriting game, enabling a shift from clunky forms to real-time, verifiable risk data.

In this episode, host Anthony Hess sits down with Alex Jomaa, Chief Underwriting Officer at Onda, to explore how real-time data is transforming cyber underwriting, and why it’s time the industry stopped relying on outdated processes that frustrate clients and slow brokers down.

Alex explains how Onda’s Navigator platform integrates directly with a client’s infrastructure to deliver objective, verifiable cyber risk insights, thereby eliminating the back-and-forth of long-form questionnaires. In addition, he unpacks the biggest hurdles to cyber adoption, from poor timing and over-complication to misaligned incentives and volatile pricing cycles.


You'll learn:

1. How telemetry brings scale, accuracy, and speed to cyber underwriting
2. What really stops buyers from purchasing cyber policies
3. How brokers can sell cyber coverage more effectively
4. The key signals Onda uses to assess cyber hygiene and risk quality
5. Why market volatility is damaging long-term trust in cyber insurance

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Get in touch with Alex Jomaa on LinkedIn: https://www.linkedin.com/in/alex-jomaa-b84b8520/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

When the market softened, Ridge didn’t follow the crowd. Here’s how discipline became their competitive edge.

In this episode, host Anthony Hess sits down with Greg Markell, President & CEO at Ridge Canada Cyber Solutions Inc., for a candid conversation on what it takes to build a sustainable cyber MGA.

Greg shares how Ridge has resisted the pull of chasing market share during soft cycles—maintaining its underwriting standards since 2020—and why he believes cyber risk transfer must be earned, not assumed. He unpacks Ridge’s strategy of building proprietary underwriting tools in-house, explains why AI is an efficiency enhancer (not a replacement for people), and introduces the company’s new “risk marketplace,” which helps brokers turn declines into actionable paths to coverage.


You’ll learn:

1. Why consistent underwriting is Ridge’s strategy for long-term profitability
2. Why cyber coverage should depend on client maturity, not market capacity
3. How Ridge balances internal tech and AI with human-led underwriting
4. What Ridge’s “risk marketplace” offers when clients aren’t ready for coverage
5. Why trusted vendor partnerships are core to a strong claims experience

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Get in touch with Greg Markell on LinkedIn: https://www.linkedin.com/in/gregmarkell/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

What if the biggest threat to your cyber claims portfolio isn’t ransomware—but a spreadsheet buried in someone’s inbox?

In this episode, host Anthony Hess chats with John Spiehs, Head of Claims at Converge, about what’s shifting in the cyber claims space—and what insurance professionals should have on their radar.

John breaks down how Converge is leading efforts to simplify Business Interruption (BI) claims with a cleaner, more intuitive, top-down approach. He also digs into the growing exposure around data privacy, where even small incidents can trigger costly class actions. Finally, he explains what’s getting lost as the market softens, why vendor relationships matter more than price tags, and the kind of talent today’s claims teams really need.


You'll learn:

1. Why BI claims are evolving, and how Converge is simplifying the process
2. Why data privacy and class actions are emerging as cyber’s new frontier
3. Why soft market dynamics threaten underwriting discipline
4. How poor email habits can explode breach costs overnight
5. What defines a strong vendor partnership, beyond cut-rate solutions

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Get in touch with John Spiehs on LinkedIn: https://www.linkedin.com/in/john-s-b981337/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

Cyber insurers can’t just assess risk—they need to actively protect businesses from evolving threats.

In this episode, host Anthony Hess welcomes Daniel Woods, Principal Security Researcher at Coalition, to explore how cyber insurers can move beyond risk transfer and take an active role in cybersecurity. Daniel explains how Coalition’s mission-driven approach sets it apart, and why active insurance has an edge in an era of escalating threats.


You'll learn:

1. Why cyber insurers must go beyond risk assessment and actively protect policyholders
2. How web privacy litigation from the plaintiffs’ bar mirrors cybercriminal tactics
3. The biggest blind spots in systemic cyber risk, and why a privacy casualty catastrophe is worth thinking about
4. How insurers can build real-time risk mitigation into their coverage models
5. The future of cyber insurance: Where the industry is headed and how insurers can stay ahead

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Get in touch with Daniel Woods on LinkedIn: https://www.linkedin.com/in/daniel-woods-82555199/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

Can your cyber insurance policy really deliver when it counts? Find out what separates a winning policy from a risky gamble.

In this episode, host Anthony Hess welcomes David Anderson, Vice President of Cyber at Woodruff Sawyer, to explore the evolving cyber insurance landscape. David dives into the current trends shaping the market, sharing insights into what 2025 holds for privacy underwriting, ransomware risks, and premium stabilization. He reveals the common missteps that leave organizations vulnerable and offers actionable strategies to ensure your cyber insurance policy performs effectively in the event of a claim.


You'll learn:

1. Why privacy underwriting is the focal point of 2025 renewals
2. How policy misalignment can lead to disastrous claims outcomes
3. The must-have policy elements for manufacturing and tech firms
4. Strategies to improve collaboration between CISOs and financial buyers
5. Why underwriter scrutiny is shifting from quantity to efficacy of tools

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Get in touch with David Anderson on LinkedIn: https://www.linkedin.com/in/dava988/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

How can insurers, brokers, and clients all win through proactive risk management? Discover the strategies reshaping the cyber insurance ecosystem.

In this episode, host Anthony Hess sits down with Sidd Gavirneni, Global Product Owner, Digital Risk Management at HSB. With a background spanning cybersecurity, entrepreneurship, and InsurTech innovation, Sidd shares his insights into transforming the cyber insurance landscape. He highlights how pre-breach services benefit insurers, brokers, and clients. This episode also explores personal cyber insurance, AI’s dual role in cybersecurity, and the value of partnerships in the cyber insurance ecosystem.


You'll learn:

1. Why pre-breach solutions are key to reducing claims and enhancing client trust
2. How the insurance industry can unlock the potential of personal cyber coverage
3. The challenges of data utilization in underwriting and ways to overcome them
4. The role of AI as both a cybersecurity asset and a growing threat
5. How closer collaboration between insurers and cybersecurity vendors drives innovation

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Get in touch with Sidd Gavirneni on LinkedIn: https://www.linkedin.com/in/siddgavirneni/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!

In a market defined by uncertainty, is it possible to ever be ‘good’ at cyber insurance? Daniel Kasper thinks not—at least for now.

In this episode, Daniel Kasper, CEO of QualRisk Cyber Insurance Center, joins host Anthony Hess to explore why the cyber insurance market is still in its infancy. Drawing from examples like the ransomware epidemic of 2019-2022, Daniel explains how the lack of historical systemic event data, a fast-evolving threat landscape, and inherent unpredictability make cyber insurance uniquely challenging.


You'll learn:

1. Why a standardized framework for cyber events could revolutionize the industry
2. How to balance data-driven decisions with expert judgment in an imperfect market
3. What makes cyber insurance uniquely difficult to master in today’s evolving landscape
4. The consolidation wave reshaping the MGA sector and what it means for market players
5. Why mastering cybersecurity fundamentals is essential for insurance professionals

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Get in touch with Daniel Kasper on LinkedIn: https://www.linkedin.com/in/daniel-kasper-cyber/


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About the host Anthony Hess:
Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.

Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: ahess@asceris.com.

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Thanks to our friends at SAWOO for producing this episode with us!