Keyboard Samurai

Your cybersecurity provider could be doing everything in its contract, and your business could still have gaps nobody owns.

In this episode, I walk through five cybersecurity questions every CEO, CFO, COO, and business owner should ask. We'll look at the technology your business depends on, who's accountable for protecting it, what happens when something suspicious occurs at 11:30 on a Friday night, and why having backups doesn't necessarily mean you can recover.

You'll leave with practical questions for your next leadership meeting, even if you don't speak fluent cybersecurity.

Free Business Cyber Risk Scorecard:
https://advisor.vilogics.com/businesscyberriskscorecard

Takes less than 7 mins, no tech questions, don't wait until there's an incident to know your protected. Find out for free now.

Follow The Keyboard Samurai on Spotify for more practical conversations about technology, cybersecurity, and business leadership.

00:00 Why business leaders need cyber clarity

02:30 What does your business depend on?

06:13 Who owns cybersecurity risk?

09:54 Who can access critical systems?

13:00 Who detects and responds to threats?

16:56 Business Cyber Risk Scorecard

18:31 Could your business actually recover?

22:26 Five questions for your next meeting

A vendor has a SOC 2 report. How much confidence should that really give you?

Host Wil Klu talks with Bill Deller, a shareholder at Schneider Downs who helps lead its IT risk advisory practice, about AI and third-party risk management. They explore where AI makes vendor reviews faster, why security questionnaires aren't going away, and why a SOC 2 report isn't the full story. If you manage vendors, lead IT or security, or make business decisions about third-party risk, this conversation will help you ask better questions.

In this episode:

Learn where AI improves vendor due diligence and where it falls short.

Find out why automated answers can frustrate clients.

Understand the difference between a SOC 2 audit and a risk assessment.

Hear why auditor quality and incentives matter.

Examine the costs and benefits of AI-powered risk reviews.

Explore security frameworks beyond SOC 2.

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Connect with Bill Deller on LinkedIn. https://www.linkedin.com/in/bill-deller/

AI agents can touch more data, make more decisions, and create more privacy risk than most companies can see.

Host Wil Klu sits down with Corey M., an analyst at the American Institutes for Research with nearly 20 years in security and experience across GRC, privacy, and engineering. They explore AI privacy, shadow AI, data brokers, agentic AI governance, and the growing problem of controlling what AI agents can access and do. For CISOs, privacy and GRC leaders, security teams, and business owners, this conversation offers a practical way to think about AI risk without throwing out the security fundamentals that already work.

Key takeaways:

• Inventory the AI agents already operating in your business

• Treat AI agents as identities with defined access and permissions

• Control what data agents can use and where that data goes

• Keep humans involved when AI makes consequential decisions

• Monitor agent activity and regularly review access

• Build AI governance around accountability, evidence, and basic cyber hygiene

Follow The Keyboard Samurai for more conversations about cybersecurity, AI, privacy, and the business decisions behind technology. If this episode was useful, share it with someone responsible for AI governance or privacy.

Find Cory:

https://www.linkedin.com/in/corymissimore/

Your physical life ends. Your digital life may keep going, and most people and businesses have no plan for what happens next.

Host Wil Klu talks with digital thanatologist Niki Weiss about digital afterlife planning, passwords and MFA, social media accounts after death, key-person risk, AI digital twins, and business continuity. Niki works with companies through Endevo.life on legacy readiness and digital resilience, helping people prepare before a crisis forces the issue. This episode is for business owners, executives, technology leaders, and anyone wondering who controls their data, accounts, and digital identity when they are no longer able to.

Key takeaways:
• Create a practical digital legacy and end-of-life plan
• Organize passwords, phones, logins, beneficiaries, and critical access
• Test business continuity for the permanent loss of a key employee
• Understand ghost and zombie accounts after someone dies
• Consider who may own or use AI versions of your likeness
• Treat digital resilience as part of governance and continuity

Follow The Keyboard Samurai for more conversations on cyber, technology, AI, business risk, and resilience.

Find Nikki:

• LinkedIn https://www.linkedin.com/in/nikiweiss/
• Her podcast https://www.youtube.com/channel/UCK2FUE-JxLOSkrcEo66HDug
• Endevo.life

Industrial AI can help manufacturers modernize legacy plants—but only if they understand the systems, data, people, and cybersecurity risks involved.

Host Wil Klusovsky speaks with Bryan DeBois, Director of Industrial AI at RoviSys, about bringing AI into real manufacturing and operational technology environments. Bryan explains how industrial AI connects with PLCs, HMIs, digital twins, and manufacturing data to improve processes without replacing every older machine. They also discuss IT/OT convergence, OT cybersecurity, deep reinforcement learning, and why experienced humans must remain part of critical decisions.

Key takeaways:

Understand how OT system integrators connect the plant floor

Learn how AI can optimize legacy manufacturing equipment

Explore digital twins and deep reinforcement learning

Identify cybersecurity concerns created by IT/OT convergence

Examine the growing manufacturing expertise gap

Recognize the limits of generative AI in critical environments

Follow The Keyboard Samurai for more conversations about the business of cyber and tech. Leave a review and share this episode with someone working in manufacturing, OT, AI, or cybersecurity.

Find Bryan: https://www.linkedin.com/in/bryan-debois/

Cyber fraud is a cybersecurity incident with one direct goal: steal the money.

Wil Klu hosts Matt Meis, a cybersecurity professional turned full-time fraud fighter, for a plain-English look at modern financial crime. They explain how online scams, money mules, digital money laundering, account takeover, check fraud, and crypto transfers connect. This episode is for cybersecurity leaders, fraud teams, financial professionals, business owners, and anyone who wants to understand how stolen money moves and where prevention can stop it.

• Identify common cyber fraud and scam patterns

• Follow the path of money through mule networks

• Understand first-party, third-party, and synthetic identity fraud

• Learn why fast reporting can improve fund recovery

• Explore the cyber fraud kill chain and fraud intelligence

• See how brand impersonation creates financial and reputation risk

Follow The Keyboard Samurai and leave a review. Find Matt on LinkedIn, read the Sec Fraud Ops newsletter, and check out his book, Survive Online.

Find Matt:

LI: https://www.linkedin.com/in/matthew-meis/

Newsletter: https://secfraudops.substack.com/

Book: https://www.learncybersecurity.net/book

AI is making penetration testers faster, but it still cannot replace the judgment needed to prove real business risk.

Wil hosts Nat Shere, Product Security Manager at Skillable and a penetration tester with more than 10 years of experience, for a practical look at AI penetration testing. They break down where AI helps, where automated pentesting falls short, and why finding more vulnerabilities does not matter unless a tester can prove exploitability and impact. This episode is for CISOs, security leaders, buyers, and cybersecurity professionals trying to separate useful AI tools from expensive scanner theater.

Key takeaways:

• Learn how AI automates repetitive testing and supports deeper exploit research

• Compare AI pentesting tools with vulnerability scanners and manual pen tests

• Judge reports by evidence, repeatable steps, and business impact

• Understand the privacy risks of sending customer data to public AI models

• See why hallucinations, scope, and creative testing still need an expert

• Explore how AI may reshape entry-level cybersecurity career paths

Follow The Keyboard Samurai and leave a review for more plain-English conversations about cyber, technology, and business.

Find Nat: https://www.linkedin.com/in/nathaniel-shere/

AI can help cybersecurity teams move faster, but speed creates new questions about control, accountability, and whether humans can keep up.

Wil Klusovsky, host of The Keyboard Samurai, talks with Carl Stern, VP of Information Security at Age of Learning and a cybersecurity leader with more than 25 years of experience. They discuss building cybersecurity programs in the age of AI, securing agentic AI, using automation for threat intelligence and GRC, and protecting the next generation of cyber talent. The conversation then moves beyond today’s tools into AI governance, artificial general intelligence, regulation, and the future role of human judgment.

• Strengthen cybersecurity fundamentals as AI accelerates attacks

• Secure AI agents through identity and access controls

• Apply AI to threat intelligence, third-party risk, and compliance work

• Examine how automation changes entry-level cybersecurity careers

• Separate LLM capabilities from the risks of AGI

• Consider why thoughtful AI regulation is moving too slowly

Follow The Keyboard Samurai for more conversations about cybersecurity, technology, business, and leadership. Leave a review and share the episode with someone thinking seriously about AI risk.

Find Carl: https://www.linkedin.com/in/carlstern/

Buying a company means inheriting its cyber risk, technical debt, and every forgotten system still humming in the corner.

Wil Klu, host of The Keyboard Samurai, sits down with Orville Williams, VP of Cybersecurity and Risk at Trilon Group, to explain what cybersecurity looks like during mergers and acquisitions. Drawing on his work across 14 partner firms, Orville shares how teams uncover legacy hardware, licensing gaps, shadow IT, unknown VPNs, and phishing risk while moving acquired companies toward a common security baseline. This episode is for executives, deal teams, CISOs, CIOs, and IT leaders responsible for cybersecurity due diligence or post-merger integration.

You’ll hear how to:

• Bring security into the M&A process earlier

• Price hidden integration and remediation costs

• Set a 30-to-60-day cybersecurity integration plan

• Improve asset visibility and find unknown systems

• Deploy practical controls such as MFA, EDR, and email security

• Protect employees from phishing, impersonation, and payment fraud

Follow The Keyboard Samurai for more business-first cybersecurity conversations, and share this episode with someone responsible for the next acquisition.

Find Orville: https://www.linkedin.com/in/orville-williams-510986230/

Ransomware response gets a lot harder when panic, money, law enforcement, insurance, and attackers all collide.

Wil hosts Kurtis Minder, author of Cyber Recon, longtime cyber operator, former CEO, and ransomware negotiator, for a grounded conversation on cyber espionage, dark web intelligence, ransomware negotiation, and personal cyber hygiene. Kurtis explains what human-led threat intelligence looks like, why negotiation is partly psychology, and how victims can make better decisions under pressure. This episode is for cyber leaders, business executives, founders, and anyone who wants to understand how cyber risk works in the real world.

Key takeaways:

• Learn how cyber espionage supports threat intelligence

• Understand what happens during ransomware negotiation

• See why response requires calm leadership, not just technical skill

• Explore how attackers use supply chains and personal data

• Improve your thinking around cyber hygiene and risk

Find Kurtis:

www.kurtisminder.com

https://www.cyberreconbook.com/

https://www.linkedin.com/in/kurtisminder/

Follow The Keyboard Samurai for more conversations on cyber, tech, business, and leadership. Leave a review and share this episode with someone responsible for cyber risk or business resilience.