Keyboard Samurai

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 lo...

AI agents need governance before they get access to your business. In this episode of The Keyboard Samurai, host Wil Klu talks with Christophe Foulon about agentic AI governance, AI identity management, data governance, and the business risks created when AI agents can act inside real systems. Christophe brings 20+ years in tech and IT, with experience across Microsoft 365, Purview, cloud moderniz...

AI adoption is no longer just an innovation project. It’s a business, security, and workforce transformation problem all at once. In this episode, Wil Klu sits down with Matt Sharp, CSO at Xactly and co-author of The CISO Evolution, to talk about how companies should approach AI adoption when the rules are still being written. They cover AI governance, cybersecurity risk, design partnerships, lear...

Threat actors don’t always "break in" anymore. They log in with real credentials. Wil hosts Randall Jackson, CISO at Income Research and Management, for a clear conversation on modern cyber attacks, identity compromise, AI-powered phishing, MFA fatigue, vulnerability prioritization, and the real pressure CISOs face. Randall brings 30+ years in IT and cyber, with experience across MSPs, M...

Cyber insurance is not a checkbox. It is risk transfer, and the details matter. Host Wil Klu talks with Will Brooks of U.Kon, formerly FifthWall, about how cyber insurance really works, why many businesses are underinsured, and how leaders should connect cybersecurity risk to financial impact. This episode is for business owners, CFOs, CISOs, CIOs, MSPs, and advisors who need to understand cyber p...

Manufacturing cybersecurity is not about buying every tool. It is about knowing what can hurt the business, what matters first, and how to fund the right work. In this episode of The Keyboard Samurai, host Wil Klu talks with Craig Duckworth, Director at Barry-Wehmiller Design Group, continuing conversation from from  ⁨@industrialcybersecurityinsider⁩  podcast about OT cybersecurity, industrial ris...

Cars are collecting business data, and most security programs are pretending they are still just transportation. Wil Klu hosts Merry Marwig, VP of Global Communications and Advocacy at Privacy4Cars, to unpack why corporate cars, rentals, fleet vehicles, and personal vehicles used for work need to be treated like endpoints. They talk through the data stored in modern vehicles, why infotainment syst...

Cybersecurity gets messy when teams buy tools before they understand the business. In this solo episode of The Keyboard Samurai, host Wil Klu breaks down how to build a cybersecurity program that fits the business instead of drowning it in tools, compliance checkboxes, and noise. Wil walks through the real sequence: business mission, risk appetite, compliance baseline, asset visibility, business i...

Building control systems are no longer invisible infrastructure. They’re business risk, safety risk, and operational resilience risk. Wil Klu hosts Fred Gordy, SVP of Secure Connected Solutions at KMC, to unpack what leaders need to understand about BCS, ICS, OT cybersecurity, and secure buildings. Fred shares lessons from decades working with system integrators, asset owners, consultants, and man...

Cybersecurity is easier to grow in when you stop trying to do it alone. Host Wil Klu talks with Ken Fishkin, a 20-year consultant, Loewenstein Sandler cybersecurity professional, and president of the ISC2 New Jersey Chapter, about how community changes careers. They dig into cyber meetups, mentorship, internships, public speaking, career transition, and why local security communities can create re...

Mobile fraud is evolving fast, and most leaders still do not understand where the real exposure lives. Wil Klu hosts Ian Matthews, founder and president of WMC Global, for a clear conversation on fraud, abuse, cyber, AI, and telecom risk. They unpack how RCS messaging, iMessage, SIM-enabled devices, and AI-generated scam campaigns are changing the threat landscape, and why mobile messaging fraud i...

Startup sales gets romanticized. The reality is trust, repetition, better questions, and a strong mental game. Host Wil Klu sits down with Jordan Benjamin to talk about what it really takes to sell inside a startup, build credibility before you have a big brand, and stay effective when the pressure stacks up. Jordan brings experience from startups, larger growth companies, and years spent helping...

Why do some MSPs and MSSPs grow while others stall, even in a hot market? Wil Klu hosts Jay McBain for a grounded conversation on the vendor and partner ecosystem shaping MSP and MSSP growth. They get into managed security services, channel partnerships, MDR vs MSSP positioning, white-label trust issues, platform strategy, and why better marketing and sales maturity are now essential for growth. T...

AI is moving faster than governance, and that gap is where risk starts to grow teeth. Wil Klu hosts Patrick Sullivan, VP of Strategy and Innovation at Align, for a sharp conversation on AI governance, shadow AI, business risk, and responsible adoption. This episode is for executives, CISOs, CIOs, GRC leaders, and business owners who know AI can create value but do not want to create chaos in the p...

AI in cybersecurity is full of noise. This episode helps you separate hype from risk. Host Wil Klu sits down with Walter Haydock, founder of StackAware, to talk about AI governance, ChatGPT security, vendor risk, and what companies should actually do when AI adoption moves faster than security. If you lead cyber, IT, compliance, privacy, or product, this episode gives you a practical way to think...

Cybersecurity marketing fails when founders talk features and buyers need business outcomes. In this episode, host Wil Klu talks with Jordan Snapper, aka Dr. Cyber, about what actually works in cybersecurity GTM. Jordan helps cyber founders with positioning, content, and growth, and this conversation gets into the real problems behind weak messaging, bad targeting, and wasted budget. If you are a...

Cybersecurity startup GTM is not about running more demos. It’s about understanding trust, attention, and channel economics. In this episode, host Wil Klu talks with Konnor Andersen, a cybersecurity GTM leader who has helped startups scale sales and marketing teams. They unpack why CISOs can’t take endless vendor meetings, how risk and credibility drive buying decisions, and why channel partners p...

Cybersecurity doesn’t win by caring more. It wins by making decisions easier. Host Wil Klu sits down with Drew Simonis (nearly 30 years in cybersecurity, 20 years as a CISO/deputy CISO) to talk about why cyber leaders lose executive trust, how to translate cyber risk into business context, and why “perfect security” often breaks the business. This is for CISOs, security leaders, and business leade...

Security awareness training should change behavior, not just generate metrics. Wil Klu talks with Robert Siciliano (30+ years in security awareness training) about human-centric cybersecurity and why most employee training fails to create real security culture. They unpack trust psychology, fear and denial, and why phishing simulation training can’t carry the whole program. If your people “do the...

If your AI security plan starts and ends with “LLM,” you’re already behind. Wil talks with cybersecurity architect Roman Kruglov explains why “AI” is not one risk bucket and how security changes across LLMs, SLMs, RAG, and data-specific models. We talk on-prem vs cloud, API security basics that still get missed, and the bigger problem most teams ignore: data labeling, DLP, and permissions hygiene....

Fast SaaS growth exposes problems most teams don’t see until it’s too late. In this episode of The Keyboard Samurai Podcast, I break down what happens when revenue, customers, and expectations scale faster than the systems meant to support them, with Steve Doty and Chris Goodman of Defensible Technology as the conversation drivers. We talk about how compliance milestones like SOC 2 create a false...

Most organizations say they want to modernize their cybersecurity stack. What they usually mean is buying more tools. In this episode of The Keyboard Samurai Podcast , I break down what modernizing security actually looks like with Ben Wilcox —and why most “modern” security programs are still built on fragmented data, disconnected tools, and the wrong definition of risk. We talk about why moderniz...

Most cybersecurity leaders lose the boardroom before the conversation even starts. In this episode of The Keyboard Samurai Podcast , I sit down with Jeffery Wheatman to break down why board-level cybersecurity conversations fail, and what executives actually care about when risk is on the table. Jeffery pulls back the curtain on how boards think, why security teams struggle to get traction, and ho...

In this episode of Keyboard Samurai , I sit down with Megan Killion , founder of Pisces Growth, to unpack why fear-based security messaging shuts small business owners down—and why most cybersecurity sales fail before they even start. Megan breaks down what SMB buyers actually care about, how words like “cybersecurity” trigger mental spam filters, and why selling risk without understanding the bus...

Most startups think if MSPs like their product, they’ll buy it. That assumption quietly kills a lot of good ideas. In this episode of Keyboard Samurai , I sit down with Jeremy Young , Community Growth Strategist at Huntress, to break down what it actually takes to bring products to MSPs and scale a startup in the channel. We dig into the difference between interest and real demand , why MSP feedba...