Keyboard Samurai

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...

Most startup founders think speed is their advantage. In this episode of Keyboard Samurai, I sit down with Baxter Lanius, CEO of Alternative Payments to unpack why moving fast often hides the real problems that quietly derail startups. We talk about founder psychology, pressure-driven decision making, and the patterns that repeat long before a company fails. Not because founders aren’t smart, but...

Most cybersecurity products don’t fail because of bad tech. They fail because they don’t solve a real business problem. In this episode of The Keyboard Samurai, host Wil sits down with Rob Allen, Chief Product Officer at  ⁨@ThreatLocker⁩  to break down what it actually takes to build security products that matter. We cover: Why cybersecurity is still an unsolved problem The difference between solv...

AI is being adopted faster than any technology in history. Security isn’t keeping up. In this episode of Keyboard Samurai, Wil sits down with cybersecurity legend Bob Carver to break down what’s actually happening inside today’s AI and LLM ecosystem and why many organizations are already exposed without realizing it. We cover: • Why AI security is the “Wild West” right now • How InfoStealers and s...

In this episode of Keyboard Samurai, host Wil Klu sits down with Carolyn Healey, a veteran B2B tech marketer and fractional CMO specializing in AI strategy, AI policy, and marketing transformation. With 30 years of experience guiding small and mid-sized tech companies, Carolyn dives deep into how generative AI is reshaping content creation, marketing workflows, team structures, and customer commun...

In this episode of Keyboard Samurai, host Wil sits down with Kevin Apolinario, widely known online as KevTech IT Support. a senior SOC analyst, technical trainer, and one of the most recognized educators in the help desk, sysadmin, and cybersecurity community. Kevin shares his unconventional journey from 12 years in the restaurant industry, four years with the NYPD, and eventually into IT support...

In this episode, Wil talks with Rock Lambros, CEO of Rock Cyber and a leader in OWASP AI Security initiatives, about what security and business leaders need to know about AI, agentic systems, governance, and emerging risks. What you will learn: Why most AI pilots fail and how Shadow AI increases attack surface and compliance risk How to build practical AI governance, KPIs, and business value track...

In this episode of Keyboard Samurai , host Will Klusovsky sits down with cybersecurity legend Dr. Eric Cole, a former CIA professional hacker who helped build the early internet and has since become one of the most influential voices in security leadership. This conversation digs into the real business of cybersecurity: why security leaders must learn to think like CEOs, how to translate technical...

In this episode of Keyboard Samurai, host Wil Klu (Wil Klusovsky) sits down with Jay Aigner, founder of JDA QA, to explore the critical overlap between Quality Assurance (QA), DevSecOps, and cybersecurity. They dig into why so many security issues start as QA misses, how poor planning and misaligned expectations in the SDLC (Software Development Lifecycle) lead to costly vulnerabilities, and why “...

In this episode of Keyboard Samurai, host Will Klusovsky sits down with Lauren Zabierek, Senior Vice President for the Future of Digital Security at the Institute for Security and Technology (IST), to dive deep into the concept of Secure by Design, a movement transforming how software security is built, measured, and sustained. Lauren shares insights from her 22 years across national security, the...

In this episode, host Wil Klu sits down with Dr. Kion Ahadi, CEO of LegalMart and author of “Humanity Reimagined in the Age of AI,” to explore how artificial intelligence is transforming leadership, ethics, and the human experience in the digital age. Together, they dive deep into: ✅ The biggest leadership shifts required in the era of AI ✅ Why the “honeymoon phase” of AI is over and what comes...

🎙 AI for the Rest of Us – with Sairam SundaresanIn this episode of The Keyboard Samurai, Wil Klusovsky sits down with Sairam Sundaresan, a veteran AI engineer, educator, and author of AI for the Rest of Us. With 15+ years in the field spanning autonomous vehicles, mobile, data centers, and space science, Sairam breaks down artificial intelligence in a way anyone can understand. 💡 They cover: • Th...

In this episode of The Keyboard Samurai, host Wil Klusovsky (aka Wil Klu) sits down with renowned ethical hacker, author, and mentor Philip Wylie — a legend in the offensive security community. Philip shares his journey from IT admin during the dot-com boom to teaching penetration testing and mentoring the next generation of cybersecurity professionals. Together, they explore how modern pen testin...

In this episode of The Keyboard Samurai, Wil sits down with Mike Holcomb, Cybersecurity Fellow at Fluor, to talk about the high-stakes world of OT (Operational Technology) security. From massive industrial control systems to securing the shop floor, Mike shares real stories and hard-earned lessons from building one of the largest OT security practices in the world. We also speculate and have some...

Cyber insurance isn’t just a policy, t’s the safety net your business needs when ransomware hits. In this episode of The Keyboard Samurai, host Wi sits down with Joe Earl, cyber insurance broker at C3 Insurance and host of Ransomware Rewind. Joe shares real stories from the front lines, including how a trucking company negotiated down a $250K ransom and recovered from a crippling attack. Together,...

What does the future of Governance, Risk & Compliance (GRC) really look like? 🚀In this episode, I sit down with AJ Yawn, current of a Aquia, Host of  ⁨@Cybertakes⁩  , Co-Founder of ByteChek and GRC innovator ... we unpack how compliance is evolving, why traditional frameworks are breaking down, and what modern leaders need to do to keep pace. We cover: ✅ The biggest shifts shaping GRC in 202...

Wil sits down with Marcel Velica of Eventbrite, to unpack what cyber leadership looks like in the age of AI. They explore how AI is reshaping the threat landscape, the boardroom’s role in cybersecurity, the rise of deepfakes and automated phishing, and why governance and risk ownership matter more than ever. 🎙️ Learn how CISOs and business leaders can: → Move beyond compliance checkboxes to real r...

What does it really take to reach the C-Suite? In this episode of The Keyboard Samurai, Wil sits down with Emma J Eyre, an executive leader who’s spent 20+ years building leadership teams across tech and then some. They dig into the data behind high-performing teams, what separates average leaders from C-level executives, and what you need to do to prepare and get to the "C-Level". If yo...

🎙️ Former ISC² Board Chair Reveals the Truth About Cybersecurity Certifications Ever wonder if cybersecurity certifications are worth it? Dan Houser, a 24-year security veteran and former ISC² Board Chair, joins host Will Klu to expose what certifications REALLY mean in today's market. In this episode, discover: ✅ Why CISSP is still the "gold standard" after 25+ years ✅ The critica...

In this episode of The Keyboard Samurai Podcast, Wil sits down with Dom Vogel, cybersecurity leader, keynote speaker, and fractional CISO, to explore the power of empathy, authenticity, and kindness in leadership. With 20+ years in cybersecurity from corporate trenches to entrepreneurship Dom shares candid insights on: ✅ Why corporate culture “choked him out” and pushed him toward building his ow...