Keyboard Samurai

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 impact analysis, risk assessment, frameworks, budget, roadmap, and execution. This is for executives, CISOs, CIOs, IT leaders, and security teams who need a practical way to build or mature a cybersecurity program.Key takeaways:• Build cyber around the business mission• Treat compliance as the baseline, not the goal• Identify assets, data, owners, and critical processes• Use business impact to prioritize cyber risk• Turn gaps into a funded cybersecurity roadmap• Build programs for resilience, monitoring, vulnerability management, and recoveryFollow The Keyboard Samurai for more practical conversations on cybersecurity, business, and leadership.

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 manufacturers. This episode is for CISOs, CIOs, facility leaders, building owners, and executives who need to understand how cyber risk shows up in the physical world.Key takeaways:• Know what you have, how it’s connected, and who has access• Understand how BCS differs from ICS and traditional IT• Reframe building security around operational resilience• Learn why downtime, safety, and public perception change the risk conversation• Hear real-world examples from commercial buildings, hospitals, and facilitiesFollow The Keyboard Samurai for more conversations on cyber, tech, leadership, and business risk.Find Fred on Linkedin: https://www.linkedin.com/in/fredgordy/

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 real opportunities for students, practitioners, CISOs, vendors, and people trying to break into cybersecurity.Key takeaways:• Why cybersecurity community is more than networking• How virtual events helped people connect during COVID• How mentorship and internships help people enter cyber• Why career changers need relationships, not just resumes• How volunteering builds speaking, leadership, and event skills• What makes SECON a practitioner-driven cyber conferenceFollow The Keyboard Samurai for more conversations on cybersecurity, leadership, career growth, and the business side of cyber.Find Ken : https://www.linkedin.com/in/kfishkin/

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 is getting harder to detect and stop. This episode is built for cyber leaders, fraud teams, telecom operators, and executives who need a better handle on mobile scam risk and business impact.Break down the difference between SMS spoofing, brand impersonation, and RCS abuseLearn why carriers lose visibility when traffic shifts into encrypted channelsUnderstand how phone farms and SIM boxes power large-scale scam campaignsSee how AI helps attackers test and improve fraud messaging in real timeExplore the regulatory and data-sharing barriers slowing down enforcementFollow The Keyboard Samurai for more conversations with Wil Klu on cyber risk, technology, leadership, and the business side of security. Leave a review and share this episode with someone responsible for fraud, telecom, or cyber strategy.Find Ian: https://www.linkedin.com/in/iancsmatthews/Read more here: Read more here: https://www.linkedin.com/pulse/navigating-end-to-end-encrypted-messaging-abuse-ian-matthews-dus5e

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 people improve performance without burning out. Together, they unpack startup sales strategy, inbound marketing, AEO and SEO content, customer-centric discovery, multi-threading, and the mindset tools that help sellers keep going when deals stall.Key takeaways:• Why startup sales depends on belief, messaging, and early trust• How useful content supports both inbound and outbound sales• Why customer goals, plans, and challenges beat self-centered discovery• How multi-threading improves your odds in larger B2B deals• What founders and sellers can do to stay productive without burning out• How simple systems can help quiet the mental noise in salesFollow The Keyboard Samurai for more conversations with Wil Klu on sales, leadership, cybersecurity, tech, and the business side of growth. If this episode helped, leave a review and share it with someone building or selling in a startup.Find Jordan on LinkedIn: https://www.linkedin.com/in/jordanbenjamin/

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. This episode is for MSP owners, MSSP leaders, channel teams, and cybersecurity vendors trying to understand where the market is headed and how to compete more clearly.Key takeaways:• Why services revenue is the real engine behind channel growth• How white-label security services can help or hurt buyer trust• What smaller MSPs need to know about enterprise deals and realistic ICPs• Why platform choices matter more as cybersecurity vendors consolidate• How to package managed security offers so buyers understand the value• Why AEO is becoming the next major marketing shift for MSPs and MSSPsFollow The Keyboard Samurai for more on the business side of cybersecurity, managed services, and partner growth. If this episode helped sharpen your thinking, leave a review and share it with another operator in the channel.Find Jay on LinkedIn: https://www.linkedin.com/in/jaymcbain/

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 process. You’ll hear how to think about AI use cases, risk appetite, policy, training, and why business language matters if you want leadership to actually make good decisions. Key takeaways:• Why “we banned AI” is not the same thing as governance• How shadow AI shows up inside real organizations• What a legitimate business case for AI should look like• Why AI risk has to be framed in business terms, not just technical ones• How training and role-based guidance reduce ignorance and misuse• Why fast AI adoption without guardrails creates long-tail risk Follow The Keyboard Samurai for more episodes on cyber risk, executive communication, and the business realities behind modern technology. Leave a review and share this episode with the leader who thinks policy alone will keep AI in its lane.Find Patrick: https://www.linkedin.com/in/the-patrick-sullivan/

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 about AI security without getting lost in buzzwords. They also unpack ISO 42001, data retention, model training, and why “self-hosted AI” is not automatically the safer option.Key takeaways:• Break down the biggest myths around AI cybersecurity and SaaS risk• Understand how data retention and model training affect AI security• Learn the first 3 steps to build AI governance inside an organization• Evaluate third-party AI vendor risk when visibility is limited• See why ISO 42001 is becoming important for AI compliance and readiness• Hear how new laws may shape AI governance requirementsFollow the show for more episodes on cybersecurity, AI governance, GTM, and the business of tech. If this episode helped you, leave a review and share it with a leader who needs a clearer view of AI risk.find Walter https://www.linkedin.com/in/walter-haydock/

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 founder, cyber marketer, SDR, AE, or security leader trying to grow a cybersecurity company, this is a sharp look at founder-led growth, LinkedIn strategy, buyer trust, and how to turn content into real pipeline.You’ll hear about:• Why cyber startups should not lean on Gartner too early• How to position a security product around outcomes, not features• Why LinkedIn founder-led growth beats relying only on company pages• How Reddit, comments, and AMAs can drive trust and content ideas• Why MQLs fall short and sales-ready conversations matter more• How marketing can better support sales with stronger content and enablementFollow Keyboard Samurai for more episodes on the business of cyber, tech, GTM, and executive decision-making. Leave a review and share this episode with a founder or marketer building in cybersecurity.Find Jordan: https://www.linkedin.com/in/jordansnapper/

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 protect their long-term relationships above everything else. If you’re a founder, CRO, or GTM leader in cyber, this episode will sharpen how you think about growth.Key takeaways:Why “just 20 minutes” is a broken approach in cybersecurity salesHow trust drives the CISO buying processWhat channel partners expect before they engageThe real economics behind VAR relationshipsWhen federal vs commercial GTM becomes a strategic forkFollow the show for weekly conversations on the business of cybersecurity and tech, and leave a review if this episode helped you think differently.Find Konnor: https://www.linkedin.com/in/konnorandersen/https://cyberbuildingblocks.substack.com/

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 leaders who want clearer conversations, faster alignment, and less security theater.Key takeaways:• Business context beats “business terms” for exec buy-in• If your message flops, blaming the audience is the failure• “Perfect vs good enough” is a leadership decision, not a slogan• SOC 2 often reduces sales friction and builds trust at scale• Relationships grow when security leads with a servant mindsetFollow the show, share this episode with a leader who needs it, and leave a review if it helped you think differently.Follow the showhttps://www.youtube.com/@KeybdSamuraihttps://www.linkedin.com/in/wilklu/Find Drew on LI: https://www.linkedin.com/in/drew-simonis/

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 training” but still don’t care, this is a blueprint for making security personal and practical.Key takeaways:Why “lecture-style” security awareness gets tuned outHow trust-by-default makes people vulnerable to scamsThe missing layer: digital literacy (passwords, MFA, password managers)How live, dialogue-based training drives behavior changeMoving from awareness to security appreciationFollow the show, share this episode with your CISO or HR lead, and leave a review if it helped. More resources at www.wilklu.meFind Robert www.protectnowllc.com

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. You’ll also hear why Copilot can surface what SharePoint search never would, and why identity (including non-human identities) is the next battlefield.Key takeaways:How to compare LLM vs RAG security risksWhy data labeling + DLP matter before you deploy AICopilot, SharePoint/Teams sprawl, and “public is public”Governance templates and guardrails that don’t block deliveryWhy identity is becoming the new perimeterFollow the show, leave a quick rating, and share this episode with the person pushing “AI” in your org.

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 sense of security, why operational maturity lags behind growth, and how security and process debt quietly become growth blockers.This episode covers:Why SOC 2 is a starting point, not a finish lineHow SaaS growth reveals gaps in security and operationsThe difference between being compliant and being resilientWhy teams underestimate the cost of security and process debtHow misaligned systems slow deals, erode trust, and increase riskWhat founders and operators should fix before growth forces the issueIf you’re building or scaling a SaaS company, this episode reframes security, compliance, and operations as growth infrastructure—not checkboxes.This isn’t about fear.It’s about staying ahead of your own success.Find Chris & Steve: https://www.linkedin.com/in/stevedoty/https://www.linkedin.com/in/christopher-goodman-007/

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 modernization isn’t a technical exercise, how operational risk should drive security decisions, and why identity has quietly become the biggest risk surface in most environments.This conversation covers:Why the board cares about operational risk, not toolsHow disconnected security platforms create blind spotsWhy SOC, GRC, and user awareness can’t operate in silosIdentity as the dominant risk driver in modern environmentsWhy automation and AI fail without clean data and defined processThe coming identity problem created by AI agentsIf you’re responsible for security strategy, modernization, or explaining cyber risk to the business, this episode reframes how to think about tools, data, and outcomes.This isn’t about buying more technology.It’s about building a system that actually works.Find Ben:https://www.linkedin.com/in/ben-wilcox/#podcast #cybersecurity #cyber #tech #MSS #MSP #startup

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 how translating cyber risk into business impact is the difference between influence and irrelevance.We cover:What boards really care about (and what they don’t)Why acronyms, jargon, and technical detail kill credibilityThe difference between owning risk and advising on riskWhy checkbox compliance creates a false sense of securityHow to frame cyber issues in terms of money, operations, and accountabilityWhat CISOs get wrong when communicating with executivesIf you’re a CISO, security leader, or executive trying to get buy-in at the board level, this episode is a masterclass in speaking the language of decision-makers.This isn’t about better slides.It’s about better conversations.

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 business destroys trust.We cover:Why SMB owners shut down the moment you say “cybersecurity”How fear-based selling signals you don’t understand the businessWhy SMBs care more about money and time than hypothetical breachesThe difference between compliance-driven buyers and everyone elseWhy niching and speaking the buyer’s language mattersHow to qualify out early instead of wasting sales cyclesIf you sell cybersecurity, run an MSP, or market to SMBs, this episode will change how you think about messaging, demand, and trust.This isn’t about scare tactics.It’s about meeting buyers where they actually are.Find Megan here:LinkedIn: ⁠https://www.linkedin.com/in/megankillion/

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 feedback can be misleading, and how founders get stuck building products people admire but won’t pay for.This conversation covers:Why demos and praise don’t equal demandSelling to MSPs vs selling through MSPsWhy “the product sells itself” is a dangerous mythHow product-led growth really works in the MSP spaceThe role of sales enablement in startup survivalWhy founder-led sales breaks at scaleIf you’re building a cybersecurity product, selling into MSPs, or trying to scale a startup without wasting years chasing the wrong signals, this episode will save you time and pain.This isn’t theory.It’s hard-earned channel reality.Find Jeremy here:LinkedIn: https://www.linkedin.com/in/jayoung1216Email: [email protected]

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 because stress, ego, and urgency change how leaders think and act.This conversation explores:• Why smart founders repeat the same mistakes• How speed can lock bad decisions into a startup’s foundation• The difference between momentum and real progress• How pressure alters leadership behavior• When advisors help and when founders stop listening• Early warning signs founders usually missIf you’re a startup founder, operator, or advisor, this episode will change how you think about growth, leadership, and what actually causes startups to break under pressure.This isn’t about hustle or tactics.It’s about the decisions that quietly shape everything that comes next.Find Baxter: LI: https://www.linkedin.com/in/baxterlaniusiv/Email: [email protected]: 917-744-6597 (text or call)startup founder psychology, why startups fail, startup decision making, founder leadership pressure, early stage startup mistakes, scaling a startup

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 problemThe difference between solving symptoms vs fixing root causesWhy complex threats often need simple controls, not more analyticsHow “block everything, allow by exception” changes security outcomesWhy UX and product usability decide whether security tools succeedHow customer advisory boards shape better productsWhy attackers no longer need endpoint access to cause damageThis conversation is a must-listen for:Founders, product leaders, CISOs, MSPs, and anyone building or buying security products.Links & ResourcesRob: https://www.linkedin.com/in/threatlockerrob/ThreatLocker: https://www.threatlocker.comhttps://www.youtube.com/@ThreatLockerSubscribe for weekly conversations on cyber & tech biz, GTM, and building products that actually work.

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 stolen credentials quietly fuel modern breaches• Why LLMs and MCPs are becoming a new attack surface• Hallucinated code, slop squatting, and AI-driven supply chain risk• Why visibility, context, and secure-by-design still matter more than toolsBob brings decades of experience from the front lines of threat hunting, large-scale networks, and early AI warnings to explain what’s breaking first and what security leaders are missing.If you work in cybersecurity, run a tech company, or rely on AI to move faster, this is a conversation you need to hear before the risks catch up.Find Bob: https://www.linkedin.com/in/bobcarver/

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 communication.You’ll hear a candid exploration of practical AI adoption inside real marketing teams; what works, what breaks, and what absolutely must be governed before businesses roll out AI tools. Carolyn and Wil also discuss the growing tension between creativity and automation, the future of design and content roles, the rise of “shadow AI,” and how companies should think about data privacy when using LLMs.Whether you're a cybersecurity leader, a technology marketer, or a founder trying to scale content without scaling headcount, this conversation breaks down actionable insights you can apply immediately, including:• How small-to-mid-size tech companies can use AI to amplify content output• The right way to build brand voice, workflows, and guardrails using custom GPTs• Why human review still matters even when AI gets you 80% of the way there• What businesses get wrong about blogging, SEO, AEO, and thought leadership• How to avoid the growing risks of shadow AI and LLM data exposure• The real-world impact of AI tools on design, video creation, and marketing opsFind Carolyn on LinkedIn: https://www.linkedin.com/in/carolynhealey/Website: servicemarketing.comFind Wil on LinkedIn: https://www.linkedin.com/in/wilklu/

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 and cybersecurity. This conversation dives deep into the realities of the help desk, the skill gaps aspiring cybersecurity pros overlook, and the truth about working with executives, SOC teams, audits, and the everyday chaos of IT.Whether you're breaking into IT, transitioning into cybersecurity, or managing technical teams, this episode delivers real-world insight into:- How help desk and customer-facing roles create stronger cybersecurity professionals- Why communication and “translating tech to business” is one of the most critical career skills- What it’s really like supporting C-suite executives- Why fundamentals—networking, operating systems, IAM, troubleshooting, matter more than certifications- How SOC analysts and IT teams can collaborate more effectively- The personality traits hiring managers actually look for in junior talent- Why cybersecurity careers are impossible to succeed in without being curious, trainable, and willing to ask questionsIf you’re exploring IT, cybersecurity, help desk, SOC analysis, or want to understand how real teams operate behind the scenes, this episode is a must-listen.Find Kevinhttps://www.linkedin.com/in/itprofessionalkevinapolinario/https://www.youtube.com/@KevtechITSupport

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 riskHow to build practical AI governance, KPIs, and business value trackingKey agentic AI risks including identity gaps, cascading hallucinations, tool poisoning, model driftThe questions to ask before buying AI or agentic tools for your SOCHow leaders can safely accelerate AI adoption without creating new liabilitiesFind Rock here:• LinkedIn: https://www.linkedin.com/in/rocklambros/• Website: https://rockcyber.comAI securityOWASP AI, agentic AI, cybersecurity leadership, CISO strategy, AI governance, LLM security, Shadow AI, SOC automation, AI compliance, model drift, AI risk management, enterprise AI

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 risks into business language, why seatbelts and security share more history than you think, and the mindset shift that turns cybersecurity from a roadblock into a business enabler.Dr. Cole breaks down the future of cyber resilience, the maturity gap facing organizations today, the myths that still plague security teams, and why selling cybersecurity isn’t sleazy, it’s essential for survival. From OT and manufacturing risks to boardroom communication, he shares decades of experience with humor, clarity, and a whole lot of hard-won wisdom.If you work in cybersecurity, lead a team, or want to understand how cyber actually drives business value, this episode will sharpen your thinking and elevate your strategy.Topics Include:• The evolution of cybersecurity from the 90s to now• How to speak the language of CEOs and boards• Risk, cost, and value as the real drivers of security decisions• Why prevention alone is dead-detection and resilience matter most• Cybersecurity’s maturity problem and how to fix it• Privacy, generational shifts, and changing expectations• Asset management, resource allocation, and budget justification• Turning cybersecurity into a business advantage• The psychology of communication and influence in security leadershipPerfect for: CISOs, security leaders, technical practitioners, founders, cybersecurity students, and anyone curious about how cyber and business intersect.Find Dr. Eric Cole on LinkedIn: https://www.linkedin.com/in/ericcole1/Find Wil on LinkedIn: https://www.linkedin.com/in/wilklu/

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 “bolt-on security” after release is a recipe for disaster.✅ You’ll Learn:How QA fits into modern DevSecOps and SDLCThe true cost of skipping testing and secure designWhy QA and cybersecurity share the same challenges in proving valueHow to build trust-based client relationships through education, not fearWhy hyper-targeted outreach beats mass sales every timeWil and Jay also share lessons on building thought leadership, owning your local market, and creating long-term business value through education, transparency, and community building.This episode blends technical insight, business strategy, and real-world GTM wisdom, perfect for leaders in software, security, and tech services who want to ship faster, safer, and smarter.Find Jay on LinkedIn: https://www.linkedin.com/in/jayaigner/Find Wil on LinkedIn: https://www.linkedin.com/in/wilklu/

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 U.S. military, intelligence community, and private sector, explaining how misaligned incentives in software manufacturing created systemic cybersecurity risks and what it takes to fix them.Together, Wil and Lauren explore:- What Secure by Design really means and why it matters for every business.- The U.S. government’s role in shifting cybersecurity responsibility from the most vulnerable (like hospitals and small utilities) to the manufacturers.- How organizations can embed security into culture, leadership, and product design, not just code.- The evolution from checklist-based frameworks to outcome-based security.- Lessons from aviation and automotive safety that can guide the digital future.Whether you’re a cybersecurity leader, developer, policymaker, or tech founder, this conversation unpacks the cultural, economic, and policy forces shaping a safer digital world.Find Lauren on LinkedIn:https://www.linkedin.com/in/laurenz1010/Find Wil on LinkedIn:https://www.linkedin.com/in/wilklu/cybersecurity podcast, secure by design, cybersecurity leadership, software security, digital safety, national cybersecurity strategy, cybersecurity policy, Institute for Security and Technology, Lauren Zabierek, Will Klu, keyboard samurai, CISA, software development security, cyber resilience, cybersecurity culture

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 next✅ How shadow AI and ethical blind spots are creating new risks✅ What governments and companies are getting wrong about AI governance✅ How bias, bad data, and “AI experts” without expertise threaten real progress✅ The balance between automation, emotional intelligence, and human connection✅ Why loneliness, mental health, and generational change must factor into the future of work.This conversation goes beyond technology. It’s about humanity, leadership, and the choices shaping our collective future. If you lead people, build technology, or care about the impact of AI on our world, this episode will challenge how you think about innovation, ethics, and the future of work.🧠 Listen now to hear how leaders can evolve with, not against, AI.Find Dr. Kion here:LinkedIn: https://www.linkedin.com/in/kionahadiWebsite: https://kionahadi.comAI leadership, Future of Work, Ethical AI, Cybersecurity Podcast, Tech Leadership, Digital Transformation, Artificial Intelligence Ethics, Human in the Loop, LegalTech, Data Governance, Workplace Culture, Leadership in AI, Keyboard Samurai, Wil Klu, Dr Kion Ahadi

🎙 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:• The evolution of AI from traditional machine learning to neural networks• Why modern AI is really “autocomplete on steroids”• How to bridge the communication gap between engineers and business leaders• What AI debt is and why it’s already hitting companies hard• The truth about security, governance, and AI-assisted coding• A brilliant analogy that explains how image generation actually worksIf you’ve ever wondered how AI really “thinks,” what’s behind tools like ChatGPT, or how to stay relevant in an AI-powered world, this episode is your field guide.🧠 Perfect for: business leaders, technologists, product managers, cybersecurity pros, and anyone trying to understand AI without a PhD.📘 About Sairam’s book:AI for the Rest of Us is an illustrated, plain-English introduction to artificial intelligence written for non-coders and non-mathematicians who still want to understand what’s happening under the hood.Find Sairam on LinkedIn: https://www.linkedin.com/in/sairam-sundaresan/Pre-order "AI for the Rest of Us" https://www.amazon.com/dp/B0F29THNLTLearn AI along with 22k+ learners from top tech firms in silicon valley: https://newsletter.artofsaience.com

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 testing has evolved, why assumed-breach testing is critical today, and how M&A (mergers and acquisitions) pose unseen security risks.💡 You’ll learn:→ Why pen testing isn’t as simple as “breaking in” anymore→ How assume-breach scenarios reveal real organizational risk→ The security pitfalls hiding inside M&A integrations→ Why mentoring, teaching, and community are vital for the next wave of cybersecurity talent→ How ethical hacking has changed — and why it’s never been more importantWhether you’re a CISO, security leader, aspiring pen tester, or just curious about what goes on inside the hacker mindset, this episode will leave you with practical insights, industry wisdom, and a renewed sense of why mentorship matters in cybersecurity.Find Phil: https://www.linkedin.com/in/phillipwylie/https://www.youtube.com/ ⁨@PhillipWylie⁩  https://x.com/PhillipWyliehttps://www.instagram.com/phillipwylie/

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 "lessons learned" from the ongoing incident at Jaguar, Land Rover causing a company wide shut down currently. 🔍 What you’ll learn:Why OT cybersecurity is different from IT security, and why many teams still get it wrongHow to design security into industrial environments from day oneReal challenges facing critical infrastructure, manufacturing, and engineering firmsPractical advice for leaders building or maturing OT security programsWhether you’re a CISO, security leader, or just curious about the hidden world of industrial cybersecurity, this conversation will change how you think about protecting what really keeps our world running.🎧 Tune in now and subscribe to The Keyboard Samurai for more insights from the front lines of cybersecurity.Find Mike: LI: https://www.linkedin.com/in/mikeholcomb/web: https://www.mikeholcomb.com/YT: https://www.youtube.com/ ⁨@utilsec⁩ 

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, we break down:✅ How cyber insurance actually works (beyond the fine print)✅ What insurers look for in your security posture✅ The biggest misconceptions about coverage and payouts✅ Why small and mid-sized businesses are prime ransomware targets✅ Practical steps to reduce premiums and improve resilienceIf you’re a business leader, CISO, or IT decision-maker, this conversation will give you the inside view on bridging risk management, insurance, and cybersecurity.🎧 Tune in now to learn how to protect your business from both hackers and financial fallout.Find Joehttps://www.linkedin.com/in/joeerle/

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 2025 and beyond✅ Why automation and AI are changing compliance forever✅ How security and business leaders can align risk with growthIf you’re a CISO, security leader, or business exec, this conversation is packed with practical insight on building smarter, faster, and more human-centric GRC programs.🎧 Tune in to learn how to future-proof your compliance strategy today.Find AJ: LinkedIn: https://www.linkedin.com/in/ajyawn/YT: https://www.youtube.com/ ⁨@Cybertakes⁩ 

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 risk management→ Balance AI’s power for defenders with its use by attackers→ Build governance programs to keep employees (and data) safePerfect for security leaders, IT pros, and executives who want to understand AI’s real impact on cybersecurity leadership.Find Marcel on LinkedIn: https://www.linkedin.com/in/marcelvelica/

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 you’re a cyber/tech leader, founder, or aspiring executive, this conversation will give you actionable insights on leadership, growth, and navigating the path to the top.Find Emma on LinkedIn:https://www.linkedin.com/in/emmajeyre/Her firm Obsidianhttps://www.obsidianblack.org/

🎙️ Former ISC² Board Chair Reveals the Truth About Cybersecurity CertificationsEver 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 critical difference between education and training (and why it matters for your career)✅ How to study the RIGHT way✅ Red flags that separate real security pros from pretenders✅ Why employers can't find qualified cybersecurity talent✅ Career advice for breaking into cybersecurity in 2025+✅ The hidden impact of AI and IoT on security careersDan shares insider insights from his time at ISC², including why judgment-based certifications like CISSP are so challenging and valuable, plus practical study strategies that actually work.Whether you're studying now, hiring security professionals, or considering a career change into cybersecurity, this episode delivers actionable insights from someone who helped shape the certification industry.Guest: Dan Houser - 24-year cybersecurity veteran, former ISC² Board Chair & Treasurer, Oracle Cloud Security ProfessionalFind Dan: https://www.linkedin.com/in/dan-houser/Host: Wil Klusovsky (Wil Klu) - Cybersecurity executive and industry veteran🎧 Subscribe to Keyboard Samurai for more cybersecurity career insights and industry wisdom!

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 own path✅ How empathy and authenticity make cybersecurity leaders more effective than fear-driven management✅ The balance between technical expertise and human connection in security leadership✅ Lessons from coaching tech executives who struggle to lead with humanity✅ Practical ways to build stronger teams, better communication, and a culture that people want to followThis conversation isn’t just for cybersecurity pros—it’s for any leader, founder, or executive who wants to build trust, inspire their team, and grow with resilience.🔍 Key Topics CoveredLeadership in cybersecurityFractional CISO insightsSpeaking & coaching for tech leadersBuilding authentic cultureWhy kindness is a competitive advantageFind Dom:Linkedin: https://www.linkedin.com/in/domvogel/Web: https://www.vogelleadershipcoaching.com/👉 Don’t forget to subscribe for more candid conversations with cybersecurity and tech leaders.

In this episode of Keyboard Samurai, Wil sits down with cybersecurity veteran Craig Taylor of Cyberhoot a 30-year industry pro who blends psychology and cyber know-how to tackle one of the toughest challenges in security: human behavior.Craig shares how he built a phishing awareness and EU-wide training program that actually changes behavior, not just checks compliance boxes. From his early days convincing companies to buy their first firewalls, to founding his own firm dedicated to cyber literacy, Craig reveals:✅ Why most training fails (and how to fix it)✅ How psychology and operant conditioning can improve security culture✅ Lessons learned running phishing simulations that people don’t ignore✅ What European companies get right—and wrong—about compliance training✅ Practical tips for CISOs and security leaders to boost resilience through peopleWhether you’re a CISO, SOC manager, or security leader trying to reduce risk at scale, this conversation delivers battle-tested insights you can apply right now.🎧 Listen to learn how to turn phishing training from a checkbox into a cultural advantage.Find Craig: Linkedin: https://www.linkedin.com/in/craigmtaylor/Web: https://cyberhoot.com/

Tired of the same boring security awareness training? So is Amy Stokes-Waters, CEO of The Cyber Escape Room Company. In this episode, we explore how she’s transforming cybersecurity culture with interactive, gamified escape rooms that make learning unforgettable.We dive into:✅ Why traditional security awareness fails✅ How gamification and storytelling boost engagement✅ Real-world escape room scenarios for phishing, insider threats & OT security✅ Using “think like a hacker” training to change behaviorWhether you’re a CISO, security leader, HR manager, or just someone tired of checkbox training, you’ll learn fresh ways to engage teams, build security culture, and actually make it stick.Listen in and see why flipping the script might be the best thing you can do for your security program.Find Amy: Linkedin: https://www.linkedin.com/in/amystokeswaters/Web: https://www.cyberescaperoom.co/

In this episode of Keyboard Samurai, Heather Noggle joins Will to unpack how cybersecurity and tech firms can gain a competitive edge by rethinking how they attract, train, and retain talent.We cover:✅ Why soft skills matter more than ever✅ How Gen Z is reshaping workplace expectations✅ Fixing broken cybersecurity career paths✅ Why degrees don’t equal capability✅ The power of clarity in job roles and trainingWhether you're a leader, HR pro, or future CISO—this is your playbook for building the next wave of great talent.🎧 Listen now and subscribe for more unfiltered insights on cyber, culture, and growth.Find Heather: https://heathernoggle.com/https://www.linkedin.com/in/heathernoggle/

In this episode of The Keyboard Samurai, Wil sits down with Sam and Michael, the founders behind HOU.SEC.CON, to unpack what it really takes to lead in security, build trust at scale, and create one of the most community-driven cyber events in the country.You’ll hear practical insights on:→ Why great leaders make their teams look good→ How to stay grounded when others see you as the expert→ Translating technical skill into business influence→ The role of trust in both cybersecurity and leadership→ How storytelling beats technical jargon every timeThis is a must-listen for security professionals, startup leaders, and anyone shaping culture in high-stakes environments.Practical. Real. No fluff.Find them: Michael: Farnum: https://www.linkedin.com/in/mfarnum/Sam Van Ryder: https://www.linkedin.com/in/svanryder/https://www.houstonseccon.com/

Why Security Culture Fails (And How to Fix It)In this episode, Wil sits down with Mike Williams, President of Appalachia Technologies, to unpack what really drives a strong security culture. It’s not just about tools or policies. It’s about leadership, intentional programs, and turning security into a shared mission. Learn how to engage employees, get leadership buy-in, measure meaningful KPIs, and make security a true business differentiator.Perfect for CISOs, IT leaders, and security pros ready to move beyond checkbox compliance.Find Mike: https://www.linkedin.com/in/mike-williams-8092842/https://appalachiatech.com/

What really makes a great cybersecurity consultant?In this episode, Will Klusovsky sits down with Ryan Rosado—Air Force veteran, security advisor, and startup mentor—to break down what most people get wrong about consulting in the cyber world.Whether you're a hands-on engineer stepping into advisory, or a seasoned consultant looking to refine your edge, this conversation delivers hard-earned wisdom, candid stories, and actionable takeaways.🔑 Topics we cover:↳ Why consulting isn’t just “doing the work”↳ How to build trust with clients (even when telling hard truths)↳ Teaching soft skills like tact, business acumen, and adaptability↳ The role of personal branding in long-term consulting success↳ Why feedback is the most underused growth tool↳ How companies should train (and retain) their consultants👀 Don’t just be billable. Be better.—📌 Connect with Ryan on LinkedIn: https://www.linkedin.com/in/ryanrenerosado/

Building a Cyber Biz From Scratch: Zero Plan, Pure GritWhat does it really take to build a business in cybersecurity as a first-time founder with no funding, no roadmap, and no safety net?In this episode, Wil sits down with Joe Head, founder of Molto, to break down the raw, real journey from recruiter burnout to building a thriving branding and marketing agency for cybersecurity companies. Joe shares how he started with nothing but his industry knowledge and scaled by listening to client needs, not by chasing perfect plans.You’ll learn:Why early-stage execution is more important than over planningHow to package your expertise and sell it fastThe power of iteration, network-building, and trusting the processThe traps of perfection, imposter syndrome, and building aloneJoe’s approach is gritty, practical, and deeply human. If you’re a founder, freelancer, or consultant in cybersecurity, this episode is for you.Connect with Joe on LinkedIn: https://www.linkedin.com/in/joehead1

GRC isn't about paperwork. It's about business impact.Wil and Tom Richards break down how to deliver GRC services clients actually want. They cover the mindsets that kill value, how to align with real business goals, and why outcome-based thinking beats checkbox compliance every time.Perfect for MSPs, consultants, or anyone building security programs that work in the real world.Find Tom on Linkedin: https://www.linkedin.com/in/tsr-etp/

What happens when a security leader becomes a founder?In this episode of The Keyboard Samurai, Wil sits down with Stas, Founder and CEO of Comply, to unpack what it really takes to go from building security programs to building a company.They break down the hard-earned truths every founder hits:What happens when the builder shouldn't be the CEOHow to transition from operator to people leaderWhen to let go of ego, and when to double downHow to burn capital smart before revenue hitsThey also cover practical lessons on hiring interns like future executives, sizing your offers across different markets, and building a network that drives real inbound growth.Whether you're pre-revenue or scaling into new markets, this is a blueprint you can use right now.Watch the full episode to learn how to scale without stalling.Find Stas: Linkedin: https://www.linkedin.com/in/stas-bojoukha/web: https://compyl.com/

This week, Wil sits down with cybersecurity & AI specialist Joseph Cardin to dive deep into the overlooked frontier of AI: not just using it for defense, but defending it. From insecure GPU infrastructure to the coming tidal wave of edge-deployed models, Joe breaks down why AI security is the next OT ripe with opportunity and riddled with risk. Whether you're at an MSSP or building security into a product, you'll want to hear how threats are evolving and what proactive leaders are doing about it now. This one’s all edge, no fluff. Let’s hack into it.Find Joe:Linkedin https://www.linkedin.com/in/josephcardin/Bluesky: @joecarden.bsky.social

What do psychology, finance, and cybersecurity have in common? Everything, when it comes to influence. Jackie McGuire joins Wil Klusofsky to unpack how emotional intelligence and decision-making theory reshape how we sell cyber. From why CISOs freeze to how sales content actually fails, this episode exposes the hidden human dynamics that make or break deals. If you sell, market, or build for the cybersecurity space, this episode rewires your approach.Find Jackie on LInkedin: https://www.linkedin.com/in/jackiesinsecurity/

What if your next hire wasn’t human? In this episode, Wil Klusovsky sits down with Randy Blasik, co-founder of The Compliance Aid, the first AI-powered cybersecurity auditing team, to unpack how AI is radically transforming MSPs, MSSPs, and security service orgs.They cover the real story behind AI in cyber: where it works, where it fails, and how to build AI-driven operations that scale faster and cost less, without sacrificing quality.👉 Whether you're running a service org or scaling your security stack, this episode will show you how to stop overhiring and start deploying intelligence.✅ How to use AI to reduce burnout & boost delivery✅ Why "just experimenting" with AI isn't enough✅ How to train AI like a team member, not a tool If you're still debating AI, you're already behind.🎧 Listen in to learn how the smartest teams are turning AI into margin, scale, and competitive edge.Find Randy @ Linkedin https://www.linkedin.com/in/thecomplianceaide/Web: https://www.thecomplianceaide.com/YT @randyblasik7066

In this episode of The Keyboard Samurai, Will Klusofsky chats with cybersecurity strategist Jeffrey Wheatman about the brutal truth of selling cyber tech to the business. From storytelling to sales misalignment, they break down why blinky lights don’t close deals, and how to actually get through to execs, investors, and boards. If you're building, selling, or marketing cybersecurity products or services, this one’s a masterclass in cutting through the noise and connecting to business impact.Find Jeffrey: https://www.linkedin.com/in/jnwheatman/