PODCAST · business
Keyboard Samurai
by Wil Klu
This is a podcast about the business of cyber & tech. Host Wil Klusovsky (Wil Klu) brings on guests leading the industry. We discuss topics to help businesses and individuals improve across all areas of cybersecurity. There is no product pitching, it's a contribution to the industry to help educate, inform, and maybe entertain. If you'd like to reach out to Wil for services, content, contributions, to be on the podcast or anything else visit www.wilklu.me and use the contact form. Follow wil @ linkedin.com/in/wilklu
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Niki Weiss - Digital Thanatology: Planning Your AI and Digital Legacy
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 continuityFollow 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-JxLOSkrcEo66HDugEndevo.life
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Bryan DeBois -Industrial AI, Digital Twins, and Safer OT Automation
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 floorLearn how AI can optimize legacy manufacturing equipmentExplore digital twins and deep reinforcement learningIdentify cybersecurity concerns created by IT/OT convergenceExamine the growing manufacturing expertise gapRecognize the limits of generative AI in critical environmentsFollow 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/
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Matt Meis - How Cyber Fraud, Money Mules, and Laundering Work
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 riskFollow 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
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Nat Shere — AI Didn’t Kill Pentesting. It Made Judgment More Valuable.
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 pathsFollow 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/
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Carl Stern - AI Governance, Cyber Risk, and the Future of Work
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 slowlyFollow 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/
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Orville Williams - Securing M&A Integration Without Importing Hidden Risk
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 fraudFollow 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/
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Kurtis Minder - Dark Web Intelligence and Real-World Cyber Risk
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 riskFind Kurtis: www.kurtisminder.comhttps://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.
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Christophe Foulon - Agentic AI Governance Starts With Identity
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 modernization, regulated industries, and hybrid environments.Key takeaways:• Start AI governance with intent, access, and ownership• Treat AI agents as non-human identities with real risk• Threat model agents before they touch sensitive systems• Use clearer context to reduce token spend and bad outputs• Build the business case for specialized AI tools• Connect AI productivity to security, compliance, and business outcomesFollow The Keyboard Samurai for more conversations on cyber, AI, leadership, and the business side of technology.Find Christophe on Linkedin: https://www.linkedin.com/in/christophefoulon/
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Matt Sharp - AI Adoption Needs Agility And Business Outcomes
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, learning curves, small language models, token costs, and the growing pressure to turn AI experiments into real business outcomes.Key takeaways:• Why AI adoption requires agility, not fixed best practices• How CISOs can help secure fast-moving AI bets• Why teams need hands-on AI learning, even without production use• How token costs and prompt quality may change workforce value• Why private equity and investors are pushing AI toward measurable outcomes• How design partnerships can help security teams keep paceFollow The Keyboard Samurai for more conversations on cyber, AI, leadership, and the business side of technology.Find Matt: https://www.linkedin.com/in/ciso-mba/https://www.cisoevolution.com/His book: https://www.amazon.com/CISO-Evolution...Co authored with Rock Lambros who was also on KBS: https://open.spotify.com/episode/1hC2q4dwvLqfJ65SHqqWdr?si=3GtedE4sRy6BCXteD2Bf-A
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Randall Jackson - Modern Cyber Attacks and Identity Security
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, MSSPs, and financial services. This episode is for business leaders, CISOs, IT leaders, and anyone trying to understand how cybersecurity works in the real world now.Topics covered:• Why identity compromise changed the attack model• How AI makes phishing cleaner and harder to spot• Why once-a-year security training is not enough• How FIDO keys, MFA, PAM, and zero trust reduce risk• How CISOs prioritize vulnerabilities through business context• When outsourcing, managed security, or fractional CISO help makes senseFollow The Keyboard Samurai for more practical conversations on cyber, tech, leadership, and business risk.Find Randall: https://www.linkedin.com/in/randall-jackson-41ciso/
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Will Brooks - Quantifying Cyber Risk Before Buying Insurance
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 policies without getting buried in insurance jargon.Key takeaways:• Why cyber insurance got more serious after COVID and ransomware growth• How to think about policy limits based on actual business loss• Why CISOs often understand the risk, but CFOs need the dollars• What MSPs and consultants can say without trying to sell insurance• Why add-on cyber coverage may not be enough• How comprehensive cyber insurance covers more than one type of incidentFollow The Keyboard Samurai for more plain-English conversations on cybersecurity, business risk, and technology leadership.Find Will: https://www.linkedin.com/in/wi1bo/
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Craig Duckworth - Manufacturing industry: cybersecurity risk and business impact
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 risk, cyber insurance, business impact analysis, and security budgeting. Craig brings real-world industrial cybersecurity experience from systems integration, risk mitigation, and manufacturing environments where old assets, new connectivity, and limited budgets collide. This conversation is for manufacturing leaders, CIOs, CISOs, IT teams, OT teams, and executives who need a clearer way to protect production.Key topics covered:→ Turning OT cyber risk into business impact→ Prioritizing security spend when budget is limited→ Protecting legacy manufacturing systems→ Explaining cyber risk to leadership and boards→ Understanding cyber insurance limits→ Building a practical security roadmap→ Knowing when to use outside partnersFollow The Keyboard Samurai for more conversations on cyber, technology, leadership, and the business side of security.Wil: https://www.linkedin.com/in/wilklu/viLogics: https://www.linkedin.com/company/vilogicswww.vilogics.comCraig: https://www.linkedin.com/in/craigaduckworth/BW Design Group: https://www.linkedin.com/company/barry-wehmiller-design-group/http://www.bwdesigngroup.com/
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Merry Marwig - The Forgotten Endpoint in Cyber - Cars
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 systems create real privacy and security risk, and how CISOs can build vehicle data deletion into policies, vendor contracts, and lifecycle processes.In this episode:• Why cars are overlooked endpoints in cybersecurity programs• What sensitive data can remain inside infotainment systems• How fleet vehicles can expose corporate and employee data• Why NIST 800-88 and certificates of deletion matter• What CISOs should require from automotive vendors• How vehicle privacy affects companies and consumersFollow The Keyboard Samurai for more plain-English conversations on cyber risk, leadership, and the business side of technology.Find Merry: https://www.linkedin.com/in/marwig/
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Wil Klu - Build a Cybersecurity Program That Fits the Business
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.
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Fred Gordy - Secure Building Control Systems Before The Breach
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/
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Ken Fishkin - Building Cybersecurity Community That Creates Real Careers
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/
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Ian Matthews - Why Mobile Messaging Fraud Is Harder to Stop
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
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Jordan Benjamin - How Startup Sellers Win Without Burning Out
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/
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Jay McBain - Managed Services Partner Strategy for Growth in 2026
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/
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Patrick Sullivan - How to Govern AI Before It Governs You
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/
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Walter Haydock - AI Governance, Vendor Risk, and ChatGPT Reality
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/
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Jordan Snapper - Cybersecurity Marketing That Actually Creates Buyer Trust
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/
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Konnor Andersen - Cybersecurity Startup GTM: CISO Time, Trust, Channel Reality
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/
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Drew Simonis - Don't Care about Cyber so much
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/
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Robert Siciliano - Human-Centric Security Training
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
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Roman Kruglov - AI is more than LLMs: How Model Choice Changes Risk
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.
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Steve Doty & Chris Goodman - When SaaS Growth Outruns their Cyber Systems
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/
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Ben Wilcox - Modernizing Cyber Tech Stack
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
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Jeffery Wheatman - Cyber Board Conversations
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.
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Megan Killion - Selling Cybers to SMBs isn't about Security
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/
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56
Jeremy Young- Bringing Products to MSPs & Startup Scaling
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]
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55
Baxter Lanius - Tech Start Up Stories
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
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54
Rob Allen - Building Security Products That Actually Solve Real Problems
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.
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53
Bob Carver - Wild West of AI & Cybersecurity
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/
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52
Carolyn Healey - Tech Marketing in the Age of AI
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/
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51
Kevin Apolinario - Cyber & IT Career Insights
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
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50
Rock Lambros - AI Security for Business Leaders
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
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49
Dr. Eric Cole - Business of Cybersecurity: Risk, Politics, and Translation
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/
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48
Jay Aigner - QA - Cyber DevSecOps
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/
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47
Lauren Zabierek - Secure By Design
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
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46
Dr Kion Ahadi - The Future of Work and Leadership in Tech
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
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45
Sairam Sundaresan - AI for the Rest of Us Book
🎙 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
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44
Philip Wylie - Evolution of Ethical Hacking
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/
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43
Mike Holcomb - OT Security & Jaguar Land Rover Incident
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
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42
Joe Erle - Cybersecurity Insurance
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/
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41
AJ Yawn - The Future of GRC
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
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40
Marcel Velica - Cyber Leadership in the Age of AI
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/
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39
Emma j Eyre - Getting to the C Level
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/
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38
Dan Houser - Certifications in Cyber & IT
🎙️ 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!
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37
Dominic Vogel - The Power of Empathy, Authenticity & Kindness
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.
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ABOUT THIS SHOW
This is a podcast about the business of cyber & tech. Host Wil Klusovsky (Wil Klu) brings on guests leading the industry. We discuss topics to help businesses and individuals improve across all areas of cybersecurity. There is no product pitching, it's a contribution to the industry to help educate, inform, and maybe entertain. If you'd like to reach out to Wil for services, content, contributions, to be on the podcast or anything else visit www.wilklu.me and use the contact form. Follow wil @ linkedin.com/in/wilklu
HOSTED BY
Wil Klu
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