Keyboard Samurai

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 leadership

Perfect 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 SDLC

The true cost of skipping testing and secure design

Why QA and cybersecurity share the same challenges in proving value

How to build trust-based client relationships through education, not fear

Why hyper-targeted outreach beats mass sales every time

Wil 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/kionahadi

Website: https://kionahadi.com

AI 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 works

If 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/B0F29THNLT

Learn 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 important

Whether 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/PhillipWylie

https://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 wrong

How to design security into industrial environments from day one

Real challenges facing critical infrastructure, manufacturing, and engineering firms

Practical advice for leaders building or maturing OT security programs

Whether 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 resilience

If 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 Joe

https://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 growth

If 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) safe

Perfect 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/