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 sense

Follow The Keyboard Samurai for more practical conversations on cyber, tech, leadership, and business risk.

Find Randall: https://www.linkedin.com/in/randall-jackson-41ciso/

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 incident

Follow The Keyboard Samurai for more plain-English conversations on cybersecurity, business risk, and technology leadership.

Find Will: https://www.linkedin.com/in/wi1bo/

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 partners

Follow 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/vilogics

www.vilogics.com

Craig: https://www.linkedin.com/in/craigaduckworth/

BW Design Group: https://www.linkedin.com/company/barry-wehmiller-design-group/

http://www.bwdesigngroup.com/

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 consumers

Follow 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/

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 recovery

Follow 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 facilities

Follow 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 conference

Follow 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 abuse

Learn why carriers lose visibility when traffic shifts into encrypted channels

Understand how phone farms and SIM boxes power large-scale scam campaigns

See how AI helps attackers test and improve fraud messaging in real time

Explore the regulatory and data-sharing barriers slowing down enforcement

Follow 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 sales

Follow 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 MSSPs

Follow 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/