Keyboard Samurai

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

What happens when a security leader becomes a founder?

In this episode of The Keyboard Samurai, Wil sits down with Stas, Founder and CEO of Comply, to unpack what it really takes to go from building security programs to building a company.

They break down the hard-earned truths every founder hits:

What happens when the builder shouldn't be the CEO

How to transition from operator to people leader

When to let go of ego, and when to double down

How to burn capital smart before revenue hits

They also cover practical lessons on hiring interns like future executives, sizing your offers across different markets, and building a network that drives real inbound growth.

Whether you're pre-revenue or scaling into new markets, this is a blueprint you can use right now.Watch the full episode to learn how to scale without stalling.

Find Stas:

Linkedin: https://www.linkedin.com/in/stas-bojoukha/

web: https://compyl.com/

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

Find Joe:

Linkedin https://www.linkedin.com/in/josephcardin/

Bluesky: @joecarden.bsky.social

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

Find Jackie on LInkedin: https://www.linkedin.com/in/jackiesinsecurity/

What if your next hire wasn’t human? In this episode, Wil Klusovsky sits down with Randy Blasik, co-founder of The Compliance Aid, the first AI-powered cybersecurity auditing team, to unpack how AI is radically transforming MSPs, MSSPs, and security service orgs.They cover the real story behind AI in cyber: where it works, where it fails, and how to build AI-driven operations that scale faster and cost less, without sacrificing quality.

👉 Whether you're running a service org or scaling your security stack, this episode will show you how to stop overhiring and start deploying intelligence.

✅ How to use AI to reduce burnout & boost delivery

✅ Why "just experimenting" with AI isn't enough

✅ How to train AI like a team member, not a tool

If you're still debating AI, you're already behind.

🎧 Listen in to learn how the smartest teams are turning AI into margin, scale, and competitive edge.

Find Randy @

Linkedin https://www.linkedin.com/in/thecomplianceaide/

Web: https://www.thecomplianceaide.com/

YT @randyblasik7066

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

Find Jeffrey: https://www.linkedin.com/in/jnwheatman/

In this episode of Keyboard Samurai, host Wil Klu sits down with Nat Shere, Director of Technical Services at Craft Compliance, to break down what pen testing should look like. From hiring red teamers to avoiding scan-in-a-box vendors, Nat shares war stories, hiring tips, and how to extract real value from your testing program. Whether you're building a team or buying services, these insights will save you money and headaches.

Perfect for CISOs, MSSP leaders, tech leaders, and anyone who's ever read a pen test report and thought, “...that’s it?”

Find Nat: Linkedin: https://www.linkedin.com/in/nathaniel-shere/

Thinking of breaking into InfoSec consulting? Greg Schaffer spills decades of wisdom—what to do, what not to do, and why most fail before they start. Whether you're dreaming of becoming a vCISO or just want to avoid rookie mistakes, this episode is packed with gritty truths, business smarts, and a few laughs to keep it real.

Find Greg:

LinkedIn: https://www.linkedin.com/in/gregoryschaffer/

YT: https://www.youtube.com/ ⁨@vciso⁩ 

Spotify: https://open.spotify.com/show/3A9PI9NlmBbSKAhHGivspV?si=2f2ddd1fba474616

In this episode of Keyboard Samurai, Wil sits down with Sly Gittens—Microsoft strategist and founder of Tech Simplified—to unpack the real strategies behind career growth in cybersecurity. From why your network is more powerful than your resume, to the brutal mistakes that stall careers before they even start, this episode delivers raw insight with zero fluff. Whether you're just breaking into tech or leveling up your leadership game, this conversation will change how you think about relationships, value, and visibility. Don't just connect—connect with purpose.

Find Sly @

web: https://www.sgtechsimp.com/

YT: https://www.youtube.com/ ⁨@TechSimplifiedAI⁩ 

LinkedIN https://www.linkedin.com/in/slygittens/

Host Wil Klu guides an insightful conversation with Dani and Ben about modern cybersecurity marketing—blending strategy, psychology, and storytelling. Together, the trio explores how to use data intelligently, engage technical audiences authentically, and elevate the industry’s narrative beyond fear-based messaging.

Find Dani:

LinkedIn: https://www.linkedin.com/in/daniarad/

Web: https://www.cybersynapse.io/

Find Ben:

LinkedIn:https://www.linkedin.com/in/benjaminnsiegel328/Web: https://www.linkedin.com/company/the-cybernest/