Keyboard Samurai

Building a Cyber Biz From Scratch: Zero Plan, Pure GritWhat does it really take to build a business in cybersecurity as a first-time founder with no funding, no roadmap, and no safety net? In this episode, Wil sits down with Joe Head, founder of Molto, to break down the raw, real journey from recruiter burnout to building a thriving branding and marketing agency for cybersecurity companies. Joe sh...

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...

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 W...

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 securit...

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 c...

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 an...

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 o...

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...

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:...

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...

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.cybers...

Wil sits down with Jen, Co-Founder & COO of Legato security and talks about how the plethora of tools and the confusion around the cybersecurity landscape can give you a "false sense of security." Find Jen on LInkedIn: https://www.linkedin.com/in/jennifergreulich/ Legto Security: https://www.legatosecurity.com/

Wil sits down with Reanna Schultz to talk about managing a Security Operations Center (SOC), and all that goes with it. We hit on the technical trials and tribulations, the keys to managing these complicated teams and the right ways to build and run one for you clients or business. Find Reanna: Linkedin: https://www.linkedin.com/in/reanna-schultz/Youtube: https://www.youtube.com/  ⁨@CyberSpeakLabs...

Wil sits down with Derek to discuss the importance of mental health in cybersecurity, specifically how leaders need to be aware of it and how to take care of their teams, and themselves. You can find Derek "The Cyber Warrior" Scheller @ cyberwarriorstudios.com Linkedin https://www.linkedin.com/in/dschellerjr/ YT: www.youtube.com/@CyberWarriorStudios

This week we chat with Ron about managing client expectations, how do you set them, making sure both sides know what in scope & out of scope, the value of having these conversations and more! Find Ron on LinkedIN https://www.linkedin.com/in/ron-sharon/

Wil sits down with Neal Foard of storyfire.net, a man with a powerful ability to tell stories and help shape viewpoints. We discuss why storytelling works so well and how as cybersecurity professionals we need to learn to use it. Helping in our day to day efforts, marketing, sales and more. Find Neal at www.storyfire.net Linkedin: https://www.linkedin.com/in/neal-foard/Tiktok: https://www.tiktok.c...

Ross author of "Cyber for Creators" and host of Inside the Network sits down with Wil to discuss the emerging markets for cybersecurity, the VC landscape, product creation and a ton more in this episode. Find Ross: -Linkedin: https://www.linkedin.com/in/rosshaleliuk/ -blog: https://ventureinsecurity.net/ -podcast: https://insidethenetwork.co/ Grab his amazon best seller: https://www.amaz...

Wil talks with Joel Fulton, Founder & CEO of Lucidum about the importance of mental health in the cybersecurity industry, how leaders can manage / prevent burn out. We talk about putting some perspective on the work we do which while is important, not more important than our lives. You can find Joel -on Linkedin https://www.linkedin.com/in/drjoelfulton/ -web https://lucidum.io/

Wil talks with Jess discussing her time in the Federal and Public Sector working as a CISO and the value & challenges of it. Find Jess @ Linkedin: https://www.linkedin.com/in/jessica-hoffman-cissp/

Wil talks with CEO of High Wire Networks, Ed Vasko about the challenges and risks surrounding technical debt in cybersecurity. Find Ed @ https://www.linkedin.com/in/ed-vasko-cissp-a146283/

Wil talks with Chris about the right and wrong things to do when marketing in cybersecurity. Demand gen, lead gen, digital, ads, client profiles, journeys and more.

Bare Knuckles & Brass Tacks podcasters George Kamide & George Al-Koura joined me for a discussion about buying & selling security. We have all sides of the table for this one. We discuss the value of relationships, how to properly build them, how to engage CISOs, how to listen to your clients and a ton more... Check them out at: https://www.bareknucklespod.com/ George K - https://www.l...

Wil & Chad discuss some of the key things to consider when building a new security product, such as business problem being solved, how to develop and manage the product, finding your ICP and more. You can find Chad on LinkedIN https://www.linkedin.com/in/chadboeckmann/ Chad currently manages the team and delivery at https://trustmapp.com. Check out what they are doing.

Peter & Wil discuss the nuances of resources working in other countries, including overcoming preconceived notions from potential clients and how businesses can benefit. You can find Peter & his company Nearshore Cyber @ Linkedin: https://www.linkedin.com/in/schawacker/ Community: https://www.nearshorecyber.community/ X: https://x.com/PeterSchawacker Bsky: https://bsky.app/profile/nearshor...

We talk with Pete about recuriting in cybersecurity, some of the facts and fiction around our talent gap and how business can get the talent they need and retain it. You can find Pete on Linkedin @ https://www.linkedin.com/in/petestrouse/ And listen to his podcast Talent Gap Fireside Chat @ https://www.linkedin.com/company/talent-gap-fireside-chat/