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 demand

• Selling to MSPs vs selling through MSPs

• Why “the product sells itself” is a dangerous myth

• How product-led growth really works in the MSP space

• The role of sales enablement in startup survival

• Why founder-led sales breaks at scale

If 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/jayoung1216

• Email: [email protected]

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 miss

If 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]

Phone: 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

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 problem

The difference between solving symptoms vs fixing root causes

Why complex threats often need simple controls, not more analytics

How “block everything, allow by exception” changes security outcomes

Why UX and product usability decide whether security tools succeed

How customer advisory boards shape better products

Why attackers no longer need endpoint access to cause damage

This conversation is a must-listen for:Founders, product leaders, CISOs, MSPs, and anyone building or buying security products.

Links & Resources

Rob: https://www.linkedin.com/in/threatlockerrob/

ThreatLocker: https://www.threatlocker.comhttps://www.youtube.com/@ThreatLocker

Subscribe for weekly conversations on cyber & tech biz, GTM, and building products that actually work.

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 tools

Bob 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/

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 ops

Find Carolyn on LinkedIn: https://www.linkedin.com/in/carolynhealey/

Website: servicemarketing.com

Find Wil on LinkedIn: https://www.linkedin.com/in/wilklu/

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 Kevin

https://www.linkedin.com/in/itprofessionalkevinapolinario/

https://www.youtube.com/@KevtechITSupport

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 risk

How to build practical AI governance, KPIs, and business value tracking

Key agentic AI risks including identity gaps, cascading hallucinations, tool poisoning, model drift

The questions to ask before buying AI or agentic tools for your SOC

How leaders can safely accelerate AI adoption without creating new liabilities

Find Rock here:

• LinkedIn: https://www.linkedin.com/in/rocklambros/

• Website: https://rockcyber.comAI security

OWASP AI, agentic AI, cybersecurity leadership, CISO strategy, AI governance, LLM security, Shadow AI, SOC automation, AI compliance, model drift, AI risk management, enterprise AI

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