Keyboard Samurai

Wil Klu
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This is a podcast about the business of cyber & tech. Host Wil Klusovsky (Wil Klu) brings on guests leading the industry. We discuss topics to help businesses and individuals improve across all lines of the business from services, product, marketing, operations, sales and tech. There is no product pitching, it's a contribution to the industry to help educate, inform, and maybe entertain. If you'd like to reach out to Wil for services, content, contributions, to be on the podcast or anything else visit www.wilklu.me and use the contact form. Follow wil @ linkedin.com/in/wilklu

  1. 5D AGO

    Roman Kruglov - AI is more than LLMs: How Model Choice Changes Risk

    If your AI security plan starts and ends with “LLM,” you’re already behind. Wil talks with cybersecurity architect Roman Kruglov explains why “AI” is not one risk bucket and how security changes across LLMs, SLMs, RAG, and data-specific models. We talk on-prem vs cloud, API security basics that still get missed, and the bigger problem most teams ignore: data labeling, DLP, and permissions hygiene. You’ll also hear why Copilot can surface what SharePoint search never would, and why identity (including non-human identities) is the next battlefield. Key takeaways: How to compare LLM vs RAG security risks Why data labeling + DLP matter before you deploy AI Copilot, SharePoint/Teams sprawl, and “public is public” Governance templates and guardrails that don’t block delivery Why identity is becoming the new perimeter Follow the show, leave a quick rating, and share this episode with the person pushing “AI” in your org.

    23 min

  2. JAN 31

    Steve Doty & Chris Goodman - When SaaS Growth Outruns their Cyber Systems

    Fast SaaS growth exposes problems most teams don’t see until it’s too late. In this episode of The Keyboard Samurai Podcast, I break down what happens when revenue, customers, and expectations scale faster than the systems meant to support them, with Steve Doty and Chris Goodman of Defensible Technology as the conversation drivers. We talk about how compliance milestones like SOC 2 create a false sense of security, why operational maturity lags behind growth, and how security and process debt quietly become growth blockers. This episode covers: Why SOC 2 is a starting point, not a finish line How SaaS growth reveals gaps in security and operations The difference between being compliant and being resilient Why teams underestimate the cost of security and process debt How misaligned systems slow deals, erode trust, and increase risk What founders and operators should fix before growth forces the issue If you’re building or scaling a SaaS company, this episode reframes security, compliance, and operations as growth infrastructure—not checkboxes. This isn’t about fear.It’s about staying ahead of your own success. Find Chris & Steve: https://www.linkedin.com/in/stevedoty/ https://www.linkedin.com/in/christopher-goodman-007/

    42 min

  3. JAN 24

    Ben Wilcox - Modernizing Cyber Tech Stack

    Most organizations say they want to modernize their cybersecurity stack. What they usually mean is buying more tools. In this episode of The Keyboard Samurai Podcast, I break down what modernizing security actually looks like with Ben Wilcox—and why most “modern” security programs are still built on fragmented data, disconnected tools, and the wrong definition of risk. We talk about why modernization isn’t a technical exercise, how operational risk should drive security decisions, and why identity has quietly become the biggest risk surface in most environments. This conversation covers: Why the board cares about operational risk, not tools How disconnected security platforms create blind spots Why SOC, GRC, and user awareness can’t operate in silos Identity as the dominant risk driver in modern environments Why automation and AI fail without clean data and defined process The coming identity problem created by AI agents If you’re responsible for security strategy, modernization, or explaining cyber risk to the business, this episode reframes how to think about tools, data, and outcomes. This isn’t about buying more technology.It’s about building a system that actually works. Find Ben:https://www.linkedin.com/in/ben-wilcox/ #podcast #cybersecurity #cyber #tech #MSS #MSP #startup

    22 min

  4. JAN 17

    Jeffery Wheatman - Cyber Board Conversations

    Most cybersecurity leaders lose the boardroom before the conversation even starts. In this episode of The Keyboard Samurai Podcast, I sit down with Jeffery Wheatman to break down why board-level cybersecurity conversations fail, and what executives actually care about when risk is on the table. Jeffery pulls back the curtain on how boards think, why security teams struggle to get traction, and how translating cyber risk into business impact is the difference between influence and irrelevance. We cover: What boards really care about (and what they don’t) Why acronyms, jargon, and technical detail kill credibility The difference between owning risk and advising on risk Why checkbox compliance creates a false sense of security How to frame cyber issues in terms of money, operations, and accountability What CISOs get wrong when communicating with executives If you’re a CISO, security leader, or executive trying to get buy-in at the board level, this episode is a masterclass in speaking the language of decision-makers. This isn’t about better slides.It’s about better conversations.

    21 min

  5. JAN 10

    Megan Killion - Selling Cybers to SMBs isn't about Security

    In this episode of Keyboard Samurai, I sit down with Megan Killion, founder of Pisces Growth, to unpack why fear-based security messaging shuts small business owners down—and why most cybersecurity sales fail before they even start. Megan breaks down what SMB buyers actually care about, how words like “cybersecurity” trigger mental spam filters, and why selling risk without understanding the business destroys trust. We cover: Why SMB owners shut down the moment you say “cybersecurity” How fear-based selling signals you don’t understand the business Why SMBs care more about money and time than hypothetical breaches The difference between compliance-driven buyers and everyone else Why niching and speaking the buyer’s language matters How to qualify out early instead of wasting sales cycles If you sell cybersecurity, run an MSP, or market to SMBs, this episode will change how you think about messaging, demand, and trust. This isn’t about scare tactics.It’s about meeting buyers where they actually are. Find Megan here: LinkedIn: ⁠https://www.linkedin.com/in/megankillion/

    25 min

  6. JAN 3

    Jeremy Young- Bringing Products to MSPs & Startup Scaling

    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: jeremy@huntress.com

    22 min

  7. 12/27/2025

    Baxter Lanius - Tech Start Up Stories

    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: baxter@alternativepayments.io 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

    22 min

  8. 12/20/2025

    Rob Allen - Building Security Products That Actually Solve Real Problems

    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.

    23 min
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About

This is a podcast about the business of cyber & tech. Host Wil Klusovsky (Wil Klu) brings on guests leading the industry. We discuss topics to help businesses and individuals improve across all lines of the business from services, product, marketing, operations, sales and tech. There is no product pitching, it's a contribution to the industry to help educate, inform, and maybe entertain. If you'd like to reach out to Wil for services, content, contributions, to be on the podcast or anything else visit www.wilklu.me and use the contact form. Follow wil @ linkedin.com/in/wilklu

Information

  • Creator
    Wil Klu
  • Years Active
    2024 - 2026
  • Episodes
    61
  • Rating
    Clean
  • Copyright
    © Wil Klu
  • Show Website
    Keyboard Samurai