Best Small Business Cyber Security Guy Podcasts (2025)

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NSITSP Spotlight: Ryan Redmond of Optrua (EP 916) 31:36

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1d ago31:36

31:36

I chat with Ryan Redmond, founder of Optrua and a long-time advocate for smarter sales, better systems, and industry progress. Ryan walks us through his background in CRM and ERP, shares why MSPs struggle with sales automation, and explains the challenges facing IT professionals when adopting Microsoft Dynamics and integrating it with existing busi…

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Don’t VPN for Me, Argentina (EP 915) 43:13

6d ago43:13

43:13

I share the latest MSP field story—helping a client whose remote staffer in Argentina couldn’t connect via VPN. What starts as a routine setup turns into a wild ride through blocked IPs, throttled Starlink connections, and Argentina’s secret war on VPNs. Hear how Ubiquiti’s VPN options, Microsoft 365 authentication quirks, and a dash of Duo MFA fin…

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#87: How to Use AI to Create a Competitive Advantage Without Losing Control 24:22

6d ago24:22

24:22

AI can fuel your edge—or leak your data. In this episode, RealVNC CPO/CTO Neil Gad joins David to unpack zero-trust, workspace segmentation, and why 94% of orgs saw identity/access incidents last year. Learn concrete steps to harness AI without losing control.By Extra Something Media

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MSP Journey: Kyle Kenyon, The Pro Tech Guy (EP 914) 1:07:22

13d ago1:07:22

1:07:22

Uncle Marv welcomes back Kyle Kenyon, “The Pro Tech Guy,” for a lively, no-fluff conversation about cybersecurity, running an MSP, and working smarter — not harder. Kyle opens up about his origins, growing his space, and moving away from “man in the van” operations toward a more structured MSP approach. They dive into key challenges like client edu…

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Man in the Van vs. MSP: 10 Years Later (EP 913) 1:05:32

13d ago1:05:32

1:05:32

Uncle Marv hosts a special 10-year reunion with Chad Kempt of Fast Computers to revisit their classic “Man in the Van vs. MSP” debate and explore how the world of solo techs and small MSPs has evolved. They dig into shifting vendor landscapes, realistic service models, and why being lean, documented, and relationship-driven still wins in today’s ma…

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Meet the Aggressively Friendly Tara Rummer (EP 912) 38:49

16d ago38:49

38:49

Ever wonder how someone leaps from an art history degree to leading automation in the MSP world? In this episode, Tara Rummer, Channel Captain at Immy Bot and Advisor with Immense Networks, sits down to unpack her real journey—facing down imposter syndrome, championing neurodiversity, and finding her “aggressively friendly” groove. From early days …

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NSITSP Spotlight: Diana Giles, Skyline IT (EP 911) 23:42

19d ago23:42

23:42

This episode explores why professionalism, certification, and ethics matter more than ever in the IT sector. Diana Giles talks about her rise as a recognized industry leader, the transition from side hustle to full-time business, and the benefits of clear communication for IT consultants. Hear insights from Diana’s teaching career and community inv…

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Synology Reverses Drive Policy (EP 910) 49:51

20d ago49:51

49:51

This episode opens with a bombshell: Synology finally reversed its drive compatibility policy for NAS units, allowing IT pros and businesses to use third-party drives again—a move that’s sent shockwaves through online forums and social media. I discuss the implications for MSPs and what it means for client storage setups. Next, DattoCon coverage re…

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#86: Are You Drowning In Account Sprawl, And Don't Know It? 23:16

20d ago23:16

23:16

Are you sure every login in your company is legit? Cybersecurity leader Matt Topper exposes the hidden chaos of account sprawl—where forgotten logins and shadow SaaS tools quietly drain budgets and open doors for hackers. Learn how simple, free steps can tighten security and save thousands.By Extra Something Media

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AI Rewrites Marketing 32:55

20d ago32:55

32:55

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Ambulance Chasing Goes Cyber (EP 909) 22:12

23d ago22:12

22:12

Hear from Bradley Gross, one of the tech industry’s top attorneys and founder of Bradley Gross, PA. With over 20 years representing MSPs, Brad shares what every IT pro must know as lawsuits skyrocket around ransomware events. The conversation covers the specifics of contract language, rising legal standards, and how vendor agreements now shape your…

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AI and Marketing Growth 35:56

24d ago35:56

35:56

AI and Marketing are reshaping how businesses operate and grow. In this episode of The Backstory on Marketing and AI, we explore the role of revenue operations, automation, and AI enabled Market Research. Learn how companies can move beyond founder-led sales and create scalable, repeatable revenue engines. Discover why recurring revenue is essentia…

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Ubiquiti - The MSP Game Changer (EP 908) 1:05:08

27d ago1:05:08

1:05:08

Join Uncle Marv and veteran MSP Tom Wyant as they dive deep into the Ubiquiti ecosystem for IT professionals. Discover real-world tips for replacing SonicWall and Cisco hardware, advanced UniFi management, and transitioning to cost-effective network hardware for MSPs. Whether you’re an Ingenious, Synology, or Cisco fan, get candid pros and cons plu…

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AI and Marketing Future 45:27

27d ago45:27

45:27

AI and Marketing are reshaping industries at lightning speed. In this episode of The Backstory on Marketing and AI, we dive deep into how AI is transforming workflows, advertising, and education. We explore the DRIVE-F framework that empowers professionals to interact with AI effectively. Learn why providing direction, defining roles, and focusing …

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MSP Spotlight: Tech Brews LLC (EP 907) 45:42

28d ago45:42

45:42

This episode explores the journey of Kevin Dutkiewicz launching Tech Brews, his approach to serving underserved small businesses, the struggles with business administration, and the philosophy of running a modern MSP without the typical minimums. Uncle Marv and Kevin debate the realities of break-fix models, Trunk Slammer myths, and community-drive…

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#85 – What Happens When A Fortune 5 Company Fails Cybersecurity 101 19:26

27d ago19:26

19:26

Even Fortune 5 firms fail at Cybersecurity 101. Paul Tracey discusses how small businesses and even home users can block the same attacks.By Extra Something Media

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The Future of AI in IT Services (EP 906) 34:09

28d ago34:09

34:09

Uncle Marv sits down again with Jermaine Clark, Sherweb’s Senior Manager of AI Readiness, for a lively discussion about how managed service providers can drive real business results with AI. Jermaine walks through Sherweb’s robust AI initiatives, including training, certification, and hands-on guides for automating onboarding, ticketing, and custom…

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AI and Marketing Insights 29:08

29d ago29:08

29:08

AI is changing marketing at lightning speed. In this episode of The Backstory on Marketing and AI, we explore how AI enabled Market Research is disrupting digital strategies and reshaping industries. Key themes include: How AI accelerates research and campaign design Why adding humanity to AI content matters Navigating HIPAA compliance in healthcar…

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#84 - Is Your Data Secure When You Use AI? 28:52

1M ago28:52

28:52

Is Your Data Secure When You Use AI? Navy intel veteran, engineer, and attorney Cordell Robinson reveals how AI handles your data, what to share, and practical steps to protect privacy, comply with standards, and avoid mistakes.By Extra Something Media

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AI in Marketing Today 39:33

1M ago39:33

39:33

Artificial Intelligence is no longer a futuristic idea—it’s here, and it’s transforming marketing. In this episode of The Backstory on Marketing and AI, we explore how AI and Marketing intersect to reshape strategy, personalization, and growth. We dive into AI enabled Market Research, showing how businesses can use data-driven insights to predict c…

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AI Readiness for MSPs: Jermaine Clark (EP 905) 33:04

1M ago33:04

33:04

Jermaine Clark of Sherweb sits down with Uncle Marv to discuss what AI readiness means for MSPs, sharing practical advice, personal stories, and vendor insights. The conversation tackles how the rapid adoption of AI has shifted the balance between MSP expertise and client knowledge, emphasizing the need for a security-first approach and regular dat…

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Kimmel & Free Speech in Tech (EP 904) 40:15

1M ago40:15

40:15

Ever felt pressured to keep quiet in your business or IT community? Uncle Marv unpacks what Jimmy Kimmel’s comeback teaches IT pros about the freedom to speak in the face of political and industry pressure. With real stories of cyberbullying, shady marketers, and systemic bias, Marv reminds us that doing the right thing means accepting the risk—and…

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AI in Marketing Today 42:07

1M ago42:07

42:07

This episode of The Backstory on Marketing and AI explores how artificial intelligence is changing marketing strategy and execution. Key topics include: AI enabled Market Research Forecasting ROI before spending Omnichannel marketing strategies The role of human creativity alongside AI Real-world campaign lessons We discuss how AI tools optimize ad…

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MSPX 2.0: The Future of MSP Contracts (EP 903) 30:13

1M ago30:13

30:13

I’m joined by Matt Yesbeck, the innovative co-founder of MSPX, a groundbreaking online marketplace empowering MSPs to buy, sell, and value managed services contracts with confidence. Matt brings deep industry experience as a builder of smart, secure business solutions for IT providers. Together, we unpack the new features of MSPX 2.0, including tru…

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Building Better MSPs with Bret Erickson (EP 902) 23:11

1M ago23:11

23:11

If you want a truly no-BS look at life as a Managed Service Provider, this is the episode you can’t miss. I’m joined by Bret Erickson—owner of Passkey Technology up in Golden Valley, Minnesota, and a founding force within the National Society of IT Service Providers (NSITSP). Bret shares how he went from gigging as a musician all over the country t…

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AI and Marketing Insights 28:55

1M ago28:55

28:55

In this episode of The Backstory on Marketing and AI, we explore how AI is revolutionizing post-sale customer experiences. Discover how brands can use AI and Marketing to reduce churn, drive loyalty, and deliver personalized journeys. Learn why the ownership experience is more than unboxing—it’s about ongoing engagement, care, and usage. We discuss…

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AI and Marketing Insights 33:53

1M ago33:53

33:53

In this episode of The Backstory on Marketing and AI, we explore how AI and Marketing combine to transform business growth. Learn how AI enabled Market Research drives smarter decisions, efficiency, and scale. Key topics include: Why AI is a force multiplier for marketers. The complexity paradox and risks of automating bad processes. How entreprene…

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Your Customer Is Your Paycheck: Why It Matters (EP 901) 55:18

1M ago55:18

55:18

On this episode of the IT Business Podcast, I dig deep into why customer service often misses the mark—sharing both hilarious and infuriating stories from recent tech support calls and product woes. You’ll hear about my battles with big brands like Samsung and Bosch, porting nightmares with Fusion Connect, and wins with vendors who still “get it”—p…

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AI and Marketing Growth 32:04

1M ago32:04

32:04

In this episode of The Backstory on Marketing and AI, we dive into how AI and Marketing combine to help businesses grow. Learn how AI enabled Market Research powers smarter decisions and bridges the gap between sales and marketing. We explore how AI systems automate lead qualification, appointment setting, and customer engagement while maintaining …

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AI Marketing Power 23:25

1M ago23:25

23:25

In this episode of The Backstory on Marketing and AI, we explore how AI and Marketing are transforming the future of e-commerce. Discover how AI enabled Market Research is helping companies build smarter customer segments, optimize messaging, and improve conversions. We discuss: How AI powered analytics connect surveys, reviews, and Shopify data in…

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EXPOSED: The £200k Mistake 90% of Small Businesses Make (Dave From IT Isn’t Supposed To Run Your Technology Strategy!) 40:35

1M ago40:35

40:35

Most small business owners think CIO stands for "Chief I-Fix-Everything Officer" and CISO means "Chief I-Worry-About-Security Officer." In this episode, Noel Bradford (actual CIO/CISO) breaks down what these executive roles actually do and why your business desperately needs this strategic thinking - without the six-figure salary. Discover how frac…

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AI Marketing Attribution 37:40

1M ago37:40

37:40

AI is changing how marketers measure campaigns and scale growth. In this episode of Backstory on Marketing and AI, we dive into attribution, frameworks, and customer acquisition. Discover how Wicked Reports uses first-party data to track real conversions. Learn why cold traffic measurement is critical for sustainable growth. Understand why ad platf…

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AI and Marketing Transformation 35:50

2M ago35:50

35:50

In this episode of the Backstory on Marketing and AI, Mark Donnigan, a virtual CMO, shares his insights into how AI is changing the marketing landscape for B2B startups. Mark discusses the importance of small teams using AI tools to scale quickly and efficiently. He dives into the role of AI in content generation, the future of marketing, and how b…

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81 Security Patches + Windows 10’s Final Countdown: What Every Business Owner Must Know 12:50

2M ago12:50

12:50

September 2025 Patch Tuesday Show NotesSeptember 2025 Patch Tuesday: Critical Business Update Special Edition with Graham Falkner Microsoft's September Patch Tuesday brings 81 security fixes, including 9 critical vulnerabilities already being exploited by attackers. This episode provides essential business guidance for small business owners navigat…

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#83 - Zero Cost Pathway to American Cybersecurity 27:44

2M ago27:44

27:44

Frustrated by cybersecurity losses? Guest Larry Clinton, President of the Internet Security Alliance (ISA) proposes a zero-cost solution. By eliminating redundant regulations and creating a tuition-for-service program, we can enhance our defenses and train 10,000 new cyber pros annually.By Extra Something Media

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MSP Spotlight: Ron & Sydney of C Solutions IT (EP 900) 1:07:44

2M ago1:07:44

1:07:44

Unlock the real story of managed services as Ron and Sydney join Uncle Marv to discuss adapting tech stacks, surviving documentation disasters, and why hands-on fieldwork still matters. Learn how to leverage networking, win as a small MSP, and hear wild stories—from hard drive crushing to Florida’s reptile wrangling Python Challenge. Florida Man Ar…

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AI and Marketing Transformation 32:22

2M ago32:22

32:22

Sameer Narkar, CEO of Konnect Insights, discusses how AI is revolutionizing the marketing landscape. From social listening to competitive benchmarking, Sameer explains how AI tools are empowering brands to optimize their marketing strategies and customer experience. Discover how Konnect Insights helps brands securely analyze data from multiple chan…

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ScaleCon 2025 Preview with Taher Hamid (EP 899) 24:13

2M ago24:13

24:13

Discover why ScaleCon is called the “best MSP conference ever” as Uncle Marv and Tahir discuss what sets it apart: practical strategies, zero sales pitches, and a focus on what works. Tahir shares raw stories from last year’s event, including how attendees drove enormous revenue jumps and learned game-changing marketing strategies. Listen for tips …

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How AI is Transforming Marketing 33:43

2M ago33:43

33:43

In this episode of The Backstory on Marketing and AI, we discuss how AI is reshaping the marketing landscape, particularly in market research. John Long of Thynk.ai provides insights on how businesses can leverage AI to drive growth, improve customer experience, and optimize sales processes. We dive into the practical applications of AI in lead gen…

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AI and Marketing at Scale 43:15

2M ago43:15

43:15

This episode of The Backstory on Marketing and AI explores how AI enabled Market Research and influencer automation are reshaping marketing. Our guest from Stack Influence shares how micro and nano influencers outperform celebrities by creating authentic connections and driving higher conversions. We cover: Why micro and nano influencers deliver st…

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#82 - The Phishing Paradox: Why Security Training Might Be Making You MORE Vulnerable 34:14

2M ago34:14

34:14

Discover the surprising reason security training may be making you an easy target for hackers, and the better way to fight back. With CyberHoot CEO Craig Taylor.By Extra Something Media

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Podnutz Pro Replay “Time to Make the Donuts” (EP 898) 1:02:39

2M ago1:02:39

1:02:39

Floods, failed DIY, and donut debates! This episode covers everything from home catastrophes to the practical realities of IT support when clients do things their own way. This episode with Matt delivers more laughs, hard lessons, and hands-on IT advice than a week in the field. Why listen: Learn how a simple bathtub disaster led to a total home ov…

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AI in Marketing & Projects 29:20

2M ago29:20

29:20

In this episode of The Backstory on Marketing and AI, we explore how AI enabled Market Research is reshaping project management and beyond. Most large projects today suffer from cost overruns and delays. AI is providing a solution by forecasting risks, automating reporting, and enabling smarter scheduling. From construction to utilities and data ce…

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Smarter Strategy with AI 26:09

2M ago26:09

26:09

AI is reshaping the marketing landscape. In this episode of The Backstory on Marketing and AI, we explore how AI enabled Market Research empowers companies to replace guesswork with clarity. Ground Control Research has developed Telemetry, a service that provides AI powered insights to guide strategy. From defining the right target market to refini…

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AI's Impact on Content Marketing 25:56

2M ago25:56

25:56

In this episode, Jon Gilham discusses how AI is changing the landscape of content marketing. He talks about Originality.ai, a tool that helps marketers detect AI-generated content, optimize readability, and ensure fact-checking. Jon shares insights into how marketers can use AI responsibly and avoid AI-generated spam in their content. From plagiari…

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Starting an MSP in 2025 (EP 897) 58:18

2M ago58:18

58:18

Matt Mulcahy shares the blueprint for launching MSP Cyber in 2025. We cover what it really costs, what tools matter, where MSPs are going wrong with value, and why combining IT with digital marketing is a game-changer. Why Listen: Learn the real startup costs of an MSP today Why Miami’s IT market is still wide open Shifting value away from just hel…

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AI and Marketing Insights 33:38

2M ago33:38

33:38

AI and Marketing are reshaping how companies engage with customers. In this episode of the Backstory on Marketing and AI, we dive into how customer experience (CX) and AI-enabled Market Research create real-world business impact. Key topics include: Why personalization at scale is essential. How startups fail without product-market fit. The importa…

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Thriving as a Solo MSP (EP 896) 35:08

2M ago35:08

35:08

Ever been told, “You’re too expensive”? Yeah, me too. In this episode, I share how I deal with prospects who quote me lower rates from “their guy” — and why I never match those prices. Instead, I focus on flipping the conversation to value, downtime costs, and the trust that keeps clients with me for decades. Why Listen: Learn why I never match low…

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Did SonicOS 7.3 Stop Akira? (EP 895) 55:13

2M ago55:13

55:13

After conversations with Cory Clark of SonicWall and Reddit’s MSP community, I lay out the facts and why poor practices—not firewalls—are usually the weak link. I also share my hands-on Ubiquiti deployments (cameras, gateways, doorbells), how Cable Finder through Telarus helped me sign two clients on the spot, and review the CoolPie 3-in-1 SSD Clon…

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Cut Costs & Hire Faster (EP 894) 24:53

3M ago24:53

24:53

What if you could slash your hiring time from 44 days to just 5? In this can’t-miss interview, Chris Keith of Hirexe shares how his AI-powered platform is turning chaos into clarity for MSP recruitment. From scraping “real CV” data to delivering vetted candidates at lightning speed, Chris reveals the secrets behind his revolutionary process and how…