Best MSP Insider Podcasts (2025)

1
MSP Automation: Unlocking Efficiency with AI With Ashley Cooper 55:11

3d ago55:11

55:11

In this episode of MSP Insider, we're diving deep into the often overlooked but massively impactful world of open source and how it's revolutionizing the MSP industry. Summary: Learn how community-driven resources and open source tools can transform your MSP, streamline operations, and enhance service delivery. Plus, discover why AI isn't just a bu…

1
Inside Empath's $2M Raise: Wes Spencer Discusses Community Investment for MSP Growth 22:45

7d ago22:45

22:45

Wes Spencer, co-founder of Empath, a training and education platform for managed service providers (MSPs), discusses a unique funding model that diverges from traditional venture capital. Instead of seeking investment from typical VCs, Empath successfully raised $2 million from industry insiders, primarily MSPs themselves. This approach fosters ali…

1
Unlocking AI for SMBs: Data Readiness, Cybersecurity, and Community-Driven Investments with Hunter Jensen and Barbara Paluszkiewicz 37:42

44m ago37:42

37:42

Small and mid-sized businesses are increasingly curious about how to leverage artificial intelligence (AI) to enhance their operations. As they explore the potential of AI, they are asking critical questions about implementation, automation, and customer engagement. Experts Hunter Jensen and Barbara Paluszkiewicz discuss the challenges these busine…

1
How Startups Can Tackle Security Debt to Unlock Revenue: A Discussion with Brian Haugli 29:13

19h ago29:13

29:13

Brian Haugli, CEO of SideChannel, discusses the critical distinction between security debt and technical debt, emphasizing that while technical debt is a common challenge for CIOs, security debt is a more specific issue that often arises in startups. He explains that startups frequently prioritize speed to market over security, leading to vulnerabi…

1
The New MSP Model: Combining Automation, Emotional Intelligence, and E-Commerce for Success 16:44

2d ago16:44

16:44

The podcast discusses a transformative vision for building a managed services provider (MSP) that shifts away from traditional models focused on infrastructure management and reactive maintenance. Instead, it advocates for creating a tech services business that empowers small and mid-sized organizations to drive revenue through technology. The spea…

1
AI Fuels Infinite Workdays, Job Cuts at Amazon, and New Trends in IT Service Partnerships 14:45

3d ago14:45

14:45

AI is increasingly becoming a double-edged sword in the workplace, as highlighted by a recent Microsoft report. While artificial intelligence tools are intended to enhance productivity, they are inadvertently contributing to an "infinite workday," leading to heightened employee burnout. The report reveals alarming trends, such as 40% of workers che…

1
SMBs Overconfident in Cybersecurity; SEC Deregulates Amid Rising AI Threats and New Investments 18:53

4d ago18:53

18:53

Small and medium-sized businesses (SMBs) are exhibiting a dangerous overconfidence in their cybersecurity readiness, with a significant gap between their perceived capabilities and actual security measures in place. A recent report reveals that while 71% of SMBs feel confident in managing major cybersecurity incidents, only 22% have an advanced cyb…

1
AI's Impact on SMBs: Revenue Gains, Cloud Growth, and New Tools from Zoom, MailChimp, Microsoft 15:50

5d ago15:50

15:50

Small and medium-sized businesses (SMBs) are increasingly recognizing the importance of adopting artificial intelligence (AI) to stay competitive in the market. A recent survey indicates that 97% of small businesses utilizing voice AI agents have seen revenue increases. However, many SMBs still perceive AI as complicated or unnecessary, with 63% ex…

1
I Got Scammed 7:50

4d ago7:50

7:50

And it could happen to you too. On this week's episode of Bite Size Cyber Crime I detail an actual scam I fell for and emphasize that anyone can be a victim of a scam anywhere on the internet.By Chloe Thonus

1
Unlocking Profitability: Andrew Bolton's Unique Approach to Tech Support for Seniors 25:20

6d ago25:20

25:20

Andrew Bolton, CEO and co-founder of TechRescue, has developed a unique approach to delivering technical services specifically tailored for seniors. With a growing client base of nearly 1,000 seniors on a monthly subscription model, Bolton's company focuses on providing empathetic and personalized tech support. Unlike traditional managed service pr…

1
AI's Jagged Age: Memory Limits, Retrieval Bots, and Legal Battles Over Encryption and Privacy 18:01

8d ago18:01

18:01

AI models have a defined memory ceiling, which is reshaping the ongoing debates surrounding copyright and data privacy. Recent research from Meta, Google DeepMind, Cornell, and NVIDIA reveals that large language models have a fixed memorization capacity of approximately 8.6 bits per parameter. This finding clarifies the distinction between memorize…

1
Microsoft 365 Copilot's Security Flaw, AI in Misinformation, and Emerging Cybersecurity Solutions 14:41

9d ago14:41

14:41

Microsoft 365 Copilot has been identified as having a significant security vulnerability known as Echo Leak, which allows hackers to access sensitive information without user interaction. This zero-click exploit was discovered by AIM Security after three months of reverse engineering the software. Although Microsoft claims the issue has been addres…

1
O3 Pro's Launch, Reddit's Lawsuit Against Anthropic, and Cisco's New AI-Driven Networking Gear 17:14

10d ago17:14

17:14

OpenAI has launched the O3 Pro Artificial Intelligence model, which focuses on delivering enterprise-grade accuracy and enhanced tool integration, albeit at a higher cost and slower response times compared to its predecessor. The O3 Pro model is designed for complex inquiries where precision is prioritized over speed, making it particularly appeali…

1
PAX 8's AI Solutions, Apple's Developer Access, Cybersecurity Policy Changes, and MSP Support Group 14:20

10d ago14:20

14:20

PAX 8 has announced the development of the first Managed Intelligence Toolkit, set to launch in 2026, aimed at empowering managed service providers (MSPs) to deliver AI solutions at scale to small and medium-sized businesses. This toolkit will integrate various Microsoft technologies, enabling MSPs to orchestrate automation for their clients. Scott…

1
U.S. Job Growth Declines, Windows 11 Stagnates, Cyber Insurance Partnerships, CrowdStrike's Forecast 16:22

12d ago16:22

16:22

U.S. hiring continues to show modest growth, with the Bureau of Labor Statistics reporting an addition of 139,000 jobs in May, surpassing economists' expectations. However, the unemployment rate remains steady at 4.2%, marking a prolonged period of stagnation. Revisions to previous months revealed a combined loss of 95,000 jobs, raising concerns ab…

1
Malwareception: SakuraRAT is a Backdoor to Trick Script Kiddies 6:32

10d ago6:32

6:32

Malware is everywhere, even inside of other malware. One tool advertising itself as an advanced remote access trojan ended up being much more, a backdoor infecting novice hackers. This was not just a one off, however, and lead to the discovery of a massive backdoored malware campaign infecting other hackers and gaming cheaters. Sources: https://pas…

1
From Invisible to Irresistible: Transforming Your MSP Brand With Crystal Conkle 58:11

11d ago58:11

58:11

Most MSPs don’t have a marketing problem. They have a clarity problem Crystal Conkle (CMO at The 20 MSP) breaks down what that really means—and how to fix it. If your growth feels stuck, or your marketing still sounds like everyone else… this is your episode. We cover: → Why invisibility is the real cost of copy-paste marketing → The shift from “en…

1
AI in Managed Services: Strategies for MSPs to Thrive Amidst Disruption with Stephen Hinch 25:12

14d ago25:12

25:12

Stephen Hinch, an expert in managed services and author of "Winning Through Innovation," discusses the challenges and opportunities for innovation within the corporate business model, particularly in the managed services provider (MSP) sector. He highlights the "curse of the corporate business model," where large corporations prioritize predictable…

1
AI's Impact on IT Management: Navigating Microsoft Updates, Talent Shortages, and Automation with Elliott Hyman 37:41

15d ago37:41

37:41

Elliot Hyman, CEO of the Lyra Technology Group, joins Dave Sobel to discuss the evolving landscape of IT management, particularly in light of Microsoft's new Windows Update orchestration platform. This initiative allows app developers to integrate their update processes into the Windows 11 framework, creating a more unified and controlled update ex…

1
Sherweb Launches Portal for MSPs; AI Pricing Evolves and Generative AI Risks Prompt Caution 18:27

15d ago18:27

18:27

Sherweb has launched a white-label self-service portal aimed at empowering managed service providers (MSPs) and their clients by streamlining operational tasks. This innovative platform enables clients to manage their technology licenses, subscriptions, and payments independently, reducing the need for service providers to handle routine inquiries.…

1
AI Drives MSP Success, U.S. AI Governance Changes, and Broadcom's VMware Partner Strategy Shift 14:50

16d ago14:50

14:50

New data reveals a significant divide in the managed service provider (MSP) landscape, with AI and infrastructure maturity emerging as key factors distinguishing high-growth MSPs from their lower-growth counterparts. A report from JumpCloud indicates that while 89% of MSPs saw revenue growth in 2024, only 22% achieved high growth, defined as an inc…

1
NWN's InterVision Deal, Empath's Insider Funding, AI Agents Emerge, Big Tech's Cybersecurity Moves 14:50

17d ago14:50

14:50

NWN Corporation has acquired InterVision Systems, a managed services provider known for its innovative IT solutions and a strong partnership with Amazon Web Services. This strategic acquisition aims to enhance NWN's offerings in customer experience, cybersecurity, and intelligent infrastructure, solidifying its position in the North American techno…

1
AI Certification for MSPs Debuts as ConnectWise and Kaseya Make Major Strategic Moves 15:36

18d ago15:36

15:36

ConnectWise has launched a unified MSP platform and an ASIO-powered professional services automation (PSA) solution at their IT Nation Secure event. The new offerings aim to streamline operations for managed service providers (MSPs) by providing features such as unified log management, automated alert triage, and customizable dashboards. The Connec…

1
PC Market Growth Driven by Tariffs; AI in Customer Service Faces Trust Issues Amid Breaches 14:21

19d ago14:21

14:21

ConnectWise has confirmed it was the target of a cyber attack by a nation-state threat actor, affecting a small number of its ScreenConnect customers. The company has since patched the software and implemented enhanced monitoring measures to secure its environment. This incident highlights the increasing targeting of remote monitoring and managemen…

1
MSP Customers Face Ransomware after Remote Assist Tool Compromised 6:07

19d ago6:07

6:07

Using an MSP can be handy for getting your IT set up or managing technical support without hiring a lot of full time staff, but there are risks that can come with outsourcing your IT to a third party. One MSP was compromised, leading to many customers having ransomware headaches. Sources: https://pastebin.com/hLKSqRaS…

1
How Soft Leadership is Hurting Your MSP Success With Dale Walls 56:18

17d ago56:18

56:18

Hard truth: It’s not your tech that’s holding you back. It’s your leadership. In this episode, I sat down with Dale Walls (founder of Corsica Technologies) to break down the real reason MSPs hit a wall. It’s not lack of effort. It’s not lack of ideas. It’s lack of clarity, courage, and consistency at the top. This one covers: → The quiet cost of so…

1
Maximizing Efficiency: How T2 Group Uses Hybrid Agile in Healthcare Solutions with Kevin Torf 19:47

21d ago19:47

19:47

Kevin Torf, co-founder and managing partner of T2 Group, discusses the unique approach his organization takes in delivering technology solutions to the healthcare industry. T2 Group focuses on providing a comprehensive set of services, including professional consulting, managed services, contact center operations, resource management, and software …

1
The Future of IT: Agentic AI, Market Readiness, and the Evolving Role of Industry Associations with Jay McBain and Ryan Morris 44:36

22d ago44:36

44:36

Two powerhouse experts, Ryan Morris and Jay McBain, join host Dave Sobel to discuss the emerging landscape of agentic AI, exploring the balance between hype and reality. They delve into the implications of AI technologies, particularly in the context of IT service providers and managed services. The conversation highlights the recent launch of Ater…

1
AI Security Risks Rise as IT Leaders Expand Use; Cloud Backlash and Texas Age Verification Law 15:59

22d ago15:59

15:59

A recent report from SailPoint reveals a significant contradiction in the IT sector: while 96% of IT professionals view artificial intelligence agents as a security risk, an overwhelming 98% still plan to expand their use within organizations over the next year. The study highlights that although 84% of respondents currently utilize AI agents, only…

1
MSPs on Alert: DragonForce Ransomware, ScreenConnect Abuse, and Microsoft’s Update Integration 12:23

23d ago12:23

12:23

DragonForce has emerged as a significant threat actor in the cybercrime landscape, targeting vulnerabilities in the SimpleHelp remote monitoring and management tool to execute sophisticated ransomware-as-a-service attacks against managed service providers (MSPs). Recent incidents have highlighted how attackers exploited known vulnerabilities, inclu…

1
AI Errors in Law, Databricks' AI Databases, Zoom's CEO Avatar, and Gender Employment Risks 13:31

24d ago13:31

13:31

AI's increasing presence in the legal field is raising significant concerns, particularly regarding the accuracy of information generated by these systems. Judges have reported a notable rise in AI-generated inaccuracies, with 23 instances of fake legal citations identified since May 1st. Legal data analyst Damien Chartland has documented 120 cases…

1
AI Ethics Alarm: Anthropic's Claude Four Sparks Controversy as SMBs Navigate Economic Uncertainty 14:33

25d ago14:33

14:33

Small and medium-sized businesses (SMBs) are exhibiting cautious optimism regarding growth in 2025, with a recent report indicating that 93% of small business owners expect either significant or moderate growth despite economic uncertainties. However, this optimism is tempered by a slight decline from the previous quarter and a notable shift in len…

1
Malware Spread via fake TikTok Piracy Tutorials 6:51

26d ago6:51

6:51

Piracy and accidentally getting malware go hand in hand for many, and though the days of Limewire viruses on your Linkin Park albums are mostly over, modern problems require modern solutions so attackers have moved to modern platforms to spread malware to those not interested in paying for software. Sources: https://pastebin.com/i7yriZXy…

1
Ending MSP Burnout: A Mental Health Roadmap to Breakthrough 55:28

26d ago55:28

55:28

Running an MSP can feel like a never-ending sprint—until your mind and your motivation hit a wall. In this episode, I sat down with Scott Scrogin, Strategic Initiatives Director at ConnectWise, to talk about the thing no one builds a dashboard for: burnout. We covered the real stuff—what it looks like when you’re scaling fast and still feel stuck, …

1
API Security: Indirect Prompt Injection Threats and the Rise of AI-Driven Exploits 38:54

29d ago38:54

38:54

API security has evolved from being primarily an infrastructure issue to a complex challenge centered around language and design flaws. Jeremy Snyder, CEO of Firetail, discusses the findings from their latest state of API security report, emphasizing the alarming rise of indirect prompt injection as a significant threat in AI-integrated systems. As…

1
AI Breakthroughs: Claude Opus 4, OpenAI's $6.5B Deal, and Atera's IT Autopilot for 40% Workloads 18:29

29d ago18:29

18:29

Anthropic has launched its latest AI models, Claude Opus 4 and Claude Sonnet 4, which are designed to enhance coding capabilities and problem-solving skills. Claude Opus 4 is touted as the most powerful model to date, capable of autonomously handling long tasks for several hours and outperforming competitors like Google's Gemini and OpenAI's models…

1
AI in SMBs, Washington's New Tech Tax, and Major Cybersecurity Breaches: What You Need to Know 17:43

1M ago17:43

17:43

Small businesses are increasingly adopting artificial intelligence (AI) technologies, particularly in personalized email marketing, which has become a primary channel for nearly 19% of small to mid-sized businesses in 2025. Despite the growing interest, many businesses face challenges in implementation, with 35% citing a lack of familiarity with AI…

1
Build 2025: Microsoft’s AI Agent Revolution Meets Google’s Hyper-Personalized AI Strategies 15:40

1M ago15:40

15:40

Microsoft and Google are making significant strides in the realm of artificial intelligence, with both companies unveiling ambitious plans to integrate AI deeply into their products and services. Microsoft’s Build 2025 conference showcased its vision of transforming the operating system into an AI agent platform, emphasizing the development of auto…

1
Transforming Customer Service: AI's Role in Augmenting Human Interaction and Satisfaction with Kate O'Neill 18:14

1M ago18:14

18:14

Kate O'Neill discusses the impact of AI and automation on business and human flourishing in her latest book, "What Matters Next." She introduces the concept of a now-next continuum, which helps leaders navigate the uncertainty of the future by connecting past knowledge with present realities and future possibilities. This framework aims to empower …

1
Tech Spending Caution: Consumer Sentiment vs. Economic Data, Plus MIT AI Paper Controversy 11:04

1M ago11:04

11:04

A historic gap between consumer sentiment and economic data is raising concerns about future tech spending. Despite positive economic indicators, such as a steady unemployment rate and a slight increase in the Consumer Price Index, consumer confidence is faltering, as evidenced by a significant drop in the Consumer Sentiment Index. Analysts from Ba…

1
Coinbase Insiders Bribed to Hand Over Data to Scammers 6:02

1M ago6:02

6:02

Coinbase is one of the largest crypto exchanges, but when corrupt employees are compromised into handing over data to scammers, a series of social engineering attacks took place. The scammers demanded a ransom, but Coinbase fired back. Sources: https://pastebin.com/dTZR6hKwBy Chloe Thonus

1
The Hard Truth About MSP Profitability and Exit Strategy with Arlin Sorenson 1:08:08

1M ago1:08:08

1:08:08

You can’t outwork a broken model. That’s where this episode starts—and where a lot of MSP owners get stuck. I sat down with Arlin Sorensen (VP Ecosystem Evangelism of ConnectWise) to unpack the kind of growth that looks good on the surface… but still leaves you frustrated, burned out, or stuck at a ceiling you can’t break through. This one’s about …

1
Navigating DMARC Complexity: Insights from EasyDMARC's CEO on Email Security for SMBs with Gerasim Hovhannisyan 22:39

1M ago22:39

22:39

Gerasim Hovhannisyan, CEO of EasyDMARC, discusses the complexities and challenges of implementing DMARC (Domain-based Message Authentication, Reporting & Conformance) in the cybersecurity landscape. He shares his personal journey, which began after experiencing a significant financial loss due to an email phishing attack. This incident prompted him…

1
Protecting Data and Models: Cybersecurity Insights and Pricing Strategies for AI Solutions with James D. Wilton and Bryant Tow 33:54

1M ago33:54

33:54

The discussion centers around the intersection of artificial intelligence (AI), cybersecurity, and monetization strategies, emphasizing the dual challenges of protecting data and AI models while also effectively pricing these solutions. Experts Bryant Tow and James D. Wilton explore the urgent risks posed by AI, including threats to company data an…

1
Cox and Charter Merger, Proofpoint's $1B Acquisition, and the Rise of Shadow AI in Education 12:38

1M ago12:38

12:38

Charter Communications has announced its acquisition of Cox Communications for $34.5 billion, a significant move that will merge two of the largest internet service providers in the United States. This merger is expected to require approval from the Federal Communications Commission due to Cox's critical operational licenses. The combined entity pl…

1
AI in Action: Radiologists Thrive, Data Silos Persist, and LastPass Expands SaaS Monitoring 17:09

1M ago17:09

17:09

Data silos are significantly hindering AI innovation, as highlighted by a recent report from Infanti. The survey of over 1,200 IT and cybersecurity professionals revealed that more than half of the respondents experience isolated data within their organizations, leading to inefficiencies and slow security responses. Nearly 30% of IT professionals r…

1
Europe's Vulnerability Database Launches as U.S. Cybersecurity Falters; AI Adoption Trends Revealed 14:51

1M ago14:51

14:51

The European Vulnerability Database (EUVD) has officially launched, providing a vital platform for monitoring critical security flaws amid challenges faced by the U.S. in cybersecurity funding and management. This initiative aims to enhance transparency and deliver essential information on vulnerabilities, addressing gaps left by the U.S. Common Vu…

1
Rise in Remote Work Drives New Ventures; Insurers Address AI Risks as CISA Alters Info Sharing 13:33

1M ago13:33

13:33

Remote work is driving a significant startup boom, reshaping the IT services market. A recent study indicates that companies with higher levels of remote work during the COVID-19 pandemic have seen a notable increase in employee startups, with an estimated 11.6% of new business formations attributed to this trend. Despite major corporations reinsta…

1
U.S.-China Tariff Agreement Fuels Market Growth; AI Layoffs and AEO Shift Digital Marketing Focus 17:22

1M ago17:22

17:22

The recent U.S.-China tariff truce has led to a significant surge in global markets, with the U.S. reducing tariffs on Chinese goods from 145% to 30% and China lowering its tariffs on American imports from 125% to 10%. While this agreement has provided short-term relief, it has also triggered caution among Chief Information Officers (CIOs), who are…

1
Pearson Breached Via Exposed GitLab Token 5:30

1M ago5:30

5:30

Pearson is an education giant, providing learning tools and standardized assessments across many fields, schools, and organizations. Recently they were breached by what was likely a series of relatively minor mistakes. Sources: https://pastebin.com/YemUE0XiBy Chloe Thonus

Podcasts Worth a Listen

MSP Insider Podcasts

Podcasts Worth a Listen