The podcast discusses the evolving landscape of cybersecurity for small and mid-market businesses, emphasizing the dual threats posed by advanced artificial intelligence tools and a resurgence of ransomware attacks. As cybercriminals leverage AI for sophisticated phishing and impersonation tactics, traditional security measures are becoming obsolete. Organizations are urged to adopt enterprise-grade solutions, such as unified security platforms and zero-trust frameworks, to protect their operations. The introduction of secure browser technologies is highlighted as a critical step in enhancing defenses against the 95% of security incidents linked to browser vulnerabilities.

A significant decline in the number of active Windows PCs, with 400 million devices disappearing in three years, indicates a shift in consumer behavior towards mobile devices and tablets. This trend reflects a broader change in endpoint strategy, as the traditional perimeter dissolves and the focus shifts from device management to user and data control across platforms. The implications of the upcoming end of support for Windows 10 in October 2025 may further influence this trend, as users may opt not to invest in new devices.

The podcast also covers Microsoft's new security measures aimed at preventing incidents similar to the CrowdStrike meltdown, which caused extensive damages. The company plans to move third-party security drivers out of the Windows kernel to enhance reliability and reduce risks. Additionally, Microsoft is offering extended security updates for Windows 10 users, allowing them to continue receiving support even after the end of support date. This initiative reflects a commitment to improving system stability and addressing vulnerabilities.

Finally, the discussion touches on the broader implications of AI in various sectors, including its impact on the workforce and democratic processes. The podcast highlights concerns about AI's role in elections and education, as well as the ethical challenges arising from its use. The conversation emphasizes the need for businesses to manage the complexities of AI, including compliance and creativity loss, while pushing back against inflated vendor claims. This approach will help build trust and ensure that organizations can navigate the rapidly changing digital landscape effectively.

Three things to know today

00:00 400 Million Missing PCs Mark the End of the Endpoint Era—MSPs Must Evolve or Fade

06:04 From Kernel Changes to Cyber Insurance: Why Structural Resilience Now Defines MSP Value

10:23 From Productivity to Manipulation: The Expanding and Uneven Impact of AI Across Sectors

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Microsoft is facing significant challenges in promoting its Copilot AI assistant within enterprises, as many employees show a preference for OpenAI's ChatGPT. This trend highlights a competitive shift in the corporate sector, where companies are increasingly recognizing the advantages of generative AI solutions. Despite Microsoft's efforts, including a notable implementation plan by Amgen Inc. for 20,000 employees, the growing strength of OpenAI suggests a changing landscape in AI adoption. The struggle to sell Copilot internally reflects broader issues of product-market fit, as users often favor consumer-grade options over sanctioned tools.

The impact of AI on managed service providers (MSPs) is also noteworthy, as a recent report indicates that AI-driven platforms are beginning to replace traditional tools. This shift is expected to reduce the number of product categories from 13 to 7, leading to increased interoperability among services. While AI-powered automation can lower operational costs, it poses market challenges, particularly for MSPs that may need to pivot from troubleshooting to delivering strategic insights. The caution expressed by Kaseya's CEO underscores the importance of integrating fragmented customer data for effective AI solutions.

Legal developments surrounding AI training data are reshaping the copyright landscape. A federal judge ruled in favor of Anthropic, allowing the company to train its AI models on legally purchased books without needing permission from authors, classifying this practice as fair use. However, the ruling is limited to physical books and does not absolve Anthropic from a separate trial regarding the alleged piracy of millions of books. Similarly, Meta Platforms secured a legal victory, but the court's decision does not confirm that its use of copyrighted materials qualifies as fair use, indicating a complex and evolving legal environment for AI training.

The podcast also highlights ongoing disparities in the IT leadership pipeline, particularly regarding diversity. Recent data shows little change in the demographic makeup of IT leadership, with a significant majority being white and male. The challenges faced by women and people of color in securing leadership roles are exacerbated by rigid criteria in executive searches. As larger companies scale back diversity efforts, there is an opportunity for smaller firms to differentiate themselves by fostering inclusive cultures, as exemplified by OIT VoIP, which received recognition for its commitment to diversity in technology.

Four things to know today

00:00 AI Reality Check: Fragmented Data, Poor UX, and Platform Consolidation Derail Enterprise and MSP Hype

04:42 Fair Use but Not Free Reign: Courts Back AI Training on Books—with Major Caveats

07:28 Smaller Tech Firms Like OITVOIP Show How Inclusion Can Be a Competitive Advantage

10:32 Collaboration Reimagined: OpenAI, Anthropic, and Rewst Redefine the Future of Work with AI-First Tools

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ConnectWise is currently facing a significant crisis of trust as attackers exploit its signed software to distribute malware. This alarming trend has seen a notable increase in infections since March 2025, primarily due to poor signing practices that allow malicious users to embed harmful code within legitimate applications. Reports indicate that the ConnectWise ScreenConnect remote access tool was the most commonly abused legitimate tool in 2024, with a staggering 56% of all active threat reports involving remote access tools. The rise in phishing schemes utilizing ConnectWise samples has raised concerns about the security measures in place and the implications for managed service providers (MSPs).

Despite the increasing number of breaches, a recent survey revealed that 76% of MSP leaders remain confident in their cybersecurity efforts, even as nearly 70% reported experiencing multiple cyber breaches in the past year. This disconnect between confidence and reality poses a significant problem, as many MSPs recognize the need to improve their defenses but feel ill-equipped to guide customers through complex regulatory changes. The situation is further complicated by sensationalized reports of massive data breaches, which can divert attention from verified security threats and contribute to a false sense of security.

The podcast also highlights the ongoing Salt Typhoon hack, which has reportedly led to major U.S. telecommunications companies instructing their incident response teams not to seek evidence of the intrusion. This directive raises concerns about the scale of the breach and the lack of accountability within the telecom sector, where deregulation has diminished incentives for companies to invest in security measures. Experts warn that this willful ignorance sets a dangerous precedent, particularly in critical infrastructure, and emphasizes the need for a reevaluation of vendor liability in the face of such breaches.

In response to the evolving challenges faced by MSPs, several vendors have introduced new tools and features aimed at improving operational efficiency and security. Synchro's Universal Billing feature aims to streamline billing processes, while Manage Engine's MSP Central platform seeks to enhance service delivery and device management. Additionally, Hornet Security has launched an AI Cyber Assistant to bolster cybersecurity for Microsoft 365 users. These developments indicate that while vendors are recognizing the challenges MSPs face, they often lag behind in providing the necessary solutions, underscoring the importance of selecting platforms that prioritize practical integration and real-world impact.

Three things to know today

00:00 Legit Tools, Real Breaches: ConnectWise Malware Surge and Telecom Hacks Highlight Systemic Security Failures

06:54 MSP Tools Evolve as Syncro, ManageEngine, and Hornetsecurity Target Profitability, Consolidation, and AI Security

09:47 Bitdefender, Pia and Nexus IT Signal Strategic Evolution in the MSP and Security Landscape

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Gartner predicts that by 2027, artificial intelligence (AI) will be responsible for half of all business decisions, either through full automation or partial augmentation. This shift is driven by the increasing pressure on technology companies to deliver returns on their AI investments, with small and mid-sized businesses (SMBs) rapidly adopting these tools. However, a significant skills gap remains, as 95% of SMBs report needing more training to effectively utilize AI. The report emphasizes the importance of human oversight to ensure data quality and governance, suggesting that companies prioritizing AI literacy training could see revenue increases of up to 20%.

Despite the enthusiasm for AI, a study from Stanford University reveals that professionals prefer using AI for automating mundane tasks rather than more complex responsibilities. The research indicates a strong desire for human control in the workplace, highlighting a disconnect between the tasks companies assign to AI and what workers actually want to automate. This gap presents an opportunity for managed service providers (MSPs) to bridge the divide by focusing on human-centered workflow design and aligning AI deployment with employee expectations.

In the realm of productivity tools, OpenAI and Anthropic are making strides with new integrations that enhance user interaction with AI. OpenAI is testing a feature that allows users to analyze emails and manage schedules through ChatGPT, while Anthropic's CLAWD code has improved its toolchain for developers. These advancements signify a shift in how end users will expect to interact with their tools, pushing providers to adapt their roles from managing infrastructure to managing intelligence and intent.

Broadcom's recent changes to VMware's licensing model have raised concerns among smaller customers, with reports of cost increases significantly impacting their budgets. While Broadcom claims that many of its top customers are adopting the VMware Cloud Foundation, the dissatisfaction among smaller clients indicates a need for IT providers to offer migration services and alternative solutions. The current landscape presents a critical moment for providers to assist clients in navigating these changes, ensuring they find resilient and appropriately priced platforms that meet their needs.

Four things to know today

00:00 From Hype to Help: AI Decision-Making Surges, But Poor Guidance Risks Undermining Gains

05:23 OpenAI and Anthropic Expand AI Agents Into Daily Workflow—IT Providers Must Now Govern Behavior, Not Just Systems

07:44 Efficiency Is the New MSP Battleground: Martello and WatchGuard Highlight Operational ROI

10:35 Broadcom’s VMware Pivot Forces MSPs to Choose Sides: Enterprise Loyalty or SMB Exodus

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Small business resilience is masking deeper economic strains, as recent surveys reveal that while many small businesses report growth and have maintained or increased their workforce, a significant portion still feels the adverse effects of current economic conditions. Despite 56% of small businesses indicating growth and 90% maintaining or increasing their workforce, 43% of entrepreneurs express that the economic landscape is detrimental to their operations. This contradiction highlights a fragile optimism among small businesses, which may continue to invest in technology but will demand more tangible value for their expenditures.

In contrast, the sentiment among large corporate CEOs has plummeted, with the CEO Economic Outlook Index dropping to its lowest level since 2020. Over 40% of CEOs anticipate workforce reductions in the next six months, reflecting widespread concerns about hiring, investment, and sales growth. This decline is attributed to uncertainties surrounding trade policies, which could have ripple effects on vendor spending and longer sales cycles, particularly impacting high-end managed service providers (MSPs) that cater to mid-market or enterprise clients.

The podcast also discusses the challenges posed by data blind spots in strategic planning, as federal hiring freezes and budget cuts are beginning to affect the quality of economic data produced by the U.S. government. The erosion of reliable statistics complicates decision-making for both policymakers and service providers, making it increasingly difficult to advise small businesses on risk and compliance. Additionally, a significant drop in employee confidence, particularly among young workers, raises concerns for MSPs managing support desks, as anxiety may lead to higher turnover and a greater need for effective communication and leadership.

Finally, the episode highlights the rapid growth of the managed services sector, with projections indicating that the market will reach $608 billion globally. Companies like NinjaOne, Halo PSA, and Nerdio are experiencing significant growth, driven by their focus on user experience and cloud-based solutions. The competitive landscape is shifting, with smaller players outpacing larger incumbents, emphasizing the need for MSPs to choose their platforms strategically and adapt to the evolving demands of the market.

Three things to know today

00:00 Growth Without Confidence: SMBs Forge Ahead as Economic Signals Flash Caution for IT Advisors

06:15 GenAI Growth Plans Clash with Security Concerns as AI Search Disrupts Digital Visibility

10:38 MSP Sector Surges to $608B as Platform Wars Reshape PSA/RMM Landscape

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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 businesses face, particularly regarding data readiness and cybersecurity. They emphasize the importance of understanding specific use cases and ensuring that companies have the necessary infrastructure and security measures in place before deploying AI solutions.

Hunter highlights that many organizations, especially those that have been around for a while, struggle with data quality and governance. He notes that businesses often have "skeletons in their data closets," which can hinder effective AI deployment. Barb adds that for companies to safely utilize AI, they must have robust cybersecurity measures, including data loss prevention and user training. This foundational work is crucial to protect sensitive information and ensure compliance with regulations.

The conversation also touches on the rising costs and complexities associated with private AI infrastructure. Hunter explains that while public large language models (LLMs) can be effective for certain tasks, businesses dealing with confidential information may benefit from self-hosted models. He points out that, in some cases, hosting AI solutions locally can be more cost-effective than relying on third-party services, especially as usage scales up.

Finally, the discussion shifts to the evolving landscape of investment in the managed service provider (MSP) sector. Barb notes that many small MSPs are undervaluing their businesses, often expecting high multiples that may not be realistic. Hunter observes a trend where venture capitalists are less willing to invest in pre-revenue companies, pushing entrepreneurs to demonstrate customer traction before seeking funding. Both experts agree that the MSP community is adapting to these changes, with new models of community-driven investment emerging to support smaller businesses.

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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 vulnerabilities that accumulate as they defer compliance and security measures. This accumulation of security debt can hinder their growth and create significant risks, as they may lack the necessary security practices and awareness when they eventually need to address these issues.

Haugli highlights the role of managed service providers (MSPs) in helping their clients navigate these challenges. He argues that MSPs should not only provide technical support but also act as trusted advisors, guiding clients to understand the business implications of cybersecurity. By framing security as a means to unlock revenue and reduce friction in sales cycles, MSPs can help clients see the value in investing in cybersecurity measures. This approach positions MSPs as heroes in the eyes of their clients, as they provide essential business advice that can lead to increased revenue.

The conversation also touches on the evolving role of virtual Chief Information Security Officers (vCISOs) in the cybersecurity landscape. Haugli asserts that the demand for vCISOs is growing, particularly as regulations increasingly require organizations to have dedicated cybersecurity leadership. He emphasizes that vCISOs offer a cost-effective solution for smaller businesses that cannot afford a full-time CISO, providing them with strategic guidance and expertise to build robust security programs.

Finally, Haugli discusses the need for a national cybersecurity standard in the U.S. to address the patchwork of existing regulations. He argues that without enforceable standards, organizations will continue to struggle with compliance and security, leading to increased costs and confusion. By drawing parallels to other regulated industries, he advocates for greater accountability among software vendors and emphasizes the importance of compartmentalization in cybersecurity practices, which can help organizations mitigate risks and protect sensitive information.

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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 speaker emphasizes the importance of hiring empathetic, business-savvy individuals who can engage with clients on a human level, rather than relying solely on technical expertise. This new approach prioritizes emotional intelligence and relationship-building over conventional help desk support.

The proposed team structure includes tech concierges who act as relationship managers, business process advisors who focus on optimizing client operations, automation specialists who streamline processes, and generalist troubleshooters who handle unique challenges. This model eliminates the traditional tiered support system, allowing for direct resolution or automation of issues. By humanizing the front-end interactions and automating backend processes, the MSP can deliver meaningful outcomes that genuinely benefit clients.

Automation is positioned as a foundational element rather than just a feature, with the speaker advocating for the use of cloud-native management platforms and workflow automation tools. These technologies enable teams to focus on high-value advisory roles rather than mundane tasks. The podcast also highlights the potential of using AI to enhance team capabilities, making it a tool for amplifying human efforts rather than replacing them. This shift allows for a more efficient operation that prioritizes client relationships and business outcomes.

Finally, the discussion touches on the financial aspects of running an MSP, emphasizing the importance of profitability over mere growth metrics. The speaker suggests that a lean team can effectively manage a smaller number of high-value clients, leading to sustainable business practices. The podcast concludes with advice on whether to build a new MSP from scratch or acquire an existing one, recommending a partnership approach to leverage complementary skills and enhance overall success in the industry.

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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 checking emails by 6 a.m. and a 16% increase in meetings scheduled after 8 p.m. This shift indicates that work is encroaching on personal time, suggesting a need for companies to rethink their time management and workflow strategies to prioritize high-impact tasks over busy work.

Amazon's CEO, Andy Jassy, has acknowledged that AI efficiency gains will result in job cuts within the company, reflecting a broader trend of AI adoption across various sectors. Gallup's research shows that AI usage among U.S. employees has nearly doubled, with significant increases among white-collar workers. However, despite the growing integration of AI, concerns about job displacement remain relatively unchanged, with only 15% of employees fearing automation will eliminate their jobs in the near future.

The podcast also discusses the transformative impact of autonomous software agents on small to mid-sized businesses, as outlined in PAX 8's report. The findings indicate that a majority of mid-sized enterprises are already deploying AI, with a notable emphasis on the need for organizations to adapt to new operational standards. The report suggests that IT service providers must shift their focus from merely selling AI tools to becoming organizational strategists that help clients redesign workflows and manage time effectively.

Finally, the episode touches on the evolving landscape of the technology channel, emphasizing the necessity for vendors and partners to adapt to emerging trends. The shift from product-based selling to outcome-based solutions is becoming essential for survival in a competitive market. As traditional marketing development funds decline, the call for performance-based partnerships is more pressing than ever, urging IT service providers to demonstrate their value and influence in driving client success.

Four things to know today

00:00 Microsoft Warns of ‘Infinite Workday’ as AI Blurs Work-Life Boundaries

06:19 OpenAI’s Defense Deal and MCP Push Signal AI’s Transition from Tool to Infrastructure

08:58 MiniMax Launches One-Million-Token Open Model, Undercutting Cost of GPT-4 by Orders of Magnitude

10:40 Techaisle: Channel Faces Structural Shakeup as Outcome-Based, Risk-Sharing Models Replace Old Playbook

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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 cybersecurity posture. This disconnect presents a critical opportunity for IT service providers to step in with strategic, outcome-focused solutions that emphasize not just tools, but comprehensive cybersecurity strategies.

The landscape of cybersecurity is evolving, with SMBs increasingly recognizing the importance of cyber resiliency. Reports indicate that 68% of small businesses and 89% of mid-market firms understand the need for quick recovery from incidents, yet many still lack formal security protocols. As the market for cybersecurity solutions is projected to grow significantly, reaching an estimated $70 billion by 2034, the demand for effective strategies is more pressing than ever. The rise of cloud-based security solutions and zero-trust architecture is indicative of this shift.

Regulatory changes are also impacting the cybersecurity landscape, as the SEC withdraws proposed regulations that would have required investment firms to establish written cybersecurity policies. This deregulation creates a trust vacuum that IT providers can fill by offering managed compliance and risk mitigation services. The convergence of regulatory retreat and escalating cyber threats underscores the need for proactive security measures, as the responsibility for cybersecurity increasingly shifts to the market.

Amid these challenges, advancements in email security, particularly through DMARC adoption, show promise in combating phishing attacks. However, the rapid proliferation of generative AI applications is creating new vulnerabilities, complicating the security landscape. IT service providers are urged to capitalize on foundational security measures while also addressing the emerging risks associated with AI. The evolving cybersecurity environment presents both challenges and opportunities for providers who can adapt and innovate in response to these shifting dynamics.

Four things to know today

00:00 SMBs Overconfident, Underprepared: Cybersecurity Misalignment Fuels $70B Market Surge

05:00 SEC Pullback Leaves Cyber Gaps as Ransomware and Zero Trust Shape 2025 Risk Landscape

08:50 From DMARC to Shadow AI: Why Cybersecurity Now Requires Dual-Front Defense

11:45 Bifurcation in IT Services: MSP-Centric Tools and Vertical Platforms Signal Strategic Divide

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