Nett Lynch, a cybersecurity leader and strategic VCIO advisor, discusses the importance of translating complex security frameworks into actionable business outcomes. She emphasizes that clients are primarily concerned with their business goals and overcoming obstacles rather than the technical details of security frameworks. To effectively communicate the value of security investments, it is crucial to understand the client's business operations, including financial flows and growth aspirations. By framing security solutions in terms of efficiency and reduced friction, Lynch argues that IT professionals can better engage clients and demonstrate the tangible benefits of security measures.

Lynch also addresses the challenge of risk management in cybersecurity, noting that security experts can only reduce risk rather than eliminate it entirely. She highlights the necessity of having conversations with senior leadership to assess risk tolerance and make informed decisions about security investments. By conducting thorough assessments and breaking down security measures into manageable steps, IT providers can guide clients in making decisions that align with their risk appetite and business objectives.

The discussion further explores the shared responsibility model in cybersecurity, where both service providers and clients have roles to play in managing security risks. Lynch points out that while vendors are responsible for the tools they provide, the ultimate responsibility for risk management lies with the client. This partnership approach is essential for effective cybersecurity, as it requires active participation from both parties to address vulnerabilities and implement necessary measures.

Finally, Lynch shares her insights on the future of vCISO services, cautioning against the potential commercialization of the role, which could undermine its advisory nature. She advocates for professionalization within the industry to ensure that those claiming to be cybersecurity experts possess the necessary skills and knowledge. As AI technology continues to evolve, Lynch expresses a mix of excitement and caution, recognizing its potential impact on the industry while remaining aware of the risks associated with its adoption.

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Two sophisticated ransomware groups, Akira and Lynx, are increasingly targeting managed service providers (MSPs) and small businesses by exploiting stolen credentials and vulnerabilities. Together, they have compromised over 365 organizations, with Akira targeting major firms like Hitachi Vantara and Lynx focusing on critical infrastructure, including a CBS affiliate in Chattanooga, Tennessee. Both groups utilize double extortion tactics, combining file encryption with data theft to pressure victims into paying ransoms. This shift in tactics highlights the evolving threat landscape for MSPs and small businesses.

In response to the growing cybersecurity threats, the U.S. Cybersecurity and Infrastructure Security Agency has released Thorium, an open-source platform designed for malware and forensic analysis. Thorium can automate tasks and process over 10 million files per hour, empowering IT professionals without in-house malware analysis capabilities to conduct effective preliminary analyses. This tool aims to enhance cybersecurity operations and better manage risks associated with complex malware threats.

Additionally, SonicWall has issued a warning to its customers to disable SSL Virtual Private Network (VPN) services due to active ransomware attacks targeting its systems. Meanwhile, Google's AI-powered bug hunter, Big Sleep, has identified 20 security vulnerabilities in popular open-source software, raising concerns about the reliability of AI-generated bug reports. A newly discovered prompt injection vulnerability in Google's Gemini AI chatbot poses serious security risks, enabling attackers to craft convincing phishing campaigns without relying on links or attachments.

The podcast also discusses the alarming rise in cybersecurity incidents, particularly social engineering attacks, which have tripled in the first half of 2025. A report from Level Blue indicates that social engineering now accounts for 39% of initial access incidents, with fake CAPTCHA schemes rising dramatically. Furthermore, the report highlights the risks associated with unauthorized AI tool usage, revealing that 97% of organizations lack adequate access controls, exposing sensitive data to potential threats. This underscores the need for organizations to strengthen their defenses and educate users on emerging threats.

Four things to know today

00:00 Attackers Up Their Game: Ransomware Hits MSPs, SonicWall Vulnerable, and Google’s AI Found Exploitable

05:53 Social Engineering Surges as Shadow AI Breaches Drive Up Cyber Costs and Risk Exposure

08:35 Neglected Tech, Rising Risk: Email and Printers Still Expose Businesses to Modern Threats

11:04 From Ransomware to Retirements: Vendor Shifts Reveal Risks and Realignment in the IT Channel

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Artificial intelligence agents are significantly transforming the landscape of software-as-a-service (SaaS) pricing, moving away from traditional per-seat licenses towards usage and outcome-based models. Gartner predicts that by 2030, 40% of enterprise spending on software will shift to these new pricing structures, prompting businesses to reassess how they perceive value in digital operations. As AI features become more prevalent in enterprise software, organizations must navigate potential risks such as data silos and vendor lock-in, emphasizing the need for transparent pricing and governance strategies.

The podcast discusses the growing concerns surrounding AI's impact on the workforce, with a survey revealing that 61% of white-collar workers fear job displacement within three years. Despite these fears, many workers report that AI has enhanced their creativity and productivity, suggesting that AI should be viewed as a tool for augmentation rather than replacement. This perspective can facilitate smoother adoption of AI technologies, positioning service providers as trusted change managers.

In the realm of security, Microsoft faces scrutiny over a critical vulnerability in its new NLWeb protocol, which could allow unauthorized access to sensitive files. Meanwhile, Cloudflare has accused the AI startup Perplexity of violating no-crawl directives by stealthily scraping content from websites, raising concerns about unauthorized data access. Additionally, Anthropic's research highlights how AI personalities can be influenced by training data, underscoring the importance of data governance in AI development.

The episode also touches on Delta Airlines' clarification regarding its AI-assisted dynamic pricing model, which aims to use aggregated data rather than individual customer information. In the fashion industry, the use of AI-generated models has sparked debate over authenticity and representation, as brands seek cost-effective solutions for content creation. Overall, the discussion emphasizes the need for service providers to balance AI's cost-saving potential with the importance of maintaining trust and authenticity in consumer-facing applications.

Four things to know today

00:00 AI Agents Drive SaaS Pricing Shift, Raise Vendor Lock-In Concerns, and Reshape Worker Attitudes

04:45 OpenAI Releases First Open-Weight Models in Six Years as AI Security and Ethics Face Fresh Challenges

09:50 Delta Defends AI Pricing as Non-Personalized, While Fashion Faces Backlash Over AI-Generated Models

12:47 Microsoft Ends Windows 11 SE, Debuts Edge AI Copilot, as SentinelOne Expands into Generative AI Security

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Small and medium-sized businesses (SMBs) are increasingly investing in artificial intelligence (AI), with a significant portion planning to allocate between $25,000 and $1 million towards technology this year. A recent GTIA survey revealed that 63% of SMBs believe AI will be the most impactful technology in the next two years, and 65% of executives view technology as crucial for achieving business goals. Despite economic uncertainties, 35% of these businesses intend to invest unexpected financial gains into cutting-edge technology, indicating a strong desire for innovation. Notably, many SMBs are purchasing technology directly from vendors, signaling a shift in the market dynamics.

The labor market for small businesses is showing signs of change, with a report indicating a decrease in unfilled job openings. While 33% of small business owners reported unfilled positions in July, down from 36% in June, the challenges of finding qualified workers persist. A net 14% of small business owners plan to hire new employees in the upcoming quarter, particularly in skilled trade sectors like construction and transportation. This commitment to growth amidst a tight labor market suggests that automation and AI solutions may become more appealing to SMBs as they seek to enhance efficiency.

Major tech companies are reporting strong earnings, with Microsoft leading the way. The company achieved a revenue of $76.4 billion for the fourth quarter of its fiscal year, driven by a 34% increase in Azure cloud services. Amazon and Google also reported significant revenue growth, particularly in their cloud services, with Amazon's AWS generating $30.9 billion. The competitive landscape is shifting, as Microsoft’s Bing is gaining market share from Google, highlighting the importance of AI integration in driving business success.

Concerns about the integrity of economic data are rising, particularly following the recent job report that showed the weakest job creation since 2010. The report's findings prompted political controversy, including the firing of the Bureau of Labor Statistics Commissioner by President Trump. Experts warn that declining survey response rates and limited resources threaten the accuracy of critical economic indicators. This situation raises alarms about the reliability of data used for economic forecasting, emphasizing the need for trustworthy metrics in navigating the current economic landscape.

Three things to know today

00:00 AI Demand, Tight Labor, and Vendor Direct Sales Redefine the SMB Technology Landscape

05:16 Microsoft Posts Record $76.4B Quarter, Azure Up 34%, Bing Gains Search Share from Google

10:10 Buyers Reject Multiyear SaaS Contracts Amid Rapid AI-Driven Product Changes

13:03 Weak Jobs Data Spurs Political Shake-Up as Trump Fires BLS Commissioner, Raising Trust Concerns

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Austin McChord, co-founder and chairman of Slide, discusses the launch of his new BCDR startup, which aims to serve managed service providers (MSPs) with a fresh approach. Drawing from his experience at Datto, McChord emphasizes the importance of maintaining a strong culture and alignment with MSPs, which he feels has eroded in recent years. He addresses comparisons between Slide and Datto, explaining that while there are similarities in vision, Slide is built on a completely different technological foundation, utilizing NVMe flash storage to enhance performance and user experience.

McChord expresses a commitment to ensuring Slide remains an independent company, learning from the challenges faced during Datto's journey, including its acquisition and the subsequent cultural shifts. He highlights the importance of setting clear values and operational controls to prevent a repeat of past experiences. The conversation delves into the lessons learned from building Datto, particularly regarding business operations and the unpredictability of public markets, which can lead to unwanted outcomes for company culture and employee satisfaction.

The discussion also touches on the impact of AI in the tech landscape, with McChord noting that while AI can enhance efficiency, it currently struggles with tasks that require deep expertise. He believes that AI's potential lies in automating mundane tasks and improving configurations, but warns against rushing to implement AI solutions that may not yet be fully developed. McChord emphasizes the need for MSPs to understand the limitations of AI and to focus on building strong relationships with new small businesses that are emerging in the tech space.

Finally, McChord shares his philanthropic endeavors, including transforming an abandoned power plant into a public park. He expresses excitement about projects that prioritize social returns over economic ones, and how these initiatives allow him to apply business principles to create positive change. His passion for building and creating, whether in business or philanthropy, drives his current pursuits and future aspirations.

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Dave Sobel interviews Raffi Jamgotchian, founder and CEO of Triada Networks, about the current landscape of AI adoption in the financial services sector, particularly among small to medium-sized investment firms. Jamgotchian notes that while some clients are eager to embrace AI, others remain hesitant, mirroring trends seen with cloud technology. For those leaning into AI, Triada Networks is focusing on proof of concepts, helping clients structure their data effectively to leverage AI tools, especially in data analytics and research.

Regulatory considerations play a significant role in how firms approach AI implementation. Many of Jamgotchian's clients operate in regulated environments, which affects their choice of data models and the types of large language models (LLMs) they can use. The challenge lies in handling sensitive, non-public information without risking regulatory violations. As firms navigate these complexities, the importance of data preparation becomes evident, with varying levels of readiness among clients impacting their ability to utilize AI effectively.

Cybersecurity is a critical aspect of the conversation around AI and data management. Jamgotchian highlights that clients are increasingly proactive in seeking guidance on cybersecurity implications related to their business decisions. This shift is attributed to a combination of heightened regulatory scrutiny and a growing awareness of cybersecurity risks in the market. The conversation has evolved from being initiated by service providers to clients actively engaging in discussions about their cybersecurity needs.

Looking ahead, Jamgotchian emphasizes the importance of monitoring regulatory developments, particularly from organizations like FINRA and the FCC, as they relate to AI. He anticipates that AI-related lawsuits will emerge, prompting changes in laws that could impact managed service providers (MSPs). The conversation concludes with a recognition that while the MSP landscape is evolving, the core mission of solving business problems through technology remains unchanged, and those who adapt will thrive in the future.

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Dan Wensley, the new CEO of GTIA, discusses his vision for the organization, emphasizing the importance of expanding membership and enhancing the value provided to both member companies and individual members. With 2,411 member companies and over 212,000 individual members, Wensley aims to grow these numbers by effectively communicating the benefits of membership, particularly to IT service providers (ITSPs). He highlights the need for a broader conversation within the community to foster growth and engagement.

Wensley addresses the challenges of ensuring that vendors do not dominate discussions within the organization. He believes that collaboration between vendors and IT service providers is essential for mutual benefit, particularly in areas like AI and managed services. By creating a platform for these conversations, GTIA can facilitate valuable exchanges that drive innovation and support the needs of its members.

The conversation also touches on GTIA's philanthropic efforts, with Wensley announcing a significant increase in charitable giving, totaling $1.5 million this year. He explains that the organization is committed to supporting technology-driven initiatives, particularly in education and underprivileged communities. Members will have a say in where these funds are allocated, ensuring that the giving aligns with the values and interests of the community.

Finally, Wensley emphasizes the importance of focusing on people as a key pillar of GTIA's strategy. He plans to engage with members to understand their needs and aspirations better, while also promoting the inclusion of younger generations in the industry. By leveraging both the experience of long-standing members and the fresh perspectives of newcomers, GTIA aims to create a vibrant and dynamic community that fosters growth and advancement for all.

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Michael George, CEO of Syncro, and Dee Zepf, Chief Product Officer, discuss the evolving landscape of managed service providers (MSPs) and the transformative potential of AI in their operations. They reflect on how automation has been a longstanding goal in the industry, but recent advancements in AI and technology have accelerated this evolution. The conversation highlights Syncro's strategic shift towards leveraging AI and automation to enhance their platform, particularly through the launch of their XMM platform, which integrates RMM, PSA, and Microsoft 365 management.

The XMM platform aims to simplify the management of Microsoft technologies for MSPs, allowing them to deliver better security and efficiency to their clients. Dee shares insights on the rapid adoption of this platform among existing partners, emphasizing how it has streamlined operations and improved security management. The discussion also touches on the competitive landscape, with Michael noting that while Microsoft is increasingly moving towards the MSP space, Synchro views their relationship as complementary rather than competitive.

As the conversation progresses, they explore the importance of workflow efficiency for small and midsize businesses, suggesting that MSPs should focus on enhancing their service offerings to remain competitive. Michael emphasizes the need for MSPs to evolve from traditional IT support roles to strategic partners that help clients leverage AI and automation effectively. This shift is seen as crucial for MSPs to differentiate themselves in a market where many are at risk of falling behind.

Finally, the discussion delves into the implementation of AI technologies within Syncro's products, particularly in areas like smart ticket management and sentiment analysis. Dee explains the challenges of measuring the quality of AI-generated responses and the importance of maintaining a human element in the process. They conclude by encouraging MSPs to start small with AI implementations, helping clients understand its potential and gradually integrating more advanced solutions into their operations.

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Rania Succar, the new CEO of Kaseya, discusses her vision for the company at a crucial time for both Kaseya and the managed service provider (MSP) ecosystem. With Kaseya facing scrutiny over customer service and billing practices, Succar emphasizes the importance of innovation and a cultural reset to strengthen relationships with MSP partners. She believes that Kaseya has the potential to be a leader in driving outcomes for small businesses through its partnerships with MSPs, which are essential for helping these businesses adopt cutting-edge technology. 

Succar outlines four key values that will guide Kaseya's next chapter: measuring success based on the profitability and revenue growth of MSP partners, delivering innovation that benefits these partners, enhancing the overall customer experience, and investing in the community. She acknowledges the frustrations MSPs have expressed regarding customer service and billing practices, and she highlights specific steps Kaseya is taking to address these issues, including the end of high watermark pricing and improvements in customer support. 

The conversation also touches on the importance of internal culture and employee retention at Kaseya. Succar emphasizes the strength of her leadership team and the need for a culture that empowers employees to make decisions at all levels. By fostering a customer-centric and innovative environment, she aims to improve the overall experience for both employees and customers, ultimately leading to better service quality. 

Looking ahead, Succar shares her vision for leveraging AI and automation to enhance Kaseya's offerings for MSP partners. She recognizes the challenges SMBs face in adopting AI and emphasizes the need for collaboration between Kaseya and MSPs to unify data and create effective solutions. By focusing on these areas, Succar aims to position Kaseya as a leader in helping small businesses navigate the evolving technology landscape.

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AI is revolutionizing the hiring process by enhancing human interaction and focusing on skills rather than traditional resumes. Brett Waikart, co-founder of Skillfully, explains how their platform utilizes AI to create realistic job simulations that allow candidates to demonstrate their skills in a practical setting. This approach addresses the challenges posed by the influx of AI-generated applications, enabling employers to filter through the noise and identify the most qualified candidates efficiently.

Skillfully's innovative method shifts the hiring paradigm from merely assessing resumes to evaluating actual performance in job-related tasks. For instance, in sales roles, candidates can engage in simulations that mimic real-life scenarios, such as handling customer objections or conducting discovery conversations. This hands-on experience not only provides employers with a clearer picture of a candidate's capabilities but also significantly reduces the time and cost associated with the hiring process.

The platform also plays a crucial role in preparing students for the workforce by offering them access to these simulations through partnerships with educational institutions. This experiential learning allows students to practice and refine their skills before entering the job market, creating a feedback loop between employers and universities. As a result, students gain valuable insights into the skills required in their desired careers, making them more competitive candidates.

Looking ahead, Skillfully aims to expand its capabilities by incorporating multimodal simulations that assess not only traditional skills but also the ability to leverage AI tools effectively. This evolution will help employers identify candidates who can excel in their roles by utilizing AI to enhance their productivity. By focusing on both skill validation and the human element of hiring, Skillfully is paving the way for a more efficient and equitable employment landscape.

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