Business of Tech: Daily 10-Minute IT Services Insights

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 providers, TechRescue positions itself as a "tech therapist," emphasizing the importance of human connection and understanding in every interaction. This approach is particularly vital when dealing with a demographic that may not be as tech-savvy, as Bolton highlights the evolving nature of senior users who are increasingly engaged with technology.

The inspiration for TechRescue stemmed from Bolton's personal experiences with his family, particularly his grandmother's struggles with technology. Recognizing a gap in the market for services that cater to seniors, he and his team have created a supportive environment where every call is treated as a priority. The company employs individuals with backgrounds in sociology and psychology rather than traditional tech support roles, ensuring that empathy and communication are at the forefront of their service. This human-centric approach has proven effective, as Bolton notes that most calls are not about complex tech issues but rather simple, everyday problems that seniors encounter.

TechRescue operates on a subscription model, offering services at $50 per month or $400 annually. The company has established metrics to maintain profitability while ensuring quality service. Bolton explains that they have a structured process for handling calls, aiming to resolve issues efficiently while still allowing for personal interaction. By focusing on the emotional and psychological aspects of tech support, TechRescue has carved out a niche that resonates with both seniors and their families, who often seek assistance for their elderly relatives.

Looking ahead, Bolton envisions expanding TechRescue's reach, potentially into international markets. However, he acknowledges that the biggest challenge lies in finding the right personnel who can deliver the empathetic service that defines their brand. As the company continues to grow, it remains committed to its mission of providing accessible and compassionate tech support to seniors, reinforcing the idea that technology should enhance, rather than complicate, their lives.

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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 alignment and advocacy among investors, who are also customers, but it raises important questions about scalability and governance. The conversation delves into the implications of having investors who are directly involved in the product's development and direction.

The investment structure utilized by Empath is based on Y Combinator's SAFE notes, which allow for a straightforward and fair investment process without changing control of the company. Spencer explains the importance of ensuring that investors are qualified, adhering to SEC regulations to protect non-professional investors. This structure not only simplifies the investment process but also limits the amount each investor can contribute, ensuring a diverse group of stakeholders who are genuinely invested in the company's mission.

Spencer highlights the demographics of their investors, primarily consisting of CEOs from established MSPs with significant revenue. These investors are motivated by a desire to influence the vendor ecosystem positively and to have a say in the direction of the platform they use. The governance model established by Empath ensures that while these investors have a voice, they do not have control over the company's day-to-day operations, allowing for a balance between investor input and the leadership team's vision.

As Empath continues to grow, Spencer acknowledges the potential need for future funding rounds, including the possibility of engaging with venture capitalists. He emphasizes the importance of maintaining transparency with investors and being responsible stewards of their contributions. The conversation concludes with Spencer expressing confidence in the company's trajectory, aiming for sustainable growth while remaining committed to the community-driven approach that defines Empath.

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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 memorized data and generalized knowledge, indicating that larger datasets do not necessarily lead to increased memorization of specific data points. This understanding is crucial as it informs the operational mechanisms of AI models and addresses concerns related to copyright infringement.

Sundar Pichai, CEO of Google, has introduced the term "artificial jagged intelligence" to describe the current phase of AI development, highlighting the non-linear progress and the challenges faced by researchers despite significant advancements. Pichai's perspective reflects the mixed performance of AI models, which can exhibit extraordinary capabilities alongside notable errors. This sentiment is echoed by deep learning researcher Andrej Karpathy, emphasizing the unpredictability of AI performance and the need for a more nuanced understanding of its capabilities.

The rise of AI retrieval bots is transforming how users access information online, with a significant increase in traffic from these bots. Companies like OpenAI and Anthropic are deploying these bots to summarize content in real-time, moving away from traditional search methods that provide links to multiple sources. This shift poses challenges for content publishers, as the growth of retrieval bots indicates a changing economic landscape where content is increasingly consumed by AI first, with human users following. Publishers may need to rethink their engagement strategies to adapt to this new reality.

In the broader context of technology and cybersecurity, WhatsApp's intervention in a legal case concerning encryption and privacy rights highlights the growing role of platforms in surveillance debates. Additionally, the U.S. Cybersecurity and Infrastructure Security Agency faces leadership challenges amid a talent exodus, raising concerns about its operational effectiveness. As the IT services industry evolves, the integration of AI into various sectors, including hiring and cybersecurity, underscores the importance of execution, interoperability, and trust in automation. The future of technology will depend on how well businesses can navigate these changes and support their clients in making informed decisions.

Four things to know today

00:00 AI’s Jagged Reality: Study Reveals Limits to Model Memory as Bots Redefine the Web Economy

05:35 Cybersecurity Crossroads: WhatsApp Joins Apple in Legal Fight as U.S. Agency Leadership Crumbles

08:29 AI Matures Into Infrastructure Layer as IT Vendors Shift Focus to Outcomes and Execution

11:51 Legal Tech, GenAI, and Fast Food Bots All Show One Thing: Hype Doesn’t Equal Success

This is the Business of Tech.   

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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 addressed and no customers were affected, experts warn that this flaw reflects deeper security concerns in AI systems, reminiscent of vulnerabilities seen in software two decades ago. The incident raises critical questions about the security of AI agents that have ambient access to data and the need for rethinking endpoint protection and trust boundaries.

OpenAI's latest threat report reveals that state-level actors, including those linked to North Korea and Russia, are exploiting ChatGPT for cyber operations. The report outlines ten operations that were shut down, including the generation of fake job applications and social media content aimed at spreading disinformation. Notably, some campaigns were traced back to China, showcasing the use of AI in creating deceptive online personas. This highlights the strategic use of AI by malicious actors, emphasizing the need for heightened awareness and security measures.

ConnectWise is facing scrutiny over its recent digital certificate updates, urging customers to update their ScreenConnect, Automate, and ConnectWise RMM solutions. The company is attempting to distance itself from a previously disclosed nation-state breach while addressing concerns raised by a third-party researcher regarding configuration data handling. The rushed certificate rotation has led to reduced confidence among customers, especially given the recent history of exploitation of ScreenConnect. This situation underscores the importance of transparency and trust in vendor relationships, as well as the need for managed service providers to audit their update processes.

New tools from Huntress, Netgear, and Varonis signal a shift towards more automated and resilient security solutions. Huntress has launched a Threat Simulator to enhance user engagement in security training, while Netgear's acquisition of Exium aims to simplify networking and security for managed service providers. Varonis has introduced a Model Context Protocol Server to integrate AI tools into its data security platform. These developments reflect a growing trend in cybersecurity towards realism, automation, and simplification, emphasizing the need for IT service providers to adapt and align with these evolving security landscapes.

Three things to know today

00:00 From Copilot to Cybercrime: How AI Agents Are Creating New Frontlines in Espionage and Misinformation

05:54 ConnectWise Urges Immediate Updates Amid Certificate Rotation, Rekindling Security Concerns After Prior Breach

08:45 Automation, Engagement, and Recovery: Security Vendors Roll Out Tools That Align with MSP Priorities

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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 appealing to businesses and developers. However, the pricing structure, set at $20 per input and $80 per output, may limit access for smaller businesses and mid-market clients, potentially widening the gap between larger enterprises and smaller players in the tech landscape.

The launch of O3 Pro coincides with OpenAI's significant growth, reporting 3 million business users and $10 billion in annual recurring revenue, a remarkable increase since the previous year. To support this growth, OpenAI has partnered with Google Cloud Service, diversifying its computing capabilities and reducing reliance on Microsoft. This partnership highlights a shift in the competitive landscape of artificial intelligence, as both companies prioritize meeting the massive computing demands of their clients.

In addition to OpenAI's developments, DeepSeek has announced improvements to its R1 AI model, enhancing its capabilities in mathematics, programming, and logic while reducing hallucination instances. Meanwhile, Reddit has filed a lawsuit against Anthropic for allegedly using its data without permission to train AI systems, emphasizing the ongoing conflict between social media platforms and AI firms over data usage and user privacy. This legal battle underscores the importance of data sourcing and compliance for AI providers.

Cisco Systems has introduced new routers and switches aimed at optimizing AI deployments in campus environments, collaborating with NVIDIA to enhance network management through automation. Apple has also announced that Intel-based Macs will no longer receive major software updates, marking a significant transition to its in-house processors. Lastly, Evergreen Services Group has reached a milestone with its 100th acquisition of a managed IT service provider, indicating the scalability of the buy-and-hold strategy in the IT services sector and the evolving landscape of ownership frameworks.

Four things to know today

00:00 OpenAI’s o3-pro Targets High-Stakes AI Workloads as Adoption Soars Past 3 Million Users

06:06 ChatGPT Dominates, But AI Market Fractures Amid Legal Risks and New Model Momentum

10:06 Cisco Launches Smart Networking Gear as Apple Phases Out Intel Macs

12:31 Evergreen Hits 100 MSP Acquisitions, $1B in Revenue, Signals Global Expansion with REDD Deal

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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 Chason, CEO of PAX 8, emphasized the evolution of MSPs from managing infrastructure to managing intelligence, positioning them as architects of digital transformation. However, the term "Managed Intelligence Provider" has been criticized for being reductive, as IT service providers must maintain flexibility to address a wide range of digital needs beyond just intelligence.

Apple has also made significant strides in the AI landscape, announcing plans to open its foundational AI technology to third-party developers. This shift comes as Apple faces scrutiny regarding its competitiveness in the evolving AI market. Additionally, Apple has introduced a new naming convention for its operating systems, moving from version numbers to a year-based system, which aims to simplify its previous approach. The company has also launched iPadOS 26, enhancing multitasking capabilities and user interface, while a recent research paper from Apple has raised doubts about the effectiveness of AI reasoning models, suggesting they struggle with complex problems.

In a notable shift in U.S. cybersecurity policy, President Trump has rolled back key provisions established by the Biden administration, particularly concerning federal software acquisition rules and cybersecurity measures related to quantum computing and AI. This new executive order emphasizes limiting cyber sanctions to foreign actors and alters previous cybersecurity directives, which could impact the landscape of U.S. cybersecurity. The appointment of Brett Leatherman as the assistant director of the FBI's Cyber Division aims to strengthen efforts against cybercrime, although the Federal Communications Commission is currently facing challenges due to a lack of quorum, hindering its ability to address critical issues.

Lastly, the MSP Owners Group has been launched by Juan Fernandez to support small to mid-sized MSPs, focusing on community-driven growth rather than traditional private equity models. This initiative aims to help struggling providers grow while maintaining their core values, emphasizing that trust and relationships are the real assets in an MSP. The rise of alternative models rooted in peer support and sustainable growth represents a significant evolution in MSP financing, offering owner-operators more nuanced paths for collaboration and exit strategies in a maturing M&A landscape.

Four things to know today

00:00 New Pax8 AI Toolkit Says ‘Manage Intelligence,’ But Smart MSPs Will Manage Outcomes

02:57 Apple Opens AI Tools to Developers While Quietly Questioning the Tech’s Limits

06:33 Trump Rolls Back Cyber Rules as FBI Appoints New Cyber Chief Amid FCC Paralysis

09:58 MSP Owners Group Emerges as Third Path for Providers Seeking Growth Without Selling Out

This is the Business of Tech.   

Supported by: Syncro

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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 about the overall health of the labor market. While wage growth remains consistent at 3.9%, sectors such as healthcare and leisure are thriving, whereas manufacturing and professional services are experiencing declines. This mixed landscape reflects economic uncertainty that is affecting hiring decisions, particularly among smaller firms.

The adoption of Windows 11 has plateaued, with its market share slightly decreasing to 43.22% as Windows 10's share rises to 53.19%. Despite this stall, experts predict a gradual increase in Windows 11 adoption through the end of the year. However, the looming end of support for Windows 10 on October 14 poses a significant risk, as half of the world's PCs will be left without mainstream support. Service providers are encouraged to prepare for a migration wave by utilizing automated tools to assess upgrade eligibility and prioritize device refreshes.

In the realm of cybersecurity, UConn is enhancing its cyber insurance marketplace by partnering with BlackPoint Cyber and Cork Protection. These collaborations aim to empower managed service providers (MSPs) with better risk management tools and insurance options. As cyber risk financing merges with prevention strategies, MSPs are positioned as key players in this evolving landscape. The need for providers to understand insurance language and align their security offerings with underwriting requirements is becoming increasingly critical.

CrowdStrike has issued a soft revenue forecast for the second quarter, leading to a decline in its stock price. The company anticipates revenue between $1.14 billion and $1.15 billion, falling short of analyst expectations. This downturn is attributed to reduced government and enterprise spending on cybersecurity products amid economic pressures. For managed service providers, this situation serves as a reminder to diversify their vendor portfolios to mitigate operational risks associated with vendor concentration. The episode underscores the importance of balancing security efficacy with vendor resilience in a challenging market.

Four things to know today

00:00 Growth Slows, Gaps Widen: Jobs Up 139 K, Unemployment Steady, AI-Exposed Roles Shrink and Talent Budgets Surge

06:27 Windows 11 Plateau Meets Windows 10 Sunset: Half of Business PCs Face October 2025 Deadline—MSPs Positioned to Monetize the Refresh Wave

08:49 From Detection to Dollars: UKON’s Insurance Engine, Blackpoint’s 24×7 Defense, Cork’s Risk Insights and Guardz’s $56 M Raise Signal Security-Finance Convergence

11:53 CrowdStrike’s Lower-Than-Expected Q2 Outlook and $29 M Outage Bill Spotlight the Hidden Cost of Vendor Concentration for MSPs

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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 profits over disruptive innovation. This focus often stifles creativity and risk-taking, leading to a reliance on incremental improvements rather than groundbreaking advancements. Hinch emphasizes that while corporations can excel in incremental innovation, they struggle with disruptive changes that require longer-term investment and risk.

As the conversation shifts to the current landscape of managed services, Hinch notes that many MSPs are still small, often relying on vendors for innovation rather than developing it themselves. He points out that while there are around 40,000 MSPs in the U.S., a significant portion of them are not profitable. This situation creates a competitive environment where smaller MSPs must find innovative ways to attract customers and differentiate themselves from the larger, investor-backed companies that provide the tools they use.

The discussion then turns to the impact of artificial intelligence (AI) on the MSP market. Hinch believes that AI represents a disruptive technology that can enhance service delivery, particularly in automating tier-one support tasks. However, he cautions that MSPs should not expect to develop these AI solutions independently; instead, they should look to their vendors for advancements that can improve efficiency and service quality. He advises MSPs to engage with their suppliers about how AI can be integrated into their operations in practical and beneficial ways.

Finally, Hinch encourages MSPs to focus on foundational innovations and automation before diving into more complex applications of AI. He stresses the importance of maintaining consistent uptime and predictable performance while leveraging AI to enhance these core values. By asking the right questions and seeking sustainable innovations from their vendors, MSPs can position themselves to thrive in a rapidly evolving technological landscape, ensuring they do not fall victim to the pitfalls that have affected other industries in the past.

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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 experience similar to that of mobile operating systems like iOS. Hyman emphasizes that while this could streamline the user experience, it may also pose challenges for third-party patch management tools, raising questions about the future of these applications in a Microsoft-dominated ecosystem.

The conversation delves into the tension between standardization and customization in IT services. Hyman reflects on the importance of standardization for efficiency and stability within managed service providers (MSPs), while also acknowledging the need for flexibility to meet diverse customer requirements. He highlights that the complexity of the Windows environment means there will likely be room for both first-party and third-party solutions, as customers have varying preferences and needs.

As the discussion shifts to artificial intelligence (AI), Hyman shares insights from recent surveys indicating a disconnect between business leaders and IT executives regarding technology readiness. He notes that while AI has the potential to enhance productivity, many organizations are still grappling with its implementation. Hyman believes that the current stage of AI adoption is akin to the early days of the internet, suggesting that significant changes and value creation are on the horizon as businesses learn to integrate AI into their operations.

Finally, Hyman addresses the challenges in the labor market, particularly the decline in entry-level job opportunities for new graduates. He emphasizes the importance of investing in talent development within organizations, advocating for a "build first" approach to hiring. By fostering a culture of continuous learning and adaptation, Hyman envisions a future where technology service providers can elevate their role in the business ecosystem, ultimately becoming invaluable partners for small and medium-sized businesses.

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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. According to Rick Stern, Senior Director of Platform at Sherweb, this autonomy not only expedites the resolution of simple requests but also allows MSPs to concentrate on strategic initiatives. The portal features automated invoicing, curated service catalogs, and integrated chat support, and is already in use by over 450 MSPs following a successful pilot program.

The podcast also discusses the evolving landscape of artificial intelligence (AI) pricing models, with companies like Globant and Salesforce adopting usage-based approaches. Globant has introduced subscription-based AI pods that allow clients to access AI-powered services through a token-based system, moving away from traditional effort-based billing. Salesforce is experimenting with flexible pricing structures, including conversation and action-based models, to better align with the value delivered by AI services. These shifts indicate a critical inflection point in how AI services are monetized, emphasizing the need for IT service providers to rethink their offerings in light of usage-based economics.

Concerns regarding the unauthorized use of generative AI tools in organizations are highlighted by a report from Compromise, which reveals that nearly 80% of IT leaders have observed negative consequences from such practices. The survey indicates significant worries about privacy and security, with many IT leaders planning to adopt data management platforms and AI monitoring tools to oversee generative AI usage. Additionally, advancements in AI are showcased through a Stanford professor's AI fund manager that outperformed human stock pickers, while a study reveals limitations in AI's ability to make clinical diagnoses from radiological scans.

The podcast concludes with a discussion on the role of the Chief Information Security Officer (CISO), which is facing an identity crisis due to its increasing complexity and the misalignment of its responsibilities. Experts suggest reevaluating the CISO role to better address modern cybersecurity threats. The episode also touches on the implications of generative AI in education, highlighting concerns about its impact on critical thinking and learning processes. Overall, the podcast emphasizes the need for IT service providers to navigate the evolving landscape of AI and cybersecurity with a focus on governance, accountability, and sustainable practices.

Four things to know today

00:00 Sherweb’s White-Labeled Portal Signals MSP Shift Toward Scalable, Client-Centric Service Models

03:31 AI Forces Billing Revolution: Globant and Salesforce Redefine How Tech Services Are Priced

06:49 From Shadow AI to Specialized Tools: Why Governance, Not Hype, Defines AI’s Next Phase

12:46 From CISOs to Classrooms to Code: Why AI Forces a Strategic Rethink Across the Enterprise

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