n this episode of the podcast, host Dave Sobol interviews Nelson Gomes, the CEO of Portalia Group, who shares insights from his extensive career in the managed services provider (MSP) industry. Nelson recounts his journey, starting with the founding of Priority One Group in 1997, which initially focused on IT services before evolving into an MSP with a specialization in healthcare. After merging with Medicus IT in 2019, he experienced significant growth, ultimately leaving the organization in 2024 while remaining a shareholder. This transition allowed him to expand his expertise and prepare for new ventures.

The conversation delves into the dynamics of mergers and acquisitions (M&A) in the MSP sector, particularly from the buyer's perspective. Nelson emphasizes the importance of cultural fit and vertical focus, particularly in healthcare, when considering an acquisition. He reflects on the growth trajectory of Medicus IT, which expanded from approximately $17 million to nearly $75 million in revenue during his tenure. This growth underscores the potential benefits of strategic partnerships in the MSP landscape, especially for those looking to scale their operations.

As the discussion shifts to the challenges facing MSPs in the coming year, Nelson identifies human capital and operational maturity as the top concerns. He highlights the difficulty in finding skilled personnel who can bridge the gap between technology and business needs, particularly in a competitive market. Nelson advocates for the hiring of business analysts who can help organizations leverage technology to achieve better business outcomes, emphasizing the need for MSPs to evolve their service offerings beyond traditional IT support.

Finally, the episode touches on the impact of artificial intelligence (AI) on the healthcare sector and the broader MSP industry. Nelson notes that while AI is becoming increasingly integrated into healthcare operations, the readiness of organizations to adopt such technologies hinges on effective data governance. He encourages MSPs to focus on preparing their data infrastructure to maximize the benefits of AI, while also being cautious about the pace of adoption. The conversation concludes with Nelson sharing his enthusiasm for working with MSPs and offering his contact information for those interested in further discussions

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Dave Sobel engages in a conversation with Mark Ralls, the president of Auvik, a company specializing in network monitoring and management. The discussion begins with an exploration of the transformative potential of automation and AI in the IT landscape. Ralls emphasizes Auvik's role in proactively monitoring networks, providing customized alerts, and integrating critical data into platforms used by their partners. He highlights the importance of ensuring that technicians receive relevant information in a timely manner, which is crucial for effective troubleshooting.

As the conversation progresses, Ralls shares insights into Auvik's recent feature release called North Star, which enables technicians to visualize network paths and identify issues more efficiently. This feature aims to streamline the troubleshooting process, allowing technicians to pinpoint problems quickly. Ralls expresses excitement about the future of automation and AI, indicating that Auvik is actively working on expanding its automation capabilities to enhance the overall user experience.

The discussion then shifts to the challenges and opportunities within the realm of SaaS management. Ralls explains Auvik's differentiated approach to SaaS management, particularly in addressing shadow IT and security risks associated with shared credentials. He underscores the importance of proactive alerting and monitoring to help partners manage costs and improve security. Ralls believes that Auvik's focus on security within SaaS management is a significant value-add for their partners, setting them apart from other vendors in the market.

Finally, Ralls reflects on the evolving dynamics in the MSP space, where the balance between vendor consolidation and best-of-breed solutions continues to shift. He emphasizes Auvik's commitment to putting partners first, offering flexible solutions that cater to their needs, whether through direct engagement or integration with other platforms. As the episode concludes, Ralls shares his optimism for the future, noting a resurgence in growth within the MSP community and Auvik's ongoing efforts to support their partners with innovative tools and solutions.

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Dave Sobel engages in a thought-provoking conversation with Jon Murchison, CEO of BlackPoint Cyber, about the current state of cybersecurity policies and practices. They discuss the initiatives surrounding "secure by design" and "secure by default," emphasizing the challenges faced by managed IT service providers in implementing these ideals. Jon expresses skepticism about the immediate impact of these policies on the ground level, noting that while they are well-intentioned, they often fall short of practical application in real-world scenarios.

The discussion shifts to the dynamics of responsibility and liability within the cybersecurity landscape. Jon highlights the disparity between software vendors and service providers regarding accountability when security breaches occur. He argues that while security providers should be held liable for secure code design and regular penetration testing, the complexities of cybersecurity make it difficult to assign blame definitively. This nuanced perspective underscores the need for a balanced approach to liability that encourages innovation without stifling progress.

As the conversation progresses, Jon shares his insights on the Cybersecurity Maturity Model Certification (CMMC) and its potential as a broader standard. He acknowledges the foundational value of existing frameworks like NIST and ISO but critiques their lack of practical guidance for organizations. Jon advocates for a more prescriptive approach that focuses on actionable steps for hardening security measures, rather than vague compliance requirements that can lead to checkbox exercises.

Finally, Jon emphasizes the critical importance of identity management in cybersecurity. He explains how threat actors have evolved their tactics, often exploiting legitimate credentials to navigate networks undetected. The episode concludes with Jon discussing the future of posture management and the need for improved security measures around automation, highlighting the ongoing challenges and opportunities in the ever-evolving cybersecurity landscape.

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In this episode of the podcast, host Dave Sobel sits down with Joel Abramson, the managing partner at TopDown Ventures, to discuss the intricacies of venture capital in the managed services provider (MSP) software space. With a background that includes significant experience in the MSP industry, including the sale of a large MSP to TELUS, Joel shares insights into the investment thesis of TopDown Ventures, which focuses on early-stage MSP software companies. The conversation highlights the importance of understanding the unique challenges faced by MSPs and how that knowledge informs their investment strategy.

Joel elaborates on the stages of investment, emphasizing that TopDown Ventures primarily targets seed and early series A companies, typically those nearing their first million in annual recurring revenue. He explains that the firm aims to assist these companies in scaling by providing not just capital but also valuable insights into product development and market strategies. The discussion touches on the lessons learned from operating MSPs and how those experiences shape their approach to identifying promising investment opportunities.

A significant part of the conversation revolves around the challenges MSPs face when transitioning from service-based businesses to product development. Joel points out that while many MSPs may have ideas for tools, the leap to creating a viable product requires a different skill set and understanding of the market. He stresses the importance of distinguishing between features and fully-fledged products, as well as the need for a strong foundation and vision to ensure long-term success in the competitive landscape of MSP software.

Finally, Joel discusses the collaborative model employed by TopDown Ventures, which includes leveraging a network of advisors from the MSP community to support portfolio companies. He outlines the decision-making framework used by the investment committee, which involves thorough due diligence and strategic discussions about potential success and challenges. As the episode concludes, Joel shares his outlook for the future, highlighting ongoing opportunities in cybersecurity and productivity tools, particularly those enhanced by AI, as areas of focus for the firm moving forward.

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Host Dave Sobel interviews Jeff Totten, the founder and CEO of Evergreen, a company that takes a unique long-term investment approach in the managed services provider (MSP) space. Jeff shares insights into Evergreen's philosophy, which is heavily inspired by Berkshire Hathaway's model of acquiring businesses with the intent to build and hold them for the long haul. This strategy emphasizes the importance of investing in people and maintaining the culture of the companies they acquire, ensuring that founders can feel proud of their legacy even after selling their businesses.

Jeff discusses the dual challenge of people management that Evergreen faces: nurturing their internal team while also investing in the leadership of the acquired companies. He highlights the role of their chief people officer in sourcing and retaining top talent, as well as the importance of preserving the local culture of the businesses they partner with. By injecting additional talent into these organizations, Evergreen aims to enhance the existing culture rather than disrupt it, fostering an environment where employees can thrive and grow.

The conversation also delves into Evergreen's decision-making framework, which prioritizes focusing on key areas such as acquisitions and talent placement. Jeff explains how they utilize first principles thinking and consider the long-term implications of their decisions, ensuring that they align with the company's values and mission. He emphasizes the importance of measuring success through customer and employee satisfaction, as well as organic growth, which is vital for the sustainability of their business model.

As the episode wraps up, Jeff reflects on Evergreen's recent international expansions and the lessons learned from entering new markets. He notes the differences in maturity levels among MSPs in various regions and the importance of building local trust. Looking ahead to 2025, Jeff identifies new customer acquisition and the integration of AI and robotic process automation (RPA) as key focus areas for Evergreen, underscoring the potential for these technologies to enhance service delivery and operational efficiency in the MSP sector.

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host Dave Sobel sits down with Kelvin Tegelaar, the CTO of Lime and founder of CyberDrain, to discuss the evolving landscape of SaaS management and the innovative approach taken by CyberDrain. Tegelaar introduces the Cyber Drain Improved Partner Portal (CIPP), an open-source, multi-tenant management solution specifically designed for Microsoft 365. He highlights the need for affordable management tools in the MSP space, which often suffer from high pricing models. By offering a free and open-source tool with optional support, Teglar aims to democratize access to essential management resources for MSPs.

The conversation delves into the dynamics of community involvement in open-source projects. Tegelaar shares insights on how CyberDrain has fostered a vibrant community of contributors, many of whom are system administrators rather than traditional developers. This community-driven approach not only enhances the product but also creates a sense of camaraderie among users. With around 7,000 active MSPs utilizing SIP, Tegelaar notes that a significant portion is opting for the paid support model, while others engage in self-hosting and community support.

Tegelaar also discusses the balance between commercial interests and community contributions, emphasizing the importance of maintaining a clear separation between CyberDrain and his MSP, Lime. This separation helps avoid conflicts of interest and ensures that the focus remains on delivering value to all users. The episode highlights the collaborative relationship between CyberDrain and Microsoft, where Tegelaar's insights and feedback from the MSP community are used to enhance Microsoft's Lighthouse product, showcasing a unique partnership that benefits both parties.

As the episode wraps up, Tegelaar reflects on the future of AI in the MSP space, particularly the potential of large language models (LLMs) to create meaningful applications that go beyond simple tasks. He emphasizes the need for practical implementations that genuinely assist engineers and service providers. 

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The episode begins with a recap of the previous year's forecasts, assessing their accuracy and relevance in the rapidly evolving tech landscape. Host Dave Sobel highlights the increasing reliance of businesses, particularly in healthcare and finance, on Managed Service Providers (MSPs) to navigate the complex compliance requirements stemming from a surge in state-level data privacy laws across the U.S.

Sobel discusses the role of artificial intelligence (AI) and machine learning in transforming IT operations, noting the advancements in self-healing systems and predictive maintenance. He acknowledges the growing interest in AI-driven solutions, particularly in the context of operational efficiency and proactive issue resolution. However, he also points out areas where his predictions fell short, such as the anticipated rise of deepfake detection services and the appointment of AI systems as board members in major corporations.

As he transitions to his predictions for 2025, Sobel emphasizes the potential of generative AI to revolutionize data reporting and accessibility for businesses. He envisions a future where AI can dynamically analyze and summarize data, making insights readily available to users without the need for specialized skills. Additionally, he predicts that autonomous IT systems will become more mature and accessible to small and medium-sized businesses (SMBs), allowing MSPs to offer enhanced managed services that focus on strategic outcomes.

The episode concludes with a series of bold predictions for the coming year, including the mainstream adoption of decentralized MSP models, the emergence of AI co-governance frameworks, and the integration of fraud prevention services into standard cybersecurity offerings. Sobel encourages listeners to consider these strategic ideas as they plan for 2025, emphasizing the importance of adapting to the evolving technological landscape.

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The episode opens with a focus on Anthropic's new tool, Clio, which is designed to enhance AI observability by identifying threats and unknown harms associated with its AI chatbot, Claude. Clio has already proven its utility by detecting a coordinated spam network attempting to manipulate search engine optimization. Anthropic aims to share Clio's methodologies with other AI labs to promote safer AI practices, emphasizing the importance of governance frameworks for service providers offering AI solutions.

The episode also delves into the ongoing challenges of diversity within IT leadership. Host Dave Sobel presents data from a recent survey that reveals little change in the demographic makeup of IT leadership, with a significant majority being white and male. Despite some tech workers believing their workplaces are making strides in diversity, equity, and inclusion, the statistics indicate that progress has been slow. The discussion highlights the need for continued monitoring of these demographics to assess the effectiveness of DEI initiatives, especially as budget cuts and leadership support wane.

In a segment titled "Experts Warn," the podcast addresses the misuse of AI technologies in disinformation campaigns, specifically referencing Eleven Labs' AI voice generation technology being used in a Russian influence operation. This incident underscores the potential risks associated with generative AI, as well as the growing concerns among business leaders regarding AI fatigue and burnout. Sobel notes that while many organizations are exploring AI solutions, they often lack clear guidelines for implementation, which can lead to challenges in managing employee use of these tools.

Finally, the episode concludes with a significant market shift in the remote monitoring and management (RMM) sector, where Kaseya has overtaken ConnectWise as the leading provider. Sobel discusses the implications of this change, including Kaseya's aggressive pricing strategies and the potential risks associated with their approach. He encourages service providers to evaluate vendors based on sustainable innovation and customer satisfaction rather than just market share. The episode wraps up with a call for organizations to establish comprehensive strategies for AI implementation, ensuring that they remain competitive while effectively managing the associated risks.

Four things to know today

00:00 AI Observability Gets Real: Anthropic’s Clio Detects Threats and Offers a Blueprint for Safer AI

03:09 Same Story, Different Quarter: IT Leadership Still Struggles With Diversity

05:25 AI Voices, Burnout, and Big Bets: Why Guardrails and Guidance Are Your Best AI Tools

10:00 Big Shift in RMM: Kaseya Tops ConnectWise, But Can They Hold the Crown?

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There is a significant surge in AI leadership and investment within organizations, highlighting a 70% increase in the number of chief AI officers from 2023 to 2024. This trend indicates a growing commitment to AI technology in the corporate landscape, with many companies opting to fill these roles with talent from major tech firms. The report emphasizes that as enterprises ramp up their AI initiatives, the chief AI officer role is becoming increasingly vital, particularly in publicly traded companies and private enterprises alike.

Host Dave Sobel also shares insights from a report by Logic Monitor, revealing that 81% of enterprises plan to boost their investments in AI-powered IT operations in the coming year. The need for improved performance and resilience drives this shift, with many organizations already utilizing AI for tasks like anomaly detection and proactive IT operations. However, challenges remain, including difficulties in integrating AI with existing infrastructures and concerns about data privacy, which are critical considerations for businesses moving forward.

The episode further explores the evolving landscape of AI chatbots, with updates from OpenAI, Anthropic, and Google. OpenAI has launched real-time video capabilities for ChatGPT, enhancing user interaction, while Anthropic's new CLAWD 3.5 Haiku model boasts impressive performance metrics. Google has introduced AgentSpace, a service designed to help enterprises create and deploy AI agents. Sobel notes that while these advancements are incremental rather than groundbreaking, they hold significant potential for productivity, particularly in data-heavy industries.

Finally, the episode delves into Broadcom's successful integration of VMware, which has resulted in substantial profit increases and a significant drop in costs. Despite the positive financial outlook, concerns arise as Ingram Micro announces it will cease business relationships with Broadcom and VMware in many regions, citing challenges in delivering optimal technology outcomes. Sobel reflects on the implications of these developments for the channel strategy and the broader tech landscape, suggesting that the financial success of Broadcom may not be adversely affected by these changes.

Three things to know today

00:00 AI Leadership and Investments Surge—Will It Stick or Fold Back Into the C-Suite?  

05:12 AI Chatbots Get Smarter (Again): OpenAI, Anthropic, and Google Tweak for Productivity

08:03 Broadcom’s VMware Overhaul Delivers Big Profits—But Not Everyone’s Cheering

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Host Dave Sobel welcomes back Gerwai Todd, CEO of both PIA and TimeZest, to discuss the unique challenges and strategies involved in leading two organizations simultaneously. Gerwai emphasizes the importance of having a strong team and effective communication, highlighting the implementation of the Entrepreneurial Operating System (EOS) in both businesses. He shares how the time zone difference with his Australian team allows for a more balanced workload, enabling him to manage his responsibilities across both companies effectively.

The conversation shifts to the practical adoption of automation and artificial intelligence (AI) in the IT industry, particularly in the context of service management. Gerwai explains that AI is simply another tool in the software toolbox, which can help solve new business challenges when applied correctly. He discusses the importance of training AI models to understand specific industry use cases, such as interpreting IT tickets, and the need to mitigate issues like AI hallucinations to ensure commercial viability.

Gerwai elaborates on the journey of integrating AI into service desk operations, noting that while the technology has advanced, it still requires human oversight. He describes how the goal is to enhance the efficiency of ticket resolution by understanding the intent behind service requests. By using a collaborative approach, technicians can guide the AI in making accurate assessments, which in turn helps improve the model's performance over time.

Finally, the discussion touches on the importance of data organization and governance for solution providers. Gerwai emphasizes that having a structured approach to categorizing tickets—such as using type, subtype, and item classifications—can significantly enhance the effectiveness of AI implementations. He concludes by encouraging organizations to standardize their processes to better prepare for the integration of advanced technologies, ultimately leading to improved service delivery and operational efficiency.

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