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Damien Stevens - From a High School Dropout to a Tech Leader

Damien Stevens: From a High School Dropout to a Tech Leader

In this episode of “Sunny’s Silver Linings” podcast, Sunny Kaila, CEO of IT By Design, brings to you the inspiring growth journey of Damien Stevens, Founder & CEO of Servosity. The conversation delved into Stevens’ entrepreneurial journey, the evolution of the managed services provider (MSP) industry, and the importance of differentiation and resilience. 

Key Learnings from Damien Stevens’ Journey: 

  • Embrace Unconventional Paths: Success can come from non-traditional routes. 
  • Differentiate or Die: Standing out requires unique strengths and clear strategies. 
  • Leverage Personal Experiences: Turn personal challenges into business opportunities. 
  • Adopt a Go-Giver Mindset: Provide value to build trust and partnerships. 
  • Focus on Talent Acquisition: Build a strong talent pipeline to access top candidates. 

The Early Days: A Tech Enthusiast Emerges 

Damien Stevens recounted his unconventional path, starting with his impatience to leave high school. He dropped out at 14 and a half, opting for a GED and a technical college. By 17, he nearly graduated with an associate degree in robotics. His entrepreneurial spirit led him to start his first business in web development and later transition into an MSP, even before the term became widely used. 

The Entrepreneurial Bug 

Stevens reflected on his early days as a tech enthusiast, providing tech support for friends and family. The advent of the internet and web applications presented a new opportunity, leading him to focus on building websites and web applications. This niche focus set him apart in the industry, despite the risks involved. 

The Shift to Managed Services 

Both Stevens and Sunny shared their experiences of starting with a break-fix model before transitioning to managed services. Stevens recalled the challenges of managing growth, emphasizing the importance of having the right culture, team and processes in place. He highlighted the value of recurring revenue models, which allowed for better financial management and stability. 

Advice for MSPs: Embrace Change and Differentiate 

Stevens offered valuable advice for MSPs, stressing the need to embrace change and differentiate themselves in a crowded market. He highlighted the importance of self-reflection to identify unique strengths and areas of expertise. Stevens shared his mantra, “differentiate or die,” urging MSPs to develop a clear strategy to stand out from the competition. 

Leveraging Unique Abilities 

Sunny and Damien discussed the significance of leveraging unique abilities and experiences to create value. Stevens shared his journey of founding Servosity, driven by a personal experience of data loss. He initially hesitated to share this story, but eventually embraced it, realizing that many MSPs faced similar challenges. This led to the development of Servosity’s unique offering, which combined software with people and processes to ensure reliable backup testing and data recovery. 

The Importance of Giving Back 

Stevens emphasized the importance of a go-giver mindset, inspired by his own experiences. He shared Servosity’s approach of providing their backup testing process for free, allowing MSPs to benefit regardless of whether they became clients. This altruistic approach not only helped the industry but also established Servosity as a trusted partner. 

Building a Winning Team 

Towards the end of the conversation, Sunny sought Damien’s insights on hiring, developing and retaining top talent. Stevens highlighted the importance of viewing talent acquisition as a funnel, like a sales pipeline. He advocated for developing a robust talent pipeline to ensure the best candidates are available when needed. Stevens also stressed the importance of understanding one’s unique strengths and building a team that complements those abilities. 


Damien Stevens’ journey from a high school dropout to a successful tech entrepreneur is a great example of the power of resilience, self-reflection and differentiation. His insights on embracing change, leveraging unique strengths and fostering a go-giver mindset offer valuable lessons for MSPs and entrepreneurs alike. 

For more content like this, be sure to follow IT By Design on LinkedIn and YouTube, check out our on-demand learning platform, Build IT University, and be sure to register for Build IT LIVE, our 3-day education focused conference, September 9-11, 2024 in Orlando, FL!