Want to learn the secrets of navigating success in the MSP space? Learn it in this episode of our “Sunny’s Silver Linings” podcast.

In this episode of the “Sunny’s Silver Linings” podcast, Celeste Ryan, Chief People Officer of Evergreen Services Group and Christopher Caprio, CEO of Focus Technology share their insights on the challenges faced by small to medium-sized businesses in the channel and lessons they could learn. 

Focus and Specialization: 

Celeste emphasized the importance of focus for startups, urging them to identify their core strengths and excel in those areas. She highlighted the success stories of MSPs that honed in on their ideal customers and use cases, leading to more referrals and overall success. The lesson here is clear: do more of what you’re good at and less of what you’re not. 

Financial Planning and Cash Management: 

Chris, drawing from his CFO background, stressed the significance of cash flow management and financial planning. He encouraged businesses to understand all costs, create budgets and make assumptions for short to medium-term planning. Knowing the numbers, including customer acquisition costs, marketing expenses and sales budgets, is crucial for making informed business decisions. 

Building a Positive Company Culture: 

When discussing company culture, Chris emphasized the top-down approach, highlighting the role of leadership, especially the CEO, in setting the tone for the entire organization. Clear communication, setting expectations and hiring individuals who align with the company’s culture are key elements. Both speakers agreed that a positive culture contributes to employee satisfaction and, subsequently, to attracting new talent. 

Avoiding Common Mistakes: 

Celeste shared insights into common mistakes MSPs make, such as the reluctance to delegate or invest in a team. Startups often fall into the trap of trying to do everything themselves, leading to burnout and distractions. Both experts emphasized the importance of hiring a strong team and empowering them to make decisions, ultimately contributing to a faster-growing and more successful company. 

Learning from Mistakes: 

In terms of personal lessons learned, Chris highlighted the significance of first impressions. Acknowledging that MSPs often focus on client satisfaction, he emphasized the critical 30-60 day onboarding period and the need to set clear expectations. Chris recognized the importance of creating a positive initial experience, ensuring a solid foundation for long-term relationships with clients. 

Attracting and Retaining Talent: 

On the topic of talent acquisition and retention, Celeste discussed the interconnection of these challenges. She recommended focusing on creating an excellent employee experience to turn existing employees into advocates who attract new talent through referrals. Additionally, she highlighted how investing in individuals earlier in their careers has proven to foster loyalty and navigating success in the long-term. 

Chris added an interesting perspective on talent acquisition, noting that the shift to remote work during the COVID-19 pandemic allowed his company to tap into talent from various geographic locations, significantly expanding their pool of potential hires. 


Celeste and Chris provided valuable insights for startups and SMBs in the MSP space. Their advice spans multiple facets of business—from focusing on core strengths and financial planning to building a positive company culture and strategically managing talent. The lessons shared reflect a holistic approach to business growth and navigating success, emphasizing the interconnected nature of various business elements. 

Watch: Navigating Success in the MSP Space with Chris Caprio and Celeste Ryan

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About Sunny’s Silver Linings Podcast

“Sunny’s Silver Linings” is a top MSP channel podcast hosted by the CEO of IT By Design, Sunny Kaila. Sunny and his guests cover a wide range of MSP- and talent-based topics, including leadership, corporate culture, MSP services, cybersecurity, customer service, talent growth and retention, and strategies to achieve success in the channel. Listen now to take your business to the next level!

You can check out all our episodes here. You can also listen to “Sunny’s Silver Linings” podcast episodes on all the top streaming platforms, including Apple Podcasts, Spotify, Amazon Music, iHeart Radio, etc.

About IT By Design

With more than two decades of experience as a technology services provider—first as an MSP, and then for MSPs—IT By Design (ITBD) helps clients navigate the volatile technical landscape. As the authority on MSP-trained technical talent, it understands the challenges its customers face when recruiting team members. ITBD addresses those issues through many solutions: dedicated staffing, 24x7x365 NOC services, helpdesk solutions, RMM virtual admin, vCIO consulting, security, employee and client engagement software, and professional services. ITBD is headquartered in New Jersey and has facilities in India and the Philippines.