Now That's IT: Stories of MSP Success

What does it take to build a $20M MSP without a traditional sales team? In this episode of Now That’s IT: Stories of MSP Success, Chris Massey sits down with Simon Marcil, co-founder of S3 Technologies and creator of Propel Your MSP, to explore the power of retention, strategy, and AI-driven innovation. Simon shares how S3 grew by focusing on client value and strategic alignment, why tracking prof...

What happens when a family-owned computer repair shop faces the recession, changing technology, and the challenges of scaling? James Thompson of ECS Technology Solutions shares how he transformed his father’s local IT business into a thriving managed service provider (MSP). In this episode of Now That’s IT: Stories of MSP Success , host Chris Massey dives into James’s journey of turning obstacles...

When the stakes are high, and the systems are down, who do governments and enterprises in the Netherlands call? Bart Lageweg, founder of Bizway, has built one of Europe’s most trusted MSPs by running toward the toughest IT challenges—cyberattacks, ransomware recovery, and compliance-critical crises. In this episode of Now That’s IT: Stories of MSP Success , host Chris Massey sits down with Bart to...

In this episode of Now That’s IT , Aaron Betts shares his remarkable journey—from launching his first MSP in 2005 and losing it all during the financial crisis, to taking a corporate detour, burning out, and ultimately returning to lead Intelesys as President. Aaron opens up about the hard-earned lessons of entrepreneurship, the shift from break/fix to managed services, and how a life-altering hea...

Modern cyberattacks aren’t just technical—they’re personal. And Rob Shapland knows how to exploit the human element better than anyone. In this episode, Chris Massey sits down with Rob to unpack the wild world of social engineering—from sneaking into corporate offices disguised as a delivery driver to using AI voice clones to bypass MFA. With over 200 successful break-ins (all authorized, of cours...

What does it take to grow from a solo IT freelancer to the founder of a thriving Managed Services Provider with a 25-person team and a bold vision for the future? In this episode of Now That’s IT: Stories of MSP Success , we sit down with Barinder Hans , founder and CEO of Red Rhino , to explore his journey from building PCs at his dining table to leading one of Canada’s most respected MSPs. Barin...

What does it take to go from defending national secrets to defending MSPs? In this episode of Now That’s IT: Stories of MSP Success , Robert Johnston—former Pentagon cyber operator, DNC breach responder, and co-founder of Adlumin—shares his journey from military red teams to building one of today’s fastest-growing cybersecurity platforms. We unpack how Robert transitioned from CrowdStrike to launc...

In this episode of Now That’s IT: Stories of MSP Success , host Chris Massey sits down with Craig Fisher and David Izen of Technica Solutions to uncover how a chance meeting—and a well-timed kebab—sparked a complete transformation of their MSP business. Craig and David share how they moved beyond the limitations of a technical-first approach to build a thriving, growth-driven MSP. They dive into t...

In this episode of Now That’s IT: Stories of MSP Success , we sit down with Vinod Paul , President of Managed Services at  Align , to explore how a bold decision to focus exclusively on one vertical— financial services —transformed the company from a solid MSP into a global leader. Vinod shares the behind-the-scenes story of walking away from millions in revenue, standardizing their tech stack, an...

What happens when your business partners are also your brothers? For Kevin Stock, CEO of RCR Technology Group, it meant building a managed service provider grounded in trust, clear roles, and shared values. In this episode, Kevin shares how a side hustle fixing computers became a full-scale MSP—powered by family dynamics, small-town reputation, and a relentless focus on doing right by clients. He...

When John McCoy walked away from a high-paying corporate job, he wasn’t chasing freedom—he was answering a calling. In this episode, John shares how his commitment to helping others led him to launch MidSolv , an MSP rooted in community and built on trust. But it wasn’t until he caught a ransomware attack in real time that his purpose fully crystallized: protecting clients from the threats they di...

What happens when the right product meets the right moment—and the right voice? In this episode of Now That’s IT: Stories of MSP Success , we sit down with Tim Barton-Wines, the dynamic force behind Halo PSA’s meteoric rise. Tim shares his unexpected journey from selling vodka in a wine shop to transforming Halo from a little-known help desk tool into one of the fastest-growing PSA platforms in th...

What if getting fired was the best thing that ever happened to your career? In this episode of Now That’s IT: Stories of MSP Success , host Chris Massey sits down with Chris Kraiss , founder of ClearPath Technology , to discuss his journey from corporate IT to building a thriving MSP —and the setbacks that shaped his success. Chris shares: ✅ How getting fired pushed him to launch his own MSP ✅ T...

In this special recap episode of Now That’s IT: Stories of MSP Success , host Chris Massey and producer Stephen McNulty, are joined by guest John Joyce, revisit nine of the most memorable episodes from the podcast’s 45-episode journey. From navigating the 2008 financial crisis to building thriving MSPs with resilience, transparency, and collaboration, this episode dives deep into the inspiring sto...

In this episode of Now That’s IT: Stories of MSP Success , we sit down with Paul Cashmore, co-founder of Solace Global Cyber, to explore his incredible journey of transforming a traditional MSP into a leading MSSP. Paul shares how his passion for cybersecurity and a service-first mindset fueled rapid growth, while also addressing the challenges MSPs face in today’s evolving IT landscape. Discover...

In this episode of Now That’s IT: Stories of MSP Success , we sit down with Alex Stanton, a seasoned entrepreneur and industry innovator, to explore his remarkable journey from a teenage web developer to the founder of one of the largest MSPs in the Inland Northwest. Alex shares candid insights on scaling a business, navigating industry shifts, and the lessons learned while building a legacy in IT...

In this episode of Now That’s IT: Stories of MSP Success , we sit down with Benji Sawyer, the high-tech guru behind Sawyer Solutions, to explore his journey from the brink of burnout to building a thriving MSP grounded in balance, compassion, and purpose. Benji opens up about the challenges of working 100-hour weeks, the pivotal moment that forced him to reassess his approach, and the strategies h...

When Dustin Bolander entered the world of managed services, he never anticipated where his journey would lead. Starting as a helpdesk technician, he worked his way up to co-owning a thriving MSP. But as Dustin shares with host Chris Massey, the transition to becoming an innovator in cyber insurance was anything but straightforward. In this episode of Now That’s IT: Stories of MSP Success , Dustin...

In this episode of Now That's IT: Stories of MSP Success , we dive deep into the remarkable growth story of Real IT Care, a thriving MSP based in Pennsylvania. Co-owners Zane Patalive and Kenny Steinbacher share how they transformed a nonprofit IT initiative into a flourishing business, navigating partner changes, adopting the Entrepreneurial Operating System (EOS), and embracing new strategi...

In this episode of Now That’s IT: Stories of MSP Success , we sit down with Brandon Layhew, President and Managing Partner of ByteTime, to explore his incredible journey from sales success to leading a thriving MSP. Brandon shares how he turned a stagnant IT company into a fast-growing MSP by blending a service-first approach with cutting-edge cybersecurity offerings. For current and aspiring MSP...

In this episode of Now That’s IT: Stories of MSP Success, we dive deep with Stephen Riddick, President of CSP, Inc., as he shares his unconventional journey from contemplating law school and ski-bumming in Jackson Hole to mastering enterprise sales at Cisco. Stephen knew he couldn’t just walk into his family’s business—he needed to earn his place by proving himself outside the company. Discover ho...

This week, we’re doing something a little different. We're excited to share an episode from another podcast sponsored by N-able: Beyond the Horizon: Future Focused MSP Insights . In this episode, Forward Together: Why Open Ecosystems Drive MSP Growth , David Weeks discusses how open platforms and ecosystems are shaping the future for MSPs, and why collaboration is key to driving growth in thi...

In this episode of Now That's IT: Stories of MSP Success , we sit down with Brad Walser, the founder and CEO of Walser Technology Group, to uncover the remarkable journey of growing a successful Managed Service Provider (MSP) in the heart of small-town Salisbury, North Carolina. With over 20 years of experience, Brad shares his insights on how he transformed a side hustle into a thriving IT b...

In this episode of Now That's IT: Stories of MSP Success , we sit down with Dave Wilkeson, the founder and CEO of MSP Advisor, to uncover the key strategies that propelled him from a tech hobbyist to a renowned leader in the Managed Service Provider (MSP) industry. Dave shares invaluable insights into the critical role of financial discipline in scaling an MSP, offering candid advice he wishe...

In this episode of Now That's IT: Stories of MSP Success , we sit down with Boyd Smith, the founder and president of TechKnowledgey, to explore his incredible journey from being self-employed to becoming a successful business owner. Boyd shares his unique perspective on the crucial differences between being self-employed and owning a business, highlighting the importance of building a reliabl...