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 profitability per client matters, and how simple, continuous improvements can transform both service...
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 into opportunities, including: Transitioning from break/fix to managed services — and convincing h...
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 explore how Bizway thrives in the “firefighter” role of managed services. They discuss: How Bart ...
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 health scare reshaped his leadership style. He shares how he's rebuilding company culture, redefining...
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 course), Rob shares what IT leaders and MSPs are still getting wrong—and how to fix it. They cover: Wh...
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. Barinder shares: How he transitioned from break-fix work to a fully managed services modelThe challenges ...
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 launching Adlumin, a company that reimagines MDR and XDR for modern MSPs, why simplicity and automation...
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 the hard decisions, including shedding old habits, embracing EOS (Entrepreneurial Operating System)...
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, and saying no to clients who didn’t fit—all in pursuit of scalable, high-value growth. The result? A...
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 opens up about the challenges of transitioning from break/fix to managed services, giving up cont...
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 didn’t see coming. From mandating a security upgrade for every customer—before they even asked—to sh...
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 the MSP space. You’ll hear how Halo earned trust without private equity, how a £10 Reddit campaign h...
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 ✅ The moment he realized he had to fire bad clients to grow ✅ Why mentorship and partnerships were game-c...
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 stories that define the MSP community. Highlights include lessons on leadership, partnerships,...
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 how Paul developed a risk-based approach to cybersecurity, handled high-stakes ransomware incident...
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. We dive into the challenges MSPs face today, from rising cyber insurance costs to the evolving e...
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 he used to create a sustainable, people-first business. Discover how Benji transitioned from techni...
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 takes us through the critical pivot points that shaped his career and ultimately led him to found ...
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 strategies for growth. Listen as Zane and Kenny discuss the pivotal moment when one of their founding partners ...
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 leaders, this episode is packed with actionable insights on leveraging strong client relationships...