Now That's IT: Stories of MSP Success

Sep 11, 2025

Small Changes, Big Impact: How Simon Marcil Uses Continuous Improvement to Scale

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 delivery and customer relationships. He also reveals how S3 integrates AI into daily operations—from ti

Aug 28, 2025

Passing the Torch: How James Thompson Turned a Family Business into a Thriving MSP

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 his father it would workBuilding a support group for family-owned businesses to navigate unique challeng

Aug 14, 2025

Chasing Cyber Crisis: Bart Lageweg on Thriving in High-Stakes IT

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 turned a solo IT operation into a leading cybersecurity-focused MSPThe strategy behind small, frequent

Jul 31, 2025

From Burnout to Believer: Why Aaron Betts Came Back Stronger

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 success, and guiding his MSP toward a $10M vision—all while empowering his team to think bigger. Wheth

Jul 17, 2025

Deepfakes, Disguises, and Deliveries: How Rob Shapland Hacks Human Weakness to Build Stronger Security

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: Why the human layer is still the biggest vulnerability in securityHow attackers are already using AI for

Jul 3, 2025

Freelancer to Founder: How Barinder Hans Built Red Rhino

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 of hiring his first employee after 10 years soloWhy culture, documentation, and leadership were key to

Jun 19, 2025

From Pentagon to Product Leader: Robert Johnston’s Mission to Transform Cybersecurity

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 matter more than ever, and how AI is reshaping both threats and responses in real time. Whether you ru

Jun 5, 2025

It Takes Two: The Story of Technica’s Transformation

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), joining peer groups, and making bold moves to scale their business. Listeners will gain insights into

May 22, 2025

Why Focus Wins: Vinod Paul on Align’s MSP Success

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? Align grew from 75 to 300 employees, expanded into 31 countries, and became a trusted name in one of the most

May 12, 2025

Built on Trust: Kevin Stock on Leading a Family-Run MSP That Lasts

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 control as a founder, and leading through tough seasons—including a rocky start to what ultimately became t

Apr 24, 2025

A Mission to Protect: John McCoy’s Path to MSP Ownership

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 shifting his entire client base to fully managed services, John’s story is one of bold leadership, cybers

Apr 10, 2025

From Help Desk to Headliner: How Tim Barton-Wines Earned the MSP Spotlight

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 helped build a global footprint, and why saying “no” to acquisition has become their boldest strategic m

Mar 27, 2025

Scaling from Setbacks: How Chris Kraiss Built a Thriving MSP

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-changers for scaling his business ✅ The importance of company culture in attracting and retaining top tal

Jan 2, 2025

Leaders Helping Leaders: 9 Memorable Stories of MSP Success

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, and finding purpose through adversity. Whether you’re an MSP veteran or just curious about the space, this re

Dec 19, 2024

Achieving Rapid Growth with Cybersecurity & Service: Paul Cashmore's IT Evolution

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 incidents, and built a culture of innovation and adaptability. Whether you’re an MSP owner looking to scale, an

Dec 5, 2024

Thinking Bigger: Alex Stanton on Leadership, Innovation, and the Future of IT

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 expectations of tech-savvy clients. Alex offers his perspective on how MSPs can move beyond commoditized

Nov 21, 2024

Burnout to Balance: Benji Sawyer’s Journey to Sustainable MSP Leadership

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 technician to CEO, the lessons he learned about scaling without sacrificing culture, and the steps he took to

Nov 7, 2024

Pivot Points: Dustin Bolander’s Journey from MSP Leadership to Reinventing Cyber Insurance

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 Beltex—a groundbreaking cyber insurance policy built specifically for MSPs. From navigating the challen

Oct 24, 2024

Unlocking Growth: The Real IT Care Transformation

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 retired, accelerating their decision-making and unlocking a 40% growth surge. Discover how EOS helped t

Oct 10, 2024

Sales, Service, and Security: How Brandon Layhew Leads ByteTime

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, evolving your services, and embracing cybersecurity to drive business growth. Learn how Brandon navig