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 model The challenges...
Jul 03, 2025•34 min•Season 3Ep. 8
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 m...
Jun 19, 2025•37 min•Season 3Ep. 7
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), ...
Jun 05, 2025•37 min•Season 3Ep. 6
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? Alig...
May 22, 2025•38 min•Season 3Ep. 5
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...
May 12, 2025•41 min•Season 3Ep. 4
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 shif...
Apr 24, 2025•28 min•Season 3Ep. 3
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 hel...
Apr 10, 2025•55 min•Season 3Ep. 2
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...
Mar 27, 2025•34 min•Season 3Ep. 1
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 find...
Jan 02, 2025•54 min•Season 2Ep. 26
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,...
Dec 19, 2024•22 min•Season 2Ep. 25
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 exp...
Dec 05, 2024•36 min•Season 2Ep. 24
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 technici...
Nov 21, 2024•31 min•Season 2Ep. 23
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 Be...
Nov 07, 2024•41 min•Season 2Ep. 22
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 re...
Oct 24, 2024•37 min•Season 2Ep. 21
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, ...
Oct 10, 2024•36 min•Season 2Ep. 20
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 how he leveraged his experience at a global tech giant and an MBA from Duke to transform CSP from a ha...
Sep 26, 2024•37 min•Season 2Ep. 19
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 this space. It’s a must-listen for anyone looking to stay ahead in the evolving world of managed services. A...
Sep 12, 2024•16 min•Season 2Ep. 18
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 business, all while navigating the unique challenges of a rural market. Brad’s story is a masterclass in s...
Aug 29, 2024•40 min•Season 2Ep. 17
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 wishes he could give his younger self. Listeners will learn how Dave successfully navigated the complex waters...
Aug 15, 2024•35 min•Season 2Ep. 16
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 reliable team and creating robust systems. Discover how Boyd navigated the challenges of the Great Recession, ma...
Aug 01, 2024•45 min•Season 2Ep. 15
In this episode of "Now That's IT: Stories of MSP Success," we sit down with Marco La Vecchia, the Chief Revenue Officer at Produce8, to uncover the secrets behind his remarkable success in the managed service provider (MSP) industry. From his early days at N-able to his leadership roles at AVG and Fully Managed, Marco has consistently driven growth and innovation through strategic sales initiatives. Marco shares his journey from an aspiring professional golfer to a key player in the MSP world, ...
Jul 18, 2024•27 min•Season 2Ep. 14
Hear from Tim Clarkson, founder and managing director of OxygenIT, who shares his remarkable journey from struggling to surviving to thriving. Tim discusses the challenges of transitioning from accounting to IT, founding his MSP, and navigating severe financial hardships. Learn how he turned his business around by focusing on financial transparency, team alignment, and operational efficiency. Tim's story is packed with practical insights and strategies that every Managed Service Provider (MSP) o...
Jul 08, 2024•43 min•Season 2Ep. 13
Lisa Niekamp-Urwin the Founder, President, and CEO of Tomorrow's Technology Today, shares her incredible journey from project management to establishing a full-service support company. Lisa delves into her early career challenges, the motivation behind starting her business during an unemployment phase, and the values that drive her team. She provides insights into transitioning from break-fix services to managed services, the importance of marketing, and the power of networking. Lisa also speak...
Jun 20, 2024•21 min•Season 2Ep. 12
Chris Massey sits down with Charles Weaver, co-founder and CEO of MSP Alliance—the world's largest industry association and certification body for cloud computing and managed service professionals. They delve into the early days of the managed services industry, discussing its evolution from the 90s dot-com era to today. Learn about the challenges and triumphs of pioneering MSP executives, the creation of industry standards, and the ongoing need for compliance and regulation. Charles also reflec...
Jun 06, 2024•33 min•Season 2Ep. 11
Sit down with James Bartrop, the founder and managing director of ShadowSafe, a leading cybersecurity and IT services MSP based in Brisbane, Australia. James takes us through his incredible journey from a solo entrepreneur grappling with the early challenges of running his own business to building a scalable and successful MSP. Discover how James navigated the ups and downs of the MSP world, from working in a national IT firm to striking out on his own, and the pivotal moments that shaped his pa...
May 23, 2024•31 min•Season 2Ep. 10
In this revealing episode of "Now That's IT," Luis Giraldo, Chief Experience Officer at ScalePad, shares his unique journey from a world-class musician to a revered MSP advocate, discussing cthe pivotal transitions and decisions that shaped his career and how his background in music provided a rhythmic foundation for his innovative approach to MSP advocacy. Tune in as Luis provides actionable insights on navigating vendor relationships, leveraging personal experience to foster industry change, a...
May 09, 2024•42 min•Season 2Ep. 9
Doug Alexander's story is nothing short of remarkable, showcasing his transition from the sales battlefield to the c-suite to the boardroom. With riveting tales from his EMC sales days and insights into his aggressive methodology, Doug's narrative is a treasure trove for anyone looking to inject entrepreneurial vigor and a competitive edge into their career. Join us as we peel back the curtain on how to morph a complacent lifestyle business into a growth juggernaut. Doug shares his playbook on i...
Apr 25, 2024•53 min•Season 2Ep. 8
Mark Sangster, cybersecurity expert and Chief of Strategy at Adlumin, brings his rich experience from BlackBerry, Intel, and Cisco, and delves into the intricacies of cybersecurity strategies that can empower MSPs. Mark and N-able's Chris Massey explore valuable perspectives for owners and leaders of MSP, highlighting effective practices in risk management, the importance of a robust security posture, and insights into the MSP market's evolving challenges. Tune in for an in-depth conversation th...
Apr 11, 2024•28 min•Season 2Ep. 7
From the pages of English literature to the scientific studies, to leading growth for an MSP. That's the narrative arc Bente Roycroft, CEO of Accurate Network Services, shares with us, painting a vivid picture of her transition from environmental consulting to leading a thriving IT business. Bente reveals how an appreciation for the written word set the stage for triumphs in hiring, HR, accounting, and strategic business planning. The chemistry between Bente and her business partner, Luke Willia...
Mar 28, 2024•35 min•Season 2Ep. 6
Unlock the secrets of IT compliance as we're joined by Bill Smeltzer, Chief Strategy Officer at Focus Technology Solutions. Bill brings a treasure trove of expertise, particularly on the intersection of healthcare and IT. We explore the compliance challenges that small medical practices face and how these hurdles are steering them towards affiliations with larger entities. Bill's strategic insights reveal the pivotal role of outsourced compliance partners in today's complex regulatory landscape,...
Mar 07, 2024•39 min•Season 2Ep. 5
