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 talent
✅ His real-time insights on leadership, fearlessness, and strategic growth

Whether you're an MSP owner, IT leader, or thinking about making the leap, Chris’s story is packed with real-world lessons on resilience, business strategy, and scaling with confidence.

🎧 Listen now and learn how to turn setbacks into success!

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 retrospective offers actionable insights and a look at what’s to come in Season 3.

Listen now and join the conversation shaping the future of IT.

Matt Hutter:

Side Hustle to Successful MSP: Matt Hutter on Starting and Growing His Business

An intriguing narrative of Matt Hutter who transformed his side gig into a thriving enterprise, all while navigating the tumultuous terrains of a recession and family life.

 

Brandon Layhew

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

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.

 

Bente Roycroft

Customer to CEO: Bente Roycroft on Transforming Accurate Network for Growth

Bente Roycroft, CEO of Accurate Network Services, paints 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. 

 

Ted Clouser

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 IT leader navigating cybersecurity complexities, or a tech enthusiast curious about industry evolution, this episode is packed with actionable insights and inspiration.

Key Topics Covered:

• Transitioning from MSP to MSSP: Lessons for IT leaders.
• Risk as a growth driver: Building cybersecurity services that scale.
• Handling ransomware recovery: Real-world examples and strategies.
• Recruiting and training top talent in a competitive field.

Join host Chris Massey as we uncover the strategies behind Paul’s success and explore what it takes to thrive in the fast-changing IT and cybersecurity space.

🎧 Tune in now and take your MSP to the next level!

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 services to become strategic partners for their clients. Plus, he introduces his latest venture, Think Purple, and its mission to solve organizational challenges through human-centric digital transformation.

Whether you’re an MSP owner navigating growth, a tech leader seeking inspiration, or simply curious about the future of IT, this episode is packed with actionable insights and thought-provoking ideas.

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 foster empathy and care at the core of his MSP. Whether you're striving for growth, searching for work-life harmony, or looking to inspire a values-driven team, Benji’s story offers actionable insights and a fresh perspective on what it means to lead in today’s MSP industry.

Tune in to learn how you can balance ambition with well-being and build a business that thrives without burning out.

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 challenges of transforming a break-fix MSP to embracing the intricacies of cyber insurance, Dustin sheds light on what it takes to thrive in an industry that’s constantly evolving.

He reveals hard-learned lessons about managing client relationships, understanding the hidden risks in traditional insurance policies, and the importance of keeping MSPs involved in the claims process. Along the way, Dustin provides candid insights into why he believes MSPs can and should play a critical role in reshaping the cyber insurance landscape.

Whether you’re an MSP executive looking to grow your business or simply interested in the intersection of IT services and insurance, this episode will leave you with actionable ideas on how to innovate, adapt, and stay ahead in a fast-changing marketplace.

Key Takeaways:

• Dustin’s early experiences in MSP ownership and the path to scaling a break-fix model
• How the concept for Beltex emerged as a response to the insurance industry’s blind spots
• Strategies for MSPs to navigate the challenges and benefits of specialized cyber insurance
• Why staying involved in incident response can lower costs and strengthen client trust

Tune in for an insightful conversation that explores the evolution of an MSP leader into a pioneer of channel-friendly cyber insurance.

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 them streamline operations, build a stronger culture, and create a clear path forward for Real IT Care.

This episode is packed with valuable insights for MSP owners, executives, or anyone aspiring to build a successful MSP. You’ll learn:

• The critical role that EOS can play in scaling your business.
• How to maintain strong client relationships while navigating leadership changes.
• Strategies to foster a winning culture that retains top talent and drives growth.

Whether you're facing similar challenges or looking for a roadmap to take your MSP to the next level, this episode will leave you inspired and equipped with actionable takeaways.

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 navigated challenges, adapted to industry changes, and turned adversity into an opportunity to propel ByteTime forward.

Whether you’re looking to strengthen your MSP’s sales strategy, enhance your service offerings, or build a robust cybersecurity foundation, Brandon’s story offers valuable lessons for every MSP leader. Tune in to discover how to balance sales, services, and security to position your MSP for long-term success.

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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 hardware-centric company into a thriving Managed Service Provider. Whether you’re an MSP owner looking to scale or an aspiring entrepreneur seeking inspiration, Stephen’s story of growth, leadership, and strategic vision is packed with insights and actionable takeaways. Don’t miss this compelling episode on what it truly takes to earn your leadership in the IT world!

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

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.

After you finish listening, be sure to subscribe to Beyond the Horizon so you don’t miss any of their upcoming episodes.

 We’ll be back in two weeks with our conversation with Stephen Riddick.

In this episode of Beyond the Horizons, Pete Roythorne is joined by David Weeks, VP of Community at N-able, to delve into the transformative concept of open ecosystems for Managed Service Providers (MSPs). They discuss the evolving role of RMM tools as data aggregators, the importance of integrating diverse software, and the power of AI in enhancing business efficiency. Tune in to explore how MSPs can leverage open ecosystems to drive opportunity, mitigate risks, and ensure scalability.

 Topics Discussed:

 

1. Introduction to Open Ecosystems:

The significance of open ecosystems for MSPs, and the changing role of RMM as a data aggregator.

2. Data Aggregation and Business Insights:

Utilizing data from your RMM to build pipelines and identify sales opportunities, and how data aggregation helps MSPs understand customer needs and trends.

3. Integration and Interoperability:

The necessity of MSPs to use a range of software tools beyond a single vendor's offerings. Challenges and benefits of bi-directional integrations and communication between tools.

4. AI and Automation in MSP Operations:

The role of AI and Robotic Process Automation (RPA) in managing data and making decisions, plus how AI enhances the scalability and efficiency of MSPs.

5. Vendor Relationships and Best-of-Breed Tools:

The risk of single-vendor tool stacks and the importan

N-able also produces Beyond the Horizon. Hosted by industry veterans, this podcast delves deep into the findings of the annual MSP Horizons Report, providing actionable insights to transform your IT business. Listen & Subscribe Wherever You Get Your Podcasts.

'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.

Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.

This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.