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 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.

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