Join Chris Tate in this fascinating episode of Tate Talks as he welcomes Len DiCostanzo, a true industry pioneer who's been at the forefront of the MSP space for over four decades. Len, known for his instrumental roles at Kaseya and Autotask, shares his unique perspective on how the IT services landscape has transformed from its nascent stages to today's complex ecosystem.In this conversation, Len delves into:The Dawn of MSPs: Travel back to the late 90s and early 2000s as Len recounts the very beginnings of managed services, the limitations of early tools, and the quest for a "single pane of glass."The Rise of PSA & RMM: Hear firsthand how Professional Services Automation (PSA) and Remote Monitoring and Management (RMM) tools revolutionized the industry, and Autotask's journey from a startup to a global powerhouse.The Challenge of Shadow SaaS: Len introduces the concept of "Shadow SaaS" and explains why managing clients' SaaS ecosystems is the next critical frontier for MSPs, offering a massive opportunity to regain control and enhance security.Building a Channel: Gain insights from Len's extensive experience helping vendors build effective "go-to-market" strategies with MSPs, and why collaboration remains a cornerstone of the industry.Future-Proofing Your MSP: Len shares his top advice for MSPs looking to push forward in 2025 and beyond, highlighting key areas like SaaS management, cybersecurity platforms, and the burgeoning impact of AI.Beyond the Grind: Discover what Len does to relax when he's not busy shaping the tech world, from pickleball and skiing to spending quality time with his son on the golf course.This episode is a must-listen for anyone in the MSP community—from veterans who remember the early days to newcomers looking to understand the foundational shifts and future direction of the industry. Len's insights are a testament to how far we've come and where the opportunities lie.MSP ToolkitAffireMusic - https://www.purple-planet.com

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