Why Cybersecurity Is Becoming Every Company’s Biggest Risk episode artwork

EPISODE · May 25, 2026 · 22 MIN

Why Cybersecurity Is Becoming Every Company’s Biggest Risk

from Legends N Leaders · host Ben Weiss

Every company is becoming a technology company.But most businesses still aren’t prepared for the cybersecurity, AI, and infrastructure challenges that come with it.In this episode of LegendsNLeaders, we sit down with Roger Lewis, CEO of CMIT Solutions, to discuss scaling a national technology brand, the future of managed IT services, and how AI is changing business operations.Since taking over CMIT, Roger has helped grow the company from $68M to $150M in revenue while building a service-driven organization designed to bring enterprise-level IT and cybersecurity support to small and mid-sized businesses across North America.Before CMIT, Roger worked at IBM supporting NASA and the Space Shuttle program — experiences that shaped his philosophy around scalable systems, operational discipline, and mission-critical execution.We discuss:The future of AI and cybersecurity for businessesWhy SMBs are increasingly targeted by cyber threatsHow managed IT services are evolvingBuilding a franchise-based technology company at scaleCreating a culture centered around service and trustWhat leadership looks like during rapid technological changeThis episode is a deep dive into entrepreneurship, cybersecurity, AI, leadership, and the systems powering modern business.#RogerLewis #Cybersecurity #AI #Technology #BusinessPodcast #Leadership #ITServices #Entrepreneurship #ManagedServices #Innovation #LegendsNLeaders

Every company is becoming a technology company.But most businesses still aren’t prepared for the cybersecurity, AI, and infrastructure challenges that come with it.In this episode of LegendsNLeaders, we sit down with Roger Lewis, CEO of CMIT Solutions, to discuss scaling a national technology brand, the future of managed IT services, and how AI is changing business operations.Since taking over CMIT, Roger has helped grow the company from $68M to $150M in revenue while building a service-driven organization designed to bring enterprise-level IT and cybersecurity support to small and mid-sized businesses across North America.Before CMIT, Roger worked at IBM supporting NASA and the Space Shuttle program — experiences that shaped his philosophy around scalable systems, operational discipline, and mission-critical execution.We discuss:The future of AI and cybersecurity for businessesWhy SMBs are increasingly targeted by cyber threatsHow managed IT services are evolvingBuilding a franchise-based technology company at scaleCreating a culture centered around service and trustWhat leadership looks like during rapid technological changeThis episode is a deep dive into entrepreneurship, cybersecurity, AI, leadership, and the systems powering modern business.#RogerLewis #Cybersecurity #AI #Technology #BusinessPodcast #Leadership #ITServices #Entrepreneurship #ManagedServices #Innovation #LegendsNLeaders

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Why Cybersecurity Is Becoming Every Company’s Biggest Risk

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This episode was published on May 25, 2026.

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Every company is becoming a technology company.But most businesses still aren’t prepared for the cybersecurity, AI, and infrastructure challenges that come with it.In this episode of LegendsNLeaders, we sit down with Roger Lewis, CEO of CMIT...

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