Oracle, Microsoft, SAP: Why Old-Timers Thrive in Cloud & AI episode artwork

EPISODE · Jan 27, 2026 · 5 MIN

Oracle, Microsoft, SAP: Why Old-Timers Thrive in Cloud & AI

from Cloud Wars Live with Bob Evans · host Bob Evans

In today's Cloud Wars Minute, I debunk the myth that legacy vendors like Oracle, Microsoft, and SAP can’t thrive in the cloud and AI era.Highlights00:10 — I want to talk about why Oracle, Microsoft, and SAP are thriving and being leaders in the industry in both cloud and AI. Why is this happening? Especially because, if you look back, we kept hearing this conventional wisdom that the legacy vendors were going to be just blown away, wiped out by these new cloud-native companies and startups, right?00:42 — That the traditional companies here — the fifty-somethings — Oracle, Microsoft, SAP, IBM, and others, were just too old. They were fuddy-duddies. They couldn’t make the turn. They didn’t get cloud. They didn’t understand it, and these hotshot new companies were just going to blow them away.01:36 — We see these companies not just holding their own, but actually being pioneers. Oracle, now number two on the Cloud Wars Top 10; Microsoft, number three; SAP, number four. They’re doing the AI economy as well, and a big part of that is tied directly to the fact that these companies have all been around for almost 50 years or more.02:22 —Oracle, 49 years. Microsoft, 51 years. SAP, 54 years. They’re wearing those sort of Boomer ages as badges of honor, and doing incredibly well in the marketplace here because they’re able to use their expertise with every sort of technology ever invented.03:04 — One of the ways that conventional wisdom in this business plays out is this notion of a zero-sum game, where there’s a limited, finite supply of assets or resources or market share — total addressable market. I mean, that’s just absolutely absurd.04:15 — This is not a zero-sum game, and these so-called experts who try to preach that and guide decision-making based on that just don’t get it. They’re applying a model that fits some other industries that certainly does not here, and it’s actually quite harmful to follow that. Visit Cloud Wars for more.

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Oracle, SAP, and Microsoft use decades of experience to lead cloud-driven business transformations.

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