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

Bob EvansBy Bob EvansJanuary 27, 20262 Mins Read
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Welcome to the Cloud Wars Minute — your daily cloud news and commentary show. Each episode provides insights and perspectives around the “reimagination machine” that is the cloud.

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.

Highlights

00:10 — 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.

AI Agent & Copilot Summit is an AI-first event to define opportunities, impact, and outcomes with Microsoft Copilot and agents. Building on its 2025 success, the 2026 event takes place March 17-19 in San Diego. Get more details.

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.

AI Agent & Copilot Summit is an AI-first event to define opportunities, impact, and outcomes with Microsoft Copilot and agents. Building on its 2025 success, the 2026 event takes place March 17-19 in San Diego. Get more details.

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.


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Bob Evans

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Cloud Wars

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Cloud Wars Founder Bob Evans actively analyzes the Cloud and AI categories through video reports, in-depth analyses, and interviews with the Cloud and AI market’s leaders and innovators. He’s also the creator of the Cloud Wars Top 10, a ranking and ongoing analysis of the world's most influential tech companies driving digital business and the digital economy. Bob is recognized as a world-class strategic communicator focused on emerging business strategy, disruptive innovation, and forward-looking leadership.

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