⚠ The Greenfield GapModerate threat

The whole edifice of enterprise switching costs protects the enormous installed base of companies that grew up on Microsoft — but it does far less to win the next generation, and that is the quiet danger. A startup founded today is as likely to begin life on Google Workspace, a fleet of Macs, a clutch of best-of-breed cloud tools, and an open-source stack as on Microsoft's rails. It never builds the Active Directory dependency, never accumulates the data gravity, never trains its people in the Microsoft grammar — so there is simply nothing to rip out.

The danger is generational and slow. Microsoft's grip on the large incumbent enterprise is nearly total and nearly unshakable, but companies are born and die, and if each new cohort of fast-growing firms is less Microsoft-centric than the last, the moat comes to protect a shrinking share of the economy's future even as it dominates its present.

Microsoft is not passive here. It courts startups aggressively, offers generous cloud credits, and has made Azure, VS Code, GitHub, and TypeScript genuinely beloved¹ by exactly the cloud-native builders who might otherwise skip it. Many greenfield companies, on reaching real scale, adopt Microsoft's enterprise tools anyway, because that is what large organizations still run on.

A low-to-moderate, long-horizon worry. The installed base is safe for a very long time, but the composition of the future customer base is genuinely contestable, and a careful owner watches whether the next generation of great companies is being born inside Microsoft's tent or outside it.