The build-vs-buy trap operators keep walking into

Somewhere between a 50-person operator and a 500-person one, every leadership team has the same conversation: we have four vendors, three of them do not talk to each other, and our people spend an hour a day moving data between them. Do we keep buying, or do we build?

The real question is not build vs buy

The real question is: which two or three capabilities are actually core to how we win, and which fifteen are commodities we just need to work? Operators who get this right buy the commodities (email, calendar, accounting, payroll) and build — or pay someone to build — a thin integration layer plus the two or three core workflows that make them different.

The trap I see most often

Buying a best-of-breed tool for every function and hoping a Zapier graveyard glues them together. This works until you need to answer a real question across three of them, and suddenly the answer is three hours of CSV exports. That is the tax you pay for picking safe fifteen times.

If it takes more than a day to answer a board-level question with your current stack, your stack is no longer your stack — it is a museum.

A framework that actually works

• List the three questions leadership should be able to answer in under a minute. Those are the core.
• For each, identify which system is the source of truth — if the answer is a spreadsheet, you have found your build target.
• Everything else is commodity. Buy the cheapest tool that does the job without breaking your data contracts.
• Invest the saved budget in the integration layer and the three core workflows. That is where the moat lives.

The operators who get this right stop feeling like their tech stack owns them. The ones who do not, eventually hire a Chief of Staff whose job is largely to move CSVs between tools. That is an expensive outcome to accept.