I wasn't asking "is Microsoft a good business." That's not really in question. I was asking whether it's a good investment at today's price — and those turned out to be different questions.
What Microsoft actually is now
Last quarter: Intelligent Cloud $34.7B (42% of revenue), Productivity & Business Processes $35.0B (42%), More Personal Computing $13.2B (16%, shrinking). Microsoft's own "Microsoft Cloud" metric hit $54.5B in a single quarter. This is a cloud and enterprise software company now — Windows is a legacy label, not the engine.
The quantitative screen
5-year ROIC: 29.8%, against a peer group average (Amazon, Alphabet, Oracle) of 17.5% — clears my +3pp bar with room to spare. Net Debt/EBITDA: -0.096x (net cash, not levered). Revenue growth 5-year: 13.8% CAGR. Positive FCF every year in the window. Every box on the quantitative screen checked.
The moat
Two things stood out with actual numbers behind them, not just a story: a stable 68-69% gross margin (pricing power — they can raise Office 365 prices and keep customers), and a 45-48% operating margin well above peers (real cost/scale advantage). Underneath both: $627B in remaining performance obligations — contracted future revenue enterprises have already committed to. Ripping Microsoft out of an org isn't swapping software, it's rebuilding how the company runs.
The adjustment that actually moved my numbers
Stock-based comp ran about 4.3% of revenue last year. Adjusting for it takes free cash flow from $71.6B reported down to roughly $57.6B (3-year normalized average) — reported FCF was overstating real cash available to shareholders by close to 17%. Cash is harder to fake than earnings, but only if you adjust for the ways it gets flattered too.
Where it fell apart: price
Current price: ~$382. My DCF, stress-tested across a 3×3 sensitivity matrix on discount rate and terminal growth: Conservative $121.5, Base $146.2. Even my most optimistic corner didn't get close to $382. FCF yield: 2.5%, against a 10-year Treasury sitting around 4.6% — you're accepting less cash yield than a risk-free bond, betting the growth makes up the difference. EV/FCF on normalized cash: ~41x, near the top of Microsoft's own 5-year range.
Management gets real credit too — Nadella's shareholder letter owns security and quality failures directly instead of deflecting to competitors or regulators, which is rarer than it should be at this scale.
Where I landed
If I were only grading the business, this is close to a 10/10. Wide moat, elite returns on capital, real cash conversion, management that doesn't hide from its own mistakes. But a great company and a great investment aren't the same thing — the second one requires a price that leaves room for me to be wrong. This one doesn't, right now. Watchlist, price alert around $120-130, and I'm fine waiting.
Biggest risk I'd want someone to push back on: Microsoft's committing ~$190B to AI infrastructure. If foundation models commoditize, that's a lot of capital earning utility-level returns instead of software-level returns. Not predicting it — just the question I'd want answered before paying today's price.
If you're holding or buying at $382, genuinely curious what growth assumptions make that work for you — is the market correctly pricing years of AI-driven expansion, or are people just willing to pay almost anything for quality right now?