MS-DOS licensed the IBM PC into existence, Windows put it on every desk, and Office made it permanent. By the end of the century Microsoft was the most valuable company in the world — and the Department of Justice’s central case.
IPO at $21 a shareMarket
Four employees become billionaires and roughly a thousand become millionaires; the office-park legend of option wealth starts here.
Closed $0.09549 that month
Windows 95Product
A launch covered like a moon landing — Start buttons, midnight queues, and the desktop monopoly cemented. The stock has already multiplied sixty-fold since the IPO.
The ruling lands as the bubble bursts. Microsoft keeps growing profits — and the stock goes sideways for thirteen years while search, phones, and social all happen somewhere else.
Found guilty of monopolyCrisis
Judge Jackson rules Microsoft abused its Windows monopoly and later orders a breakup. The remedy is overturned on appeal, but the stock spends the next fifteen years de-rating anyway.
Closed $34.88 that month
Ballmer replaces GatesLeadership
The CEO change is weeks before the Nasdaq peak. Ballmer triples revenue over his tenure — and the market pays less for each dollar of it every year.
Closed $48.94 that month
Vista ships late; iPhone ships firstCrisis
Five years in the making, Vista lands to shrugs months before Apple reveals the computer of the next decade. Microsoft’s mobile answer never arrives.
A new CEO kills the phone, ships Office on iPhone, and bets the company on Azure. The multiple re-rates before the revenue fully arrives — the market finally believes the transition.
Nadella becomes CEOLeadership
The head of the cloud division gets the job and immediately starts governing as if Windows were a product, not a strategy.
Closed $38.31 that month
LinkedIn for $26BDeal
The largest software acquisition yet — a professional graph bolted onto Office and Dynamics, and an early sign the new Microsoft will pay for position.
Closed $51.17 that month
The $1B bet on OpenAIProduct
A research lab gets Azure-scale compute and Microsoft gets an option on whatever deep learning becomes. It looks eccentric for years.
A $1B bet on OpenAI becomes Copilot everywhere, and Azure becomes the default landlord of the AI build-out. Forty years in, Microsoft is again priced as the platform everyone else rents.
The rates repricingCrisis
Like every durable grower, Microsoft gives back a third of its value as the easy-money era ends — its cheapest valuation in five years, days before ChatGPT goes public.
Closed $232.13 that month
Copilot everywhereProduct
ChatGPT becomes a product line: GitHub, Office, Bing, Azure. Investors start pricing Microsoft as the toll booth on enterprise AI.
Closed $247.81 that month
The second $3T companyMarket
Thirty-eight years after a $21 IPO, the market caps a software subscription business above three trillion dollars.
Closed $397.58 that month
Activision closes for $69BDeal
The largest tech acquisition ever survives two years of regulators — gaming becomes a side bet inside a much larger platform.
