What if you bought Microsoft in 1990?
US Tech · Software. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play800.0× · S&P 500 same money: $19,429
$1,000 in Microsoft at the start of 1990 would be worth about $800,000 today — 800.0 times your money, and ahead of the S&P 500 over the same stretch.
The story
Microsoft entered the 1990s owning the operating system on nearly every PC, and Windows 95 plus the Office suite turned that position into one of the most profitable franchises in corporate history. By 2000 the shares traded at a valuation that assumed the good times would compound forever, just as the US government was arguing in court that Microsoft had abused its monopoly. The company avoided a break-up, but the stock did not avoid gravity.
What followed was a famously flat decade. Under Steve Ballmer profits kept rising while the share price drifted, as investors fretted about missing search, smartphones and the shift to the web. Satya Nadella took over in 2014, embraced the cloud with Azure, moved Office to subscriptions and stopped treating Linux as an enemy. An early, large bet on OpenAI then positioned Microsoft at the centre of the generative AI boom. Someone who bought at the 2000 peak waited the better part of fifteen years to break even, then watched the shares multiply many times over.
The lesson: A great business bought at a silly price can still deliver a lost decade; Microsoft's profits grew for years while its 2000 valuation slowly deflated.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 1990 | $0.6 | $800,000 | $19,429 | 800.0× |
| 1995 | $3.00 | $160,000 | $14,783 | 160.0× |
| 2000 | $40.00 | $12,000 | $4,626 | 12.0× |
| 2003 | $20.00 | $24,000 | $7,727 | 24.0× |
| 2005 | $27.00 | $17,778 | $5,763 | 17.8× |
| 2007 | $30.00 | $16,000 | $4,789 | 16.0× |
| 2008 | $35.00 | $13,714 | $4,626 | 13.7× |
| 2010 | $30.00 | $16,000 | $6,071 | 16.0× |
| 2012 | $27.00 | $17,778 | $5,312 | 17.8× |
| 2015 | $46.00 | $10,435 | $3,301 | 10.4× |
| 2018 | $86.00 | $5,581 | $2,519 | 5.6× |
| 2020 | $160 | $3,000 | $2,092 | 3.0× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 1990, turning $1,000 into $800,000. The S&P 500 from that same year: $19,429.
On this day
- 30 January 2007: Windows Vista launches to consumers
- 13 March 1986: Microsoft goes public
- 4 April 1975: Microsoft is founded in Albuquerque
- 25 April 2019: Microsoft reaches a $1 trillion market value
- 27 June 2008: Bill Gates' last day as a full-time Microsoft employee
Now try it without hindsight. The wheel decides the year and the asset class, you pick the position, ten seconds a pick, and we simulate to today. Microsoft is one of 258 positions on the wheel — including the ones that went to zero.
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