What if you bought Oracle in 1990?
US Tech · Software. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play1000.0× · S&P 500 same money: $19,429
$1,000 in Oracle at the start of 1990 would be worth about $1,000,000 today — 1000.0 times your money, and ahead of the S&P 500 over the same stretch.
The story
Oracle, co-founded by Larry Ellison in 1977, built the relational database that much of corporate America ran on, then expanded into business applications. The shares rose more than a hundredfold during the 1990s and collapsed with the rest of tech in 2000 and 2001. Ellison responded with a series of acquisitions, including a bruising hostile takeover of PeopleSoft completed in 2005 and Sun Microsystems in 2010, and Oracle became a steady, cash-generating compounder with a reputation for aggressive licence audits.
For much of the 2010s it was seen as late to the cloud, and the share price reflected that. The acquisitions of NetSuite in 2016 and health-records firm Cerner in 2022 added scale but also debt. The story changed with the AI boom: Oracle's cloud infrastructure became a supplier of computing capacity to AI labs, and huge contracts announced in 2025 sent the stock soaring before worries about borrowing and the economics of data centres pulled it back. A long holder in 2026 still sat on a large gain.
The lesson: Leverage amplifies a narrative in both directions; Oracle's debt-funded AI build-out turned its sleepy stock into a volatile bet on a few large customers.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 1990 | $0.2 | $1,000,000 | $19,429 | 1000.0× |
| 1995 | $1.90 | $105,263 | $14,783 | 105.3× |
| 2000 | $25.00 | $8,000 | $4,626 | 8.0× |
| 2003 | $11.00 | $18,182 | $7,727 | 18.2× |
| 2005 | $13.00 | $15,385 | $5,763 | 15.4× |
| 2007 | $17.00 | $11,765 | $4,789 | 11.8× |
| 2008 | $22.00 | $9,091 | $4,626 | 9.1× |
| 2010 | $24.00 | $8,333 | $6,071 | 8.3× |
| 2012 | $26.00 | $7,692 | $5,312 | 7.7× |
| 2015 | $45.00 | $4,444 | $3,301 | 4.4× |
| 2018 | $47.00 | $4,255 | $2,519 | 4.3× |
| 2020 | $53.00 | $3,774 | $2,092 | 3.8× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 1990, turning $1,000 into $1,000,000. The S&P 500 from that same year: $19,429.
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. Oracle is one of 258 positions on the wheel — including the ones that went to zero.
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