What if you bought Expedia in 2005?
US Tech · Travel. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play10.4× · S&P 500 same money: $5,763
$1,000 in Expedia at the start of 2005 would be worth about $10,417 today — 10.4 times your money, and ahead of the S&P 500 over the same stretch.
The story
Expedia started in 1996 as a division of Microsoft, one of the software giant's experiments in online services. It was spun off, then acquired in stages by Barry Diller's media and internet group IAC, which in turn spun it off as a separate listed company in 2005. Expedia grew into a portfolio of travel brands including Hotels.com and, later, Trivago, while the shares moved sideways for most of its first decade as an independent company and fell in the financial crisis.
Growth came by consolidation. In 2015 alone Expedia bought Travelocity, Orbitz and HomeAway, owner of the vacation rental site Vrbo, positioning itself against Airbnb. It also spent heavily on marketing to Google, which was simultaneously a key traffic source and a potential competitor. Booking Holdings outgrew it, and the pandemic in 2020 forced deep cost cuts and a hasty consolidation of its sprawling technology systems. From 2005 to 2026 the shares rose roughly tenfold.
The lesson: Paying for customers is expensive; online travel agencies spend heavily on Google advertising, so a big chunk of their revenue flows straight to a potential rival.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 2005 | $24.00 | $10,417 | $5,763 | 10.4× |
| 2007 | $21.00 | $11,905 | $4,789 | 11.9× |
| 2008 | $32.00 | $7,812 | $4,626 | 7.8× |
| 2010 | $26.00 | $9,615 | $6,071 | 9.6× |
| 2012 | $29.00 | $8,621 | $5,312 | 8.6× |
| 2015 | $85.00 | $2,941 | $3,301 | 2.9× |
| 2018 | $120 | $2,083 | $2,519 | 2.1× |
| 2020 | $108 | $2,315 | $2,092 | 2.3× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2007, turning $1,000 into $11,905. The S&P 500 from that same year: $4,789.
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. Expedia is one of 258 positions on the wheel — including the ones that went to zero.
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