What if you bought Priceline / Booking in 2000?
US Tech · Travel. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play11.7× · S&P 500 same money: $4,626
$1,000 in Priceline / Booking at the start of 2000 would be worth about $11,702 today — 11.7 times your money, and ahead of the S&P 500 over the same stretch.
The story
Priceline launched in 1998 with a novel idea, letting travellers 'name your own price' for airline seats and hotel rooms, and a famous pitchman in William Shatner. It went public in 1999 amid wild enthusiasm, then lost the vast majority of its value as the dot-com bubble burst and its model proved less exciting than the advertising. By 2003 the shares had lost about 97 percent.
Its salvation came from an unlikely corner. In 2004 and 2005 Priceline bought two small European hotel booking firms, Active Hotels and Booking.com, for modest sums. Booking.com, with its huge inventory of independent European hotels and relentless online advertising, grew into the largest online travel agency in the world, and Priceline later added Agoda, Kayak and OpenTable. In 2018 the company renamed itself Booking Holdings, acknowledging which brand really mattered. The pandemic shut travel down in 2020, but bookings recovered quickly. A buyer at the 2003 low saw one of the great returns of the century.
The lesson: Small acquisitions can matter more than big ones; Priceline's cheap purchase of Booking.com eventually became almost the entire value of the company.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be | Multiple |
|---|---|---|---|---|
| 2000 | $470 | $11,702 | $4,626 | 11.7× |
| 2003 | $15.00 | $366,667 | $7,727 | 366.7× |
| 2005 | $25.00 | $220,000 | $5,763 | 220.0× |
| 2007 | $45.00 | $122,222 | $4,789 | 122.2× |
| 2008 | $115 | $47,826 | $4,626 | 47.8× |
| 2010 | $220 | $25,000 | $6,071 | 25.0× |
| 2012 | $470 | $11,702 | $5,312 | 11.7× |
| 2015 | $1,150 | $4,783 | $3,301 | 4.8× |
| 2018 | $1,750 | $3,143 | $2,519 | 3.1× |
| 2020 | $2,050 | $2,683 | $2,092 | 2.7× |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2003, turning $1,000 into $366,667. The S&P 500 from that same year: $7,727.
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. Priceline / Booking is one of 258 positions on the wheel — including the ones that went to zero.
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