What if you bought Uber in 2020?
US Tech · Apps. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play2.7× · S&P 500 same money: $2,092
$1,000 in Uber at the start of 2020 would be worth about $2,667 today — 2.7 times your money, and ahead of the S&P 500 over the same stretch.
The story
Uber, founded in 2009 in San Francisco, turned the phone into a taxi dispatch system and then spent the 2010s fighting city regulators, taxi lobbies and its own culture. It raised enormous sums of private money to subsidise rides around the world, and its founder Travis Kalanick was pushed out in 2017 after a run of scandals over workplace conduct and aggressive tactics. Dara Khosrowshahi took over and began cleaning up.
The 2019 IPO priced at 45 dollars and quickly traded below it, as investors balked at years of heavy losses. The pandemic nearly emptied the ride business in 2020, but food delivery through Uber Eats boomed and kept the company going. Price increases, cost cuts and scale then did what sceptics had doubted: Uber posted its first full-year operating profit in 2023 and began buying back stock. By 2026 its main open question was whether self-driving cars would be its partner or its replacement. A buyer at the start of 2020 had more than doubled their money.
The lesson: Network businesses can take a decade of losses to show their real economics; Uber's critics were right about the cash burn and wrong about the endpoint.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be |
|---|---|---|---|
| 2020 | $30.00 | $2,667 | $2,092 |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2020, turning $1,000 into $2,667. The S&P 500 from that same year: $2,092.
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. Uber is one of 258 positions on the wheel — including the ones that went to zero.
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