What if you bought PayPal in 2018?
US Tech · Payments. The hindsight answer, year by year, against the only benchmark that matters.
Could you have picked it? Play0.9× · S&P 500 same money: $2,519
$1,000 in PayPal at the start of 2018 would be worth about $946 today. A plain S&P 500 index fund over the same years would have made more — the boring option won.
The story
PayPal started in 1998 out of a merger between Peter Thiel's Confinity and Elon Musk's X.com, survived early fraud epidemics and was bought by eBay in 2002. In 2015 eBay spun it off, Venmo included, and PayPal became a favourite of growth investors as online shopping expanded and the pandemic pushed even more spending online. By mid-2021 the shares had risen roughly sevenfold from the spin-off.
The pandemic trade then reversed. Growth slowed sharply, Apple Pay and other wallets competed hard at checkout, and Venmo proved popular but difficult to monetise. PayPal stock fell by around three quarters from its peak, and Alex Chriss, appointed chief executive in 2023, focused on profitability rather than user numbers. The business continued to generate substantial cash, but the shares stayed far below their highs. Anyone who bought at the start of 2018 or 2020 was showing a loss by 2026.
The lesson: Early leadership in a fast-growing market does not guarantee a lasting moat; PayPal's dominance in online checkout met rivals that controlled the phone itself.
$1,000 invested at the start of each year
| Bought in | Price then | Worth today | S&P 500 would be |
|---|---|---|---|
| 2018 | $74.00 | $946 | $2,519 |
| 2020 | $108 | $648 | $2,092 |
green = beat the S&P 500 · red = lost money
Best entry point in our set: 2018, turning $1,000 into $946. The S&P 500 from that same year: $2,519.
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. PayPal is one of 258 positions on the wheel — including the ones that went to zero.
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