The Worst Times to Invest (and Why It Didn't Matter)

By Warren Sharpe··5 min read

Every investor's worst fear: putting money in right before a crash. We looked at three of the worst possible entry points in recent history to see what would have happened if you held on.

January 2000: right before the dot-com bust

The S&P 500 dropped nearly 50% over the next two and a half years. Tech stocks were hit even harder. But $1,000 invested in the S&P 500 in January 2000 would still be worth over $7,600 today. That's a 660%+ return despite the worst possible timing.

Even more striking: $1,000 in Apple in 2000 would be worth over $319,000 today.

October 2007: right before the financial crisis

The S&P 500 would go on to lose 57% from its peak to its March 2009 low. Banks collapsed. The housing market imploded. It felt like the end.

But $1,000 invested at the 2007 peak in the S&P 500 would still be worth roughly $4,500 today. Not as dramatic as the 2000 example, but still a solid 350% return for an investor who simply held on.

February 2020: right before COVID

The market dropped 34% in about five weeks. The fastest bear market in history. But $1,000 invested in the S&P 500 in January 2020 would be worth over $2,200 today, and anyone who bought during the March 2020 low did even better.

The pattern

In every case, holding for at least 5 years produced positive returns. The stock market has recovered from every crash in history. The only investors who locked in permanent losses were the ones who sold.

Meanwhile, $1,000 kept in cash since 2000 would have the purchasing power of about $510 today. Doing nothing was the worst strategy of all.

Browse all investments to see how different stocks performed through these downturns.

For informational and educational purposes only. Not financial advice. Past performance does not guarantee future results. All calculations are based on split-adjusted closing prices from Yahoo Finance and do not account for dividends, taxes, or trading fees.