The World’s Unluckiest Investor
Meet Oliver. If bad luck were an Olympic sport, Oliver would have multiple gold medals. This is a man who once found a crisp twenty-dollar bill on the sidewalk, gleaming like a rare treasure.
He picked it up, feeling a rare moment of fortune. But five minutes later, he returned to his car to find a parking ticket tucked under the windshield wiper. The fine was more than the twenty dollars he had just found.
Whenever Oliver chooses the shortest queue at the supermarket, the cashier immediately closes the register with a brief apology. And the ice cream machine always breaks exactly when he gets to the counter, leaving him with nothing but a melted mess. If something has a one percent chance of going wrong, Oliver somehow turns it into a guarantee.
At this point, his friends don’t even call it bad luck anymore. They simply call it being Oliver.
Eventually, after months of listening to Oliver explain how the universe had personally declared war on him, his friend Ethan finally had enough. Oliver, you need to take control of your life. Start by getting a job.
Oliver agreed. That sounded simple enough. So, he started applying.
One company filled the position ten minutes before his interview. Another company canceled the role while he was sitting in the reception area. One interviewer accidentally emailed Oliver his rejection before the interview had even started.
Twenty-three interviews later, Oliver was still unemployed.
Eventually, Ethan recommended him for a position at his own company. And against all odds, Oliver got the job. A few months later, Ethan had another suggestion.
You should start investing. Oliver laughed. Investing?
Ethan, my entire life is a warning label. If I invest in the stock market, it will probably crash the next morning. But Ethan kept insisting.
Don’t try to predict the market. Just stay consistent. Eventually, Oliver agreed.
Starting in January 2021, Oliver decided he would invest five hundred dollars every month into an S&P 500 index fund. Simple. There was only one problem.
Oliver was still Oliver.
January 2021 arrived. During that month, the S&P 500 traded as low as approximately 3,663 points. A normal investor could have bought somewhere around that level.
But Oliver wasn’t a normal investor. He somehow invested his entire five hundred dollars at the highest price reached during January. 3,870.
90 points. He had successfully found the most expensive moment of the entire month. Then came February.
The market traded as low as approximately 3,726 points. But once again, Oliver invested his five hundred dollars at the exact monthly high. 3,950.
43 points. Two months into his investing journey, and Oliver had already bought at the worst possible price twice.
March, he bought at 3,994. 41, the monthly high. April, he bought at 4,218.
78, another monthly high. Every single month. If the market reached its highest point at 2:17 on a random Tuesday afternoon, that was exactly when Oliver’s investment order seemed to execute.
Statistically impossible, yet somehow completely believable when it came to Oliver. By the end of the first year, Oliver was convinced Ethan had ruined his life. Every month, his investment app would notify him, purchase complete.
And a few days later, the market would fall. Again, and again, and again.
By now, his friends had started joking about it. Whenever Oliver bought the market, everyone else prepared for a correction. Some investors watch inflation data.
Others watch interest rates. Oliver’s friends just watched Oliver. But Ethan kept reminding him, don’t stop.
So Oliver continued investing five hundred dollars every month. He didn’t skip the expensive months. He didn’t wait for a crash.
And because this was Oliver, he continued buying at the highest price reached every single month.
After two full years, Oliver had invested twelve thousand dollars. But his portfolio was worth only ten thousand, six hundred seventy-three dollars and five cents. He was down one thousand, three hundred twenty-six dollars and ninety-five cents.
A negative return of 11. 06 percent. Oliver stared at Ethan.
See? I told you this would happen. Considering Oliver’s history, the result felt almost predictable.
He had bought through the expensive market of 2021 and then watched the market fall during 2022. This was exactly the point where someone like Oliver would normally quit. But Ethan gave him the same answer, keep going.
So Oliver kept going. Another five hundred dollars in January, another five hundred in February, another five hundred in March. Market rally?
Oliver bought at the monthly high. Market recovery? Monthly high.
New all-time high? Oliver was already there. And slowly, something strange started happening.
His losses disappeared. His portfolio recovered. And eventually, it moved into profit.
For the first time in his life, Oliver began wondering whether the universe had forgotten about him.
After four years of consistent investing, Oliver had now invested twenty-four thousand dollars. His portfolio was worth thirty thousand, seven hundred eighty-five dollars and thirty-five cents. That was a profit of six thousand, seven hundred eighty-five dollars and thirty-five cents.
And a total return of 28. 27 percent. Oliver couldn’t believe it.
He had spent four years buying at the most expensive point of every month. He hadn’t timed a single purchase correctly. And yet, he was now comfortably ahead.
Apparently, even Oliver’s bad luck had limits.
But Oliver wasn’t done yet. He continued through 2025 and through the first six months of 2026. Another monthly high, then another, then another.
He bought at 6,128. 18 in January 2025. He bought at 6,945.
77 in December 2025. He bought at 7,002. 28 in January 2026.
And in June 2026, he invested his final five hundred dollars at that month’s highest level again. 7,620. 90 points.
For five and a half years, Oliver had achieved something almost impressive. He had consistently invested at the worst possible price available each month. Sixty-six consecutive monthly purchases.
Sixty-six monthly highs.
After sixty-six monthly investments, Oliver had invested a total of thirty-three thousand dollars. His portfolio was now worth exactly forty-nine thousand, four hundred fifty-six dollars and fifty-five cents. That was a profit of sixteen thousand, four hundred fifty-six dollars and fifty-five cents.
And a total return of 49. 87 percent. Read that again.
Oliver bought at the highest price reached in every single month from January 2021 through June 2026. He bought before pullbacks. He bought before corrections.
He bought during expensive markets. He bought at record highs. And after five and a half years, his thirty-three thousand dollars had grown to forty-nine thousand, four hundred fifty-six dollars and fifty-five cents.
And for the first time in his life, Oliver’s terrible luck had finally met its match. Consistency. The point isn’t that timing never matters.
Buying at lower prices would obviously have produced a better result. But Oliver’s story reveals something more important. You don’t need perfect timing to build wealth.
You don’t need to know whether the market will rise or fall next month. And you don’t need to wait forever for the perfect opportunity. Oliver’s timing was not just bad, it was mathematically terrible.
But he had one advantage. He kept going month after month, through market highs, through market declines, through fear, through uncertainty. And eventually, consistency overcame his terrible timing.
Because when it comes to long-term investing, the perfect time to invest matters far less than consistently staying invested. And if the world’s unluckiest investor could turn thirty-three thousand dollars into almost forty-nine thousand five hundred dollars, then perhaps the biggest risk isn’t buying at the wrong time. Perhaps the biggest risk is never starting at all.
