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The $21 Share That Taught a Generation About Patience McKee Financial Resources, Wealth Management Services |
On March 13, 1986, a software company from Bellevue, Washington, went public. The stock opened at $21 per share. Bill Gates, thirty years old and already a decade into building the company, watched Microsoft raise $61 million in a single day. The entire business was valued at just over half a billion dollars.
Plenty of people bought shares that morning. Most of them sold within a few years. Some held through the 1987 crash. Fewer held through the dot-com bust. Fewer still held through the long, frustrating stretch of the 2000s when the stock seemed to go nowhere.
The ones who held through all of it? They didn't just own a stock. They owned a piece of a business — and they understood the difference. |
What $21 Became
It's tempting to run the numbers. A single share purchased at the IPO, held through every stock split and reinvested dividend, would be worth a staggering sum today. The figures get thrown around in financial media every anniversary, usually with the implied message: You should have bought Microsoft.
But that framing misses the point.
The real story isn't that Microsoft went up. Lots of stocks go up. The story is that holding Microsoft — or any single stock — through forty years of volatility required something most investors don't talk about: the willingness to be uncomfortable. |
In 1987, less than two years after the IPO, markets crashed. In 2000, Microsoft was at the center of the dot-com collapse, its stock falling more than 60% from its peak. From 2000 to 2014, the stock was essentially flat while the company was mocked as irrelevant, a dinosaur being lapped by Google and Apple. Headlines asked whether Microsoft's best days were behind it.
Investors who sold during any of those moments had reasons. Good reasons, even. The ones who held didn't have better information. They had a different relationship with what they owned.
Trading vs. Owning
There's a meaningful difference between buying a stock and owning a piece of a business.
Buying a stock is a transaction. You're making a bet that the price will go up, and you're watching to see if you're right. When the price drops, the instinct is to cut your losses. When it rises, the instinct is to take profits. The emotional logic is short-term: What is this doing for me today? |
Owning a piece of a business is different. You're not betting on the price — you're betting on the company. You're asking whether the business has durable advantages, competent leadership, and a reason to exist in ten or twenty years. When the price drops, you're asking whether anything about the business has changed. If it hasn't, the drop is noise. |
That distinction sounds academic until you're living through a 60% decline and every headline is telling you to get out. That's when it becomes the only thing that matters.
The Unsexy Truth
Most people don't get rich buying IPOs. The data on this is clear: the average IPO underperforms the broader market over time. The excitement of getting in early usually costs more than it returns.
What creates wealth isn't access to the next hot stock. It's the boring, unglamorous act of staying invested through the periods when staying invested feels foolish. |
Microsoft's forty-year run wasn't a straight line. It included years of doubt, years of decline, and long stretches where the smartest analysts in the world were certain the company was finished. The investors who built meaningful wealth weren't smarter than everyone else. They simply didn't leave.
This isn't advice to buy Microsoft or any other individual stock. It's a reminder that patience isn't a personality trait some people are born with. It's a discipline — one that gets tested precisely when it matters most. |
What This Means for Your Plan
You probably don't own Microsoft from 1986. Almost nobody does. But the principle underneath this story applies to every long-term investor.
Markets will decline. Sometimes sharply, sometimes for years. Headlines will announce that everything has changed. The urge to act — to do something — will feel responsible and reasonable.
The question isn't whether you'll feel that urge. You will. The question is whether you've built a plan that accounts for it. A portfolio designed around your actual timeline. An understanding of what you own and why. A relationship with someone who can remind you, during the uncomfortable stretches, that discomfort isn't the same as danger. |
The wealth that Microsoft created for patient investors wasn't built on luck or timing. It was built on conviction — the decision, made over and over again, to stay. That's not a tech story. It's an investing story. And it's one worth remembering. |
Related Reading on Our Site
If this article resonated, you may find these pieces helpful as well:
📘 Buy-and-Hold Investing: Why Doing Nothing Is Harder Than It Sounds |
📙 From Hollywood to Wall Street: The Truth About IPO Investing |
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Written and shared by Anthony S. Owens, on behalf of the team at McKee Financial Resources, Wealth Management Services.
Disclaimer: This article is for educational purposes only and should not be considered financial, legal, or tax advice. Investing involves risk, including the potential loss of principal. Past performance is not indicative of future results. No investing strategy can guarantee a profit or protect against loss. Please consult a qualified financial professional for guidance tailored to your individual situation. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Copyright © 2026 Anthony S. Owens. All rights reserved. |