The 10 Biggest "What If I Had Invested" Moments of the Last 25 Years

If you want the number that punches you in the stomach, here it is: $1,000 in Bitcoin at the start of 2012 would be worth about $13.1 million today. $1,000 in Amazon at its 1997 IPO would be worth about $2.84 million. And even the “boring” option, a simple S&P 500 index fund bought in January 2010, would have grown to roughly $7,900.

That’s the part people remember.

What they forget is what it felt like in real time. These weren’t neat little lines drifting upward on a chart. They were messy, terrifying, high‑volatility stories where the future looked uncertain, the headlines looked awful, and selling felt smart.

That’s why this list matters. Not to make you feel bad about what you missed. To help you think more clearly about the next thing that looks crazy, early, overhyped, or dead.

Before the List: How to Read “What If” Numbers Honestly

Most “what if I had invested” posts cheat a little.

They pick a clean starting point. They use today’s price. They show the final gain. Then they quietly skip the middle, which is where real life happens.

Real investing is different. You buy when the outcome is uncertain. You hold while smart people explain why your thesis is broken. You watch 40%, 60%, or 80% of your money disappear on paper. Then you decide whether to stay in, sell out, or panic halfway through.

That middle matters more than the final number.

For the figures below, IPO scenarios start at official IPO prices, and date‑based scenarios use split‑adjusted historical closes. The S&P 500 comparison uses an index‑fund proxy so the comparison reflects what a real investor could have actually bought.

The 10 Scenarios

How to read this: “Worst crash to survive” means the roughest peak‑to‑trough decline you would have had to sit through to capture the full ride.

Asset	$1,000 Then → Today (Approx.)	Worst Crash to Survive	S&P 500 Same Period
Amazon (IPO, May 1997)	~$2,840,000	-94%	~$13,000
Apple (Jan 2007)	~$92,900	-61%	~$6,800
Netflix (Jan 2007)	~$300,000	-80%	~$6,800
Bitcoin (Jan 2012)	~$13,100,000	-87%	~$6,800
Tesla (Jan 2012)	~$204,500	-75%	~$6,800
Nvidia (Jan 2015)	~$370,000	-66%	~$3,900
Ethereum (Jan 2017)	~$240,500	-94%	~$3,400
Microsoft (Jan 2012)	~$17,700	-30%	~$6,800
Shopify (IPO, May 2015)	~$76,600	-85%	~$3,800
S&P 500 Index Fund (Jan 2010)	~$7,900	-34%	~$7,900

Returns are approximate and ignore taxes, fees, and behavioral mistakes like panic selling.

What Jumps Out Right Away

First, the raw winners are enormous.

Bitcoin and Amazon sit in a completely different universe of returns. Then comes a second tier of huge winners like Nvidia, Netflix, Ethereum, and Tesla. Then there’s a third tier that would still feel life‑changing to many investors: Apple, Shopify, and Microsoft.

Second, the S&P 500 was not weak.

Turning $1,000 into roughly $7,900 with a simple index fund is an excellent outcome for a strategy that requires almost no decision‑making.

Third, nearly all the biggest winners demanded emotional pain.

You didn’t earn Amazon by being clever for five minutes. You earned it by surviving a 94% collapse. The same pattern shows up with Bitcoin, Ethereum, Netflix, Shopify, and Tesla.

The headline gain was the reward. The crash was the admission price.

The Real Enemy Is Survivor Bias

Looking backward makes the path look obvious. Looking forward never does.

Today it feels obvious that Amazon would dominate e‑commerce, that Nvidia would power AI infrastructure, and that Apple’s iPhone changed consumer technology.

But at the time, each of those stories existed alongside dozens of others that looked equally promising and went nowhere.

That’s why regret is such a poor investing tool. Regret remembers the survivor and forgets the failures.

Many industries produce one dominant winner and a long list of companies that fade away. Remembering only the winner creates the illusion that success was obvious all along.

What the S&P 500 Benchmark Actually Says

The benchmark keeps your thinking honest.

Every time you look at a giant winning investment, compare it with what the same money would have done in a simple index fund.

That comparison reminds you that the default strategy wasn’t useless. It quietly captured the long‑term growth of the entire market.

The index fund doesn’t give you bragging rights at dinner parties. It gives you reliable participation in the overall economy.

And historically, that has been very difficult to beat consistently.

The Most Useful Lesson From This List

You do not need to capture the entire move.

Many people imagine that the only successful outcome is buying perfectly and holding flawlessly for 10 or 20 years.

That almost never happens.

A more realistic success story looks like this:

You notice something early.

You invest a small amount.

You survive the first ugly stretch.

You add gradually if the thesis strengthens.

You avoid going all‑in.

You let time do most of the work.

That approach is less dramatic, but far more survivable.

Because in almost every case on this list, position sizing mattered just as much as stock selection.

A Better Way to Use “What If” Stories

Use them as stress tests.

When an opportunity excites you, ask yourself four simple questions.

Could I hold this for 10 years?

Not “could this go up next quarter.” Could you hold it through a long period where the story looks broken?

What would a 50—80% drop do to me?

Would it annoy you? Fine.

Would it change your life? Then the position is too big.

What am I trying to beat?

Every investment competes against a simple index fund.

If your idea requires perfect timing and constant monitoring just to maybe outperform the market, that matters.

Am I okay being wrong?

You will miss great opportunities. You will also avoid disasters you never hear about.

The goal is not to catch every rocket. The goal is to build a portfolio that still works even when you miss most of them.

Try It Yourself

Build your own “what‑if” scenario for any stock, ETF, or crypto.

Then compare it with the S&P 500 over the same period.

That one comparison often changes how the entire story looks.

FAQ

Which investment on this list produced the biggest return?

Bitcoin starting in 2012 produced the largest outcome in this list, turning roughly $1,000 into more than $13 million. Amazon’s 1997 IPO also produced a multi‑million‑dollar result.

Why did these investments require surviving huge crashes?

Fast‑growing companies and new technologies often experience extreme volatility. Markets frequently underestimate and then overreact to their long‑term potential.

Why include the S&P 500 in the table?

The index fund acts as a baseline comparison. It shows what a passive investor could have achieved without picking individual winners.

Is it realistic to capture the full return of these investments?

Very few investors buy at the perfect moment and hold the entire time. The numbers illustrate the potential path, not the typical investor experience.

What’s the most practical lesson from these stories?

Keep most of your portfolio diversified and treat high‑conviction ideas as smaller, carefully sized bets.

For education only, not investment advice.