Biggest What-Ifs in Stocks (or How Investors Live with Regret)

You think you’ve got regrets because you didn’t buy Nvidia NVDA at $50 or sold Tesla TSLA at $420? Join the club.

The stock market’s history is littered with “almost” trades, missed deals, and facepalm-worthy decisions that turned out to be trillion-dollar pivots.

This is the hall of fame for what didn’t happen — and what those stories teach us about how markets (and human nature) actually work. Call it a free masterclass in greed, fear, FOMO, and the priceless value of just sitting tight sometimes.

Take it easy today, grab your cold brew and read up on the biggest what-ifs in stock market history.

🍏 Ronald Wayne: The Patron Saint of “Oops”

Our first inductee needs no introduction. But let’s do it anyway. Ronald Wayne, the third Apple AAPL co-founder, sold his 10% stake back in 1976 for the princely sum of $800. He wanted to avoid any debts if things went south. Sensible, right?

That $800 stake today would be worth more than $300 billion. That’s more than the GDP of Finland — and about 1.2 million new iPhones every single day for pretty much the rest of his life. Wayne has since said he doesn’t regret it. Which is probably the biggest lie he’s ever told.

🍿 Blockbuster’s Netflix “Pass”

In 2000, Netflix NFLX was a DVD-by-mail startup with spotty profits. Reed Hastings, Netflix’s founder, knocked on Blockbuster’s door and offered to sell the whole thing for $50 million — about the price of a Hollywood production.

Blockbuster’s execs reportedly laughed him out of the room. “People will always want to drive to a store to rent a VHS,” they said, basically. Fast forward: Netflix is worth around $560 billion, and Blockbuster is down to one store that’s mostly a selfie museum for millennials who miss rewinding tapes.

💻 Microsoft’s Lifeline That Saved Apple

In 1997, Apple AAPL was broke. Steve Jobs had returned but was days away from the company flat-lining for good. Enter Bill Gates.

Microsoft MSFT wrote Apple a $150 million check, partly to keep antitrust regulators off its back. Jobs even appeared on stage with Gates beaming in on a giant screen like Big Brother — a moment that made every Apple fan cringe.

But that deal saved Apple’s hide. The iMac was born. The iPod followed. Then the iPhone. That $150 million is now a rounding error on Apple’s $3 trillion valuation. Sometimes your greatest rival is also your best frenemy.

🔍 Google: The $750K “Meh”

Before “Google it” became a verb, Larry Page and Sergey Brin tried to sell their little search engine to Excite — the Yahoo-lite portal that dominated the ‘90s web. The price? $750,000.

Excite’s CEO said search “wasn’t that important” — one of the worst calls in tech history. Today, Alphabet GOOGL is worth over $2.1 trillion and always flashing bright on the Stock Heatmap, and Excite is a footnote in a forgotten Web 1.0 graveyard.

The lesson? Never dismiss a side project just because it doesn’t fit the spreadsheet.

💸 Masayoshi Son’s $200 Billion Slip

SoftBank’s Masayoshi Son is known for his giant, risky bets. And in 2017, he made a pretty good one: his Vision Fund scooped up a 5% chunk of Nvidia stock worth about $4 billion. He called GPUs the backbone of the AI revolution. He was right.

But by 2019, SoftBank was under pressure to tidy up its books. So Son sold the whole position for a tidy short-term profit. That stake today would be worth nearly $200 billion, given Nvidia’s rocket-fuel AI rally.

“We can cry together,” CEO Jensen Huang told Masa Son at an AI Summit in Tokyo last year. Early doesn’t always mean patient. And being “kind of right” can be the most painful lesson of all.

📊 Berkshire Hathaway: A Textile Mill’s Rebirth

Think of Berkshire Hathaway BRK.A now — a $1 trillion behemoth. Insurance, utilities, railroads, huge piles of Apple shares. But back when Warren Buffett bought it, Berkshire was a dying textile business in New England.

Buffett only bought control because he was annoyed at the CEO’s lowball tender offer. It turned into his permanent holding company. The textile side eventually went extinct — but the insurance side became the cash-printing machine Buffett used to buy everything else.

Sometimes your best trade starts with pure pettiness.

🚀 Tesla: The Short Sellers’ Pain Cave

Here’s a more recent tale. Tesla was not long ago the most shorted stock on Earth. Everyone from hedge funds to your uncle at Thanksgiving was betting on Elon’s dream to fail.

Every now and then, the short-sellers get slapped with billions of dollars in losses, because the stock shoots up out of nowhere. The most recent example? November 12, when those naysayers nursed $7 billion in wiped out cash. Bears have been torched so many times, they might as well switch sides and sell Tesla hoodies instead.

🌌 Yahoo’s Double Miss: Google and Facebook

If you think blowing one chance is bad, try blowing two. Yahoo turned down the chance to buy Google for less than a million bucks. Then years later, they offered $1 billion for Facebook (now META META) — but bungled the negotiations and tried to lower the price. Zuck said “nope.”

But back to Google, because the story didn’t end there. In 2002, Yahoo said it wanted to buy Google for $3 billion. Brin and Page said $5 billion and Yahoo said no. Then Microsoft was ready to pay $40 billion to acquire Yahoo in 2008. But Yahoo said no.

Today, Google, Microsoft, and Meta are trillion-dollar titans. Yahoo? Sold itself for $4.5 billion, mostly for its patents, in 2016 to Verizon. Talk about slipping on the same banana peel more than once.

🧃 Apple: The Splits that Keep Giving

Want a reason to love boring old “buy and hold”? Apple AAPL has split its stock five times since its 1980 IPO. If you’d bought 100 shares back then, you’d now have over 56,000 shares, plus mountains of dividends.

Next time you want to swing trade every squiggle, remember: sometimes the slowest route is the sweetest.

📝 Regret: The Only Universal Asset Class

Every trader has a “coulda, shoulda, woulda.” It’s the cost of doing business in a market that only makes sense in hindsight. Even the pros — billionaires, boards, hedge funds — have stories that make yours look tame.

Ronald Wayne reminds you that selling too soon can cost you your own island. Masayoshi Son proves being right but impatient is still being wrong. Yahoo shows that “almost” is worth exactly zero on a balance sheet.

What these stories prove is that the market’s biggest edge isn’t necessarily timing, genius, or inside scoops — it’s discipline, resilience, and sometimes a stubborn refusal to touch the sell button.

🤗 Bonus Story: Ballmer Regrets Nothing

But not every story has to be a regret story. Just look at Steve Ballmer, Microsoft ‘s former CEO. Since the early 2000s, he’s been holding his 4% stake in the software maker and that’s now worth more than $130 billion. No regrets found.

👉 What’s Your “One That Got Away”?

Now your turn: What’s your personal what-if story? Which ticker haunts you in your sleep? Drop your best missed trade or worst sell in the comments — we promise to laugh with you, not at you. Probably. Stay sharp. Stay patient!