Hammad Hassan

The Companies That Won Were Misunderstood for Years First

The competitive advantage nobody wants to talk about.

Apr 8, 2026·5 min read

In September 2016, Apple removed the headphone jack from the iPhone 7. The reaction was immediate and enormous. A petition demanding Apple reverse the decision gathered over 300,000 signatures.

The Verge called it "user-hostile and stupid." Samsung ran ads mocking the decision. Google released a parody video celebrating that the Pixel 5a still had a headphone jack.

A YouTuber proved that a headphone jack could physically fit inside the iPhone 7 without removing any major components, which made Apple's justification look even weaker. Apple's official explanation was that it took "courage."

This was mocked relentlessly, and honestly, it deserved to be. It's a bad word for what they were actually doing. But what they were actually doing turned out to be right.

Within a few years, every major competitor quietly followed. Samsung removed the jack from the Galaxy S20. Google removed it from the Pixel 6a. The same companies that had run ads mocking Apple's decision adopted the same decision. Samsung even tried to delete the ads.

AirPods became one of the most successful consumer electronics products in history. Apple and Beats ended up controlling nearly 50% of global Bluetooth headphone revenue.

The wireless audio market, which barely existed in its current form before the iPhone 7, became a multi-billion-dollar category.

The headphone jack went from universal standard to vestigial organ in about four years.

This is the pattern I want to write about: the willingness to be misunderstood for an extended period of time as a competitive advantage.

The standard version of this story focuses on the technology. Apple saw that wireless audio was the future, made a bet, and the bet paid off.

But I think the more interesting version is about the psychology.

Specifically, the psychology of the people making the decision, and why most organizations can't do what Apple did, even when the logic points the same way. Because removing the headphone jack wasn't a hard technical decision. Bluetooth existed. Wireless headphones existed. The direction was clear to anyone paying attention.

The hard part was tolerating two years of being publicly wrong. Two years of mockery, bad reviews, angry customers, and competitors using your decision as a marketing weapon.

That's not a technology problem. That's a temperament problem.

Jeff Bezos said this explicitly in his 2016 letter to shareholders:

"If you're going to take bold bets, they're going to be experiments. And if they're experiments, you don't know ahead of time whether they're going to work. Experiments are by their nature prone to failure. But a few big successes compensate for dozens and dozens of failures."

But then he added the part that I think matters more:

"Given a 10 percent chance of a 100 times payoff, you should take that bet every time. But you're still going to be wrong nine times out of ten. We all know that if you swing for the fences, you're going to strike out a lot, but you're also going to hit some home runs."

And then:

"Big winners pay for so many experiments."

Bezos built Amazon on this.

AWS was years of internal investment before the rest of the market understood what cloud computing would become.

The Kindle was sold at a loss when the ebook market barely existed. Amazon Prime launched in 2005 when the idea of paying $79 a year for free shipping sounded bizarre. In each case, the decision looked wrong for a while. And in each case, being willing to look wrong was the actual advantage.

I think this is one of the most underappreciated asymmetries in business. Most correct long-term decisions look wrong in the short term. This is almost a law.

If a decision looks obviously right to everyone immediately, it's probably not a very bold decision. The truly category-defining moves are the ones that require a period of looking foolish. And the length of that period, and your ability to tolerate it, determines whether you can make those moves at all.

Most founders can't tolerate six months of being wrong in public. Most CEOs can't tolerate a quarter of bad press. Most product teams can't tolerate a launch where the reviews are negative and the metrics dip. So they hedge. They compromise. They ship the version that nobody hates, but nobody loves.

They keep the headphone jack. The cost of this is invisible, which is what makes it so dangerous. You never see the decisions that weren't made. You never see the features that weren't removed. You never see the bets that weren't placed because someone in the room said, "But what will people say?"

The cost of intolerance for being misunderstood doesn't show up on any dashboard. It shows up years later, when you realize you're still doing what everyone else is doing, and there's no strategic distance between you and your competitors.

Apple has a long history of this specific pattern. They killed the floppy disk drive. People were outraged. They killed the CD-ROM drive. People were outraged. They killed the physical keyboard on the phone. People were outraged. In every case, the outrage lasted between one and three years, and then the rest of the industry followed. The pattern isn't just that Apple makes bold decisions. It's that they absorb the backlash without flinching.

There were no apology tours after the headphone jack. No "we hear you" blog posts. No compromise dongles shipped as a hedge. They made the decision, took the hit, and waited. They trusted time to do what explanations couldn't.

And there's a move inside the move that most people miss. Apple doesn't just remove things and wait. They remove the thing, let the frustration build, let the noise get loud, and then they sell you the solution.

The headphone jack disappeared in September 2016. For months, people complained. They bought ugly dongles. They fumbled with adapters. The pain was real and public. Then AirPods shipped. And suddenly the problem had an answer, an answer that costs $159 and locks you deeper into Apple's ecosystem.

The removal created the demand. The noise confirmed the demand. The product captured the demand. They didn't solve a problem that existed.

They manufactured a problem, waited for people to feel it, and then walked in with the fix. The floppy drive disappeared, and the USB port arrived. The CD drive disappeared, and the App Store arrived. Every removal is a setup for a sale.

But because there's a gap between the pain and the solution, it never looks like a sales strategy. It looks like courage.

Raw Notes

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