If we were to talk about Tim Cook’s flaws, I’m sure we could list a whole basketful. But if I had to pinpoint his biggest flaw, it would be this—he is not Steve Jobs.

What made Steve Jobs such an effective and visionary leader was the clarity of his values. He instilled in the Apple team an unwavering belief in—and dedication to—“innovation, design, and simplicity.” But he also had one almost “old-school” trait: an extreme emphasis on user experience.

In Jobs’ view, only by creating the best possible experience could you attract new users and build truly lasting brand loyalty.

Back in the late 1990s, when Jobs returned to Apple, which was on the brink of bankruptcy, he personally laid out the vision for us during a meeting with the advertising agency—everything must center around the user experience.

From that moment on, he was willing to “spend lavishly” on every detail that could enhance the experience, while at the same time ruthlessly rejecting—or even lambasting—any suggestion that might compromise it.

That was Jobs’ “red line”—cross it, and there would be consequences.

Now, that red line is starting to blur.

And today? That red line seems to be slowly fading away.
The latest news suggests that Apple Maps is about to start showing ads. Just like the App Store—which introduced ad placements as early as 2015 and expanded them further in 2021.

No one would consider “passively seeing ads” to be a better user experience, so why is Apple doing this?
The answer is simple—money. You can imagine how bright the eyes of the Apple board must have been when they heard about this “new revenue stream.”

No one seems to care how these ads will ultimately be received by users. Although we already live in an era where “ads are everywhere,” many still feel disappointed—that one of the wealthiest companies in the world is willing to trade a bit of its soul for some “easy money.”

“What would Jobs have done?”

Normally, I’d avoid answering hypothetical questions—they’re usually just baseless speculation. But this time is different, because I was actually there when a similar situation arose.

I remember it was around 1999. The head of the advertising agency, Lee Clow, and I were urgently called in to meet with Steve Jobs and his executive team. The topic of the meeting was: “Should we insert ads into the Mac system software?”

It sounded reasonable—“two choices, let the user decide.”

We even discussed various ways to “integrate ads”: for example, playing a Nike ad every time the system booted up; or embedding ads in system notifications, like placing a link to an ink supplier next to a “your ink is running low” alert. The discussion was lively, but no final decision was made that day.

A few days later, Steve Jobs personally told me—he had rejected the idea.

His reasoning was very straightforward: it would undermine the pure, elegant, and clean interface experience that Mac users loved. Even if users could choose between an “ad-free” or “ad-supported” version, he still didn’t want anyone to see a system that had been “polluted.”

Jobs understood that was the “crown jewel” of Apple. He would rather give up a bit of revenue than sacrifice the purity of the experience. He refused to step onto that “slippery slope,” because he knew—once you step on it, you can’t stop.

He guarded that red line well.

Does Apple still guard that line today?

Fast forward to now, and Apple’s evolution tells us this: red lines don’t last forever. How long they survive depends entirely on whether the person at the helm is willing to continue protecting them. Once no one is maintaining them, they gradually blur—and may even disappear.

For whatever reason, it’s clear that Tim Cook is no longer as obsessed with user experience as Jobs was.
If we were to ask him today, “Why are things being done now that couldn’t be done in Jobs’ era?” he’d probably respond, “Apple today is not the same as it was back then.” And he’d be right—yet that is precisely the problem.

To sum it up: the “red line” that Jobs drew protected a belief; the “red line” that Cook has erased has brought in profit. Perhaps Apple is still great—but it is no longer pure.