What is Apple's biggest mistake?
Apple’s biggest mistake was that it failed to capitalise on the iPhone.
The iPhone, released in June 2007, was perhaps the most revolutionary step in a mass-market product in the history of humanity.
It took the phone from a clumsy product with a keyboard, to a beautiful intuitive one that a 3 year old could use, with an effortless marketplace to buy apps.
It was genius.
Within 10 years nearly half the planet would have a device broadly similar to the first iPhone.
It was only until March 2010 that Android was ready to ditch its keyboard with the HTC Nexus One - that’s almost 3 years later - and it was crap compared to the iPhone.
Not only that, by 2010, the iPhone had achieved 3 billion downloads and it had over 100,000 apps.
I mean, why would anyone buy an Android when it had no apps?
From this absolutely unassailable leadership position, Apple have been absolutely assailed.
But from 100% of the keyboard-less smartphone market they’ve gone down to around 10%.

Today mobiles run on Android, just like PC’s have run on Windows for 3 decades. The iPhone is a niche player in the market it once owned. And it’s going to go more niche.
Ok, fine, Apple is making US$141bn a year from their iPhones, far more than Android make. But Android have an almost monopoly position on the operating system running smartphones and soon it will dominate the app marketplace, and long-term they'll end up making multiple times what Apple will ever make.
It’s just a matter of time.
What has been Apple's biggest strategic mistake since Steve Jobs’s death?
First, Too Many Product Versions: Apple currently has 5 different iPhone models on the market, along with 4 iPad variations - which makes 9 current models that they have to support for several years, along with all the past models they’re still supporting (two of the iPhone models are currently “past versions”, BTW).
I don’t think Steve Jobs would have approved of this, as it adds complexity & reduces their ability to be nimble in terms of product design. The more they add every year, the more they have to support, and the slower they can roll out & deploy new features across the board. Jobs liked things to be elegant. I suspect he’d limit things to 2 iPhone & 2 iPad model (big & small) in production at a time and that’s it.
Haters might respond to this by saying, “but look, Samsung is Apple’s #1 competitor and they have like 65 different models.” Yes, very true. How many of those can you name? Do you know anything about them? Do they inspire product or brand loyalty? Samsung phones are perceived as largely generic except for the Galaxy series, and they’re part of the highly-fragmented Android ecosystem, which suffers from way too much diversity across a hundred brands and a thousand models. Not something Apple should be copying.
Second, Neglecting The Cloud: Sometimes Apple is a little too hardware-centric, and the way that IOS handles photos is an example of this. Your photos get uploaded to the cloud, and then a partial copy of your library is downloaded to all your devices - and meanwhile your ability to manage the photos in the cloud is really limited.
WTF, guys? This isn’t Napster, take a lesson from Google and keep the whole library in the cloud, then download them as needed. Just one example of Apple trying to keep everything tied to the hardware, when the hardware should be a gateway, not always a destination.
Third, Failing To Pursue Business Markets: Microsoft is still in business because Apple frankly doesn’t care if business users buy its products. They remain focused on the consumer products market, but they sell premium products that are nearly enterprise-class desktop machines. It’s ridiculous, because the #1 market that could pay for Apple computers doesn’t, because Apple basically ignores them.
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