I remember when this happened. Apple’s corporate staff screwed up and didn’t have the contract done in time to have the music in by the keynote. And of course they are not going to move the keynote. So Jobs had to spin it: the small number of songs is a good thing, actually!
He was one of the best at this. PowerPC is not keeping up with Intel? Spin it! (Then switch.) Everyone hates DRM? Spin it! (Then drop DRM.) People are nervous about your antenna design? Spin it! And give ‘em a bumper. (But don’t change the antenna.)
What he said publicly was not necessarily a reflection of reality, it was whatever he thought would best position himself and his organization at that moment. In tech they called it a reality distortion field. In politics it’s called a day ending in -y. :-)
Obviously Apple did not have a problem with CD Baby because they did do the contract. And obviously they did not actually have a quality concern about the cheap $40 fee because they kept them even as it went to free.
It’s a classic small business supplier story: the big guys will do what works best for them and the little guy will have to deal with it in order to get the benefit. The most common example is how long most big businesses take to pay their small suppliers. It’s not intentionally malicious, just relative indifference. Like a big truck running over a raccoon because it’s so hard to swerve or stop.
> It’s a classic small business supplier story: the big guys will do what works best for them and the little guy will have to deal with it in order to get the benefit.
“The strong do what they can and the weak suffer what they must.” - The Melian Dialogue
Is this not a common trait among most of the high-level tech CEOs? We hear of lack of humanity across much of the tech industry when you get up to that level. All the stuff that is said about Musk, and all the others.
The main think I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children. Compared to making EVs mainstream, helping paralysed people nteract with the world, reducing traffic in LV, cutting government fraud and making reusable rockets that's pretty thin.
> The main think I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children.
You missed a word there.
The main NEGATIVE things I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children.
> Compared to making EVs mainstream,
He didn't do that, although he contributed. I can credit him with raising the consumer demand for in-vehicle assistance.
> helping paralyzed people interact with the world,
I also helped someone carry their groceries yesterday. That's a personality trait. The results of one of his many business efforts is not a personal act...although he likes to take credit.
> reducing traffic in LV,
That was a selling point for funding a different boring technology (that didn't happen) and hopefully a better transportation system (which also didn't happen) for a convenience tunnel. SR-99 is a commuter highway tunnel, with double the traffic, and the Seattle Tunnel Partners is not considered a magnate for the same reason Elon's tunnel isn't. It's just boring (literally and figuratively).
The biography regarding how NeXT came to be is quite relevant in how it all went, and how lucky it was that Apple ended up going with NeXT instead of Be.
Haven't read that book, but I am Listening to the Audiobook of "Steve Jobs in Exile: The Untold Story of NeXT and the Remaking of an American Visionary" on commutes etc. Really like the book, and you get a another view of Steve Jobs, the people behind NeXT and the industry at that time.
There is actually a Youtube video from The Computer History Museum on the book with the author and key figures from NeXT’s history [Recorded May 26, 2026] (haven't seen it yet, but looking forward to):
https://www.youtube.com/watch?v=gnNdb2wa_NE
While I don’t love Google (it’s hard to love) I actually think Sundar isn’t an asshole fwiw. Also I’m not sure if you’d put Dario in big tech circles but he seems half decent. A little too AGI pilled perhaps but definitely standing up for what he believes in.
The bar is pretty low among that population, though.
I mean, they gave money to a PAC that is trying to get legislation to control all models. He’s fine with legislation affecting Anthropic as far as I can tell, as long as it’s evenly applied. Open weight models built outside the US are going to be pretty hard to control, though.
Apple's playbook has always been to knock technology they don't have as "worthless" (Video Messaging, Copy/Paste on iPhone, ability to play multiple video formats on AppleTV, ability to encode WAV files into Apple AAC/M4P). I get that sitting in the meeting room, one would not want to piss off Steve Jobs. Real money/opportunities are sitting there on the table. But it sure would have been nice to say, "Man, this seems like the type of place that might employ a smart engineer or two.... How about you let me know when they figure out how to convert my dataset into something you can handle". Slide the paperwork back across the table, stand, button my top button of my suit jacket, say, "good day". The outcome would have been the same - Steve still would have changed his story into "we didn't want them". But in your mind, it would have been, "wow, I can't believe converting one format to another was such an arduous task".
This is pure survivorship bias talking. Being ruthless is one way to get just about anything you want, but rarely the best way and it sits with you. Even Steve Jobs spent so much time justifying his shittyness that I think on some level it didn't sit with him very well.
>A month later, Steve Jobs did a special worldwide simulcast keynote speech about iTunes. People had been criticizing iTunes for having less music than the competition. They had 400,000 songs while Rhapsody and Napster had over 2 million songs. (Over 500,000 of those were from CD Baby.)
>Four minutes in, he said something that made my pounding heart sink to my burning stomach:
>“This number could have easily been much higher, if we wanted to let in every song. But we realize that record companies do a great service. They edit! Did you know that if you and I record a song, for $40 we can pay a few of the services to get it on their site, through some intermediaries? We can be on Rhapsody and all these other guys for $40? Well we don’t want to let that stuff on our site! So we’ve had to edit it. And these are 400,000 quality songs.”
In 2003, there were 2 special events with Steve Jobs keynotes about iTunes and he's referring to the 2nd one on October 16, 2003 (deep link to that quote) :
https://www.youtube.com/watch?v=MvCJ613HORA&t=9m00s
>Whoa! Wow. Steve Jobs just dissed me hard! I’m the only one charging $40. That was me he’s referring to!
The author Derek Sivers left a lot of details out but here's how I interpret the situation ...
As prerequisite background, you can categorize "record labels" into 2 groups:
(1) the record label pays the artist for music via "advances", paying upfront recording costs, marketing etc. These are the traditional record labels like Warner, Universal, Sony, Motown, etc that "develop" the artist by making financial bets and losing money on most of the signed roster but making a profit a tiny number.
(2) the artists pay the "record label" -- where these entities are mostly used as a "distribution" intermediary. CD Baby and Tunecore would be typical examples.
Now look at the convoluted process with physical CDs that Apple forced CDBaby and other independents to use:
>The Apple guys said, “Sorry, you need to use this software; there is no other way.”
>Ugh. That means we have to pull each one of those CDs off of the shelf again, stick it in a Mac, then cut-and-paste every song title into that Mac software. But so be it. If that’s what Apple needs, OK.
That is basically a form of "proof-of-work". Apple didn't necessarily want everything from CD Baby. Instead, they just wanted the stuff CD Baby thought was worthwhile enough to expend time & effort to mess around with physical CDs.
The big labels didn't have to do that because they already did a form of "proof-of-work" via paying in advance for artists.
The issue is that Derek didn't "read between the lines" to understand what Steve Jobs and the convoluted upload process was trying to accomplish. I suppose business people could just speak plainly so they don't get mixed messages but sometimes they don't.
You forgot an important quote:
“We want the iTunes Music Store to have every piece of music ever recorded. Even if it’s discontinued or not selling much, we want it all.”
> I suppose business people could just speak plainly so they don't get mixed messages but sometimes they don't.
When you’re putting out a message to a large amount of people, no matter how much time and effort you spend trying to get the words just right so everyone understands, there’s always going to someone that misunderstands it and gets offended.
I think it's more likely that the iTunes software was just immature at that point.
What you're describing is a nice side effect of that for Apple, but the reality is they're not going to do the bitch work of importing all those songs from a hodge podge of whatever formats they're given. They didn't have a better tool available at that time to make their catalog consistent.
It's very believable that Apple felt enough urgency to rush this phase.
What do you mean for the sake of Apple? This didn't benefit Apple. He screwed with this guy for months because of a mistaken idea that the guy should have somehow known Apple's attitude towards secrecy without being told, and after months of messing him about sent him back the signed contract the second he had given up. There was no benefit to Apple here. In fact he harmed Apple by limiting their music collection in the initial stages. It's also not on the limits of ethics. It's unethical.
> should have somehow known Apple's attitude towards secrecy
I have to assume you and the author (at that time) aren't familiar enough with the corporate world to realize all discussions containing privileged information (contract details that would never get a press release) are confidential by default.
Of course Apple would never think they'd have to explain this. It's a reasonable expectation for them to have.
I work in the corporate world, I have detailed confidential discussions about technical details of upcoming products and contract details. The first thing we do in those situations is we all sign NDAs. The idea that you'd do a presentation to a hundred people and expect that information to stay confidential without specifically informing them is just absurd. Which is part of the reason Jobs just screwed him around rather than doing what you're meant to do - get the person to sign an NDA and then sue them if they break it.
Pricing details in contracts are trade secrets. You don't even need an NDA to sue someone for leaking that.
They're lucky Apple found a quick remediation. They delayed signing the contract because they had to wait and see if any damage was caused. Next steps would have been renegotiating or lawsuit.
lol, if you don’t put an NDA (or otherwise make it clear it’s a trade secret and try to protect it), you lose the protection the moment you start sending that out. Including in contracts.
You mean on the limits of being sued for. Coz this man had zero ethics anywhere in his life unless "being ethical" was somehow correlated with also making money
After reading this story, I do think Apple is bad, but from a business perspective, it makes sense. (By 'business perspective,' I mean it's immoral but profitable.)
Because if CD Baby was acting as a middleman and a gateway for indie music distribution, Apple's move to shut it out was about preventing power from becoming decentralized and keeping control concentrated in Apple's hands to position iTunes as a premium platform. On top of that, if CD Baby had monopolized the indie music market, any future platform would only need to deal with CD Baby, which would have been a burden down the line.
It was likely a strategy to capture the entire music market. Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft. I don't know what the image is like in the US. Personally, I've always thought Apple's premium strategy is terrible
> Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft.
Apple was the underdog at a point where Microsoft got its bad image by virtue of it's monopolistic practice. I can't help but think that a lot of it is a combination of inertia and MS pissing off a sufficient subset of geeks at a point where we made up a much larger proportion of the online discourse and so could set the tone. And for at least a time, in part by virtue of MS bad reputation, a subset of geeks saw Apple as a possible saviour.
It also helps that for all of its calculated business behaviour, Apple also has a reputation for better quality that makes people want to give them passes for things MS wouldn't get a pass for.
Microsoft also had more instances of being petty, (see the bit about join press releases in Jerry Kaplan's _StartUp_ https://www.goodreads.com/book/show/1171250.Startup ), vindictive (bundling Internet Explorer rather than having two separate produces, an HTML display component coded to the standard and usable by all apps and a browser application which also used it and optionally extended it), and even destructive (poster child for this is MacBasic: https://www.folklore.org/MacBasic.html but there are two many instances to note and researching more instances is left as an exercise for the reader).
At least Apple's destructiveness was mostly related to market realities and their own product (still waiting for a replacement for my Newton MessagePad --- my Samsung Galaxy Note 10+ sort of works (but not daylight viewable), my Kindle Scribe ColourSoft is quite nice, but way too limited and no 3rd party apps other than what can be done via PDFs or HTML)).
> By 'business perspective,' I mean it's immoral but profitable.
So, the purest form of evil there is?
> Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft.
They are indeed just as bad as each other. I think Microsoft just got unlucky and had a lot of bad-PR emails leak. If that had happened at Apple he'd probably have someone killed.
I was a sysadmin through the 90's and my distaste for Microsoft was that it wasn't plug and play and they would distribute software on 35 floppy disks instead of a CD-ROM. Finally their business practice. If Microsoft was unlucky, remember we make our own luck.
I remember when this happened. Apple’s corporate staff screwed up and didn’t have the contract done in time to have the music in by the keynote. And of course they are not going to move the keynote. So Jobs had to spin it: the small number of songs is a good thing, actually!
He was one of the best at this. PowerPC is not keeping up with Intel? Spin it! (Then switch.) Everyone hates DRM? Spin it! (Then drop DRM.) People are nervous about your antenna design? Spin it! And give ‘em a bumper. (But don’t change the antenna.)
What he said publicly was not necessarily a reflection of reality, it was whatever he thought would best position himself and his organization at that moment. In tech they called it a reality distortion field. In politics it’s called a day ending in -y. :-)
Obviously Apple did not have a problem with CD Baby because they did do the contract. And obviously they did not actually have a quality concern about the cheap $40 fee because they kept them even as it went to free.
It’s a classic small business supplier story: the big guys will do what works best for them and the little guy will have to deal with it in order to get the benefit. The most common example is how long most big businesses take to pay their small suppliers. It’s not intentionally malicious, just relative indifference. Like a big truck running over a raccoon because it’s so hard to swerve or stop.
> It’s a classic small business supplier story: the big guys will do what works best for them and the little guy will have to deal with it in order to get the benefit.
“The strong do what they can and the weak suffer what they must.” - The Melian Dialogue
Very interesting insight. OP essentially lost at playing chicken.
That’s a misread. You don’t play chicken with a squirrel on the road.
Always worth remembering that as well as being an innovator, Steve Jobs was often a cruel and petty man.
Is this not a common trait among most of the high-level tech CEOs? We hear of lack of humanity across much of the tech industry when you get up to that level. All the stuff that is said about Musk, and all the others.
If we are seeking role models, dont seek out petty people.
Or, everybody is flawed and we shouldn’t adopt petty traits while respecting other traits and still having aspirations.
The main think I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children. Compared to making EVs mainstream, helping paralysed people nteract with the world, reducing traffic in LV, cutting government fraud and making reusable rockets that's pretty thin.
> The main think I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children.
You missed a word there.
The main NEGATIVE things I hear about Musk is that he supported a candidate people didn't like and has a lot of different mothers for his children.
> Compared to making EVs mainstream,
He didn't do that, although he contributed. I can credit him with raising the consumer demand for in-vehicle assistance.
> helping paralyzed people interact with the world,
I also helped someone carry their groceries yesterday. That's a personality trait. The results of one of his many business efforts is not a personal act...although he likes to take credit.
> reducing traffic in LV,
That was a selling point for funding a different boring technology (that didn't happen) and hopefully a better transportation system (which also didn't happen) for a convenience tunnel. SR-99 is a commuter highway tunnel, with double the traffic, and the Seattle Tunnel Partners is not considered a magnate for the same reason Elon's tunnel isn't. It's just boring (literally and figuratively).
> cutting government fraud
That's not what happened.
You should expand your bubble.
The biography regarding how NeXT came to be is quite relevant in how it all went, and how lucky it was that Apple ended up going with NeXT instead of Be.
"Steve Jobs and the Next Big Thing"
Haven't read that book, but I am Listening to the Audiobook of "Steve Jobs in Exile: The Untold Story of NeXT and the Remaking of an American Visionary" on commutes etc. Really like the book, and you get a another view of Steve Jobs, the people behind NeXT and the industry at that time.
There is actually a Youtube video from The Computer History Museum on the book with the author and key figures from NeXT’s history [Recorded May 26, 2026] (haven't seen it yet, but looking forward to): https://www.youtube.com/watch?v=gnNdb2wa_NE
Name a big tech CEO who isn’t.
While I don’t love Google (it’s hard to love) I actually think Sundar isn’t an asshole fwiw. Also I’m not sure if you’d put Dario in big tech circles but he seems half decent. A little too AGI pilled perhaps but definitely standing up for what he believes in.
The bar is pretty low among that population, though.
Dario's attemoting to use legislative capture to stop open source models as we speak.
I mean, they gave money to a PAC that is trying to get legislation to control all models. He’s fine with legislation affecting Anthropic as far as I can tell, as long as it’s evenly applied. Open weight models built outside the US are going to be pretty hard to control, though.
I think some of them do a better job of limiting their cruelty to their job.
Jobs allegedly spent years lying about whether his daughter was his daughter. That's not necessary for Apple to succeed. That's just being a dick.
dont get to that level without being an asshole.
And used his wealth to obtain and subsequently waste a liver that could have saved an actual important person with a family.
> an actual important person
importance is now how organ donations are managed.
It is? Really? Or did you mean "not"?
Sad comment really. I could make a counterargument that it could've gone to an alcoholic who wasted his liver, which would be equally uncalled for.
Apple's playbook has always been to knock technology they don't have as "worthless" (Video Messaging, Copy/Paste on iPhone, ability to play multiple video formats on AppleTV, ability to encode WAV files into Apple AAC/M4P). I get that sitting in the meeting room, one would not want to piss off Steve Jobs. Real money/opportunities are sitting there on the table. But it sure would have been nice to say, "Man, this seems like the type of place that might employ a smart engineer or two.... How about you let me know when they figure out how to convert my dataset into something you can handle". Slide the paperwork back across the table, stand, button my top button of my suit jacket, say, "good day". The outcome would have been the same - Steve still would have changed his story into "we didn't want them". But in your mind, it would have been, "wow, I can't believe converting one format to another was such an arduous task".
Ruthless.
1 of the 3 qualities one needs to be a successful entrepreneur.
This is pure survivorship bias talking. Being ruthless is one way to get just about anything you want, but rarely the best way and it sits with you. Even Steve Jobs spent so much time justifying his shittyness that I think on some level it didn't sit with him very well.
>A month later, Steve Jobs did a special worldwide simulcast keynote speech about iTunes. People had been criticizing iTunes for having less music than the competition. They had 400,000 songs while Rhapsody and Napster had over 2 million songs. (Over 500,000 of those were from CD Baby.)
>Four minutes in, he said something that made my pounding heart sink to my burning stomach:
>“This number could have easily been much higher, if we wanted to let in every song. But we realize that record companies do a great service. They edit! Did you know that if you and I record a song, for $40 we can pay a few of the services to get it on their site, through some intermediaries? We can be on Rhapsody and all these other guys for $40? Well we don’t want to let that stuff on our site! So we’ve had to edit it. And these are 400,000 quality songs.”
In 2003, there were 2 special events with Steve Jobs keynotes about iTunes and he's referring to the 2nd one on October 16, 2003 (deep link to that quote) : https://www.youtube.com/watch?v=MvCJ613HORA&t=9m00s
(For trivia reference, the first one was April 28, 2003 : https://www.youtube.com/watch?v=NF9o46zK5Jo)
>Whoa! Wow. Steve Jobs just dissed me hard! I’m the only one charging $40. That was me he’s referring to!
The author Derek Sivers left a lot of details out but here's how I interpret the situation ...
As prerequisite background, you can categorize "record labels" into 2 groups:
(1) the record label pays the artist for music via "advances", paying upfront recording costs, marketing etc. These are the traditional record labels like Warner, Universal, Sony, Motown, etc that "develop" the artist by making financial bets and losing money on most of the signed roster but making a profit a tiny number.
(2) the artists pay the "record label" -- where these entities are mostly used as a "distribution" intermediary. CD Baby and Tunecore would be typical examples.
Now look at the convoluted process with physical CDs that Apple forced CDBaby and other independents to use:
>The Apple guys said, “Sorry, you need to use this software; there is no other way.”
>Ugh. That means we have to pull each one of those CDs off of the shelf again, stick it in a Mac, then cut-and-paste every song title into that Mac software. But so be it. If that’s what Apple needs, OK.
That is basically a form of "proof-of-work". Apple didn't necessarily want everything from CD Baby. Instead, they just wanted the stuff CD Baby thought was worthwhile enough to expend time & effort to mess around with physical CDs.
The big labels didn't have to do that because they already did a form of "proof-of-work" via paying in advance for artists.
The issue is that Derek didn't "read between the lines" to understand what Steve Jobs and the convoluted upload process was trying to accomplish. I suppose business people could just speak plainly so they don't get mixed messages but sometimes they don't.
You forgot an important quote: “We want the iTunes Music Store to have every piece of music ever recorded. Even if it’s discontinued or not selling much, we want it all.”
It seems pretty unambiguous to me.
This. I'm pretty sure the major labels were not at this meeting and it was only indies.
> I suppose business people could just speak plainly so they don't get mixed messages but sometimes they don't.
When you’re putting out a message to a large amount of people, no matter how much time and effort you spend trying to get the words just right so everyone understands, there’s always going to someone that misunderstands it and gets offended.
I think it's more likely that the iTunes software was just immature at that point.
What you're describing is a nice side effect of that for Apple, but the reality is they're not going to do the bitch work of importing all those songs from a hodge podge of whatever formats they're given. They didn't have a better tool available at that time to make their catalog consistent.
It's very believable that Apple felt enough urgency to rush this phase.
I’m a moonlit musician and this makes a lot of sense to me.
"we don’t want to let that stuff on our site!"
Me, looking at all the slop on the App Store...
Classic Steve Jobs move. On the absolute limit of ethics for the sake of Apple
What do you mean for the sake of Apple? This didn't benefit Apple. He screwed with this guy for months because of a mistaken idea that the guy should have somehow known Apple's attitude towards secrecy without being told, and after months of messing him about sent him back the signed contract the second he had given up. There was no benefit to Apple here. In fact he harmed Apple by limiting their music collection in the initial stages. It's also not on the limits of ethics. It's unethical.
> should have somehow known Apple's attitude towards secrecy
I have to assume you and the author (at that time) aren't familiar enough with the corporate world to realize all discussions containing privileged information (contract details that would never get a press release) are confidential by default.
Of course Apple would never think they'd have to explain this. It's a reasonable expectation for them to have.
I work in the corporate world, I have detailed confidential discussions about technical details of upcoming products and contract details. The first thing we do in those situations is we all sign NDAs. The idea that you'd do a presentation to a hundred people and expect that information to stay confidential without specifically informing them is just absurd. Which is part of the reason Jobs just screwed him around rather than doing what you're meant to do - get the person to sign an NDA and then sue them if they break it.
Pricing details in contracts are trade secrets. You don't even need an NDA to sue someone for leaking that.
They're lucky Apple found a quick remediation. They delayed signing the contract because they had to wait and see if any damage was caused. Next steps would have been renegotiating or lawsuit.
lol, if you don’t put an NDA (or otherwise make it clear it’s a trade secret and try to protect it), you lose the protection the moment you start sending that out. Including in contracts.
I presume you mean "the maximum physical limit of bad ethics" rather than any particular ethical standard.
On the absolute limit of ethics? This is simply not ethical anymore...
You mean on the limits of being sued for. Coz this man had zero ethics anywhere in his life unless "being ethical" was somehow correlated with also making money
After reading this story, I do think Apple is bad, but from a business perspective, it makes sense. (By 'business perspective,' I mean it's immoral but profitable.)
Because if CD Baby was acting as a middleman and a gateway for indie music distribution, Apple's move to shut it out was about preventing power from becoming decentralized and keeping control concentrated in Apple's hands to position iTunes as a premium platform. On top of that, if CD Baby had monopolized the indie music market, any future platform would only need to deal with CD Baby, which would have been a burden down the line.
It was likely a strategy to capture the entire music market. Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft. I don't know what the image is like in the US. Personally, I've always thought Apple's premium strategy is terrible
> Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft.
Apple was the underdog at a point where Microsoft got its bad image by virtue of it's monopolistic practice. I can't help but think that a lot of it is a combination of inertia and MS pissing off a sufficient subset of geeks at a point where we made up a much larger proportion of the online discourse and so could set the tone. And for at least a time, in part by virtue of MS bad reputation, a subset of geeks saw Apple as a possible saviour.
It also helps that for all of its calculated business behaviour, Apple also has a reputation for better quality that makes people want to give them passes for things MS wouldn't get a pass for.
Microsoft also had more instances of being petty, (see the bit about join press releases in Jerry Kaplan's _StartUp_ https://www.goodreads.com/book/show/1171250.Startup ), vindictive (bundling Internet Explorer rather than having two separate produces, an HTML display component coded to the standard and usable by all apps and a browser application which also used it and optionally extended it), and even destructive (poster child for this is MacBasic: https://www.folklore.org/MacBasic.html but there are two many instances to note and researching more instances is left as an exercise for the reader).
At least Apple's destructiveness was mostly related to market realities and their own product (still waiting for a replacement for my Newton MessagePad --- my Samsung Galaxy Note 10+ sort of works (but not daylight viewable), my Kindle Scribe ColourSoft is quite nice, but way too limited and no 3rd party apps other than what can be done via PDFs or HTML)).
> By 'business perspective,' I mean it's immoral but profitable.
So, the purest form of evil there is?
> Sometimes I wonder why people don't get as angry at Apple as they do at Microsoft.
They are indeed just as bad as each other. I think Microsoft just got unlucky and had a lot of bad-PR emails leak. If that had happened at Apple he'd probably have someone killed.
I was a sysadmin through the 90's and my distaste for Microsoft was that it wasn't plug and play and they would distribute software on 35 floppy disks instead of a CD-ROM. Finally their business practice. If Microsoft was unlucky, remember we make our own luck.