Jobs would have had an estimate of what it would take to copy the feature - way less than $50m, just not quite as quickly.

It surely wouldn't have made a lot of difference (to Apple) if Jobs had laughed off the bluster, and negotiated back down to pretty much any number they liked, maybe even less than $50m.

But the asshole vibe from Jobs comes from the fact that he clearly didn't value the feature that much. It was more valuable to wait for his own team to build it slower, and send the CEO away with a flea in their ear pour encourager les autres. So I'm sure that story got heard by plenty of other potential Apple acquisitions, and saved Apple a lot of money down the line.

Moral evaluation of his action I leave as an exercise for the reader.

Why is not valuing the feature that much an asshole move?

I'm sure you'll figure out a way somehow. It's amazing how far people will bend themselves out of shape over Steve Jobs.

Of course it's reasonable for anyone in business to say "you're trying to bullshit me, so I'm not doing business with you". The OP agrees, end of story.

But - Jobs might have batted away OP's amateur bravado with grace, and still bought his company for any price he wanted (probably even less than it would have cost Apple to build!). Or he could have passed them over to a subordinate be let down.

Instead Jobs personally wanted to be known for cruel honesty, and for ordering a clone of a startup that he'd changed his mind about buying. I genuinely don't know whether he succeeded because or in spite of that kind of conduct.

Would you rather Jobs had NOT been transparent, and obscured his his thoughts behind niceties? Or perhaps he should have given a 30 minute negotiation coaching session to OP for free? He could do either of these, and others might, but this is business first and not necessary.

To me this seems like the "reality distortion field".

There's just no amount of "good negotiation" that is going to get Apple up from $50m to $150m here. Apple was willing to pay an acquihire amount of money and Ali wanted an acquisition that respected the last couple years of work they put in. The two sides were pretty far apart. So they didn't make a deal. That's all there is to it.

Steve Jobs somehow pulled a trick, though, convincing Ali that the reason everything went sour is that Ali was a bad negotiator. Just because he's Steve Jobs doesn't mean he knows the "correct" valuation of your startup! He's just trying to bully Ali into revealing whether there are other offers on the table.

The principles of negotiation here are simple... Ali had to find another company willing to pay a lot more than $50m. There's no way that a lot of talking to Apple is going to change how they view a small acquihire target.

I mean, saying "I know X" when in reality you aren't 100% confident... that's completely a Steve Jobs move! How many times did he say a product was absolutely amazing, when actually it's kind of just a middling quality Apple product?

OP says he would have taken less than $150m ("we tried in vain to negotiate some lower number"). Whether that lower number would be under Apple's highest number, is unknown. So your point is well taken that "bad negotiator" is a bit subjective and assumes that a deal could have been struck.

Was it a mistake? In retrospect it would have made Ali more money, but I don't know, maybe iLike still had some chance of succeeding on its own at that point. Maybe it was just a calculated risk that didn't pan out.

Maybe the perfectly charismatic negotiator could have squeezed an extra 10% out of Apple but that just isn't that important compared to the decision of "should we sell the company for approximately 50m, or not?"

What I consider soft is lashing out over the smallest emotional slight, which Steve was famous for. I wish we would all stop pretending that the platonic ideal of a leader is having the emotional maturity of a toddler.

Exactly. The lesson of this encounter wasn't anything more than: Steve Jobs had power and was willing to use it at the drop of a hat to puff up his ego over a tiny thing. Maybe there was something strategic behind that or maybe he just had anger issues and enough power that he didn't have to do anything about them.

And this huge analysis about deceptive intent makes no sense. Of course the startup wanted a price as high as they can get.

Yet this story increased my esteem for Jobs.

Jobs knew going in that Apple could build the feature set themselves, and invited the company on the chance that they could do it faster with an aqui-hire. He'd prepared and knew his numbers also, although he didn't need or intend to discuss them.

Now, everything goes swimmingly, and then this guy asks about numbers and expresses concern that his investors won't accept that. Fair enough, legit, and Steve instantly responds "Don't worry, we'll make sure they accept it." That should be WAY MORE than enough of a statement from someone like Jobs - he and his team obviously have huge experience at this, and the guy should have dropped it, and taken back that information, now more prepared. He should also have read the room and noticed that the tenor had changed and that's as far as it should be pushed.

Now, he goes ahead and doubles down basically demanding more money. It is now just about the money. Had he stopped at "I think we're worth more", it probably would have just ended at Steve saying "I don't think so", and leaving it to Eddy, maybe they'd make a deal, maybe not.

But then he instantly doubled down again, saying "I Know it is" - basically saying he had a competing term sheet at that value — when he had nothing. If he'd actually had a $150MM term sheet, Steve might have said, "ok, we'll consider it", or "you should take that deal".

But when Steve saw that there was nothing to back up the statement, what earthly reason could he have to want to even talk with the guy anymore? His time is too valuable to talk to liars, and he instantly lost any interest in acqui-hiring them.

It's impressive how Jobs instantly saw the BS and adjusted his attitude to the new reality.

Perhaps it'd be a tad better had Jobs not flashed anger at his wasted time and interacting with liars, but instead expressed sadness at the opportunity lost - could be a bit softer, but why? The situation is the same - SJ will not want you in the company even at a $1 aqui-hire.

It's critical to understand the level of game being played, and play it well. This guy played like he was in some college seminar instead of the top pro level, and he got burned. Good he's taking it so realistically.

Very few negotiators can reverse their positions in nanoseconds and realize the better deal is no deal at all.

Steve floated $1/user. In isolation, that's a fine initial consideration.

The OP's reaction - "that means we didn't create any initial value" - is 100% accurate response.

What you do with that epiphany is what's important.

In the end, iTunes Genius Sidebar didn't last long either.

These are both pretty subjective. But Jobs only got to attack one of them. "I think" would have been even easier to attack.

The CEO in question seems to have disengaged for subjective reasons related to points surrounding his ability to perceive himself from positions of weakness. As you said, he wasn't being deceptive, more like authentic and open. This Jobs didn't care for, in the sense of offering it room in the negotiation.

Jobs rightly perceived that you can negotiate powerfully with those in positions of emotional vulnerability if you develop subjective criticisms and refine them into more objective language via generalizations. But he had his own blind spots as well; it's more like he was lucky that op didn't take a different approach...but op was in a difficult place to begin with, this being Apple's platform.

What whould have been a better approach?

But a better approach, that really depends on a lot of things. More than just words to say in the meeting context.

Anyway...

Jobs cared a lot about people as capital; he also cared about impact, creativity, and especially insight. He admired the big picture, but a huge problem for him was that he couldn't easily live in it. I think this was extremely frustrating and kept him floating in the limbo-like DMZ between daily details and the big picture.

So here's an approach I would have liked to try:

"OK, so you just heard about the software and how we think it's pretty neat. But you don't want the software. We know you're not that dull. It's really a story about our people, the developers who know Apple customers, and who have helped us build up a cult following. And we have new concepts underway that are even better. If you knew what we had planned, in the big picture, you'd sh*t your pants."

Then I'd talk about how universal the ideas are. Then because I'm a time traveler and op's situation is annoying, and I want to get in a little jab for op, maybe I'd add,

"But these days our problem is trust. Can we really trust the platform we're building on? Look at these platforms. People are stuck between two of them, at home and at work. We want to look forward and imagine what future trusted platforms look like, too. Maybe you want us to experience something like that trust in dealing with Apple, but then again maybe you're just like all the rest..."

If you use "intrinsically abstract English language in a subjective way" in multi-million dollar deals or in medicinal practice, and you stand to benefit from it, then you could very well be a liar, or if sincere extremely dangerous to others...

To the one in the receiving end, you can choose to get intimidated by a larger than life personality like Steve Jobs, and focus on what he said to you and get crushed by any admonition or, conversely, lose your head by any praise.

This is not any good. Rather, look at the situation for what it is. It’s a mini-game. Good or bad outcomes should only inform future actions, and not be allowed to take over your thought process for unnecessarily long periods.

So, "stealing the idea" is an oxymoron, like "led zeppelin".