>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.
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.
So, looking into it a bit more, iLike ended up selling for $20m to Myspace roughly a year after this story happened. It sucks for Steve Jobs to say you're full of BS, but really, if there's a mistake here, the mistake is simply not taking the $50m. Ali probably could have called up corp dev the next day and said, ha ha wasn't it funny that Steve called me a bullshitter in that meeting, anyways I accept your offer.
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?"
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.