From my many years of experience in business I can say that anytime you have a serious offer on the table you have to decide if you are willing to risk going for door number two.
You can always point to cases where people didn't sell out and ended up better but with business you have to look at the downside not just the upside. Over the years that is the biggest mistake that I have seen people make in negotiation.
I'll give you an example with domains. I'm in the process of buying a domain for a startup and the startup will pay $50,000 maybe even $100,000 for the domain. But the owner won't even engage preferring to shoot for the stars and thinks he will get a million. He won't even state a price. At this point we will cut bait and find another name. I know fully well this business (I also own names) and I know that this domain has about a 2% chance of selling for anywhere near that amount in coming years. I have domains that I've held for 15 years and have never gotten a single offer on. I've had domains that I've held for 15 years that I've sold for big money. Anytime someone comes along with a serious offer I focus on how long it will take until the next offer will come in - if ever. Business and gambling are two different things.
I have found my client another domain that they are happy with.
how is that bs ? I have a vanity domain that I'm not interested in selling.
Otoh, if I approached Marissa Mayer to buy a domain she owned I wouldn't consider "I don't want to sell" "BS".
If I approached McDonalds and wanted to buy "hamburger.com" from them (hypothetical) and they said "don't want to sell" I wouldn't consider that BS.
But this company, that is their business (domains). It is BS.
Lastly, If your vanity domain name is (hypothetically once again) "nowblog.com" maybe you aren't interested in selling it. If someone offers you $100,000 you might be interested, correct?
For a fairly popular example of some other founders who didn't accurately value their company :
Only in the minds of a few people.
The startup CEO has to be a cheerleader and biggest believer. And at the same time, the biggest realist, the most aware of the downside risks. There are times when you have to push the kool-aid aside.
"Nobody knows future."
History is littered with startups that didn't exit in frothy markets, then cratered. Timing is everything. Andrew's advisors should have been aware of the downside risks, should have had some experience with previous business cycles. IMHO they gave bad advice.
Not very many with a $6b offer
Respectfully - no. (And by that I mean respect++ - I learned a lot from your book!)
The company had been around awhile, and there was data to guide the decision. Growth rates, customer acquisition costs, engineering costs, etc. At the time of the offer, a lot about Groupon's financial model was well known. It could have led to a better decision.
So Groupon walking away from the deal could have been their only option.
That said, Google is one company that could make this sort of product work as one of the major expenses Groupon has is buying advertising.