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I wouldn't mind being advised by someone who created a business and sold it to Amazon for a billion dollars, lack of profitability notwithstanding.

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So they found the “greater fool”?

Mark Cuban also sold broadcast .com to Yahoo for 5.7 billion

I guess one could also argue in these cases that the founder started a very promising company, and the buyer failed to realize its potential.

You must be in marketing

That broadcast.com to Yahoo and Tom selling Myspace to Murdoch are 2 of my favorite flop acquisitions. Honorable mention: Digg selling its soul to their own sales team.

However, Geocities to Yahoo is one of my least fave.

I'd never heard of broadcast.com before, it is the inspiration for ROI (Radio on the Internet) and Russ Hanneman?

Probably! It was literally putting radio broadcasts on the internet. Tuning in to a radio frequency of a sporting event far away was avant garde and wanted by many. No idea why Yahoo needed to buy someone's janky website with an idea I just explained in 1 sentence, but yeah Yahoo managed to tank it from several billions of $ down to nothing in about a year.

Coulda been the first music streaming service. I hope someone has the minutes to those Yahoo board meetings and makes a cartoon out of it.

Tumblr to Yahoo for 1.1 billion in the hopes it becomes "The new PDF" was pretty good too.

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