Longreads

How financial and personal pressure took a toll on an entrepreneur:

"Before the fundraising, Sherman would push himself and others to raise as much money as possible for their businesses. After the financing closed, he began referring to venture capital as a 'fraud' and a 'sham.'

"Employees could tell something was off when Sherman announced the financing to the team.

"'He said, "This is one of the hardest things I've ever had to do. And I hope to not have to raise more money for a very long time,"' a source recalls.

"Another source also recalled Sherman saying something alarming about this last round:

"'He said, "I had no business raising that last round of financing. I hadn't made our metrics or our terms—not anything near it. But I got it done."'"

An inside look at how banks jockey for "left lead" status on an IPO—especially one as big as Facebook's:

"For the past couple of decades, Goldman Sachs and Morgan Stanley have ruled the tech IPO business, with one of the firms serving as lead manager on most of the hottest deals.

"Goldman took Microsoft, Yahoo, and eBay public, for example. Morgan won Netscape and Google. Although other firms have picked off an occasional deal over the years, when it comes to tech banking, Goldman and Morgan remain in a class by themselves. To be sure, having Morgan or Goldman take you public is no guarantee of success—they’ve banked plenty of dogs. But going public without Morgan or Goldman means signaling that you weren’t good enough for Morgan or Goldman. In other words, that your company is second-rate.

"In the last few years, though, there has been a shift in the Morgan-Goldman power balance in the Valley. Specifically, until very recently, Morgan Stanley has won almost all of the hot IPOs."

Groupon actually lost $413 million in 2010. Diving into the S-1, it turned out that Groupon only considered itself profitable because it used a peculiar accounting metric of its own creation — adjusted consolidated segment operating income, or ACSOI. Basically, Groupon was taking the money it was spending on advertising to acquire new subscribers to its email and not counting that money as a quarterly, recurring expense — but as a one-time, capital expense, the way Google might account for the cost of building a new server farm. Groupon was saying that ACSOI helped it figure out the ratio between the amount of money it needed to spend on marketing to acquire a subscriber and how much that subscriber would be worth to the company over the long haul. But marketing expenses are not typically accounted for this way, and people looked at Groupon as though it were trying to pull a fast one.