Groupon stock hit another all-time low today. That in itself is not news — the company has had a habit of setting all time lows.

But today marks the first day that Groupon dropped below the split-adjusted $7.90 paid by late-stage private investors in early 2011. (Disclosure: I have a variety of puts and several wagers against Groupon.) That round included funding from Andreessen Horowitz, Kleiner Perkins, Greylock Partners, and Technology Crossover Ventures, as well as Fidelity and T. Rowe Price. If any of them are still holding Groupon shares, they’re doing so at a loss.

In that round of close to $1 billion, Groupon insiders pocketed nearly 90% of the proceeds.

In May, I asked Benchmark VC Bill Gurley if he would ever invest in a round where insiders took so much cash.

“Probably not,” Gurley said with a laugh. “I can imagine a situation where I would. But it would raise a lot of questions and it would be a 2% likelihood situation. … I would have a lot of questions about the go-forward intent of the team.”

Recently, Groupon chairman Eric Lefkofsky, who along with his affiliated entities took nearly $400 million of that round, said that he was going to focus more of his time on his venture capital firm.

Gurley said Benchmark never took a serious look at Groupon.

“A 42% rake is really a lot,” Gurley said, referring to the portion of a merchant deal that Groupon takes. “There’s no way that value proposition can hold at 42 if someone else is doing it for 10. It can’t last. Or, everything I’ve learned about finance and business could be wrong. One of those two things.”

At today’s valuation of about $5 billion, Groupon is worth a cool billion less than Google offered for the company in 2011.

[Top image credit:  Norebbo/Shutterstock]