The Mythical Sheryl Sandberg Wink And Smile (Starring Al Pacino)

In an an email newsletter yesterday Jason Calacanis, bizarrely referring to himself as Serpico (played by Al Pacino in the 1973 movie) talks about an interaction he had with Facebook CEO Mark Zuckerberg at the Wall Street Journal’s D Conference earlier this week.

Calacanis has long been over the top critical of Facebook, even recently referring to Zuckerberg as “an amoral, Asperger’s-like entrepreneur” and says “Zuckerberg is clearly the worst thing that’s happened to our industry since, well, spam.”

So it’s not surprising that he got in Mark’s face again in person. According to Jason, he first asked Mark to play poker with him, and then made comments to Mark as they both watched Steve Jobs on stage:

Steve said the folks at Apple were really concerned that some kid might get attacked–or worse–because someone tracked them with their technology. That could never happen right? Oh wait, Facebook is under assault for just this type of issue in Australia. Details:

While the audience cheered Steve’s position, I turned to Zuckerberg behind me and said: “I hope you’re taking notes.”

Zuck laughed, and Sheryl Sandberg–the adult brought in to keep Facebook and Zuckerberg out of trouble–shot me an aggressive stare from over his shoulder.


Then, out of site from Zuckberg, she winked and smiled at me.

Well played Sandberg, well played. In one complicated glance she admonished me for busting on the Golden Child, and then sent me the clear message that she appreciated that I’ve been educating the kid.

…. at least that’s how I read it.

So that’s a pretty serious allegation – that Sheryl Sandberg, the COO and clear no. 2 at Facebook, secretly enjoys seeing Mark criticized over Facebook’s privacy missteps.

Is it true? I asked Sandberg flat out via email. Her response: “absurd.” Plus a few other off the record comments that suggested it was really absurd.

Why the repeated Serpico references (really – he says “I am Serpico.”)? He’s getting pressure from “influential people,” he says, to fall into line and support Facebook. But he’s not going to stand for it:

Walking around the D conference I felt like Serpico. It feels like I crossed the Blue Line, where technology executives don’t get into big public fights that are bad for business. There are a lot of folks who are getting rich selling Facebook shares on SecondMarket today, and there are many more people–including friends of mine–who have a large percentage of their net worth in Facebook shares.

The sad part about the situation is that the person who sent me the email demands has massive influence over the industry, the people I work with. He could buy and sell me many times over. In short, this
power broker could make my life and career in technology miserable.

In fact, he could probably get me fired… and he let me know that in so many words.

The thing is, though, that this is good for business. Jason is the master at creating controversy. And controversy is fun, up to a point. But trying to disrupt a management team by suggesting that there’s strife when there really isn’t is crossing a line.

I’ve written recently that media and blogging attacks on Facebook are getting out of hand.

We love to tear apart the people and companies that are trying to do big things. And nothing is bigger in tech right now than what Facebook is trying to accomplish – a restructuring of the Internet around a social architecture. It may be time for us all to step back and realize that we’re witnessing the creation of a massive company, one that touches the lives of half a billion people a month, on the fly.

We’re seeing sausage being made, never a pleasant experience, by a company that is inventing the sausage as they go.