Kara Swisher

Recent Posts by Kara Swisher

To VC or Not to VC: Former Square COO Rabois Leaning Toward Khosla Ventures Job


Keith Rabois, the former Square COO who left the company in the midst of unproven allegations of personal misconduct, is weighing an offer to join Silicon Valley venture firm Khosla Ventures, according to sources close to the situation, and is currently leaning toward accepting the job there.

But, that could change. In an interesting twist, the longtime entrepreneur and investor has also been in discussions with Airbnb CEO and co-founder Brian Chesky to become COO or president there.

Both the VC and the startup have been doing reference checks on Rabois, news of which has gotten out in the ever-chatty Silicon Valley scene. The Wall Street Journal reported earlier today that Rabois had been in talks with the San Francisco-based online housing rentals company.

But sources with knowledge of the situation said that Rabois — who has played the No. 2 to a string of high-profile entrepreneurs, including Peter Thiel at PayPal, Max Levchin at Slide and, most recently, Jack Dorsey at Square — seems “99 percent” ready to move into a more formal investing role.

Of course, there is still that one percent chance he might not, underscored by the eternal lure of the hot startup for serial entrepreneurs like Rabois. That said, he has also been an active angel investors for many years, with a wide-ranging portfolio, and is on many boards, including Yelp’s.

The choice of two very attractive alternatives is in stark contrast to the more tense situation for Rabois just a month ago, after accusations of sexual harassment arose related to a relationship he had with a Square employee.

Rabois has denied the allegations aimed at him and at the San Francisco payments company, which have not yet turned into a lawsuit, and has thus far been backed by Square. Rabois called the accusations by the employee “fiction” and a “shakedown.”

That said, due to the controversy around the serious workplace issue, he stepped down from his job as COO.

“At the end of the day, this is personally embarrassing to me, because when anyone’s life is exposed to a public forum, it creates quite a damaging situation,” said Rabois at the time in an interview with me. “As we looked at it, it was going to become a distraction that was going to hurt the company.”

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The problem with the Billionaire Savior phase of the newspaper collapse has always been that billionaires don’t tend to like the kind of authority-questioning journalism that upsets the status quo.

— Ryan Chittum, writing in the Columbia Journalism Review about the promise of Pierre Omidyar’s new media venture with Glenn Greenwald