Kara Swisher

Recent Posts by Kara Swisher

Khosla’s Keith Rabois Talks About Going From Internet Ops to VC-Land (Video)

I coasted down to Sand Hill Road yesterday to pay a quick visit to longtime Internet investor and operating executive Keith Rabois to talk about his new gig as a venture capitalist at Khosla Ventures.

Rabois — for those following the soap opera aspects of the story — left his job as COO of Square, the San Francisco online payments company, in the midst of unproven allegations of personal misconduct earlier this year with regard to accusations of sexual harassment related to a relationship he had with a Square employee.

After he left, Rabois considered a top job at Airbnb, the online rentals startup, as well as other places. But he eventually landed at the top-tier Silicon Valley VC firm because he wanted to turn his active informal investing experience as a longtime angel investor into the real deal.

It was a major shift, since Rabois has largely been a serious operator, having been 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.

So, I decided to check in with him since he arrived in March on how he’s liking the new life of plush offices and entrepreneur hunting. One thing is clear — Rabois has been active, making about 10 investments since he got there, including making a big bet on HealthTap, a mobile medical Q&A app.

Here’s my video interview with Rabois at Khosla’s luxe HQ (by the way, we did not discuss the Square departure, as he already did so quite publicly with me several times and also in a blog post):


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Just as the atom bomb was the weapon that was supposed to render war obsolete, the Internet seems like capitalism’s ultimate feat of self-destructive genius, an economic doomsday device rendering it impossible for anyone to ever make a profit off anything again. It’s especially hopeless for those whose work is easily digitized and accessed free of charge.

— Author Tim Kreider on not getting paid for one’s work