Deals

Keith Rabois’ next act, after Square: Khosla Ventures

Keith Rabois, the former chief operating officer of Square, has a new gig: He’s going to be a venture capitalist at Khosla Ventures.

“I love Khosla Ventures’ vision and passion for assisting the next generation of entrepreneurs,” Rabois said in a statement Khosla Ventures released this morning. “The Khosla team encourages entrepreneurs to be bold. And the team’s legendary work ethic ensures that entrepreneurs will receive the best possible assistance.”

He followed up the announcement with a tweet this morning that read, “Any bold, ambitious entrepreneurs around?”

Rabois has a long track record as an entrepreneur and angel investor. Previous to Square, he was a vice president for Slide, where he was responsible for Slide’s corporate strategy and partnerships. Prior to that, he had roles at PayPal and LinkedIn. He’s one of a circle of entrepreneurs associated with PayPal cofounder Peter Thiel, often referred to as the “PayPal Mafia” for their influence throughout Silicon Valley.

Rabois recently left Square after a company employee filed a lawsuit alleging sexual harassment. Rabois wrote a very personal blog post about his departure, acknowledging that he had a physical relationship with the man before he worked at Square, but stating that he’d not been involved in managing the employee at all.

Rabois said he was voluntarily leaving Square to avoid distracting the fast-growing company with his legal troubles. He must have left on good terms, because Square co-founder and chief executive Jack Dorsey lent his name to Khosla Ventures’ statement as well.

“I couldn’t be more excited to see two of the top entrepreneurs I know join forces at Khosla Ventures to support and coach the next generation of entrepreneurs the world over,” Dorsey’s statement read.

In 2010, Rabois answered a direct question on Q&A site Quora about whether he would ever consider becoming a VC. He noted that he would miss “the excitement and challenge of start-ups” and acknowledged the poor reputation that many VCs have among entrepreneurs.  But, he conceded that the role held some attraction for him. “As a result, at some point, I would not be shocked to invest money professionally. But I hope that I will still remember how to think different,” Rabois wrote.

Today, he followed up with a note on Quora explaining why he joined Khosla Ventures.

… what sets KV apart from other investors is that we are dedicated to a different model of venture assistance where the team and the partners bear the obligation to provide insightful guidance. In fact, I can attest that Square would not be Square today without KV’s help.

In my experience, raising capital is easy. High caliber mentoring and genuine counsel is rare. Those qualified to dispense it to a fragile startup are in short-supply. I am excited to join Khosla Ventures because we recognize that this what the most ambitious entrepreneurs crave.

Rabois currently holds board roles at Xoom (since June 2003) and Yelp (since September 2005), plus a large number of privately-held startups.

He will be a senior member of the firm, which does not use formal titles.

Photo credit: VentureBeat

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