One of tech's wealthiest workaholics is weighing his options.
Keith Rabois, who stepped down as COO of Square in the wake of a sex scandal last month, is being courted by Airbnb for a top operating job, according to the Wall Street Journal, while Kara Swisher at AllThingsD says he's far more likely to join Khosla Ventures as a partner.
Rabois doesn't exactly have to work. As a former PayPal executive and one of Silicon Valley's more successful angel investors, he has made a considerable fortune. According to a document Business Insider has reviewed, his stake in Square is worth $50 million at the company's current valuation.
He's also a board member at money-transfer company Xoom, which recently went public, and Yelp.
Yet friends describe Rabois as having a relentless work ethic. At Square, he typically worked on Sundays. So it is likely he'll end up taking on some big job.
Representatives from Khosla Ventures and Airbnb, reached Saturday evening, declined to comment.
Both career options are intriguing, but pose challenges for Rabois.
Airbnb could use an operator
Airbnb, which Rabois backed early on as an angel investor, is run by a close-knit troika of founders—CEO Brian Chesky, chief product officer Joe Gebbia, and CTO Nathan Blecharczyk. That said, the online lodging marketplace has interesting problems, including maintaining control over its fast international growth; fending off legal problems over rentals in cities like San Francisco, New York, and Amsterdam; and competition from various players.
Rabois, as an executive at PayPal, led the effort to get its payment service on the right side of the law across the United States, while fending off a fierce competitive challenge from eBay, which eventually bought the company.
Airbnb recently added a VP of engineering, Mike Curtis, from Facebook, and as Business Insider reported on Friday, added former Zappos COO Alfred Lin from Sequoia Capital to its board of directors.
Jessica Lessin at the Wall Street Journal is "still evaluating whether [Rabois] would be a good fit."
That is clearly a very active process. Rabois has taken a recent interest in getting to know the talent at Airbnb.
On LinkedIn, he recently connected to Joe Zadeh, a key programmer, and Thomas Arend, a recent hire from Twitter who heads Airbnb's international product development. That seems like an unusual level of involvement with Airbnb's technology team for someone who's just an investor.
Khosla needs another star
But given Rabois's talent for picking startups like Airbnb, a full-time investing role might make more sense.
Khosla Ventures, founded in 2004 by former Kleiner Perkins venture capitalist Vinod Khosla, has struggled to expand its bench of investors. Among the departed partners include former Facebook CFO Gideon Yu, now president of the San Francisco 49ers; Ramy Adeeb, who left to found Snip.it, a startup he recently sold to Yahoo; Ford Tamer, now CEO at Inphi; and Alex Kinnier, a former Google executive who's now at Opower.
So landing Rabois would be a coup for Khosla, and would decrease the perception that the firm is Vinod Khosla's show.
It does not hurt that Rabois had made a ton of money on paper for Khosla, which owns a stake in Square now notionally worth $462.5 million, after having led a $10 million initial financing round in 2009.
Rabois stepped down from Square after an employee at the company accused him of sexual harassment and hired a lawyer who threatened to sue Rabois and Square.
Rabois acknowledged that he had a physical relationship with the man and said it was consensual, but admitted he had never disclosed the relationship to colleagues at Square.
Square had an outside lawyer investigate, and while it didn't find evidence of harassment, a company spokesperson said Rabois displayed "poor judgment." Rabois said he resigned because the matter would inevitably create a "distraction" for Square.
At the time, Rabois said he planned to announce his next move in February. With the month winding down, it seems we'll know soon what it is.
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