a16z exec Steven Sinofsky had murky dealings with Jeffrey Epstein in his previous life working for Microsoft
Steven Sinofsky isn’t a household name outside tech circles, but he once ran the operating system on more than 90% of the world’s PCs, and now quietly sits as a board partner at one of Silicon Valley’s most powerful venture firms, Andreessen Horowitz. He’s also, as Fortune’s new investigation digs into, a former Microsoft insider who turned to Jeffrey Epstein as a seven‑figure fixer on his way out of the company.
Sinofsky joined Microsoft straight out of grad school in 1989 and climbed from software engineer to president of the Windows division, overseeing Windows 7 and Windows 8. He was once even seen as a possible successor to Steve Ballmer. When he abruptly left in 2012, his departure temporarily knocked billions off Microsoft’s market cap.
Today, he’s a board partner at Andreessen Horowitz, representing the firm on select portfolio company boards and advising founders on product, strategy, and scaling.
What that résumé doesn’t show, however, is Sinofsky’s entanglement in the murkier corners of the business world. Department of Justice documents detail how, after leaving Microsoft, Sinofsky brought on Jeffrey Epstein—an already convicted sex offender—as a paid negotiator on his exit deal. Emails, reviewed by Fortune, show Epstein critiquing drafts of Sinofsky’s resignation agreement, especially non‑disparagement language in the draft, and ultimately collecting a $1 million fee when Sinofsky secured a $14 million package.
Those same records place Sinofsky in the tight orbit through which Epstein sought influence over Bill Gates, aided by Sinofsky’s longtime partner Melanie Walker, a Gates Foundation alum who fed Epstein internal Microsoft gossip years before Sinofsky’s exit, files published by the DOJ reveal. Through a series of other interactions (Epstein document search tool JMail cites over 1,400 emails and mentions of Sinofsky in the communications), Sinofsky remained in contact with Epstein in a personal capacity until at least late 2017, and appeared to help Epstein keep tabs on various other tech figures and startups, including details on WeWork as its business model came into question, and feedback on various startup investment opportunities. Sinofsky also appeared to use Epstein as a professional sounding board, keeping him informed on the Andreessen Horowitz opportunity and an exploratory conversation he apparently had with another tech bigwig.
Sinofsky hasn’t been charged with any crime, nor accused of any wrongdoing. Sinofsky did not provide a comment to Fortune, and a16z did not immediately respond to Fortune’s request for comment. Microsoft declined to comment. Venture capitalists are known for doing their due diligence. But the question this episode raises is how much do founders know about the investors, their LPs, and the sometimes murky dealings swirling in the corridors of money and power? You can read the full story in Fortune here.
See you tomorrow,
Lily Mae Lazarus
X: @LilyMaeLazarus
Email: lily.lazarus@fortune.com
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This story was originally featured on Fortune.com